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Allocholesterol / Coprostenol / 4:5-Coprosten-3-ol
Hideaki Nishino
C27H46O1 386.654 Download ChemDraw structure file

132deg (ether-methanol) (Ref. 0002)
[a]23/D=+43.7deg (c=1 in benzene) (Ref. 0002)
Freely sol in benzene, acetone, ether, chloroform, dioxane, pyridine; less sol in methanol, alcohol (Ref. 0002)

Preparation. (Ref. 0001/0002) Separation from cholesterol. (Ref. 0003)

Deep-red color with 90% trichloroacetic acid. Positive in Rosenheim reaction, Salkowski reaction, Liebermann-Burchard reaction. (Ref. 0002) Precipitable by digitonin. (Ref. 0004)
Androsterone / Cis-androsterone / 3a-Hydroxy-17-androstanone / Androstan-3(a)-ol-17-one / 3(a)-Hydroxyetioallocholan-17-one / 3-Epihydroxyetioallocholan-17-one
Hideaki Nishino
C19H30O2 290.440 Download ChemDraw structure file
Androgenic activity. Sex determination in fetus. Maintenance of genitalia functions. (Ref. 0005/0006)
185-185.5 degC (Ref. 0006)
[a]15/D=+87.8pm1.5deg, [a]15/5461=+107.3pm1.5deg (c=1.5379 in dioxan) (Ref. 0006)
Sol in most organic solvents. Barely sol in water. (Ref. 0007)
max. 292.5pm1.0 nm, min. 232.5pm2.5 nm (ethanol) (Ref. 0008)

Isolation from male urine. (Ref. 0005/0006)
Synthesis from cholesterol. (Ref. 0009/0010)

Not precipitated by digitonin. (Ref. 0007)
16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide / 3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide 16-acetate
Hideaki Nishino
C26H36O6 444.560 Download ChemDraw structure file
Cardiotoxic steroid. Applied for Chinese medicine named Senso as cardiotonic agent. (Ref. 0011/0012/0013/0014/0015/0016)
269-272 degC (3-acetate), 233 degC (free) (Ref. 0013)
[a]20/D=+5.4deg (c=0.5 in CHCl3) (Ref. 0013)
Sol in alcohol, chloroform (Ref. 0017)
max. 300 nm (Ref. 0015)
1H n.m.r. (100 MHz), employing spin-decoupling experiments, lead to the following assignments: the pyrone ring protons, d 6.17 (Ha, Doublet, Jab 9Hz, Jac 1Hz), 8.04 (Hb, Quartet, Jab 9Hz, Jbc 2.7Hz), 7.24 (Hc), while in ring D the 17a-proton Hd appeared as a doublet at d 2.72, J 9Hz. Because Jed and Jef were both 9Hz, He corresponded to a sextet at d 5.54 with Jeg 2 Hz. The methylene protons Hf and Hg gave signals at d 2.66 and 1.9, respectively. (Ref. 0016)
m/e: 444 (M, 5%) (M for C26H36O6=444); 384 (M-60, 100%); 336 (M-60-18, 61%); 351 (M-60-18-15, 9%); 348 (M-60-36, 10%); 341 (M-60-43, 80%); 323 (M-60-43-18, 68%). Metastable ion peaks at m/e 332.0 (440 to 384), 349.0 (384 to 366), and 303.0 (384 to 341) were observed. (Ref. 0016)

Predominant constituent of dermal gland secretion, toad poison. Component of bufotoxin. (Ref. 0011/0012/0013/0014/0015/0016/0017)
A couple of methods for partial synthesis. Prepare the 16-ketone of cinobufagin, reduce 14,15b-epoxide group with chromous acetate to yield b-hydroxy ketone and a,b-unsaturated ketone. Selectively reduce the b-hydroxy ketone with Urushibara nickel A to produce alcohol, which is acetylated to provide diacetate. Treat the diacetate with HCl in methanol to give bufotalin. Alternatively reduce first the a,b-unsaturated ketone with Urushibara nickel A to allylic alcohol. After acetylation subject the olefin to hypoiodous acid or hypobromous acid, then treat the resulting halohydrin with Urushibara nickel A. Hydrogenolyze the product to bufotalin 3b-acetate. (Ref. 0018)

Hideaki Nishino
C27H44O4 432.636 Download ChemDraw structure file
Saponin useful as fish poisons. (Ref. 0025)
273-276degC, 154-155degC (diacetate) (Ref. 0023)
[a]24/546 = -52deg (chloroform or isopropanol) (Ref. 0023)
Sol in methanol, isopropanol. (Ref. 0023)
d (pyridine) 0.83 (19-Me), 0.86 (18-Me), 1.12d(21-Me, J=7Hz), 1.05d (27-Me, J=7Hz), 3.30d (26-H2, J=11Hz), 3.39dd (26-H2, J=11, 3Hz), 4.45ddd (16-H, J=7, 7, 7Hz), 3.70m (3H and 6H). (Ref. 0024)
m/e 432 (Ref. 0024)

Root of amole (California soap plant, lily family, Chlorogalum pomeridianum Kunth) (Ref. 0025)

Precipitable by digitonin. (Ref. 0019) Conversion to tigogenin. (Ref. 0023)
Cholestanol / b-Cholestanol
Dihydroxycholesterol / 3b-Hydroxycholestan / 5a-Cholestan-3b-ol
Hideaki Nishino
C27H48O1 388.669 Download ChemDraw structure file
Accumulation within the nervous system in cerebrotendinous xanthomatosis patients. (Ref. 0031)
141.5-142degC (Ref. 0026)
[a] 22/D=+28.8deg (Ref. 0026)
Freely sol in heated alcohol, ethylether, chloroform. Approximately 1 g/100 ml alcohol or 200 ml methanol. (Ref. 0028)
9.20(19-H), 9.36(18-H) (Ref. 0029)

Human feces, bilestones, eggs. (Ref. 0028) Trace amount accompanied with cholesterol in animal cells, predominant sterol of sponges. (Ref. 0030)
Synthesis by reduction of cholesterol. (Ref. 0026/0027)

Precipitable by digitonin. Negative in Liebermann-Burchard reaction. (Ref. 0026/0027)
Coprostenol / 3b-Cholestanol / Stercorin
Hideaki Nishino
C27H48O1 388.669 Download ChemDraw structure file

101degC (methanol) (Ref. 0035)
[a]18/D=+28deg (c=1.8 in chloroform) (Ref. 0036)
Sol in ethylether, chloroform, benzene. Slightly sol in methanol (1g/145 ml). Sol in water. (Ref. 0036)

Separation from cholesterol using TLC. (Ref. 0034)
Feces from human (Ref. 0032/0034) , rat (Ref. 0033) , and carnivorous animals. (Ref. 0036)
Synthesis by reduction of cholest-5-en-3-one with lithium aluminium hydride. (Ref. 0035/0037) Synthesis by catalytic hydrogenation of coprostenol. (Ref. 0002/0038/0039/0040)

Approximately 360 mg/day in human feces. (Ref. 0032/0034) Positive in Liebermann-Burchard reaction. (Ref. 0032/0033/0034) Reduction by more than one bacterial species. (Ref. 0041)
7-Dehydrocholesterol / Provitamin D3
Hideaki Nishino
C27H44O1 384.638 Download ChemDraw structure file
Immediate precursor to cholesterol. (Ref. 0051/0052)
149-150degC (Ref. 0043)
[a]20/D=-122.5deg(benzene), -113.6deg(chloroform) (Ref. 0043/0045)
Sol in ether, chloroform. Slightly sol in methanol. Insol in water (Ref. 0045)
nm(e): min. 230 (150), max. 262.5 (740), max. 271 (1,040), min. 276 (883), max. 281.5 (1,075), min. 288 (553), max. 293 (615), max. 321 (36). (Ref. 0008)

E1%/1cm (l, nm): 39.1 (2,300), 193 (2,625), 271 (2,710), 230 (2,760), 280 (2,815), 144 (2,880), 160 (2,930), 0.9 (3,210). (Ref. 0046)

Tissues of animals (Ref. 0047) , pig derma (5 % of total sterols) (Ref. 0048) , Horned snail (Buccinum undatum). (Ref. 0049/0050)
Antirachitic activity as vitamin D3 after conversion to cholecalcipherol by ultraviolet irradiation and hydroxylation. (Ref. 0051/0052)
Synthesis from cholesterol via 7-bromocholesteryl ester. (Ref. 0053/0054)

Possibly excess accumulation relates to holoprosencephalic disorder. (Ref. 0055)
Precipitable by digitonin. (Ref. 0042)
Desmosterol / 24-Dehydrocholesterol / Desmesterol
Hideaki Nishino
C27H44O1 384.638 Download ChemDraw structure file
One of precursors to cholesterol in animals. (Ref. 0056/0057/0058)
120.5-121.0degC (methanol) (Ref. 0057) 117-118degC. (Ref. 0059) 120-122degC (Ref. 0060)
[a]/D=-37.9deg, [a]27/D=-40.2 (c=1 in chloroform) (Ref. 0057)
Sol in ether, benzene, chloroform, ethanol. (Ref. 0061)
max. 320nm (E1%/1cm, 240), 433nm (E1%/1cm, 154), min. 256nm (E1%/1cm, 93), 393nm (E1%/1cm, 109), (7times10-7 M in 97% sulfate) (Ref. 0057)
1125, 1012, 900 cm-1 (THP ether) (Ref. 0057/0058/0060)
41 (18-CH3), doublet centered at 51 (J=6Hz, 21-CH3), 61 (19-CH3), 97 and 102 (26.27 methyls), 210(3a-H) and 303(24-H), 320(6-H) (Ref. 0057/0058/0060)
m/e: 91(31%), 93(48%), 95(52%), 105(37%), 107(41%), 109(33%), 117(12%), 119(44%), 121(34%), 123(15%), 129(100%), 130(17%), 131(20%), 133(26%), 135(17%), 143(20%), 145(32%), 147(22%), 149(13%), 159(25%), 161(18%), 173(12%), 213(13%), 245(12%) (Ref. 0058)

Rat skin (Ref. 0056) Chick embryo (Ref. 0057) Red algae (Rhodophyceae) (Ref. 0058) Barnacle (Ref. 0059)
Synthesis from 3b-hydroxybisnorcholenic acid and 3b-hydroxynorcholenic acid by lithium-ethylamine-induced hydrogenolysis of the methyl ether derivatives of allyl alcohol. (Ref. 0060) Synthesis from 3b-acetoxy-23,24-dinorchol-5-en-22-ol by coupling reaction between dimethylallyllithium and a bromide. (Ref. 0062) Synthesis from 16a, 17a-epoxypregnenolone by employing the potassium-assisted oxy-Cope rearrangement as a key stereodirecting process at C-20. (Ref. 0063)

Possibly excess accumulation relates to lethal multiple malformations. (Ref. 0064)
Conversion to cholesterol in vivo. (Ref. 0056)
Hideaki Nishino
C27H44O6 464.635 Download ChemDraw structure file
Molting hormone of insects. (Ref. 0065/0066/0068/0069/0075)
238-239degC (Ref. 0067/0068)
[a]20/578 = +62deg (Ref. 0067)
Sol in ethanol. (Ref. 0065)
max. 243nm (e=11,600), 293nm (e=15,800) (Ref. 0065/0068)
KBr (/cm): 1658, 1652 (Ref. 0069)
n max. 73(18-H), 107(19-H), 124 and 131(21-H), 138(26-H and 27-H) cps (Ref. 0070)
m/e (t-190deg): 446(3%), 428(29), 418(2), 413(2), 410(3), 372(3), 359(4), 348(8), 330(15), 315(18), 300(23), 279(17), 267(5), 255(8),250(13), 249(10), 99(100), 81(61) (Ref. 0071)

Silkworm (Bombyx mori) (Ref. 0072) Rhizomes (Polypodium vulgare L.). (Ref. 0073) Bracken (Pteridium aquilium L.) (Ref. 0074)
Synthesis from stigma-22-ene-3,6-dione by dividing three partial structure, A-ring, B, C-ring, and side chain. (Ref. 0068) Synthesis from 3b-hydroxy-23,24-bisnorchol-5-en-22-oic acid, readily available starting material. (Ref. 0070) Synthesis from (20S)-2b,3b-diacetoxy-20-formyl-5b-pregn-7-en-6-one by Grinard reaction with 2-methyl-3-butyn-2-oltetrahydropyran-2-yl ether, followed by hydrogenation of the triple bond, removal of the protecting groups, and hydroxylation in 14a-position. (Ref. 0071) Synthesis from methyl 14a-hydroxy-2b,3b-isopropylidenedioxy-6-oxo-22,23-bisnor-5b-chol-7-enoate. (Ref. 0074)

b-Ecdysone / 20-Hydroxyecdysone / Ecdysterone / Crustecdysone / Isoinokosterone
Hideaki Nishino
C27H44O7 480.634 Download ChemDraw structure file
Molting and metamorphosis hormone for Insecta and Crustacea. Much potent than a-ecdysone. (Ref. 0077)
240-242degC (methanol-ethylacetate) (Ref. 0079)
[a]28/D = +63deg(c=1.0, methanol) (Ref. 0080)
Sol in methanol, ethanol. (Ref. 0080)
max. 243nm (e= 10,300), 240nm (ethanol, e= 12,670), 242nm (methanol, e= 12,400) (Ref. 0067/0079/0077)
n KBr/max. 1656, 1615, 1387, 1229, 1053, 917, 878 /cm (Ref. 0079)
Pyridine-d5: 1.07(19-H), 1.20(18-H), 1.36(26- and 27-H), 1.56(21-H), 6.17(7-H) (Ref. 0079)
m/e: 480 (ecdysone+0), 462 (M-H2O), 444 (M-2H2O), 426 (M-3H2O), 408 (M-4H2O) (Ref. 0077)

Silkworm (Bombyx mori) (Ref. 0077) Crawfish (crayfish) (Jasus lalandei) (Ref. 0078) Achyranthis radix (as phytoecdysone) (Ref. 0080) Australia timber tree (Podocarpus elatus) (Ref. 0081) Lemmaphyllum microphyllum, Trillium smallii (Ref. 0082)
Synthesis from hydroxylated aldehyde precursor, (20S)-2b,3b-diacetoxy-5a-hydroxy-20-methoxycarbonylpregn-7-en-6-one. (Ref. 0079) Synthesis from 20b-hydroxy-5a-pregnane-3,6-dione via 2b,3b-diacetoxy-5a-pregn-7-ene-6,20-dione. (Ref. 0083) Stereospecific synthesis from 20bbenzoyloxy-5-pregnen-3b-ol. (Ref. 0084) Stereocontrolled total synthesis from 2b,3b,20b,-triacetoxy-5a-pregnan 6-one via acetylene-cationcyclization. (Ref. 0085)

The complete structure of natural b-ecdysone determined by a three-dimensional X-ray analysis using convolution molecule method. (Ref. 0076)
3-Hydroxyestra-1,2,5(10),7-tetraen-17-one / 1,3,5,7-Estratetraen-3-ol-17-one
Hideaki Nishino
C18H20O2 268.350 Download ChemDraw structure file
Weaker than estron, stronger than estriol. (Ref. 0091) Clinically available because of mild estrogenic hormone activity. (Ref. 0093)
237-239degC (Ref. 0087) 238-240degC (Ref. 0088) 237-240degC (Ref. 0089)
[a]15/D=+308 (dioxane) (Ref. 0088) [a]25/D=+304deg(dioxane) (Ref. 0087) [a]/D=+295deg(c=1 in ethanol) (Ref. 0089)
max. 283-285nm (Ref. 0090) 282nm (ethanol) (Ref. 0089)

loge=3.36 (282nm) (Ref. 0089)

Urine of mares. (Ref. 0088/0091)
Synthesis from 19-nortestosterone acetate via four intermediates. (Ref. 0089) Relatively simple synthesis from dienone compound. (Ref. 0092) Synthesis from estratetraene via several novel steroid intermediates and reactions. (Ref. 0093) Total synthesis from estra-1,3,5(10),8-tetraenes by oxidation with m-chloroperbenzoic acid, rearrangement of the resulting epoxide with acid, catalytic hydrogenation, and dehydration. (Ref. 0094) Synthesis by conversion of equilenine. (Ref. 0095/0096)

Ergosterol / Ergosterin / Provitamin D2
Hideaki Nishino
C28H44O1 396.648 Download ChemDraw structure file
Antirachitic activity as 1,25-dihydroxyergocalciferol. (Ref. 0102)
168degC (alcohol) (Ref. 0098)
bp0.01 = 250degC (Ref. 0098)
[a] 20/D=-135deg (c=1.2 in chloroform), [a] 20/546=-171deg(chloroform) (Ref. 0099)
Sol in heated chloroform, benzene. Slightly sol in methanol, ethanol, ether, petroleum ether. Insol in water. (Ref. 0050)
max. nm (e); 262 (6,940); 271 (10,000); 282 (10,600); 293 (6,060). min. nm (e); 230 (1,430); 263 (6,850); 275.5 (8,580); 289 (5,450); 317.5 (35) (Ref. 0008)

E 1%/1cm: nm(e); 36.1 (2,300); 175 (2,620); 173 (2,630); 253 (2,710); 217 (2,755); 268 (2,820); 138 (2,890); 158 (2,930); 0.8 (3,175) (Ref. 0046)

Ergots, yeasts, Chlorella, molds. (Ref. 0100/0101) Trypanosoma, soil amoeba, Lycopodium complanatum. (Ref. 0102)

Precipitable by digitonin. Positive in Rosenheim reaction. (Ref. 0097)
b-Estradiol / Cis-estradiol / Estradiol / 3,17-Epidihydroxyestratriene / Dihydrofollicular hormone / Dihydrofolliculin / Dihydroxyestrin / Dihydrotheelin / Compudose 365 / Dihydromenformon / Dimenformon / Diogyn / Estrovite / Femestral / Gynergon / Gynoestryl / Lamdiol / Macrodiol / Oestergon / Ovahormon / Ovasterol / Ovocyclin / Ovocylin / Perlatanol / Primofol / Profoliol / Progynon-dh
Hideaki Nishino
C18H24O2 272.382 Download ChemDraw structure file
Most potent estrogenic activity. (Ref. 0103)
173-179degC (Ref. 0104)
[a]25/D= from +76 to +83deg(dioxane) (Ref. 0104)
Hardly sol in water. Sol in organic solvents like alcohol, acetone, dioxane. Slightly sol in vegetable oil. (Ref. 0104)
max. 225, 280nm (Ref. 0104)

e=2,120 (281nm), E1%/1cm=78 (Ref. 0105)

Ovary, placenta, testis, adrenal cortex of animals. (Ref. 0104)
Total synthesis from the optically active CD-building block and m-methoxyphenacyl bromide (Ref. 0106) or (+)-carboxylic acid. (Ref. 0107)

Very weak estrogenic activity in 17a-form. (Ref. 0103)
estriol / 16a-Hydroxyestradiol / Follicular hormone hydrate / Oestriol / Trihydroxyestrin / Aacifemine / Colpogyn / Destriol / Gynasan / Hormomed / Klimax E / Klimoral / Oekolp / Ortho-gynest / Ovesterin / Ovestin / Ovo-vinces / Theelol / Tridestrin / Triovex
Estra-1,3,5(10)-triene-3,16,17-triol / 3,16a,17b-Trihydroxy-D1,3,5-estratriene
Hideaki Nishino
C18H24O3 288.381 Download ChemDraw structure file
Male and female sex hormones, influences secondary sexual characteristics, regulates female reproduction cycles. A metabolite of, and less potent than, 17b-estradiol. (Ref. 0114/0115/0116/0117/0118)
282degC (alcohol) / 268.5-269.5degC (methanol) (Ref. 0110/0111)
[a]25/D=+58pm5deg (Ref. 0110/0111)
Insol in water. Sol in alcohol, dioxane, chloroform, ether, vegetable oils. Freely sol in pyridine. (Ref. 0112)
max. 280nm (Ref. 0113)

E1%/1cm=75, e=2,150 (280nm) (Ref. 0113)

Human pregnancy urine (Ref. 0114/0115) , Human placenta (Ref. 0116/0117) , Plant sources, e.g., pussywillows (Ref. 0118)
Partial synthesis from estrone by transforming a-keto to a-glycol with sodium amalgam in dilute ethanolic acetic acid (Ref. 0111) , Synthesis from zinc-acetic acid reduction of 16-oximino-17-ketosteroids and 16,17-diketosteroids. (Ref. 0119) Synthesis from 3b-hydroxyandrostane-17-one by formation of an enol acetate of a 17-ketosteroid followed by epoxidation with perbenzoic acid. (Ref. 0120)

Precipitable by digitonin. (Ref. 0108/0109)
Estrone / Oestrone / Theelin / Folliculin / Follicular hormone / Tokokin / Thelykinin / Ketohydroxyestrin / Hiestrone / Menformon / Glandubolin / Cristallovar / Destrone / Endofolliculina / Estrol / Femidyn / Folikrin / Ovex / Kolpon / Crinovaryl / Folisan / Disynformon / Hormovarine / Oestroperos / Wynestron / Thelestrin / Kestrone / Estrusol / Estrugenone / Femestrone INJ. / Folipex / Follestrine / Follidrin / Follicunodis / Hormofollin / Oestrin / Oestroform / Ovifollin / Perlatan / Ketodestrin / Unden
3-Hydroxyestra-1,3,5(10)-trien-17-one / 1,3,5-Estratrien-3-ol-17-one
Hideaki Nishino
C18H22O2 270.366 Download ChemDraw structure file
One of estrogenic hormones. Same potent as estriol, less potent than estradiol-17b. (Ref. 0121/0122/0124/0127)
254.5-256degC (acetone), 240degC (azoate) (Ref. 0123/0124)
[a]22/D=+152deg (Ref. 0123)
3g sol in 100 ml water (25degC), 1g sol in 96% alcohol (15degC) 250ml, boiling alcohol 50ml, acetone 50ml (15degC), chloroform 110 ml (15degC), boiling benzene 145ml. Sol in diozane, pyridine, fixed alkali hydroxides. Slightly sol in ether, vegetable oils. (Ref. 0125)
max. 282, 296nm(p-dioxane, e=2300, 2130); 300, 450nm (conc.sulfate); 239, 293nm (0.1M NaOH) (Ref. 0125)
nmax (CHCl3): 1,693/cm (methyl ether) (Ref. 0126)
(chloroform)d: 1.08 (3H,s,-CH3), 3.69 (3H,s,OCH3), 6.39-6.72 (2H,m,C2H), 7.08 (1H,d,J=9Hz,C,H) (methyl ether) (Ref. 0126)
m/e 298 (M+) (methyl ether) (Ref. 0126)
E1%/1cm=77 (280nm, e = 2,080) (Ref. 0105)

Pregnancy urine of human and mares, follicular liquor of animals, human placenta, urine from bulls and stallions palm-kernel oil, date palm pollen grains. (Ref. 0120/0122/0124/0127) Moghat roots. (Ref. 0124)
Stereospecific synthesis from b-m-anisylethylmalonic ester by condensation if the sodio derivative with the acid chloride of ethyl hydrogen glutarate. (Ref. 0128) Total synthesis from tricyclic ketoester compounds. (Ref. 0123/0129/0130/0131/0132) New synthesis methods by intramolecular cycloaddition reaction of olefinic o-quinodimethane. (Ref. 0126/0133/0134/0135)

Precipitable by digitonin. (Ref. 0121/0122)
a1-Sitosterol / Citrostadienol
Hideaki Nishino
C30H50O1 426.717 Download ChemDraw structure file

164-166degC (free), 137degC (acetate), 168-172degC (benzoate) (Ref. 0136/0139)
[a]28/D = -1.7 (c=2 in chloroform), [a]25/D = -1.7 (acetate) (Ref. 0136/0139)
Sol in alcohol, benzene, pyridine (Ref. 0139)

m/e more than 200%: M(3), M-15(3), M-(15+18)(-), M-98(57), M=(98+15)(8), M-(98+18)(3), M-127(3), M-(98+15+18)(4), M-141(100), M-(139+18)(8), M-(141+18)(7), M-165(10), M-181(6), M-(165+18)(3), M-184(2), M-185(3), M-(181+18)(9) (Ref. 0140)

Wheat germ oil (Ref. 0139/0141), Corn oil (Ref. 0142), Plants (Ref. 0143)
Synthesis from D7-cholesten-3-one by methylation and reduction. (Ref. 0138)

Stereochemistry. (Ref. 0140) Precipitable by digitonin. (Ref. 0143) Same compound as citrostadienol. (Ref. 0144/0145)
b-Sitosterol / 22:23-Dihydrostigmasterol
Hideaki Nishino
C29H50O1 414.707 Download ChemDraw structure file
Antihyperlipoproteinemic agent, for prostate tumor therapy. (Ref. 0154/0155/0156) Inhibition to cholesterol absorption. (Ref. 0158/0159) Inhibition of carcinogenesis. (Ref. 0160)
140degC, 127-128degC (acetate) (Ref. 0143) 136-137degC (Ref. 0147)
[a]25/D = -37deg (c = 2 in chloroform) (Ref. 0143) -41deg (acetate) (Ref. 0147)

TMS-derivatives (MW = 486): 129(100%), 357(98%), 396(66%), 121(58%), 145(45%), 215(42%) (Ref. 0148)

Wheat germ oil, corn oil (Ref. 0142) Rye germ oil (Ref. 0149) Cotton seed oil (Ref. 0150) Tall oil (Ref. 0151) Soybean, calabar bean, rice germ (Ref. 0152) Cascara (Rhamnus purshiana) (Ref. 0153) Cinchona bark, Cinchona wax (Ref. 0153)
Stereospecific synthesis 24-ethylcholesta-5,22,25-trien-3b-ol by hydrogenation and ring opening. (Ref. 0157)

Precipitable by digitonin. (Ref. 0143/0146/0147)
g-Sitosterol / Clionasterol
Hideaki Nishino
C29H50O1 414.707 Download ChemDraw structure file
Anticholesteremic. (Ref. 0161/0162)
147-148degC (alcohol) (Ref. 0162/0163/0164)
[a]20/D = -43deg (c=1.9 in chloroform) (Ref. 0162/0163/0164)

Corn oil (Ref. 0141) Predominant sterol of soybean oil (Ref. 0162)
Stereospecific synthesis 24-ethylcholesta-5,22,25-trien-3b-ol by hydrogenation and ring opening. (Ref. 0157)

Different stereoconfiguration in C-24 from b-sitosterol. (Ref. 0165)
Stigmasterol, Anti-stiffness factor / 3b-Hydroxy-24-ethyl-D5,22-cholestadiene
Hideaki Nishino
C29H48O1 412.691 Download ChemDraw structure file
Antistiffness factor. (Ref. 0177)
144.0-144.6degC (acetate), 170degC (free) (Ref. 0170/0171/0172)
[a]22/D = -51deg (c = 2 in chloroform), [a]20/D = -55.6deg(acetate, c = 2 in chloroform) (Ref. 0171/0172)
Insol in water. Sol in organic solvents (Ref. 0172)

TMS : 484(22%), 394(35%), 255(63%), 145(32%), 133(38%), 129(100%) (Ref. 0148)

Distributed widely in plant kingdom. Calabar beans (Physostigma venenosum). (Ref. 0173) Kidney beans (Phaseolus vulgaris). (Ref. 0174) Oils from corn, coconuts, rapeseed, and soybeans. (Ref. 0170/0175/0176)

Simple purification as acetic ester bromide because of the insolubility in ethylether. (Ref. 0178)
Testosterone / Trans-testosterone / Geno-cristaux gremy / Malestrone (AMPS) / Orquisteron / Percutacrine androgenique / Primotest / Primoteston / Sustanon / Mertestate / Testobase / Virosterone / Virormone / Testryl / Testrone / Homosterone / Oreton-f / Teslen
17b-Hydroxyandrost-4-en-3-one / D4-Androsten-17b-ol-3-one
Hideaki Nishino
C19H28O2 288.424 Download ChemDraw structure file
Stimulates growth of the prostate and seminal vesicles, and promotes sperm maturation and development of male secondary sexual characteristics. (Ref. 0184/0187)
154-154.5degC (Ref. 0179)
[a]24/D = +109deg (c = 4 in alcohol) (Ref. 0179)
Insol in water. Sol in alcohol, ether, other organic solvents. (Ref. 0184)
max. 238nm (loge = 4.23) (Ref. 0181/0185)

E1%/1cm=582 (240nm, e = 16,800) (Ref. 0186)

Major hormone secreted from interstitial cells, e.g., Leydig cells in testis. (Ref. 0184/0187)
Synthesis from cholesterol via dehydroandrosterone. (Ref. 0184)

21-Acetoxypregnenolone / Acetoxanon
3b,21-Dihydroxy-5-pregnen-20-one-21-acetate / 5-Pregnene-3b,21-diol-20-one-21-acetate / Pregnenolone-21-acetate
Hideaki Nishino
C23H34O4 374.514 Download ChemDraw structure file
Synthesis as an intermediate in desoxycorticosterone acetate synthesis (Ref. 0188)
184-185deg (Ref. 0188)
Slightly sol in ether, pentane. Sol in chloroform, toluene (Ref. 0189)

Anti-inflammatory (Ref. 0188)

Hideaki Nishino
C21H36 288.511 Download ChemDraw structure file
Synthesis from corticosterone by treatments with H2, HJO4,CH3MgBr, CrO3, and Zn-Hg (Ref. 0189) Synthesis from allopregnan-3-one via allopregnanone-hydrazone (Ref. 0190) By degration of conessine (Ref. 0192) By Hofmann decomposition of 3b- and 3a- dimethylaminopregnanes (Ref. 0194)
84-85deg (acetone+methanol) (Ref. 0189)
[a]/D = +18.0deg (c = 1.388 in chloroform) (Ref. 0191)
Sol in chloroform, methanol (Ref. 0189/0190/0192) Sol in petroleum ether (Ref. 0193)

Allotetrahydrocortisone / Reichstein's Substance Dehydro-C / 11-Dehydro C
Hideaki Nishino
C21H32O5 364.476 Download ChemDraw structure file
Synthesis as 3a,21-diacetate form (Ref. 0196)
212-214deg (Ref. 0195)
[a]25/D = +94.2pm1.5deg (c = 1.45 in dioxane as 3a,21-diacetate) (Ref. 0195)

Bovine adrenal (Ref. 0195)

Androstane / 5 -Androstane / Etioallocholane
Hideaki Nishino
C19H32 260.457 Download ChemDraw structure file
Synthesis from androstandione by utilizing lead amalgam and glacial actic acid (Ref. 0197) Synthesis from androstane-3,17-diol (Ref. 0198) Synthesis by heating at 300deg under nitrogen to remove hexahydrobenzoate from androstan-17b-ol-3-one-hexahydrobenzoate (Ref. 0199)
50-50.5deg (acetone-methanol) (Ref. 0199)
[a]16/D = +2pm2deg (c = 1.22 in chloroform) (Ref. 0199)
Sol in acetone, alcohol, methanol, ether, petroleum ether (Ref. 0199)

11b-Hydroxyisoandrosterone / 11b-Hydroxyepiandrosterone
5a-Androstane-3b,11b-diol-17-one / 3b,11b-Dihydroxy-5a-androstan-17-one
Hideaki Nishino
C19H30O3 306.440 Download ChemDraw structure file

235-238deg (acetone+ether) (Ref. 0200)
[a]20/D = +84.5deg (ethanol), [a]19/D = +81.3deg (dioxane), [a]19/545 = +105deg (dioxane) (Ref. 0200/0201/0202)
Sol in ethanol, dioxane (Ref. 0200/0201/0202)

m/e = 450(M+), 435(M-15), 394(M-56), 360(M-90), 345(M-(90+15)), 270(M-2times90), 255(M-[(2times90)+15]), 214(M-[(2times90)+56]), 199(M-[(2times90)+56+15]), 156 (Ref. 0203)

Analysis by TLC and gas chromatography (Ref. 0203) Reverse-phase HPLC (Ref. 0204)
Degraded product of allopregnane-3b,11b,17a,20b,21-pentol (Reichstein's Substance A) (Ref. 0200) Adrenal cortex (Ref. 0201)

Induction of d-aminolevulinate synthase and porphyrins (Ref. 0202)

Precipitable by digitonin (Ref. 0200)
5-Androstene-3b,17b-diol / 3b,17b-Dihydroxy-5-androstene
Hideaki Nishino
C19H30O2 290.440 Download ChemDraw structure file
Synthesis from dehydroandrosterone by reduction of carbonyl-group at C17 (Ref. 0179/0181/0205)
177-178deg (Ref. 0179) 178deg (Ref. 0205) 182-183deg (Ref. 0181)
[a]18/D = -55.5deg (c = 0.4 in isopropanol) (Ref. 0179/0205)
Sol in isopropanol, insol in water (Ref. 0205)

No crest growth in capon (Ref. 0205)

Hideaki Nishino
C19H30O2 290.440 Download ChemDraw structure file
Synthesis from 5-androsten-3b-ol-16-one by the sodium borohydride reduction or by reduction of 3b-acetoxy-5-androsten-16-one to 3b-acetoxy-5-androsten-16b-ol, which is in turn tosylated and epimerized at C16 (Ref. 0206)
216-217deg (aqueous methanol) (Ref. 0206)
[a]22/D = -110deg (c = 1.09 in 95% ethanol), [a]24.5/D = -67deg (c = 0.8 in dioxane) (Ref. 0206)
Sol in ethanol, dioxane (Ref. 0206)

Tranquilizer (Ref. 0206)

Androstenedione / Androtex
Hideaki Nishino
C19H26O2 286.409 Download ChemDraw structure file
Synthesis from 5-dehydroandrosterone (Ref. 0208/0209) Synthesis from 5-androsten-3-ol-17-one (Ref. 0210) Synthesis from 4,5-androsten-17-ol (Ref. 0211) Synthesis from 5,6-dibromo-3-keto-steroids by chromous chloride dehalogenation (Ref. 0212)
142-144deg (acetone) (Ref. 0208) 173-174deg (hexane) (Ref. 0209)
[a]17/D = +2.26deg (Ref. 0210)
[a]30/D = +191deg (alcohol), [a]18/D = +185deg, [a]17/D = +197.4deg (chloroform) (Ref. 0210)
Sol in chloroform (Ref. 0210)
max. 235 nm (chloroform) (Ref. 0208)

Adrenal cortex (Ref. 0207)

5a-Androst-16-en-3a-ol / 3a-Hydroxy-5a-androst-16-ene / 16-[5a]Androsten-3a-ol
Hideaki Nishino
C19H30O 274.441 Download ChemDraw structure file
Preparation (Ref. 0199/0218)
142.5-143deg (Ref. 0213)
a20/D = +0.125deg (Ref. 0213) a16/D = +0.13pm0.02deg (Ref. 0199)
[a]20/D = +13.1pm2deg (c = 0.957 in chloroform) (Ref. 0213) [a]16/D = +13.9pm2deg (c = 0.936 in chloroform) (Ref. 0199)
Sol in chloroform (Ref. 0213)

m/e 346(M), 331(M-15), 256(M-90), 241(M-(90+15)) (Ref. 0214)

Boar testis (Ref. 0213) Human male axillary sweat (no androgenic activity) (Ref. 0214) Truffle, Tuber melanosporum (Ref. 0215)
Metabolism in vivo in boar testis (Ref. 0218) Biosynthesis in tissue (Ref. 0221/0222)
Androgenic activity in boar (Ref. 0216) Receptor binding with high affinity (Ref. 0220)

Blue-coloring in Kägi-Miescher test (Ref. 0217) Quantification by radioimmunoassay (Ref. 0219) Boars are able to find truffle even in 1 m underground. (Ref. 0223)
3b,22,23-Trihydroxy-7-oxostigmasta-5,24(28)-dien-29-oic acid g-lactone
Hideaki Nishino
C29H42O5 470.641 Download ChemDraw structure file
Synthesis of 22,23 isomers from 3-tetrahydropyran-2'-yloxy22,23-bisnorchol-5-en-24-al by aldol condensation (Ref. 0227) A new synthetic route by condensation of the 2-lithio derivative of 3-isopropylfuran with 3-tetrahydropyran-2'-yloxy22,23-bisnorchol-5-en-24-al (Ref. 0230) Synthesis from C22 aldehyde by aldol condensation (Ref. 0231)
250-255deg (Ref. 0224)
Sol in hot methanol, slightly sol in chloroform, very slightly sol in water (Ref. 0224)
max. (ethanol) 220 nm (e = 17,000) (Ref. 0224/0225)
nKBr max. 3390, 1742, 1672/cm (Ref. 0224)
Olefin protons (5.69,5.77 ppm) methyl-groups at C-18 and C-19 (0.70,1.20 ppm) (Ref. 0225)
(M+ = 470) 344,326,298,287,269,251 (Ref. 0224/0227)

Achlya bisexualis (Ref. 0228)
Steroid sex hormone. Secretion from female. Induction of formation of male antheridial hyphae (Ref. 0224/0228)

Isolation of crystal structure (Ref. 0224) Stereochemistry (Ref. 0229/0230/0231) Reviews (Ref. 0232/0233)
Azacosterol / Diazasterol
17b-[[3-(Dimethylamino)propyl]-methylamino]androst-5-en-3b-ol / N-Methyl-N-[3(dimethylamino)propyl]-17b-aminoandrost-5-en-3b-ol / 20,25-Diazacholesterol
Hideaki Nishino
C25H44ON2 388.630 Download ChemDraw structure file
Synthesis from 3b-hydroxyandrost-5-en-17-one (Ref. 0234)
146-148degC (acetone+methanol) (Ref. 0234)
[a]25/D=-54.5deg (Ref. 0234)
Sol in ether anhydride, isopropylalcohol. (Ref. 0234)

Effective application to therapy for hypercholesterolemia. Oral ingestioin, 15% decrease (0.5mg/kg body weight), 35% decrease (3mg/kg body weight). (Ref. 0234)

Preparation of dihydrochloride salt. (Ref. 0234)
Budesonide / S-1320 / Preferid / Pulmicort / Rhinocort / Sprirocort
16,17-Butylidenebis(oxy)-11,21-dihydroxypregna-1,4-diene-3,20-dione / (R,S)-11b,16a,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with butylaldehyde
Hideaki Nishino
C25H34O6 430.534 Download ChemDraw structure file
Synthesis. (Ref. 0235)
221-232degC (Ref. 0235)
[a]25/D=+98.9deg (c=0.28 in methylene chloride) (Ref. 0235)

Quantification of the epimer and impurities in HPLC. (Ref. 0237)

Pharmacodynamics. (Ref. 0236)
Anti-inflammatory effect. (Ref. 0235) Application to asthma. (Ref. 0238)

Hideaki Nishino
C24H34O4 386.524 Download ChemDraw structure file
Synthesis from 14a-hydroxycortexolone through side-chain degradation and Reformatsky reaction. (Ref. 0240) Synthesis from digitoxigenin (Ref. 0241) Synthesis from 20-ketopregnane. (Ref. 0246)
242-243degC (methanol/chloroform) (Ref. 0240/0241/0242)
[a]/D=-20deg (Ref. 0239)
Sol in alcohol, chloroform. (Ref. 0239)
nmax 3080, 2945, 1725, 1640, 1545 /cm (Ref. 0241)
pmr (100MHz) 0.71 and 0.96(18 and 19 methyls), 4.14 (3a proton), 6.25(doublet, Ha,J=10Hz), 7.28(partially masked doublet, Hc,J=2Hz), 8.85(quartet, Hb,J=10 and 2Hz) (Ref. 0241)
M+ 386, 368, 350, 325, 250, 232, 214, 207, 203, 147 (Ref. 0241)

Poison from Chinese toad (Bufo bufo Gargarizans). (Ref. 0239) Isolation from the skin of Japanese toad (Bufo vulgaris Formosus) as the 3-sulfate form. (Ref. 0243)

Cardiotonic steroid. (Ref. 0239) Block in neural transmittance (Ref. 0244/0245)

Bufogenin B / Desacetylbufotalin
Hideaki Nishino
C24H34O5 402.524 Download ChemDraw structure file
Synthesis from bufotalin. (Ref. 0247)
210-223degC (Ref. 0247)
[a]19/D=+30deg (c=1.039 in dioxane) (Ref. 0247)
Sol in dioxane. Very sparingly sol in chloroform, methanol, acetone. (Ref. 0247)

Chinese medicine (Ch'an Su, Bufo asiaticus = isolated from Bufo gargarizans Canter, a Chinese toad), or also yielded from bufotalin. (Ref. 0247)

Cardiotonic steroid. (Ref. 0247)

Calusterone / U-22550 / Methosarb
17-Hydroxy-7,17-dimethylandrost-4-en-3-one / 7b,17a-Dimethyltestosterone
Hideaki Nishino
C21H32O2 316.478 Download ChemDraw structure file
Synthesis (Ref. 0248)
127-129degC (acetone) (Ref. 0248)
[a]/D=+57deg (chloroform) (Ref. 0248)
UV max (alcohol): 243nm (Ref. 0248)

Carcinostatic agent (Ref. 0248)

Hideaki Nishino
C28H48O 400.680 Download ChemDraw structure file

157-158degC (acetone) (Ref. 0249)
[a]23/D=-33deg (22.5mg in 5ml chloroform) (Ref. 0249)

Small amounts in oils prepared from rapeseed, soybean, malt (wheat germ). (Ref. 0249)

Hideaki Nishino
C29H48O 412.691 Download ChemDraw structure file

168-169degC (chloroform-methanol) (Ref. 0251)
[a]24/D=-2deg (chloroform) (Ref. 0251)
Sol in chloroform, methanol. (Ref. 0251)

Isolation from green algae (Scenedesmus obliquus (Turpin) Kuetz, Scenedesmaceae) (Ref. 0251)

Stereoisomer of a-spinasterol. (Ref. 0251)
N20,N20-Dimethyl-5a-pregnane-3b,20-diamine / 3b-Amino-20a-dimethylamino-5a-pregnane
Hideaki Nishino
C23H42ON2 362.592 Download ChemDraw structure file
Synthesis from Acetoxy-3a-bisnorallo cholanique. (Ref. 0255)
149degC (Ref. 0255)
[a]/D=+25deg (chloroform, c=1) (Ref. 0255)
Sol in chloroform, ether. (Ref. 0255)

Extract from the bark and leaves of Chonemorpha macrophylla G. Don, Ch. Fragrans Alston, Ch. Penangensis Ridl., Apcynaceae (Ref. 0252/0253/0254)

Stereochemistry. (Ref. 0256)
16-(Acetyloxy)-14,15-epoxy-3,5-dihydroxybufa-20,22-dienolide / 14,15b-Epoxy-3b,5,16b-trihydroxy-5b-bufa-20,22-dienolide 16-acetate
Hideaki Nishino
C26H34O7 458.544 Download ChemDraw structure file

259-262degC (acetone) (Ref. 0257)
[a]20/D=+11deg (Ref. 0257)
UV max: 295nm (loge=3.72) (Ref. 0257)

Isolation from Chinese drug, Ch'an Su, prepared from Chinese toad (Bufo asiaticus=Bufo gargarizans Cantor) (Ref. 0247)

Hideaki Nishino
C27H42O4 430.620 Download ChemDraw structure file

259-261degC (chloroform+methanol) (Ref. 0259)
[a]27/D=-79.1deg (c=1.02 in chloroform) (Ref. 0258)
Sol in methanol, chloroform, ethanol. (Ref. 0258)
nnujol/max: 3095, 1655, 877/cm (vinyl-form double bond) 3350, 3295/cm (Ref. 0259)

Root of a lily of the valley (Convallaria majalis L.) (Ref. 0259)

Hideaki Nishino
C29H42O10 550.638 Download ChemDraw structure file
Synthesis from strophanthidin and acetobromrhamnose. (Ref. 0266)
235-242degC (methanol+ether) (Ref. 0260/0261)
[a]22/D=-1.7pm3deg (c=0.65 in MeoH); [a]25/D=-9.4pm3deg (c=0.72 in dioxane) (Ref. 0260/0261)
Sol in alcohol, acetone. Sparingly sol in chloroform, ethylacetate, water (1:2000). Insol in ether, petroleum ether.(Ref. 0260/0261)

Flower of a lily of the valley (Convallaria majalis L., Liliaceae). (Ref. 0263) Antiaris toxicaria Lesch, Moraceae (Ref. 0264) Ornithogalum umbellatum L., Liliaceae (Ref. 0265)

Cardiotonic drug. (Ref. 0263)

17a,21-Dihydroxy-4-pregnene-3,11,20-trione / 17-Hydroxy-11-dehydrocorticosterone / 11-Dehydro-17-hydroxycorticosterone / D4-Pregnene-17a,21-diol-3,11,20-trione
Hideaki Nishino
C21H28O5 360.444 Download ChemDraw structure file
Synthesis as a monoacetate from deoxycholic acid. (Ref. 0272) Improved preparation protocols. (Ref. 0273/0274/0275/0276/0277/0278/0279/0280/0281/0282/0283/0284) Total stereospecific synthesis as a cortisone acetate. (Ref. 0285)
220-224degC (95% ethanol) (Ref. 0267/0268/0269/0270)
[a]25/D=+209deg (c=1.2 in 95% ethanol); [a]25/546=+248deg (c=0.1 to 0.2 in ethanol); [a]25/546=+269deg (c=0.125 in benzene) (Ref. 0270/0271)
Sol in cold methanol, ethanol, acetone. Sparingly so in ether, benzene, chloroform. Insol in water. (Ref. 0267/0268/0269/0270)
UVmax: 237nm (e=14,000) (Ref. 0270)

Isolation from adrenal glands. (Ref. 0267/0268/0269/0270)

Action as a glucocorticoid. (Ref. 0270)

Cortisone phosphate
17a-Hydroxy-4-pregnene-3,11,20-trione-21-dihydrogen phosphate
Hideaki Nishino
C21H29O8P 440.424 Download ChemDraw structure file
Preparation from 17a-hydroxy-21-iodo-4-pregnene-3,11,30-trione by metathesis with silver dihydrogen phosphate in boiling acetonitrile. (Ref. 0286/0287)
198-204degC (Ref. 0286/0287)
Sol in water as a sodium salt. Insol in as a dimethylester (Ref. 0286/0287)
UV max (methanol): 238nm (e=15,200), (water): 244nm (e=15,900) (Ref. 0286)

Hideaki Nishino
C28H42O6 474.629 Download ChemDraw structure file

165-167degC (ether+petr. ether) (Ref. 0289)
[a]22/D=-39.5deg (c=1.24 in 90% ethanol) (Ref. 0289)
Sol in petroleum ether, ethanol. (Ref. 0289)
UVmax (ethanol): 218 nm (loge=4) (Ref. 0288)
lKBr/max/cm: n/OH: 3480, n/C=O: 1700, n/C=C: 1638 (Ref. 0288)
Carbon-13 NMR (Ref. 0292/0293)

Isolation from the root of Cynanchum caudatum Max., Asclepiadaceae (Ref. 0288)

Pink to yellow in color reaction by Lieberman-Burchard reaction. (Ref. 0289) Brown to violet in 84% sulfate. (Ref. 0289) Green in antimony trichloride (Ref. 0289) Yellow in tetranitromethane (Ref. 0289)
6-Chloro-1,2-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione / 6-Chloro-6-dehydro-17a-hydroxy-1,2a-methyl-eneprogesterone / 6-Chloro-1,2a-methylene-4,6-pregnadien-17a-ol-3,20-dione
Hideaki Nishino
C22H27O3Cl 374.901 Download ChemDraw structure file
Preparation as a free alcohol form. (Ref. 0294)
237.5-240degC (ethyl acetate) (Ref. 0294)
UVmax (methanol): 281nm (e=17,280) (acetate) (Ref. 0294)

Metabolism in human body (Ref. 0294)
Anti-androgenic activity as an acetate. (Ref. 0294)

11-Dehydrocorticosterone / Substance A
21-Hydroxypregn-4-ene-3,11,20-trione / D4-Pregnen-21-ol-3,11,20-trione / 17-(1-Keto-2-hydroxyethyl)-D4-androsten-3,11-dione
Hideaki Nishino
C21H28O4 344.445 Download ChemDraw structure file
Synthesis from deoxycholic acid. (Ref. 0297) Synthesis from 3a-acetoxy-11-ketobisnorcholanic acid.(Ref. 0272/0296) Synthesis from 3a-acetyl-11-ketolithocholic acid methyl ester. (Ref. 0298)
178-180degC (aq.acetone) (Ref. 0295)
[a]25/546=+299deg, 347deg (c=0.23 in benzene), [a]25/D=+258deg (alc.) (Ref. 0296)
Relatively sol in benzene. (Ref. 0295)
l max = 237.5nm (acetate), E1%=386 (Ref. 0296)

Found in adrenal cortex. Isolation of 333 mg from 1000 lbs beef glands. (Ref. 0295)

Hideaki Nishino
C28H42O 394.632 Download ChemDraw structure file
Preparation from ergosterol. (Ref. 0299) Preparation from isopyrocalciferol. (Ref. 0300)
146degC (Ref. 0300)
bp0.5=230degC (Ref. 0300)
[a]15/D=+149.2deg (c=1.9 in chloroform) (Ref. 0300)
Sol in methanol (1g/800ml), ether, chloroform, benzene. (Ref. 0300)
l max: 342.0, 325.5, 311.0, 296 nm (Ref. 0301)

Hideaki Nishino
C29H48O 412.691 Download ChemDraw structure file

144-145degC (Ref. 0302)
[a]21/D=-116deg (c=2 in chloroform) (Ref. 0302)
Sparingly sol in methanol, alcohol. Sol in other organic solvent. Insol in water.(Ref. 0302)

Almost same absorption spectrum as ergosterol. (Ref. 0302)

Separation from b-sitosterol in soybean oil. (Ref. 0302)

Delmadinone acetate
17-(Acetyloxy)-6-chloropregna-1,4,6-triene-3,20-dione / 6-chloro-17-hydroxypregna-1,4,6-triene-3,20-dione acetate / 1,6-Bisdehydro-6-chloro-17a-acetoxyprogesterone
Hideaki Nishino
C23H27O4Cl 402.911 Download ChemDraw structure file
Preparation method. (Ref. 0303)
168-170degC. (Ref. 0303)
[a]/D=-83deg (chloroform) (Ref. 0303)
UVmax (ethanol): 229, 258, 297nm (loge=4.00, 4.00, 4.03). (Ref. 0303)

Progesterone activity in oral ingestion=35 (Clauberg assay) (Ref. 0303) Antiestrogenic activity. (Ref. 0304/0305)

Application for regulation of generation in cats and dogs. (Ref. 0306)
6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione / 6a,9a-difluoro-16b-methyl-D1,4-pregnadiene-11b,17a,21-triol-3,20-dione / 6a,9a-Difluoro-16b-methylprednisolone
Hideaki Nishino
C22H28O5F2 410.452 Download ChemDraw structure file
Preparation of free alcohol form and 21-acetate. Decrease of arachidonic acid and hydroxyeicosatetraenoic acid in psoriasis. (Ref. 0309)

21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dione / 6a,9-Difluoro-11b,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate 17-butyrate / 6a,9a-Difluoroprednisolone-21-acetate-17-butyrate
Hideaki Nishino
C27H34O7F2 508.551 Download ChemDraw structure file
Preparation. (Ref. 0310/0311/0312/0313/0314)
191-194deg (methylene chloride/ether/petr. ether) (Ref. 0312)
[a]22/D=+31.7deg (c=0.5 in dioxane).(Ref. 0312)
UVmax (ethanol): 237-238nm (E1%/1cm 320). (Ref. 0312)

Anti-inflammatory action. (Ref. 0310/0311/0312/0313/0314)

Hideaki Nishino
C27H44O4 432.636 Download ChemDraw structure file

218.5-220.5degC (methanol) (Ref. 0315)
[a]21/D=-75deg (chloroform) (Ref. 0315)
Sol in chloroform, methanol (Ref. 0315)
No carbonyl bond. 25a-Sapogenin possessing two hydroxyl groups. (Ref. 0315)

Isolated from seeds of Digitalis purpurea. (Ref. 0315)

3b,12b,14,16b-Tetrahydroxy-5b-card-20(22)-enolide / 12-Hydroxygitoxigenin
Hideaki Nishino
C23H34O6 406.512 Download ChemDraw structure file
Preparation from gitoxigenin (Ref. 0318/0319)
157degC (chloroform), 154-156degC (water) (Ref. 0316/0319)
[a]20/D=+34deg (methanol) (Ref. 0319)
Sol in methanol, chloroform, pyridine. (Ref. 0316/0319)
UVmax (ethanol): 218nm (loge=4.18) (98%w/w sulfate): 230, 310, 390, 490nm (E1%/1cm 160, 130, 210, 85) (Ref. 0319)
Characteristic peaks in 3-6m (Ref. 0318/0319)

[M]/D=+138 (Ref. 0321)

Non-sugar part (aglycon) of diginatin from Digitalis lanata (Ref. 0316) Not detected in D. purpurea, D. thapsi, D. sibirica, D. lutea, D. ambigua, S. mertonensis. (Ref. 0316) Preparation by hydrolysis of diginatin. (Ref. 0316)

Cardiotonic agent (Ref. 0316)

Strong fluorescence in phosphate, which is a specific reaction to cardiotonic glycosides possessing hydroxyl group at C-16 (Ref. 0316)
Hideaki Nishino
C27H44O5 448.635 Download ChemDraw structure file

280-283degC (Ref. 0327)
[a]19/D=-81deg (c=1.4 in chloroform) (Ref. 0327)
Insol in water. Sol in 30% chloroform, 35% boiling alcohol, 100% alcohol (20degC). (Ref. 0327)
lchloroform/max: 2.81, 2.90 (hydroxyl) 10.22, 10.90, 11.14, 11.53m (spiroketal) (Ref. 0327)

Aglycon of digitonin. (Ref. 0322)

Exhibits no color reaction even by treatment with conc. sulfate. (Ref. 0327)
3,14-Dihydroxycard-20(22)-enolide / D20,22-3,14,21-Trihydroxynorcholenic acid lactone
Hideaki Nishino
C23H34O4 374.514 Download ChemDraw structure file
Synthesis from methyl-3b-acetoxy-14b-hydroxy-5b-etianate (II). (Ref. 0336) Synthesis from 15a-hydroxycortexone. (Ref. 0338) Synthesis from 21-hydroxy-20-ketosteroid. (Ref. 0339) New synthetic method. (Ref. 0340) Synthesis from deoxycholic acid. (Ref. 0341)
253degC (40% alc.) (Ref. 0331/0336)
[a]17/D=+19.1deg (c=1.36 in methanol) (Ref. 0331/0336)
Sol in alcohol, chloroform, acetone. Slightly sol in ethylacetate. Very sparingly sol in ether, water. (Ref. 0331)

Isolation from seeds of Apocinacae. (Ref. 0337)

Cardiotonic agent. (Ref. 0336)

3,12,14-Trihydroxycard-20(22)-enolide / D20,22-3b,12b,14,21-Tetrahydroxynorcholenic acid lactone
Hideaki Nishino
C23H34O5 390.513 Download ChemDraw structure file
Synthesis from deoxycholic acid (Ref. 0346)
222degC (Ref. 0342)
[a]20/546=+27.0deg (c=1.77 in methanol) (Ref. 0342)

Aglycon (non-sugar moiety) of digoxin, a cardiac glycoside, from leaves of Digitalis lanata, prepared from hydrolyzate of digixin. (Ref. 0342)

Hideaki Nishino
C18H22O2 270.366 Download ChemDraw structure file
Both of 17a- and 17b-forms can be prepared by reduction of equilin, which is found in urine of pregnant mares. (Ref. 0347)
17b-form:174.5-174.6degC (acetone), 17a-form: 205.5-205.6degC (30% ethanol) (Ref. 0347/0348)
17b-form: [a]20/D=+220deg (dioxane), 17a-form: [a]20/D=+213deg (ethanol). (Ref. 0347/0348)
Sol in alcohol, benzene. (Ref. 0347/0348)
281 nm (e=1,955) (Ref. 0347)
In 8-15m, a finger print region, different from a-dihydroequilin. (Ref. 0347)

Isolation of 17a- and 17b-forms from urine of pregnant mares. (Ref. 0349)

1/50 activity of estrone. (Ref. 0347)

Hideaki Nishino
C28H46O 398.664 Download ChemDraw structure file
Preparation form reduction of tachysterol (Ref. 0350)
125-127degC (90% methanol) (Ref. 0350)
[a]22/D=+97.5deg (chloroform) (Ref. 0350)
Insol in water. Sol in organic solvents. (Ref. 0350)
UV max: 242, 251, 261nm (E1%/1cm 870, 1010, 650) (Ref. 0350)

Increase of calcium ion concentration in blood. (Ref. 0350)

4,23-Dimethylergost-22-en-3-ol / 4a-Methyl-5a(H)-D22-23,24-dimethylcholestan-3b-ol
Hideaki Nishino
C30H52O 428.733 Download ChemDraw structure file
Stereospecific synthesis. (Ref. 0354)
220-222degC (methanol-chloroform) (Ref. 0351)
[a]/D=pm5deg (c=0.6 in chloroform) (Ref. 0351)
Sol in chloroform, methanol, ether. (Ref. 0351/0352)
100MHz, seven alkyl linked methyl signals (d0.70(3H,s)), 0.80 (3H,d,J=7Hz), 0.84 (3H,s), 0.85 (3H,d,J=7Hz), 0.94 (6H,d,J=6.5Hz, isopropyl), 0.95 (3H,d,J=6Hz), olefinic proton signal (d4.87(1H,q,J=1.2,10Hz)), proton signal due to a secondary alcohol (d3.10(1H,m)
m/e 428(26), 387(15), 370(10), 316(65), 303(24), 287(100), 271(67) (Ref. 0351/0352/0353)

Relative retention time is 1.59 (1%OV-17, 240degC) in GLC when that of cholesterol is 1.0. (Ref. 0352)
Biogenetically significant marine sterol isolated from the toxic dinoflagellate, Gonyaulax tamarensis. (Ref. 0351) Extraction from rotten soil in the Black Sea. (Ref. 0353)

Determination of structure by X-ray crystallography. (Ref. 0352)
Hideaki Nishino
C27H42O3 414.621 Download ChemDraw structure file
Preparation from yamogenin. Simple stereospecific synthesis. (Ref. 0363)
204-207degC (acetone) (Ref. 0355/0358)
[a]25/D=-129deg (c=1.4 in chloroform) (Ref. 0358)
Sol in organic solvents, acetic acid. (Ref. 0355)

Isolation from Dioscorea (Ref. 0359/0360) Isolation from Trillium. (Ref. 0355/0360) Root of Beth. (35-60% of total steroid sapogenin). (Ref. 0361)

Conversion to pregnenolone, progesterone. (Ref. 0362) Determination of configuration at C-25. (Ref. 0356)
Hideaki Nishino
C27H48O 388.669 Download ChemDraw structure file
Synthesis (Ref. 0365) Preparation by new epimerization technique. (Ref. 0366)
141.5degC (alcohol). (Ref. 0364)
[a]30/D=-35deg (c=1 in alcohol). (Ref. 0364)

Estra-1,3.5(10)-triene-3,16b,17b-triol / D1,3,5-Estratriene-3,16b,17b-triol
Hideaki Nishino
C18H24O3 288.381 Download ChemDraw structure file

289-291degC (methanol+benzene). (Ref. 0369)
[a]15/D=+76deg (c=0.297 in ethanol). (Ref. 0369)

Isolation from urine of pregnant women, human placenta. (Ref. 0367/0369)

Estrogenic activity. (Ref. 0367)

3-Hydroxyestra-1,3,5,7,9-pentaen-17-one / 11,12,13,14,15,16-Hexahydro-3-hydroxy-13-methyl-17H-cyclopenta[a]phenanthren-17-one / 1,3,5:10,6,8-Estra-pentaen-3-ol-17-one
Hideaki Nishino
C18H18O2 266.334 Download ChemDraw structure file
Total synthesis from 7-methoxy-1-keto-1,2,3,4-tetrahydrophenanthren prepared from 1-naphthylamine-6-sulfonic acid (Cleve's acid). (Ref. 0371/0372/0373) Synthesis from 1-keto-1,2,3,4-tetrahydrophenanthrene. (Ref. 0374) Synthesis from 1-keto-2-methyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene. (Ref. 0375) Synthesis as methyl ether. (Ref. 0376) Synthesis from 1,4,8(9)-trien-11b-olunder acidic condition at room temperature. (Ref. 0095) Synthesis from estra-1,3-5(10),8-tetraenes. (Ref. 0094) Synthesis by coupling of m-methoxystyrene and diazoketone. (Ref. 0377)
258-259degC (dil. alc.). (Ref. 0371)
[a]16/D=+87deg (12.8mg/1.8ml in dioxane). (Ref. 0371)
0.63g/100ml alcohol (18degC), 2.5g/100ml alcohol (boiling). (Ref. 0371)
UVmax (ethanol): 231, 270, 282, 292, 325, 340nm (logEmolar=3.85, 3.87, 3.74, 3.58, 3.68, each) (Ref. 0372)

Isolationfrom urine of pregnant mares. (Ref. 0371)

Strong estrogenic acitvity. (Ref. 0371)

b-Estradiol / (+)-Estradiol
Hideaki Nishino
C18H24O2 272.382 Download ChemDraw structure file
Enantioselective synthesis from 1,3-dihydrobenzo[c] thiophene-2,2-dioxide (Ref. 0107)
173-179degC. (Ref. 0378/0106)
[a]25/D=+76 to +83deg (dioxane). (Ref. 0378/0106)
Almost insol in water. Freely sol in alcohol, acetone, dioxane, other organic solvents. Sparingly sol in vegetable oils. (Ref. 0378/0106)
UVmax: 225, 280 nm (Ref. 0379)

Isolation from urine of pregnant mares. (Ref. 0103) Isolation from porcine ovary follicular fluid. (Ref. 0103)

The strongest estrogen in mammals. (Ref. 0103)

Properties, synthesis, and analysis as valerate. (Ref. 0380)
Estradiol benzoate
Hideaki Nishino
C25H28O3 376.488 Download ChemDraw structure file

191-196degC (alcohol). (Ref. 0381)
[a]25/D=+58 to +63deg (c=2 in dioxane). (Ref. 0381)
Sol in alcohol, acxetone, dioxane. Sparingly sol in ether, vegetable oils. (Ref. 0381/0382)

Isolation from urine of pregnant mares. (Ref. 0103) Preparation from porcine ovary follicular fluid-derived-estradiol. (Ref. 0103)

Estrogenic activity. (Ref. 0381/0382)

Ppt with digitonin. (Ref. 0381)
Estra-1,3,5(10)-triene-3,17-diol 3-[bis(2-chloroethyl)carbamate] / Estradiol 3-bis(2-chloroethyl)carbamate / Estra-1,3,5(10)triene-3,17b-diol 3-[N,N-Bis(2-chloroethyl)carbamate]
Hideaki Nishino
C23H31O3NCl2 440.403 Download ChemDraw structure file
Preparation. (Ref. 0383)
104-105degC (benzene-petr. ether) (Ref. 0383)
[a]20/D=+50deg (in dioxane) (Ref. 0383)
UVmax (alcohol): 270.7, 276.5nm (Ref. 0383)

Anti-tumor drug. (Ref. 0383)

3-Hydroxyestra-1,3,5(10)-trien-17-one / 1,3,5-Estratrien-3-ol-17-one
Hideaki Nishino
C18H22O2 270.366 Download ChemDraw structure file
Synthesis from cholesterol. (Ref. 0123) Improved protocols for synthesis of 19-norsteroids. (Ref. 0388) Synthesis via bicyclo[2,2,1]heptane as an intermediate. (Ref. 0135) Synthesis by application of boron annulation. (Ref. 0389)
dl-form: 251-254deg (acetone), d-form: 254.5-256deg (acetone) (Ref. 0123) 254.5-256deg (acetone) (Ref. 0123)
[a]22/D=+152deg (c=0.995 in chloroform) (Ref. 0123)
Sol in water (25deg): 0.003g/100ml. Sol in 96% alcohol 250ml, acetone 50ml, chloroform 110ml (1g estrone, 15degC). Sol in alcohol 50ml, benzene 145ml (1g estrone, boiling). Sol in dioxane, pyridine, fixed alkali hydroxide. Slightly sol in ether, vegetable oils. (Ref. 0123)
UVmax: 283-285nm (Ref. 0384)
Infrared spectra of estrone methyl esters. (Ref. 0385)

Found in pregnant women, pregnant mares, follicular fluids from many animals, human placenta, urine of bulls and studhorses, palm-kernek oil (Ref. 0121/0386) Roots of moghat (Clossostemon bruguieri, Sterculiaceae), pollens of Egyptian date palm (Phoenix dactylifera). (Ref. 0387)

Estrogenic activity. (Ref. 0121/0386)

Ppt with digitonin. (Ref. 0123)
Ethinyl estradiol
19-Nor-17a-pregna-1,3,5(10)-trien-20-yne-3,17-diol / 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol
Hideaki Nishino
C20H24O2 296.403 Download ChemDraw structure file
Preparation from estrone. (Ref. 0391)
145-146degC (Ref. 0391)
[a]/D=+1deg (in dioxan) (Ref. 0391)
Insol in water. Sol in the proportion of 1: 6 ethanol, 4 ehter, 5 acetone, 4 dioxane, 20 chloroform. Sol in vegetable oils, fixed alkalihydroxides solution. (Ref. 0391)
UVmax (ethanol): 281nm (e=2040pm60) (Ref. 0392)
NMR spectra. (Ref. 0392)

Estrogenic activity (application to hormonotherapy for human and animals). (Ref. 0391)

Properties (Ref. 0392)
17a-Hydroxypregn-4-en-20-yn-3-one / 17a-Ethynyltestosterone / 17a-Ethynyl-17b-hydroxy-4-androsten-3-one / 17a-Ethinyltestosterone / 17a-Ethynyl-4-androsten-17b-ol-3-one
Hideaki Nishino
C21H28O2 312.446 Download ChemDraw structure file
Preparation by addition of acetylene to dehydroepiandrosterone, followed by Oppenauer oxidation. (Ref. 0391)
269-275degC (Ref. 0391)
[a]23/D=+23.8deg (dioxane), [a]25/D=-32.0deg (pyridine) (Ref. 0391)
Insol in water. Slightly sol in alcohol, acetone, ether, chloroform, vegetable oils. (Ref. 0391)
UVmax (methanol): 241nm (E1%/1cm 513) (Ref. 0391)

19-Nor-pregn-4-en-20-yne-3,17-diol / 17a-Ethynyl-19-norandrost-4-ene-3b,17b-diol / 17a-Ethynyl-4-estrene-3b,17b-diol
Hideaki Nishino
C20H28O2 300.435 Download ChemDraw structure file
Synthesis. (Ref. 0393) Preparation as 3-acetate, 17-acetate, diacetate. (Ref. 0393)
147-149degC (Ref. 0393)
[a]/D=-39deg (EtOH) (Ref. 0393)
Sol in alcohol.(Ref. 0393)
Particularly no strong absorbance. (Ref. 0393)
nKBr/max 3300/cm (Ref. 0393)

Progesterone activity. (Ref. 0393)

Hideaki Nishino
C29H48O 412.691 Download ChemDraw structure file
Synthesis from 3b-hydroxy-20-iso-D5-cholenic acid (Ref. 0397)
124degC (methanol). (Ref. 0394)
220-230degC/0.2mm.(Ref. 0394)
[a]20/D=-38.42deg (c=5 in chloroform). (Ref. 0394)
Sol in almost all organic solvents. (Ref. 0394)

GLC. (Ref. 0140)
Isolation from Fucus vesiculosus L., Fucaceae (Ref. 0394) Isolation from marine brown algae (Phaeophyceae). (Ref. 0396)

3-Amino-5-pregnan-20-one / 3a-Amino-20-oxo-5a-pregnane
Hideaki Nishino
C21H35ON 317.509 Download ChemDraw structure file

126degC (ethyl acetate). (Ref. 0401)
[a]/D=+95deg (c=1.7, chloroform). (Ref. 0401)
Sol in organic solvents. (Ref. 0400/0401)

Isolation from Funtumia latifolia x tapf., Apocynaceae. (Ref. 0400) Found in Halorrhena febrifuga. (Ref. 0402)

Effective on liver cancer. (Ref. 0401)

Hideaki Nishino
C24H34O5 402.524 Download ChemDraw structure file

254degC (alcohol+ether). (Ref. 0404)
[a]18/D=+1.26deg (c=0.793 in methanol). (Ref. 0404)
Very sparingly sol in chloroform, acetone, water. Somewhat more sol in methanol. (Ref. 0404)
UVmax about 300nm. (Ref. 0404)

Isolation from Japanese toad (gama: Bufovulgaris formosus). (Ref. 0405) Isolation from Chinese toad (Bufo asiaticus=Bufo gargarizans Cantor). (Ref. 0247)

Digitalis-like activity. (Ref. 0406)

Gentrogenin / Botogenin
(25R)-3b-Hydroxyspirost-5-en-12-one / 20a,22A,25D-Spirost-5-en-3b-ol-12-one
Hideaki Nishino
C27H40O4 428.604 Download ChemDraw structure file
Precursor for synthesis of pharmaceutically-active steroid. (Ref. 0407)
215-216degC (methanol) (Ref. 0407)
[a]28/D=-56deg (c=1.02 in chloroform). (Ref. 0407)

Isolation from Dioscorea mexicana. (Ref. 0407) Isolation from Dioscorea spiculiflora, Dioscoreaceae. (Ref. 0409)

Gitogenin / Digin
Hideaki Nishino
C27H44O4 432.636 Download ChemDraw structure file

266-268degC (Ref. 0411)
[a]20/D=-75deg (c=1.02in chloroform) (Ref. 0414)
Sol in chloroform, hot alcohol. Sparingly sol in cold ethylacetate, ether. Insol in water. (Ref. 0414)
General absorption at aroud 230-320nm (Ref. 0414)

Isolation from seeds of Digitalis purpurea (Ref. 0410) Yielded by heating gitonin in dil.HCl. (Ref. 0322)

Cardiotonic agent. (Ref. 0410)

Not ppt with digitonin. (Ref. 0322) Ppt with digitonin. (Ref. 0411)
3b,14,16b-Trihydroxy-5b-card-20(22)-enolide / D20.22-3,14,16,21-Tetrahydroxynorcholenic acid lactone.
Hideaki Nishino
C23H34O5 390.513 Download ChemDraw structure file

234degC (Ref. 0416)
[a]20/545=+38.5deg (c=0.68 in methanol). (Ref. 0415)
Sparingly sol in alcohol, acetone, ethylacetate. (Ref. 0415/0416)
max (96% sulfate): 310, 485, 520nm (Ref. 0416)

Aglycon of gitoxin (Ref. 0415) Preparation by refluxing of gitoxin in water +alcohol+HCl. (Ref. 0415)

Cardiotonic action. (Ref. 0417)

Hideaki Nishino
C30H48O4 472.700 Download ChemDraw structure file

191-196degC (Ref. 0418), 202-203degC. (Ref. 0419)
[a]20/D=+168deg (c=1.193 in chloroform), [a]20/D=+151deg (c=0.863 in MeOH) (Ref. 0418), [a]25/D=+175pm3deg (chloroform). (Ref. 0419)
Sol in methanol, ethanol, chloroform, acetone, pyridine. Insol in water, ether, petroleum ether. (Ref. 0418/0419)
UVmax: 290mm (loge=2.0) (EtOH). (Ref. 0418)
3620, 3588, 1691/cm (Ref. 0419)

m/e = 105, 109, 119, 127, 135, 143, 172, 173, 175, 192, 309, 327, 371, 413, 439, 454, 472. (Ref. 0419)
CD(c=0.69 g/l): l(De)=340(O), 317(+3.65, inflexion), 305(+5.60, plateau), 298(+5.80), 240mm(O). (Ref. 0419)

Isolation from the tuber of Gratiola officinalis L. (Ref. 0418) Preparation by hydrolysis of gratioside extracted from Gratiola officinalis L. (Ref. 0418)

Hideaki Nishino
C27H42O4 430.620 Download ChemDraw structure file
Conversion of isoandrosterone to mixture consisting of tigogenin and neotigogenin via 18 steps, further conversion to steroidal sapogenin such as hecogenin (Ref. 0358)
264-266degC (Ref. 0358)
[a]/D=+8deg (chloroform) (Ref. 0358)
Sol in ether, ethylacetate, benzene, acetone. (Ref. 0358)

Isolation from plants, especially numerous Agave species. (Ref. 0357) Preparation method for purification. (Ref. 0357>

Hideaki Nishino
C18H24O2 272.382 Download ChemDraw structure file

168-168.5degC (Ref. 0420)
[a]23/D=-5pm4deg (0.945% in ethanol). (Ref. 0420)

Isolation from urine of pregnant mares. (Ref. 0420) Preparation by hydrogenation of equilenin in acid-ethanol. (Ref. 0421)

High estrogenic activity (rat). (Ref. 0420)

Not ppt with digitonin. (Ref. 0420) Unlike D5,7,9-estrtrienol-3-one-17, no red color reaction even by heating up to 240deg. (Ref. 0421)
Hideaki Nishino
C27H46O2 402.653 Download ChemDraw structure file

24b-epimer, 175-176degC (Ref. 0422); 24a-epimer, 182-183degC (Ref. 0424)
24b-epimer, [a]20/D=-48.2deg (c=1.06 in chloroform). (Ref. 0423>, 24a-epimer, [a]20/D=-26.8deg (c=0.672 in chloroform). (Ref. 0424)

Isolation of b-isomer from horse brain. (Ref. 0422) Isolation b-isomer from bovine spinal cord. (Ref. 0423)

Presence of two stereoisomer. Cholest-5-ene-3b,24b-diol. Cholest-5-ene-3b,24a-diol (Ref. 0424) Also called 24b-epimer as cerebrostenediol or cerebrosterol. (Ref. 0422)
Cholest-5-ene-3,25-diol / D5-Cholestene-3b,25-diol
Hideaki Nishino
C27H46O2 402.653 Download ChemDraw structure file
Preparation by treatment of 3b-acetoxy-5-cholestene-25-one with methylmagnesium. (Ref. 0425/0426) Not product of biogenesis, but oxidation of cholesterol in the air. (Ref. 0422) Efficient and simple synthesis. Regioselective protocol without forming 24-hydroxyisomer. (Ref. 0433) Synthesis of 25-hydroxycholesteryl 3b-acetate by UV-irradiation of 3b-acetoxycholestane. (Ref. 0434) Generally available synthesis method from pregnenolone and the acetate (Ref. 0428) Synthesis from 2-lithiodithian (Ref. 0428)Synthesis from stigmasterol (Ref. 0432) Synthesis from 5b-cholestan-3a,25-diol derived from lithocholic acid. (Ref. 0435) Synthesis by using (h3-allyl)palladium. (Ref. 0429)
178-180degC (Ref. 0425/0426)
[a]25/D=-39.0deg (c=1.05 in chloroform) (Ref. 0425/0426)
(CHCl3) 3620(OH), 1050, 1020, 960, 930, 910/cm (Ref. 0427/0428)
(CDCl3) d 5.33(m, H-6); 3.48(m, -CH-O); 1.19(s,H3C-C(26) and H3C-C(27)); 1.00(s,H3C-C(19)); 0.92(d,J=7Hz,CH3); 0.67(s,H3C-C(18)).
Molecular ion m/e 402 (Ref. 0427/0428/0429)

Contamination as a trace component in cholesterol preparation. (Ref. 0422)

Useful for synthesis of vitamin D3 intermediates, 25-hydroxycholecalciferol and 1,25-dihydroxycholecalciferol (Ref. 0427/0428/0430/0431/0432)
Isoestradiol / 8a-Estradiol / 8-Epiestradiol / 8-Isoestradiol-17b
8a-Estra-1,3,5(10)-triene-3,17b-diol / D1.3.5-8a-Epiestratriene-3,17b-diol
Hideaki Nishino
C18H24O2 272.382 Download ChemDraw structure file
Preparation by high-pressure hydrogenetion of dihydroequilin. (Ref. 0086) Preparation by hydrogenetion of equilenin using Raney nickle under 2800 psi at 85deg. (Ref. 0436) Stereochemistry and preparation of dl-form from dl-equilenin. (Ref. 0385)
a-form: 181degC (dil. methanol+chloroform), dl-form: 213.5-214degC (dil. methanol). (Ref. 0086)
a-form: [a]20/D=+18deg (16mg in 2ml dioxane), [a]21/D=+28deg (alc.). (Ref. 0086/0436)
Sol in methanol, chloroform.(Ref. 0086)
lmax 269mm (loge=2.66), 278mm (loge=2.49) (Ref. 0436/0385)

9b-Ergosterol / Isopyrocalciferol
Hideaki Nishino
C28H44O 396.648 Download ChemDraw structure file

112-115degC (ether-methanol) (Ref. 0437)
[a]20/D=+332deg, [a]20/546=+415deg (c=1.5 in chloroform). (Ref. 0437)
Sol in chloroform (Ref. 0437)
UV max: 262, 280nm. (Ref. 0437)

One of ergosterol stereoisomers. Ppt with digitonin. (Ref. 0437)
Isorubijervine / 18-Hydroxysolanidine
Hideaki Nishino
C27H43O2N 413.636 Download ChemDraw structure file

235-237degC (alcohol). (Ref. 0438), 236-238degC. (Ref. 0442)
[a]25/D=+6.5deg (c=0.97 in abs. ethanol). (Ref. 0438)
Sol in pyridine, alcohol, chloroform. (Ref. 0438/0439/0440)

Isolation from seeds of Veratrum, Liliaceae (Ref. 0438) Separation from V. album, V. viride. (Ref. 0438) Separation in the process of isolation of rubijervine. (Ref. 0438)

Ppt with digitonin. (Ref. 0439) Formation of 1,2-cyclopentenophenanthrene by hydrogenation. (Ref. 0439) Confirmation of isorubijervine structure as a hydroxy-solanidine by conversion to solanidine. (Ref. 0440) Resolution of (22R:NS)-configuration by X-ray analysis. (Ref. 0442)
Hideaki Nishino
C20H32O2 304.467 Download ChemDraw structure file
Praparation by treatment of 3b-hydroxy-5-androsten-17-one with methyl magnesium iodide. (Ref. 0444/0445)
205.5-206.5degC (etylacetate). (Ref. 0444/0445)
[a]20/D=-73deg (alcohol), [a]21/D=-84.5deg (c=0.977, chloroform). (Ref. 0445)
Insol in water. Very sparingly sol in organic solvent. (Ref. 0444/0445)
max. mm (E1%/1cm): 235(141), 309(155), 355(136), 390(168)[I], 438(373), 497(209). min. mm(E1%/1cm): 226(136), 258(105), 335(123), 372(123), 478(145). (Ref. 0446)

1.08(C18), 1.08(C19), 2.55(M,C4), 5.39(M,C6), 1.38(C20). (Ref. 0447)

Function as an anabolic steroid.(Ref. 0444)

17b-Hydroxy-17-methylandrosta-1,4-dien-3-one / 17a-Methyl-17b-hydroxyandrosta-1,4-dien-3-one / 1-Dehydro-17a-methyltestosterone
Hideaki Nishino
C20H28O2 300.435 Download ChemDraw structure file
Preparation by microorganism hydrogenation of 17a-methylteststerone. (Ref. 0448) Preparation by reduction of 17a-methylteststerone with SeO2. (Ref. 0449)
163-164degC (acetone+ether). (Ref. 0448)
[a]26/D=0deg (c=1.150 in chloroform). (Ref. 0448)
Sol in chloroform. (Ref. 0448)
UVmax: 245nm (e=15,600). (Ref. 0448)
In methylenechloride: 2.74m, 5.98m, 6.14m, 6.21m, 7.29m, 7.52m, 8.86m, 9.23m, 10.68m, 10.83m, 11.28m, 12.23m. (Ref. 0448)

M/D+356 (dioxan). (Ref. 0448)

Anabolic action (androgen activity). (Ref. 0448)

11b-Methoxy-19-nor-17a-pregna-1,3,5(10)-trien-20-yne-3,17-diol / 3,17-Dihydroxy-11b-methoxy-19-nor-17a-pregna-1,3,5-trien-20-yne / 17a-Ethynyl-11b-methoxyestra-1,3,5(10)-triene-3,17b-diol / 11b-Methoxy-17a-ethynyl-D1,3,5(10)-estratriene-3,17b-diol / 11b-methoxy-17a-ethynylestradiol
Hideaki Nishino
C21H26O3 326.429 Download ChemDraw structure file
Preparation. (Ref. 0450)
280degC. (Ref. 0450)
[a]20/D=+29deg (c=0.6 in EtOH). (Ref. 0450)
UVmax (ethanol): 280nm (e1%/1cm=58.4) (Ref. 0450)

Estrogenic acitivity. (Ref. 0450)

Hideaki Nishino
C27H40O1 380.606 Download ChemDraw structure file
Preparation from ergosterol. (Ref. 0451/0452/0453)
152-154degC. (Ref. 0451/0453)
[a]17/D=-11deg (c=2 in chloroform). (Ref. 0451)
Insol in water. Sol in organic solvent. (Ref. 0451/0452/0453)
Absorption maximum at around 265-270nm (ether). (Ref. 0451)
nCS2max: 3600/cm (hydroxy), 970/cm (side chain double bond), 809/cm (aromatic ring). (Ref. 0453)

Ppt with digitonin. (Ref. 0451) Stereochemistry. (Ref. 0454)
Ouabagenin / G-Strophanthidin
Hideaki Nishino
C23H34O8 438.511 Download ChemDraw structure file
Preparation by HCl-treatment of ouabain in acetone. (Ref. 0262)
235-238degC (monohydrate from water), 255-256degC (anhydr.). (Ref. 0262/0456)
+0.288deg (Ref. 0262)
[a]17/D=+11.32deg (c=1.27). (Ref. 0262)
Sol in boiling water (1g/10ml, less than 1% solubility at room temperature). Also sol in dil. alcohol. Insol in alcohol anhydride. (Ref. 0262)

Isolation from ouabain, a glycoside from Strophanthus gratus. (Ref. 0262)

LD50 (cat), mean systolic dose in frog. (Ref. 0455)

Evidence for steroid structure of ouabagenin. (Ref. 0456)
Periplogenin / 19-Desoxostrophanthidine
Hideaki Nishino
C23H34O5 390.513 Download ChemDraw structure file
Synthesis of periplogenin. (Ref. 0461/0462)
235degC (Ref. 0457/0458), 135-140degC (from MeOH-H2O). (Ref. 0461)
[a]27/D=+31.5deg (c=1.04 in alcohol), [a]20/D=+29.8deg (c=1 in methanol). (Ref. 0457/0458)
Sol in alcohol, chloroform. Sparingly sol in ether:water (1:2500). Insol in benzene, petroleum ether. (Ref. 0457/0458)

Found in the bark and wood of Periploca graece. (Ref. 0457) Found in Strophanthus eminii Asch et Pax. Apocynaceae. (Ref. 0458) In several species of Strophanthus genus. (Ref. 0461) Isolation accompanied in preparation of strophanthidine from Strophanthus eminii Asch. Et Pax., Apocynaceae. (Ref. 0457) Yielding of periplobiose (C13H24O9) and periplogenin (C23H34O5) in hydrolysis of periplocin. (Ref. 0457)

Prednisolone / Meticortelone
11,17,21-Trihydroxypregna-1,4-diene-3,20-dione / 1,4-Pregnadiene-3,20-dione-11b,17a,21-triol / 1,4-Pregnadien-11b,17a,21-triol-3,20-dione / 3,20-Dioxo-11b,17a,21-trihydroxy-1,4-pregnadiene
Hideaki Nishino
C21H28O5 360.444 Download ChemDraw structure file

240-241degC. (Ref. 0463/0464)
[a]25/D=+102deg (dioxane). (Ref. 0463/0464)
Sparingly sol in water. Sol 1g in 30ml alcohol, 180ml chloroform, 50ml acetone, methanol, dioxane. (Ref. 0465)
UVmax (methanol): 242nm (e=15,000; A1%/1cm=414) (Ref. 0463/0464)
l Nujol/max: 2.96(OH), 5.82(20-carbonyl), 6.04, 6.19 and 6.25(D1,4-diene-3-one) (Ref. 0463/0464)

Biosynthesis from cortisol by Corynebacterium simplex. (Ref. 0465)

More effective than natural corticosteroid as inflammatory drug. (Ref. 0465) Glucocorticoid stronger 3-4 times than natural cortisone, hydrocortisone in eosinopenic response and liver glycogen storage in adrenalectomized mice, thymus degeneration in untreated mice.

Prednisone / Meticorten
17,21-Dihydroxypregna-1,4-diene-3,11,20-trione / 1,4-Pregnadiene-17a,21-diol-3,11,20-trione
Hideaki Nishino
C21H26O5 358.428 Download ChemDraw structure file
Synthesis from cortisone with Corynebacterium simplex. (Ref. 0465)
233-235degC (Ref. 0463/0464)
[a]25/D=+172deg (dioxane) (Ref. 0463/0464)
Very sparingly sol in water. Sol 1g in 150ml alcohol, 200ml chloroform. Slightly sol in methanol, dioxane. (Ref. 0465)
UVmax (methanol): 238nm (e=15,500) (Ref. 0463/0464)
l Nujol/max: 3.04(OH), 5.84(11- and 20-carbonyls), 5.98, 6.16 and 6.21(D1,4-diene-3-one). (Ref. 0463/0464)

Anti-inflammatory action. (Ref. 0465) More efficient rather than natural corticosteroid. 3-4 Times stronger glucocorticoid than natural cortisone, hydrocortisone in eosinopenic response and liver glycogen storage in adrenalectomized mice, thymus degeneration in untreated mice.

11,21-Dihydroxy-17-[(1-oxopentyl)-oxy]pregna-1,4-diene-3,20-dione / 11b,17,21-Trihydroxypregna-1,4-diene-3,20-dione 17-valerate / Prednisolone 17-valerate
Hideaki Nishino
C26H36O6 444.560 Download ChemDraw structure file
Preparation from 17a,21-cyclic orthoesters. (Ref. 0466)
210-213degC (methanol). (Ref. 0466)
[a]/D=+3.5deg (dioxane). (Ref. 0466)

Glucocorticoid. (Ref. 0466)

Hideaki Nishino
C28H44O 396.648 Download ChemDraw structure file
Preparation by UV-irradiation of ergosterol suspended in benzene-alcohol solution. (Ref. 0437)
118degC (Ref. 0437)
[a]19/D=+191.5deg, [a]19/546=+235.4deg (c=2 in acetone). (Ref. 0437)
Insol in water. Sol in organic solvents. (Ref. 0437)
279nm (e=8,500) (Ref. 0468/0469)

5b-Pregnane / 17b-Ethyletiocholane
Hideaki Nishino
C21H36 288.511 Download ChemDraw structure file
Preparation from pregnanetriol-B. (Ref. 0471) Preparation from D5-3-oxy-21-acetoxy-pregnenon-20. (Ref. 0189)
83.5degC (methanol). (Ref. 0470)
[a]19/D=+20deg (c=2 in chloroform), [a]20/D=+19.6deg (in chloroform) (Ref. 0470)
Sol in chloroform, methanol. (Ref. 0470)

Isolation from urine of pregnant women. (Ref. 0470)

Androgenic activity. (Ref. 0470)

Hideaki Nishino
C21H36O2 320.509 Download ChemDraw structure file

239degC (acetone or ethanol). (Ref. 0472)
[a]20/D=+27.4deg (c=0.7 in alcohol). (Ref. 0472)
Sparingly sol in organic solvents. (Ref. 0472)

Metabolite of progesterone. Found in urine of many animals (human, bovine, horse, chimpanzee). (Ref. 0114/0472/0473)

Not ppt with digitonin. (Ref. 0472) Starting material for synthesis of progesterone. (Ref. 0473)
Hideaki Nishino
C21H32O2 316.478 Download ChemDraw structure file
Preparation from 4,11-pregnadien-3,20-dione. (Ref. 0476)
123degC (Ref. 0474)
Insol in water. Sol in organic solvents. (Ref. 0474)

Found in urine of pregnant mares. (Ref. 0474) Urine of pregnant women. (Ref. 0475)

Androgenic acitivity. (Ref. 0474/0475)

3a-Hydroxy-5b-pregnan-20-one / Pregnan-3a-ol-20-one
Hideaki Nishino
C21H34O2 318.493 Download ChemDraw structure file
Preparation by hydrolysis of sodium pregnanediol glucuronidate. (Ref. 0478)
149.5degC (hexane). (Ref. 0477/0478)
[a]13/D=+109deg (c=0.98 in ethanol). (Ref. 0477/0478)

In urine of pregnant women, pregnant hogs. (Ref. 0477)

Not ppt with digitonin. (Ref. 0477)
Hideaki Nishino
C21H34O2 318.493 Download ChemDraw structure file
Preparation from pregnandione. (Ref. 0479) Preparation from pregnandiol. (Ref. 0479)
149degC (dil.alcohol). (Ref. 0479)
Sol in ether. (Ref. 0479)

Ppt with digitonin. (Ref. 0479) Corelation as an epimer with pregnan-3a-ol-20-one. (Ref. 0479)
Hideaki Nishino
C21H34O2 318.493 Download ChemDraw structure file
Preparation from pregnanolon-acetate. (Ref. 0480)
152degC (acetone) (Ref. 0480)

Androgenic acitvity. (Ref. 0481)

20b-Hydroxy-5b-pregnan-3-one / Pregnan-20b-ol-3-one
Hideaki Nishino
C21H34O2 318.493 Download ChemDraw structure file
Yielded by acetylation, partial saponification, oxidation, and hydrolysis of pregnandiol-3(b),20(b), which is synthesized from pregnandiol-3(a),20(a). (Ref. 0481)
172degC (dil. acetone) (Ref. 0481)
Sol in methanol. (Ref. 0481)

Found in urine of pregnant women. (Ref. 0481)

High androgenic activity. (Ref. 0481)

Isomer of pregnan-20a-ol-3-one at C20-OH. (Ref. 0481) Higher melting point (172degC) than 20aisomer (152degC). (Ref. 0481)
Substanz T
20,21-Dihydroxypregn-4-ene-3,11-dione / 4-Pregnene-20,21-diol-3,11-dione
Hideaki Nishino
C21H30O4 346.460 Download ChemDraw structure file

About 210degC. (Ref. 0482)
[a]20/D=+176deg (acetone). (Ref. 0482)
240 mm (loge=about 4.2), because of keto-group. (Ref. 0482)

Found in adrenal glands. (Ref. 0482)

11b,17,20b,21-Tetrahydroxypregn-4-en-3-one / 17-(1,2-Dihydroxyethyl)androsten-3-one-11,17-diol / 4-Pregnene-11b,17a,20b,21-tetrol-3-one /4-Pregnane-11b,17a,20b,21-tetrol-3-one
Hideaki Nishino
C21H32O5 364.476 Download ChemDraw structure file

[a]20/D=+87deg (alcohol), [a]10/D=+120deg (c=2 alcohol). (Ref. 0483)
UVmax: 240nm (Ref. 0483)

In adrenal cortex. (Ref. 0483) Isolation.(Ref. 0484)

17,20,21-Trihydroxypregn-4-ene-3,11-dione / 4-Pregnene-17a,20b,21-triol-3,11-dione
Hideaki Nishino
C21H30O5 362.460 Download ChemDraw structure file

208-209degC (acetone+ether) (Ref. 0485)

In adrenal glands. (Ref. 0485)

17a,20b,21-trihydroxypregn-4-en-3-one / 17-(1,2-Dihydroxyethyl)-D4-androsten-3-on-17a-ol / 4-Pregnen-17a,20b,21-triol-3-one
Hideaki Nishino
C21H32O4 348.476 Download ChemDraw structure file
Synthesis from 17-ethynyltestosterone. (Ref. 0486)
190degC (methanol) (Ref. 0486)
[a]/D=+63deg (c=1 in dioxane) (Ref. 0486)
Sol in dioxane, chloroform, methanol. (Ref. 0486)
UVmax: 240nm (loge=4.1) (Ref. 0486)

Pregnenolone methyl ether
Hideaki Nishino
C22H34O2 330.504 Download ChemDraw structure file
Preparation methods.(Ref. 0487/0489) Synthesis of several 3b-methoxy-D5-steroid. (Ref. 0488)
123.5degC (anhydrous or dil. methanol) (Ref. 0487/0488)
+0.19(5)deg (Ref. 0487)
[a]18/D=+18deg (c=1.085 in chloroform) (Ref. 0487)
Sol in methanol, chloroform. (Ref. 0487)

Anti-inflammatory action. (Ref. 0488)

Pseudohecogenin / 4-Hecogenin
Hideaki Nishino
C27H42O4 430.620 Download ChemDraw structure file
Preparation by hydrolysis of hecogenin. (Ref. 0357)
190-191degC (Ref. 0490)
[a]20/D=+103deg (c=1.5 in chloroform), +96deg (c=1 in dioxane) (Ref. 0490)
UVmax (ethanol): 213nm (e=6,400) (Ref. 0490)
nNIJOL/max: 3320 (hydroxy), 1706 (ketone), 1688/cm (vinyl ether). (Ref. 0490)

Pyrocalciferol / 9a-Lumisterol
10a-Ergosta-5,7,22-trien-3b-ol / 9a-Lumista-5,7,22-trien-3b-ol
Hideaki Nishino
C28H44O 396.648 Download ChemDraw structure file

93-95degC (Ref. 0491)
[a]20/D=+512deg, [a]20/546=+624deg (c=0.15 in alcohol). (Ref. 0491)
Sol in alcohol. (Ref. 0491)
274, 294mm (Ref. 0491)

Distribution (Ref. 0437)

Different configuration at C-9 and C-10 from ergosterol. (Ref. 0437)
Rubijervine / Rubigervine
D5-3b-12a-Dihydroxysolanidene / Solanid-5-ene-3b,12a-diol
Hideaki Nishino
C27H43O2N 413.636 Download ChemDraw structure file

240-246degC (Ref. 0493)
[a]25/D=+19.0deg (c=1 ethanol) (Ref. 0493)
Sparingly sol in water. Sol in ethanol, methanol, benzene, chloroform. Slightly sol in ether, petroleum ether. (Ref. 0493)
1048, 1028, 1016, 1003/cm, strongest at 1048. (Ref. 0495)

X-ray analysis of structure. (Ref. 0442)

Isolation from various species from Veratrum, Liliaceae. (Ref. 0493)

Ruscogenin / Ruscorectal
Hideaki Nishino
C27H42O4 430.620 Download ChemDraw structure file

205-210degC (dried anhydride) (Ref. 0496/0497)
[a]19/D=-127deg (Ref. 0496/0497)
n max: 898, 922/cm (same strength). (Ref. 0497)

Isolation from Ruscus aculeatus L. (produces ruscogenin and neoruscogenin (1:1)). (Ref. 0497) Isolation from Sansevieria trifasciata (Ref. 0498)

Application for therapy of hemorroids. (Ref. 0497)

Hideaki Nishino
C23H34O5 390.513 Download ChemDraw structure file

265-275degC (Ref. 0499/0500)
[a]19/D=+21.1degpm4deg (c=0.521 in methanol) (Ref. 0499/0500)
Sol in alcohol, methanol, pyridine. Sparingly sol in acetone, chloroform. Sol in benzene, ether. (Ref. 0499/0500)
230nm (E1%/1cm=460, 98% sulfate) (Ref. 0500), 415nm (E1%/1cm=430, 98%sulfate) (Ref. 0500)

Isolation from Strophanthus sarmentosus. (Ref. 0499) A component of sarmentoside B, strong glycoside. (Ref. 0501)

Sarsasapogenin / Parigenin
Hideaki Nishino
C27H44O3 416.636 Download ChemDraw structure file

199-199.5deg (Ref. 0502)
[a]25/D=-75deg, [a]25/=-89deg (c=0.5 in chloroform). (Ref. 0503)
Sol in alcohol, acetone, benzene, chloroform. (Ref. 0502)
(Asym.-CH2-), 2910, 2873 (Sym.-CH3), 2864 (Sym.-CH3), 2935. (as acetate) (Ref. 0509)
326 c.p.s (C-19 methyl-group), 338 c.p.s (C-18 methyl-group), 321-326 c.p.s. (C-21,C-27 methyl-group) (Ref. 0508)

Roots of Sarsaparilla. (Ref. 0502) Yielded by hydrolysis of saponin extracted from root of Sarsaparilla. (Ref. 0502)

Ppt with digitonin. (Ref. 0502) Configuration of side chain. (Ref. 0504/0505/0506/0507)
Hideaki Nishino
C23H30O7 418.480 Download ChemDraw structure file

232-234deg (Ref. 0510/0511)
[a]15/D=+44.5pm2 (c=1.1683 in methanol), [a]23/D=+49.5deg (methanol) (Ref. 0510)
Sol in water, methanol, chloroform. (Ref. 0510)
UVmax: 218, 277.5nm (loge=4.2, 1.83) (Ref. 0511)
886-777/cm (7.8-epoxy 14b-hydroxyl) (Ref. 0513)
d5.03(C-3),d5.63(11b-proton),d3.93,d3.43,d3.20,d2.83,d2.6,d1.31, d1.13,d1.08,d1.06. (Ref. 0514)
M=418; 400[M-18]; 382[400-18]; 372[400-28(CO)]; 364[382-18]; 354[372-18, or 382-28(CO)]; 339[354-15(CH3)] (Ref. 0513)

Seeds of Strophanthus sarmentosus. (Ref. 0510) Seeds of S. courmontii. (Ref. 0515/0516) Seeds of S. amboensis, S. intermedius.(Ref. 0511) Aglycon from sarveroside. (Ref. 0510)

Hideaki Nishino
C24H32O4 384.508 Download ChemDraw structure file

232-238deg (methanol) (Ref. 0517/0518)
[a]20/D=-16.8deg (c=0.357 methanol), [a]20/D=+17.9deg (c=0.39, chloroform) (Ref. 0517/0518/0519)
Sol in chloroform, methanol. (Ref. 0517/0518/0519)
UVmax: 300nm (loge=3.72) (Ref. 0517/0518)
Presentation of IR spectra as the acetate. (Ref. 0519)

Found in Urginea burkei Baker, Liliaceae. (Ref. 0518) In bulbs of Scilla maritima. (Ref. 0520) Aglycon prepared by enzymic degradation of proscillaridin A. (Ref. 0517)

Cardiotonic agents (Ref. 0517) LD50 (cat) =0.1567mg/kg (Ref. 0518/0520)

Hideaki Nishino
C32H44O12 620.685 Download ChemDraw structure file

168-170deg (hemihydrate) (Ref. 0521)
[a]20/D=-59 to 60deg (methanol, c=1) (Ref. 0521)
Sol in lower alcohol, ethylene glycol, dioxane, glacial acetic acid. Slightly sol in water, acetone, chloroform, ethyl acetate. Insol in ether, petroleum ether. (Ref. 0521)
lmax: 300nm (loge=3.73, 96% ethanol), 295, 505nm (E1%/1cm 260, 315, 98% sulfate) (Ref. 0521)

Found in Urginea maritima (L.) Baker, Liliaceae, originated from the shore areas of the Mediterranean Sea (the bulbs had ever been utilized as cardiotonic drugs or diuretic agents). (Ref. 0521)

LD50=0.7mg/kg body weight (male mice, oral ingestion) (Ref. 0521) Cardiotonic, diuretic. (Ref. 0521) Glucosides. (Ref. 0521)

Revised structure. (Ref. 0522)
a1-Sitosterol / Citrostadienol / 24-Ethylidene-lophenol
Hideaki Nishino
C30H50O 426.717 Download ChemDraw structure file
Synthesis methods.(Ref. 0138) Cis-trans isomers at 24(28)-double bond. (Ref. 0145/0140)
164-166deg (alcohol) (Ref. 0139/0136)
[a]28/D=-1.7deg (c=2, chloroform) (Ref. 0139/0136)
Sol in alcohol, chloroform. (Ref. 0139/0136)
209mm (e=5,500) (Ref. 0137)

Found in wheat germ oils, corn oils. (Ref. 0142), Citrus fruits (Ref. 0137) Most general plant sterol. (Ref. 0142)

Ppt with digitonin. (Ref. 0139)
Solanidine / Solatubine
Hideaki Nishino
C27H43ON 397.636 Download ChemDraw structure file
Synthesis from demissidine. (Ref. 0528) Synthesis from tomatid-5-en-3b-ol. (Ref. 0528) Stereospecific synthesis.(Ref. 0529)
218-219deg (chloroform-methanol) (Ref. 0524/0527/0528)
[a]21/D=-29deg (c=0.5, chloroform) (Ref. 0527/0528)
Freely sol in benzene, chloroform. Slightly sol in alcohol, methanol. Sparingly sol in ether, water. (Ref. 0524/0527/0528)

Presence as an aglycon of solanine derived from Solanum tuberosum (potato), S. nigrum (woody-night-shade), S. lycopersicum (tomato). (Ref. 0525)

Function as an aglycon of solanine, a species of alkaloids.(Ref. 0525)

Ppt with digitonin. (Ref. 0524) Evidence for steroid skeleton by dehydrogenation with Selen. (Ref. 0524) Stereochemistry. (Ref. 0526/0442)
Solanocapsine / Solanocapsin
3-Amino-16,23-epoxy-16,28-seco-solanidan-23-ol / 3b-Amino-22,26-imino-16b,23-oxido-5a,22a,23b,25a-cholestan-23-ol / 3b-Amino-22,26-imino-16b,23-oxido-5a,22R,23S,25R-cholestan-23-ol
Hideaki Nishino
C27H46O2N2 430.666 Download ChemDraw structure file
Synthesis from solafloridine ((25R)-22,26-epimino-5a-cholest-22(N)-en-3b,16a-diol). (Ref. 0533) Synthesis from O(3),O(16)-diacetyl-solafloridine. (Ref. 0534)
213-215deg (monohydrate) (Ref. 0531)
[a]20/D=+26.3deg (c=1.80), [a]20/D=+24.9deg (c=2.13 methanol) (Ref. 0531)
Sol in methanol, chloroform. (Ref. 0531/0532)
(chloroform) 3587, 3355 (NH-atomic rotation-vibration), 3305, 1280, 1245, 1218, 1205, 1160, 1140, 1113, 1096, 1078, 1057, 1040, 1018, 1008, 965, 950, 926, 908, 880, 870, 800, 767, 698/cm (Ref. 0531)

Found in Solanum pseudocapsicum (Ref. 0530/0531) Found also in S. capsicastrum, S. hendersonii. (Ref. 0531)

Function as an alkaloid. (Ref. 0530)

Ppt with digitonin. (Ref. 0532) Stereochemistry. (Ref. 0532)
Solasodine / Solancarpidine / Solanidine-s / Purapuridine
Spirosol-5-en-3b-ol / Solasod-5-en-3b-ol / D5-20bF,22aF,27-Azaspirosten-3b-ol / 3b-Hydroxy-22(27)-imino-25a-5-furostene
Hideaki Nishino
C27H43O2N 413.636 Download ChemDraw structure file
Synthesis from diosgenin acetate. (Ref. 0536) Synthesis from (22S:25R)-16b-acetoxy-22,26-acetimino-5a-cholestan-3b-ol. (Ref. 0537) Synthesis from 26-carbomethoxy(22R,25S)22-nitro-5-cholesten-3b-ol-16-one. (Ref. 0538)
200-202deg (methanol) (Ref. 0536/0537)
[a]25/D=-98deg (c=0.14, methanol), [a]/D=-113deg (chloroform) (Ref. 0536/0537)
Freely sol in benzene, pyridine, chloroform. Sol in alcohol, methanol, acetone. Insol in ether. (Ref. 0536/0537)
10.3, 10.4, 11.2, 11.5m (azaoxaspirane bands) (Ref. 0536)

Found in eggplant, potato, belonging to Solanum family. (Ref. 0535) Aglycon of solasonine. (Ref. 0535)

Function as an alkaloid. (Ref. 0535)

Strating material for synthesis of steroidal agents. (Ref. 0536)
a-Spinasterol / a-Spinasterin / Bessisterol / Hitodesterol
Hideaki Nishino
C29H48O 412.691 Download ChemDraw structure file
Synthesis from 7-dehydrostigmasteryl benzoate. (Ref. 0541)
168-169deg (alcohol+petroleum ether) (Ref. 0539/0540)
[a]25/D=-3.6pm0.5deg (c=2.8, chloroform), [a]23/D=-1.8deg (Ref. 0541)

Isolation from spinach leaves. (Ref. 0539) Isolation from watermelon and the related vegetables. (Ref. 0540)

Needed for growth of fruit-fly, Drosophila. (Ref. 0542)

Ppt with digitonin. (Ref. 0539)
7-(Acetylthio)-17-hydroxy-3-oxo-pregn-4-ene-21-carboxylic acid g-lactone / 17-Hydroxy-7-mercapto-3-oxo-17a-pregn-4-ene-21-carboxylic acid g-lactone,7-acetate / 3-(3-Oxo-7a-acetylthio-17b-hydroxy-4-androsten-17a-yl) propionic acid g-lactone
Hideaki Nishino
C24H32O4S 416.574 Download ChemDraw structure file
Preparation. (Ref. 0543)
134-135deg (methanol) (Ref. 0543)
[a]20/D=-33.5deg (chloroform) (Ref. 0543)
Insol in water. Sol in organic solvents. (Ref. 0543)
UVmax: 238nm (e=20,200) (Ref. 0543)
8.78 p.p.m (C10-CH3) (Ref. 0544)

Rotatory dispertion curve: [f]=-2540, l=345mm. (Ref. 0544)

Diuretic. (Ref. 0543) Effective as an aldosterone antagonist. 0.4mg/oral ingestion to rat, 50% inhibition of urine sodium-potassium balance by 12mg desoxycorticosterone in adrenalectomized rat. Belonging to most efficient group among steroid 17-spirolactone. (Ref. 0543)

Stereoisomers (7b-SCOCH3) (Ref. 0544) Isolation and identification of the metabolic intermediates. (Ref. 0546) Determination of structure by X-ray diffraction. (Ref. 0545)
Squalene / Spinacene / Supraene
Hideaki Nishino
C30H50 410.718 Download ChemDraw structure file
Synthesis using geraniol. (Ref. 0553) Stereoisomer-specific synthesis. (all-trans-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene). (Ref. 0554/0556) Synthesis from 2-farnesylthiothiazoline. (Ref. 0557) Application of general synthetic method of 1,5-diene. (Ref. 0558) Synthesis of trans-cis-trans-trans isomer, and preparation of tritium-labeled squalene. (Ref. 0559)
about -75deg (Ref. 0547)
bp/25=285deg, bp/2=240deg, bp/0.15=203deg (Ref. 0547)
n20/D=1.4965 (Ref. 0547)
Insol in water. Sol in ether, petroleum ether, carbon tetrachloride, acetone. Sparingly sol in glacial acetic acid, alcohol. (Ref. 0547)
Comparison between natural and synthetic compounds. Identification of characteristic peaks at around 9-11m,12m (Ref. 0553)

Molar refraction 139.6, 139.8, 139.9 (Ref. 0547)

Shark liver oil. (Ref. 0547) Centrophorus granulosus, Spinax niger, Scymnorhinus lichia. (Ref. 0548)
Intermediate in cholesterol biosynthesis. (Ref. 0554)
Sterilizer. (Ref. 0547)

Somewhat stinks in oily state. (Ref. 0547) 12cps.viscosity at 25degC. (Ref. 0547) The flashing point, about 200degC. (Ref. 0547) Intermediate for synthesis of drugs. (Ref. 0547) Intermediate for organic pigments, synthetic rubber, aroma, surfactants. (Ref. 0551/0552) Iodine value 377.6 (Ref. 0547) Occupied 50-80% of liver oil. (Ref. 0547) Crystal structure (Ref. 0555)
Stigmastanol / b-Sitostanol / Fucostanol
Hideaki Nishino
C29H52O 416.723 Download ChemDraw structure file
Preparation from b-sitosterol. (Ref. 0147) Preparation from b-sitostenone. (Ref. 0560)
138-139deg (monohydrate, crystals), 144-145deg (dry) (Ref. 0147)
[a]20/D=+25deg (c=1.1 in chloroform) (Ref. 0147)
Sol in methanol, chloroform. (Ref. 0147)

Stigmasta-5,22-dien-3b-ol / 3b-Hydroxy-24-ethyl-D5,22-cholestadiene
Hideaki Nishino
C29H48O 412.691 Download ChemDraw structure file

170deg (Ref. 0176)
[a]22/D=-51deg (c=2 in chloroform) (Ref. 0176)
Insol in water. Sol in organic solvents. (Ref. 0176)

Isolation from phytosterols mixture extracted from soy or calabar beans. (Ref. 0176)

Anti-rigidity factor. (Ref. 0176)

Hideaki Nishino
C23H32O5 388.497 Download ChemDraw structure file

187-188degC (aceton+petroleum ether) (Ref. 0561)
[a]25/D=+14.1deg (c=1.138 in chloroform) (Ref. 0561)
UVmax: 217nm (loge=4.22, chloroform) (Ref. 0561)
11.29-11.39m and 12.81-12.87m KBr two bands-derived structure (Ref. 0562)
NMR spectra of 3-O-acetyl-tanghinigenin. (Ref. 0562)

Seeds of Cerbera tanghinin. (Ref. 0561) Aglycon of tanghinin. (Ref. 0561)

LD50 (cat)=1.016pm0.0876mg/kg body weight. (Ref. 0562)

3a,17a,21-Trihydroxy-5b-pregnane-11,20-dione / 3a,17a,21-Pregnanetriol-11,20-dione / 11,20-Pregnanedione-3a,17a,21-triol
Hideaki Nishino
C21H32O5 364.476 Download ChemDraw structure file

190degC (anhyd. ethanol) (Ref. 0564)
[a]25/D=+85.0deg (c=1.0 in 100% ethanol) (Ref. 0564)
Sol in alcohol, ethylacetate. (Ref. 0564)
Characteristic band at 1041/cm. (Ref. 0564)

In general, metabolite of cortisone in mammals. (Ref. 0563) Yielded by reduction of A-ring of cortisone in Streptomyces sp. (Ref. 0564)

Adonitoxin / Adovern
Hideaki Nishino
C29H42O10 550.638 Download ChemDraw structure file

238-240degC (Ref. 0566)
lmax=218mm (loge=4.10), lmax=219mm (loge=4.3) (Ref. 0565/0566)
1640, 1756, 1726/cm (Ref. 0566)

Isolation from plants, Adonis vernalis L., Ranunculaceae. (Ref. 0565/0566)

Adrenosterone / Reichstein's Substance G
Hideaki Nishino
C19H24O3 300.392 Download ChemDraw structure file
Total synthesis from 6-methoxy a-tetralone. (Ref. 0568) Preparation from Reichstein's Substance E, Fa. (Ref. 0198/0295)
220-224bC (alcohol) (Ref. 0483)
[a]20/D=+262pm3deg (anhydrous alcohol); [a]25/5461=+364pm5deg (c=0.18% in anhydrous alcohol) (Ref. 0483/0271)
Sol in water, 9.85(23deg),15.2(37deg) mg/100ml alcohol, acetone, ether. (Ref. 0568)
UVmax: 235nm (Ref. 0483)

Crystallographic analysis. (Ref. 0569)

Bovine adrenal cortex. (Ref. 0271/0270/0483)
Metabolism of adrenosterone-1,2-3H in control and hypothyroid patients. (Ref. 0570)
Androgenic activity. (Ref. 0483/0270/0271/0198/0295)

Aldosterone / Elektrocortin / Electrocortin / Aldocortin
11b,21-Dihydroxy-3,20-dioxopregn-4-en-18-ol; 3,20-Diketo-11b,18-oxido-4-pregnene-18,21-diol
Hideaki Nishino
C21H28O5 360.444 Download ChemDraw structure file
Total synthesis. (Ref. 0577) Synthesis via three steps from corticosterone. (Ref. 0578)
164-169degC (hydrated, 105deg) (Ref. 0574)
[a]23/D=+152.2deg (anhydr; c=2 in acetone), [a]25/D=+161deg (c=0.1 in chloroform) (Ref. 0571/0574)
UVmax: 240nm (loge=4.20 for the monohydrate; e mol 15,000 for the anhydr.) (Ref. 0574)
Hydroxyl band at 2.92m, D4-3-keto band at 6.05 and 6.18m, saturated carbonyl at 5.87m. (Ref. 0574)

A mineral corticoid secreted from adrenal cortex. (Ref. 0579) Isolation. (Ref. 0571/0572/0573/0574)

Adrenocortical steroid regulates matabolism of electrolyte and water. Synthesized in zona glomerulosa, transported by albumin. Secreted 400mg/day in human male adult. The secretion is influenced by ACTH, GH, plasma sodium/potassium ions, and renin-angiotensin system, which induces resorbing of sodium, chloride, bicarbonate ions and potassium ion from uresis. Activity can be detected at the dose of 0.05-0.01mg in rat urinary sodium retention assay. 16mg Desoxycorticosterone acetate must be needed to retain the same activity. (Ref. 0579)

Alfadolone acetate / Alphadolone acetate / GR 2/1574
3a,21-Dihydroxy-5a-pregnane-11,20-dione 21-acetate / 21-Acetoxy-3a-hydroxy-5a-pregnane-11,20-dione
Hideaki Nishino
C23H34O5 390.513 Download ChemDraw structure file
Preparation from 5a-androstane-3,17-dione. (Ref. 0580)
175-177deg (acetone-hexane) (Ref. 0580)
[a]26/D=+97deg (c=1.02 in chloroform) (Ref. 0580)
nmax(Nujol) 3500, 1755, 1718, 1200/cm. (Ref. 0580)

Constituent of anesthetic. (Ref. 0580)

Strong positive in blue-tetrazolium reaction. (Ref. 0580)
Alfaxalone / Alphaxalone / GR 2/234
Hideaki Nishino
C21H32O3 332.477 Download ChemDraw structure file
Preparation from hecogenin. (Ref. 0196)
172-174deg (ether) (Ref. 0196/0580)
[a]26/D=+113.4pm2deg (c=1.2 in chloroform) (Ref. 0196/0580)
IR spectra. (Ref. 0196)

As a constituent, Steroid I, of anesthetic, included in an injection of GLAXO CT1341 together with 21-acetoxy-3a-hydroxy-5a-pregnane-11,20-dione (Steroid II) and et al. AD50 1.79, LD50 54.7 (mg/kg mice) (Ref. 0581) Preliminary clinical application to human. Stable anesthetized state. (Ref. 0583)

The 3-acetate, m.p. 155-156deg. (Ref. 0580)
Algestone / Alphasone
16a, 17-Dihydroxypregn-4-ene-3,20-dione / 16a,17-Dihydroxyprogesterone / 4-Pregnene-16a,17a-diol-3,2-dione
Hideaki Nishino
C21H30O4 346.460 Download ChemDraw structure file
Preparation from 16-dehydroprogesterone. (Ref. 0585)
225deg (ethanol+dichloromethane) (Ref. 0585)
[a]22/D=+95deg (c=0.81 in chloroform) (Ref. 0585) [a]24/D=+97deg (Ref. 0586)
UVmax: 240nm (e=16,600) (Ref. 0585), lmax: 241-242mm (e=15,200). (Ref. 0586)
nNuiol/max 3390, 1711, 1612, 1081/cm. (Ref. 0586)

[M]/D+336. (Ref. 0586>

Anti-inflammatory action as an acetonide in topical tissues. (Ref. 0588)

Preparation of acetonide. The m.p. 176-177deg, [a]20/D=+49deg (c,1.25) (C23H32O5, water) (Ref. 0585/0588)
Algestone acetophenide / Alphasone acetophenide / P-DHP / Bovitrol / Deladroxone / Droxone
16a,17-Dihydroxypregn-4-ene-3,20-dione cyclic acetal with acetophenone / 16a,17a-Dihydroxyprogesterone acetophenide
Hideaki Nishino
C29H36O4 448.594 Download ChemDraw structure file
Preparation from 16a,17a-dihydroxyprogesterone. (Ref. 0588)
150-151deg (95% ethanol) (Ref. 0588)
[a]23/D=+51deg (chloroform) (Ref. 0588)

Unlike inactive 16a,17a-dihydroxyprogesterone as a progestagen, the acetonide exhibits three-times higher activity than progesterone. No androgenic activity, No anti-androgenic activity, estrogenic activity, anti-DCA activity, corticoid activity in a used dose. (Ref. 0588)

Stable in boiling inorganic acid. (Ref. 0588)
Allylestrenol / Gestanin / Gestanol / Orageston / Gestanyn / Gestanon / Turinal
17-(2-Propenyl)estr-4-en-17b-ol / 17a-Allylestr-4-en-17b-ol / 17a-allyl-17-hydroxy-19-nor-4-androstene / 17-Hydroxy-17a-allyl-4-estrene
Hideaki Nishino
C21H32O 300.478 Download ChemDraw structure file

79.5-80deg (Ref. 0589/0590)
Insol in water. Sol in alcohol, ether, acetone, chloroform. (Ref. 0589/0590)

Progestin (progestagen) activity in human. Maintains pregnancy by stimulating the placental function. (Ref. 0589) Inhibition of pregnenolone 3b-ol-dehydrogenase-D5-4-isomerase system in human. (Ref. 0590)

Easily oxidized. (Ref. 0589)
a-Amyrin / a-Amyrenol / Viminalol
Hideaki Nishino
C30H50O 426.717 Download ChemDraw structure file
Formation from ursolic acid. (Ref. 0597) Formation from boswellic acid. (Ref. 0598) Partial synthesis from glycyrrhetic acid and stereochemistry. (Ref. 0599)
186deg (alcohol) (Ref. 0597/0598)
bp0.7 243degC (Ref. 0597)
[a]17/D=+91.6deg (c=1.3 in benzene) (Ref. 0597/0598>
Sol in 22 parts of 98% alc. Sol in ether, benzene, chloroform, glacial acetic acid. Slightly sol in petroleum ether. (Ref. 0597)
Strong terminal methylene absorption at 887/cm (Ref. 0599)

Plants. Ficus variegata Blume, Moraceae; Balanophora elongata Blume, Balanophoraceae; Erythroxylum coca Lam; var. novogranatense Morris, var spruceanum Burck, Erythroxylaceae. Mainly the acetate, latex from Erythroxylaceae, latex from rubber tree. (Ref. 0591)

b-Amyrin / b-Amyrenol
Olean-12-en-3b-ol / 3b-Hydroxyolean-12-ene
Hideaki Nishino
C30H50O 426.717 Download ChemDraw structure file
Total synthesis of biogenetic form. (Ref. 0606) Conversion from d-amyrene to b-amyrin. (Ref. 0605)
197-197.5degC (petr. ether or alc.) (Ref. 0605)
bp0.8 260degC (Ref. 0605)
[a]19/D=+99.8deg (c=1.3 in benzene) (Ref. 0605)
Less solubility than a-form. Sol in 37 parts of 98% alcohol. (Ref. 0605)

Plants. Along with a-amyrin, found in extracted fluid of Baranophora elongata Blume, Balanophoraceae, Erythroxylum coca Lam, var novogranatense Morris, var spruceanum Burck, Erythroxylaceae, Ficus variegata Blume, Moraceae. (Ref. 0600/0601/0602/0603/0604)
Biogenetic pathway from squalene. (Ref. 0607/0608)

17-Hydroxy-6a-methylpregn-4-en-20-one / 6a-Methyl-4-pregnen-17a-ol-20-one
Hideaki Nishino
C22H34O2 330.504 Download ChemDraw structure file

190-193degC (methanol+dichloromethane) (Ref. 0613)
[a]20/D=+51deg (in chloroform) (Ref. 0613)

Progestin action as an acetate (oral ingestion to rabbits, influence to the uterus). (Ref. 0612) Formation of knot in the mammary glands when used as a contraceptive steroid for a long time (Beagle dogs). (Ref. 0611) Malignant tumor formation in the mammary glands when used as a contraceptive steroid for a long time (Beagle dogs). Estradiol, ethynylestradiol are faster removed from blood (used together with mestranol in Rhesus monkey). (Ref. 0610) Influence on the morphological structure of rhesus monkey mammary glands. (Ref. 0610)

Androisoxazole / Neo-penden
17-Methyl-5a-androstano[3,2-C]-isoxazol-17b-ol / 2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-Tetradecahydro-1,10a,12a-trimethyl-1H-cyclopenta[7,8]phenanthro[2,3-C]isoxazol-1-ol /17b-Hydroxy-17a-methylandrostano[3,2-C]isoxazole
Hideaki Nishino
C21H31O2N1 329.476 Download ChemDraw structure file

169-170degC (Ref. 0614)
[a]/D=+19deg (Ref. 0614)
UVmax (ethanol): 226nm (loge=3.71) (Ref. 0614)

High anabolic agent. low androgenic activity (Ref. 0614)

3b,11b-Dihydroxy-5a-androstan-17-one / Androstane-3b,11b-diol-17-one
Hideaki Nishino
C19H30O3 306.440 Download ChemDraw structure file

235-238degC (acetone+ether) (Ref. 0200)
[a]20/D=+84.5pm3deg (c=1.04 in ethanol) [a]19/D=+81.3deg (dioxane), [a]19/545=+105deg (dioxane) (Ref. 0200)

Recognized first as a degradated product of allopregnane-3b,11b,17a,20b,21-pentol (Reichstein's Substance A). (Ref. 0200), but isolated from adrenal cortex. (Ref. 0207/0615)

Ppt with digitonin. (Ref. 0200)
D5-Androstene-3b-16a-diol / 5-Androstene-3b,11a-diol
Hideaki Nishino
C19H30O2 290.440 Download ChemDraw structure file
Preparation from 5-androstene-3b,16b-diol via the formation of 3.16-di-p-toluenesulfonate, hydrolysis at C3, and epimerization at C16 by exchange reaction with p-toluenesulfonate acetate. Alternatively, from 5-androsten-3b-ol-16-one (hemihydrate) as a starting material, synthesis via 3b-acetoxy-5-androsten-16b-ol, tosylation at C16, and epimerization. (Ref. 0206)
216-217degC (methanol aq.) (Ref. 0206)
[a]22/D=-110deg (c=1.09 in 95% ethanol), [a]24.5/D=-67deg (c=0.80 in dioxan). (Ref. 0206)

Tranquilizer. No androgenic activity, no anabolic activity. (Ref. 0206)

Hideaki Nishino
C29H42O11 566.637 Download ChemDraw structure file

220-235degC (Ref. 0617)
[a]17/D=-3.9pm2deg (c=0.905 in methanol) (Ref. 0617)
Sol in water, alcohol. Slightly sol in ether. (Ref. 0617)
UVmax: 305,217nm (loge=1.8,4.08) (Ref. 0617/0618)

Plants. Isolation from latex (arrow poison) from Antiaris toxicaria Lesch., Moraceae (Indonesia). (Ref. 0616/0617/0618)

LD50 in cats (anhydr.); 0.116mg/kg i.v. (Ref. 0617/0618/0621)

Asiaticoside / Madecassol
2a,3b,23-Trihydroxyurs-12-en-28-oic acid O-6-deoxy-a-L-mannopyranosyl-O-b-D-glucopyranosyl-O-b-D-glucopyranosyl ester
Hideaki Nishino
C48H78O19 959.122 Download ChemDraw structure file

235-238degC (Ref. 0622)
[a]20/D=-14deg (alc.) (Ref. 0622)

Plants. Active component of Centella asiatica (L.) Urban, Umbelliferae. Trisaccharide moiety linked to the aglycone: asiatic acid(Ref. 0622)
Metabolism in rat. Hydrolysis in Caecal microflora. (Ref. 0623)
Application to therapy for wound. (Ref. 0622)

Batrachotoxinin A 20-(2,4-Dimethyl-1H-pyrrole-3-carboxylate) / 3a,9a-Epoxy-14b,18b-(epoxyethano-N-methylimino)-5b-pregna-7,16-diene-3b,11a,20a-triol,20a-ester with 2,4-dimethylpyrrole-3-carboxylic acid
Hideaki Nishino
C31H42O6N2 538.675 Download ChemDraw structure file
Partial synthesis from batrachotoxinin A. (Ref. 0626)
[a]/589=+5-10deg, [a]/300=-260deg (Ref. 0625)
UVmax (methanolic HCl): 262, 234 nm (loge=3.70,3.99), end absorption (Ref. 0626)
A sharp absorption band at 5.9m (amidocarbonyl group), 1695, 1250/cm (Ref. 0624/0625)
0.85, 1.48 (doublet), 2.25, 2.2 ; 2.25 ; 2.45, 2.35, 3.40 (2H), 5.6-6.3 (about 3H), 8.74 broad (le0.4H) (Ref. 0625)
Mass 399,2413 (C24H33NO4, 9 rings or double bonds), CH17/17(carbon skeleton C17 (potentially) highly unsaturated OH-groups in ring system), no intense C4H7NO (not ring A of samandarine), no intense C6H12NO (not ring F, no tomatidine) C4H10NO, C7H6-8NO, C7H8NO2 (NO within 4C, NO2 within 7C) (Ref. 0625/0626)

Separation from the related compound in two-dimensional TLC. (Ref. 0626)
Plants. Extraction from skin of Columbian arrow poison frog (Kokoi frog), genus Phyllobates bicolor. (Ref. 0624)

Most toxic steroidal alkaloid. No effect on non-injured skin, but cause of persisting pain. Dangerous effect on the decline patients. Selective toxicity, irreversible increase of permeability of sodium ions. LD50=1.15-2.7mg/kg mice (most toxic among the related compounds) (Ref. 0625/0626)

Rf=0.60, ED50=0.37mg/kg mice (Ref. 0625) Color reactions; (1) iodoplatinate, +; (2) Ehrlich reaction, red; (3) dimethylaminocinnamaldehyde, blue. Table of chemical properties in reactions. (Ref. 0626)
Batrachotoxinin A
1,2,3,4,7a,10,11,11a,12,13-Decahydro-14-(1-hydroxyethyl)-2,11a-dimethyl-7H-9,11b-epoxy-13a,5a-propenophenanthro[2,1-F][1,4]oxazepine-9,12(8H)-diol / 3a,9a-Epoxy-14b,18b-(epoxyethano-N-methylimino)-5b-pregna-7,16-diene-3b,11a,20a-triol
Hideaki Nishino
C24H35O5N 417.538 Download ChemDraw structure file
Partial synthesis. (Ref. 0626) Partial synthesis from 18,20-lacton compound. (Ref. 0632>
End absorption (Ref. 0625)
1645/cm (Ref. 0625)
0.85,1.42,2.30,2.66,3.42(-2H),5.5-6.3(-4H) (Reference TMS d=0.0, solvent CDCl3); 0.85(19-CH3), 1.90(d)(6.5)(21-CH3), 2.48(s)(N-CH3), 2.89(s)(18-CH2), 3.22(d)(18)(H-11), 4.57(q)(6.5)(H-20), 5.72(t)(2)(H-7), 6.24(dd)(2.5,5)(H-16)(TMS, d=0.0, CDCl3) (Ref. 0626)
m/e ion 399 C24_H33NO4, 370 C23H32NO3, (342)(C22H32NO3), 312 C20H24_O3, 294 C20H22O2, 286 C18H22O3, 279 C19H19O2, 276 C20H20O, 261 C19H17O, 224 C16H16O, 219 C17H15, (206), 184 C13H12O, (166)
C10H16NO, 88 C4H10NO, 71 C4H9N (Ref. 0626)
Crystal structure of O-p-bromobenzoate derivative. (Ref. 0631)
Separation from batrachotoxin and batrachotoxinin B, C in preparative TLC. Rf=0.54. (Ref. 0625)
Plants. Skin of Columbian arrow poison frogs (Kokoi frog), genus Phyllobates bicolor. (Ref. 0624) Skin of Phyllobates avrotaenia (Ref. 0630)

Cardiotoxin. LD50 i.v., in mice: 1mg/kg (1/10 than batrachotoxin). Weakest in major 4 species of toxic steroidal alkaloids. (Ref. 0625) Toxicity of various derivatives. 2,4,5-Trimethylpyrrole-3-carboxylate derivative, LD50=1mg/kg mice, stronger 1000-times than batrachotoxinin A. (Ref. 0626)

Color reactions; (1) iodoplatinate. +; (2) Ehrlich reaction, none (3) dimethylaminocinnamaldehyde, none. (Ref. 0625)
Betamethasone / Betadexamethasone / Flubenisolone / b-Methasone / Beta-corlan / Becort / Betafluorene / Betasolon / Betnelan / Betnesol / Tablets / Celestan / Celrstene / Celestone / Visubeta
9-Fluoro-11b,17,21-trihydroxy-16b-methylpregna-1,4-diene-3,20-dione / 9a-Fluoro-16b-methylprednisolone / 16b-Methyl-9a-fluoro-D1-hydrocortisone / 16b-Methyl-9a-fluoroprednisolone
Hideaki Nishino
C22H29O5F 392.461 Download ChemDraw structure file
Synthesis from 9a-fluoroprednisolon. (Ref. 0634) Synthesis from 3a-acetoxy-16-pregnene-11,20-dione. (Ref. 0635)
231-234degC (ethyl acetate) (Ref. 0635)
[a]/D=+108deg (acetone) (Ref. 0635)
UVmax (methanol) 238nm (e=15,200) (Ref. 0635) lNujol/max 2.90, 2.95, 5.88, 6.10, 6.15, 6.20, 11.25m

Glucocorticoid, anti-inflammatory effect (human, experimental animal), no retention activity of water and salts. (Ref. 0633/0634/0635)

Synthesis as a 21-acetate. (Ref. 0634)
Betulin / Trochol / Betulinol
Lup-20(29)-ene-3b,28-diol / Lup-20(30)-ene-3b,28-diol
Hideaki Nishino
C30H50O2 442.717 Download ChemDraw structure file

248-251degC (methanol-chloroform) (Ref. 0637)
[a]/D=+15deg, [a]/D=+20deg (diacetate) (Ref. 0637)
Sparingly sol in cold water, petroleum ether, carbon disulfide. Sol in 149 parts alcohol, 251 parts ether, 113 parts chloroform, 417 parts benzene. Sol in acetic acid. (Ref. 0637)

Plants. Isolation from outer parts of white birch barks, other barks, and lignite. (Ref. 0636) Extraction from Lemaireocereus griseus Britton, rose, Cactaceae (Ref. 0637)

Bolasterone / Myagen / U-19763
17b-Hydroxy-7a,17-dimethylandrost-4-en-3-one / 7a,17-Dimethyltestosterone
Hideaki Nishino
C21H32O2 316.478 Download ChemDraw structure file
Synthesis by reaction of D5-7-keto steroid with methylmagnesium halide or methyl lithium to obtain 7-methyl carbinol, followed by successive several reactions. (Ref. 0643)
163-165degC (Ref. 0643)

In oral ingestion to rat, myotropic activity, androgenic activity; 1, 1 in 17-methyltestosterone; 13.4, 3.0 in bolasterone (because of 7a-methyl-group). Anabolic assay in monkey, higher activity than halotestin. Accordingly, since a smaller dose of bolasterone will be enough, in clinical application, toxicity to liver shall be relatively lowered. (Ref. 0643/0644)

Boldenone / Dehydrotestosterone
17b-Hydroxyandrosta-1,4-dien-3-one / 1,4-Androstadien-17b-ol-3-one / 3-Oxo-17b-hydroxy-1,4-androstadien
Hideaki Nishino
C19H26O2 286.409 Download ChemDraw structure file
Synthesis from testosterone. Also can be synthesized from D5-17b-hydroxy-androsten-3-on. (Ref. 0449)
164-166degC (Ref. 0449)
[a]25/D=+25deg (chloroform) (Ref. 0449)
UVmax: 243-244mm (Ref. 0645)
Carbon tetrachloride, 3675, 3500 (free and associate hydroxy), 1670 (3-ketone), 1632 (D4-double bond), 1607/cm (D1-double bond) (Ref. 0645)

In anabolic action in muscle, 17-cyclopentenyl ether (Quinbolone) exerts lower toxicity to liver in oral ingestion.(Ref. 0645)

Weakly positive in Zimmermann reaction, orange-colored by spray with ethanol-sulfate.(Ref. 0645)
Bufogenin B / Desacetylbufotalin
Hideaki Nishino
C24H34O5 402.524 Download ChemDraw structure file
Prepared by removal of acetyl-group from Bufotalin. (Ref. 0247)
210-223degC (Ref. 0247)
[a]19/D=+30pm3deg (c=1.039 in dioxane) (Ref. 0247)
Very sparingly sol in chloroform, methanol, acetone. (Ref. 0247)

Animals. Separation from Chinese drug prepared from Chinese toads (Bufo asiaticus = Bufo gargarizans Cantor). (Ref. 0247)

Toxin secreted from skin glands of toads. (Ref. 0247)

Bufotoxin / Vulgarobufotoxin
Bufotalin 3-suberoylarginine ester
Hideaki Nishino
C40H60O10N4 756.925 Download ChemDraw structure file
Partial synthesis.(Ref. 0650)
198-202degC (Ref. 0647)
[a]26/D=+2.0pm2deg (c=0.9939 in MeOH) (Ref. 0647)
Sol in methanol, pyridine. Slightly sol in anhydrous alcohol. Insol in water, ether, acetone, chloroform, petroleum ether. (Ref. 0014/0015/0646/0647/0648/0649/0650)
UVmax: 295nm (loge=3.74) (Ref. 0647/0014)

Animals. Found in secretion (toad poison) from skin glands of European toad (Bufo vulgaris, Bufo bufo Gargorizans) (Ref. 0646/0014/0015/0647)

Cardiotonic steroid to promote heart function. (Ref. 0646/0014)

Hydrolyzed into bufotalin and suberylarginine. (Ref. 0014) Revised chemical structure. Not bufotalin 14-suberoylarginine ester, but 3-(hydrogen suberoyl)-bufogenin. (Ref. 0648) Determination of structure by enzymic degradation. (Ref. 0649)
Hideaki Nishino
C29H40O9 532.623 Download ChemDraw structure file

223degC (alcohol or ethyl acetate). (Ref. 0654/0657)
[a]18/D=+66.8pm1.0deg (in methanol). (Ref. 0657)
Sol in water, alcohol. Insol in ether. (Ref. 0652/0654/0657)
UVmax: 217, 310nm (EtOH, loge=4.21, 1.49). (Ref. 0657)

Isolation from hydrolyzate of Vscharidin by paper chromatography. (Ref. 0657) Isolation from milk sap of Calotropis procera Dryand., Asclepiadaceae. (Ref. 0651/0652/0653/0654) Asclepias curassavica L., Asclepiadaceae. (Ref. 0655)

Cardiotonic agent. (Ref. 0651/0652/0653/0654/0655) Lethal dose: amphibian, 0.5g/g body wt.; cat, 0.12mg/kg body wt.(Ref. 0653) Although have been applied as a private drug to wart and cancer, exerts cytotoxic activity to human tumor cells derived from nasopharynx cancer. (Ref. 0655)

Almost same structure as apocannoside, cymarin. Isolation of both forms from extract of Apocynum cannabinum L.(Apocynaceae), possessing cytotoxic activity to tumors. (Ref. 0655)
Canrenone / Phanurane
17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid g-lactone / 17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactone /17a-(2-Carboxyethyl)-17b-hydroxy-3-oxo androsta-4,6-diene lactone / 6-Dehydrotestosterone-17a-propionic acid g-lactone / 3-(3-oxo-17b-hydroxy-4,6-androstadien-17a-yl) propionic acid g-lactone
Hideaki Nishino
C22H28O3 340.456 Download ChemDraw structure file
Preparation by dehydrogenation of 17-hydroxy-3-oxo-17a-pregn-4-ene-21-carboxylic acid g-lactone. (Ref. 0543)
149-151degC (ethyl acetate) (re-melts at 165deg). (Ref. 0543)
[a]/D=+24.5deg (chloroform). (Ref. 0543)
UVmax: 283nm (e=26,700). (Ref. 0543)

Competitive agent to the action of aldosterone. Diuretic. 50% Bolck of effect of desoxycorticosterone on the ratio of sodium-potassium in urine of adrenalectomized rats by oral ingestion of 12mg. (Ref. 0543)

Cephalosporin P1
6a,16b-Bis(acetyloxy)-3a,7b-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid
Hideaki Nishino
C33H50O8 574.745 Download ChemDraw structure file

147degC (Ref. 0662)
[a]20/D=+28deg (c=2.7 in chloroform) (Ref. 0662)
Immediately sol in most organic solvents. Slightly sol in chloroform, ethanol. (Ref. 0662)
UVmax: 211nm (e=9,140). (Ref. 0662)

Produced by Cephalosporium sp. collected in Sardinia. (Ref. 0662) Production of Cephalosporium sp.harvested from sea near Sardinia. (Ref. 0662)

Antibiotics. Inhibition of proliferation of most Gram-positive bacteria. All five species of cephalosporins share the common properties to helvolic acid (antibiotic produced by Aspergillus fumigatus). Most active cephalosporin, P1, exhibits the same activity as aureomycin and terramycin. The activity of P1 is twice higher than helvolic acid (in cylinder plate method, effect to S. aureus). (Ref. 0662)

Cephalosporin P consists at least of five components, P1, P2, P3, P4, and P5. P1 is the most active one. P1 is stable in organic solvent and as sodium salt in solution (pH7.0) at room temperature. At pH8.0, slowly become inactive, and at pH9.6, rapidly inactivated. (Ref. 0662) Cephalosporin P1 is not C32H48O8, but, maybe possess one more methyl-group at C8, perhaps C33H50O8. (Ref. 0664) Revision to C33H50O8 by NMR and mass. (Ref. 0655/0666)
Cerberin / Veneniferin / Monoacetylneriifolin
Hideaki Nishino
C32H48O9 576.718 Download ChemDraw structure file

212-215degC (methanol+water). (Ref. 0668) 213degC. (Ref. 0669)
[a]27/D=-46.9deg (95% ethyl alcohol). (Ref. 0667), [a]19/D=-82deg (chloroform). (Ref. 0668) [a]23/D=-79deg. (Ref. 0669)
Sol in alcohol, chloroform, acetic acid, pyridine. Slightly sol in ethyl acetate, acetone, water. Very sparingly sol in ether, benzene. (Ref. 0671)

Plants. Seeds of Cerbera odollam Gaertn., Apocynaceae, seeds of Tanghinia venenitera Poir., Apocynaceae. (Ref. 0667) Fruits of Thevetia neriifolia. (Ref. 0669)

Toxic, but utilized as cardiotonic agent. (Ref. 0670) E.M.D.50 (mg/kg pigeon)=126.7pm7.0. Stronger than cerberoside. LD50 (mg/kg cat)=147.0pm5.7. (Ref. 0671)

Positive by Tollens' reagent. Positive by sodium nitroprusside. By treatment with conc. sulfate, the color chages from lemon-yellow to wine-red, which shows green-fluorescence. Reacted with m-dinitrobenzene, the violet color changes to indigo blue (characteristic to cardiac glycoside). Reacted with Liebermann-Burchard reagent, sows emerald green-color. Negative by Keller-Killiani reagent. In sealed tube, by treatment with dil. sulfate, cerberin reduces Benedict's solution. (Ref. 0671)
Cerberoside / Thevetin B / Thevanil
3b-[(O-b-D-Glucopyranosyl-(1 to 6)-O-b-D-glucopyranosyl-(1 to 2)-6-deoxy-3-O-methyl-a-L-glucopyranosyl)oxy]-14-hydroxy-5b-card-20(22)-enolide
Hideaki Nishino
C42H66O18 858.963 Download ChemDraw structure file

197-201degC (water) (Ref. 0672)
[a]24/D=-61.4pm1.5deg (c=1.50 in methanol). (Ref. 0672)
Sol in water, alcohol, acetic acid, pyridine. Slightly sol in ethyl acetate, acetone. Sparingly sol in ether, benzene, chloroform. (Ref. 0671)

Plants. Found in a species of Cerbera odollam Gaertn., Apocynaceae, Thevetia neriifolia Juss., (a species of Apocynaceae). (Ref. 0671)

Weaker cardiotonic drug than cerberin. E.M.D.50 (mg/kg pigeon)=150.2pm11.6, LD50 (mg/kg cat)=813.7pm78. (Ref. 0671)

Dil. sulfate-hydrolyzate shows positive reaction by Benedict's solution (indicative of sugar moiety as a component). Same aglycon as in cerberin. (Ref. 0671/0672)
Cevadine / Veratrine
(Z)-4a,9-epoxycevane-3b,4,12,14,16b,17,20-Heptol 3-(2-methyl-2-butenoate)
Hideaki Nishino
C32H49O9N 591.733 Download ChemDraw structure file
Synthesis by hydrogenation of veracevine 3-(3'-bromoangelate). (Ref. 0675)
208.5-209.5degC (Ref. 0673), 214-215degC (Ref. 0674)
[a]20/D=+12.8deg (c=3.2 in alc.) (Ref. 0673)
Sol in alcohol, ether (1g/about 15ml). Sparingly sol in water. (Ref. 0673)
Very strong absorbance in short wavelength region, but the peak cannot be detected. (Ref. 0673)
Absorbance as evidence for the presence of ether-linked carbonyl-group. Absorbance as evidence for the presence of many hydroxyl-groups. (Ref. 0674)

Plants. Seeds of Schoenocaulon officinale (Schlecht & Cham.) A. Gray (Sabadilla officinarum Brandt), Liliaceae (Sabadilla seed). (Ref. 0673/0674)

A species of Sabadilla alkaloid utilized for an insecticide. Stimulative to mucous membrane. Strong toxicity by ingestion. Strong side effect. (Ref. 0674)

Hideaki Nishino
C27H43O8N 509.632 Download ChemDraw structure file

Hydrochloride, 247degC. (Ref. 0679)
[a]17/D=-17.5deg (aq. alc.). (Ref. 0679)
Sol in water, alcohol. Slightly sol in ether. (Ref. 0679)

Plants. Alkamine (aminoalcohol) yielded by hydrolysis of cevadine. (Ref. 0677)

Structure related to alkaloids such as zygadenine and germine. (Ref. 0678) Determination of C-16 hydroxyl-group as b-orientation, C-22 hydrogen as a-orientation. (Ref. 0679) Confirmation of the orientations by X-ray crystallography. (Ref. 0680)
Chlormadinone acetate / Gestafortin / Lormin / Luteran / Verton / Lutestral / Lutoral[Syntex] / Normenon / Menstridyl / Cero
6-Choloro-17-hydroxy-pregna-4,6-diene-3,20-dione acetate; 6-Chloro-6-dehydro-17a-hydroxyprogesterone acetate / 6-Chloro-6-dehydro-17a-acetoxyprogesterone / 17a-Acetoxy-6-chloro-6,7-dehydroprogesterone
Hideaki Nishino
C23H29O4Cl 404.927 Download ChemDraw structure file
Preparation from 6a,7a-oxido-17a-hydroxy-progesterone. (Ref. 0681) Preparation from 6a,7a-oxido-D4-pregnen-17a-ol-3,20-dione-acetate. (Ref. 0682)
212-214degC (methanol or ether). (Ref. 0681), 209-211degC. (Ref. 0682)
[a]/D=+6deg (in chloroform). (Ref. 0681/0682)
UVmax: 283.5, 286nm (e=23,400, 22,100). (Ref. 0681/0682)

Progestin action (human). Application of the progestational activity for the regulation of mating season (domestic animals). (Ref. 0681/0682)

16a-Chloroestrone 3-methyl ether / Atheran
Hideaki Nishino
C19H23O2Cl 318.837 Download ChemDraw structure file
Preparation from estrone methyl ether enol acetate by reaction with chlorine and potassium carbonate in carbon tetrachloride. (Ref. 0683)
177-179degC (chloroform). (Ref. 0683)
[a]/D=+161deg (chloroform). (Ref. 0683)

Anticholesteremic agent. Applicable because of weak estrogenic activity (1/100 estron). (Ref. 0683)

6a-Chloro-17,21-dihydroxy-pregna-1,4-diene-3,11,20-trione / 6a-Chloro-1,4-pregnadiene-17a,21-diol-3,11,20-trione
Hideaki Nishino
C21H25O5Cl 392.873 Download ChemDraw structure file
Preparation as the 21-acetate by selenium dioxide dehydrogenation of 6a-chlorocortisone 21-acetate. (Ref. 0684)
The 21-acetate, C23H27ClO6, 217-219degC (acetone+hexane). (Ref. 0684)
The 21-acetate [a]/D=+144deg (chloroform). (Ref. 0684)
The 21-acetate; UVmax (ethanol): 237nm (loge=4.19). (Ref. 0684)

Use as a glucocorticoid to topical tissues. Thymolytic activity, 4; anti-inflammatory activity, 4 when the values for hydrocortisone acetate are 1, respectively, in oral ingestion to adrenalectomized rats. (Ref. 0684)

Cimigenol / Cimicifugol
Hideaki Nishino
C30H48O5 488.699 Download ChemDraw structure file

216-217degC (Ref. 0688)
[a]/D=+38.2deg (c=1.99 in chloroform). (Ref. 0688)
No characteristic absorbance. (Ref. 0688)
lKBr/max 3280/cm(OH). (Ref. 0688)
One split signal (3H, J=5-6c/sec.), belonging to secondary methyl group. (Ref. 0685)
Spectral evidence for C30H48O5 (m/e 488). (Ref. 0685/0688)
468 (osmometer) (Ref. 0688)

Plants. Triterpene genin, a species of xyloside, extracted from resin of Cimicifuga racemosa Nutt. (Actaea racemosa L.), Ranunculaceae. (Ref. 0685) Major component of Cimicifuga acerina. (Ref. 0688)

No change in heating reflux in 5% NaOH (MeOH) for 1 h. Resistant to NaIO4 (MeOH). Not absorb H2. Production of several species in mixture by heating reflux in 5% HCl (MeOH) for 1 h. No change in heating reflux in 5% AcOH for 5 h. (Ref. 0688)
4-Chlorotestosterone / Clostebol
Hideaki Nishino
C19H27O2Cl 322.869 Download ChemDraw structure file
Yielded by treatment of 4a,5-oxidoandrostane-17b-ol-3-one acetate with HCl in acetic acid, convertion to 4b-chloroandrostane-5a,17b-diol-3-one-17-acetate, and heating to remove water. (Ref. 0689) Preparation by treatment of 4x,5x-oxidoandrosta-17b-ol-3-one with 1 part of 37% HCl in acetone. (Ref. 0690)
188-190degC (acetone+hexane). (Ref. 0690)
[a]20/D=+148deg (chloroform). (Ref. 0690)
UVmax (95% ethanol): 256nm (loge=4.13). (Ref. 0690)

Anabolic action. Anabolic-androgenic ratio is 0.88 as the acetate when testosterone propionate is 0.28. (Ref. 0689)

25-(Acetyloxy)-2-(b-D-glucopyranosyloxy)-16,20-dihydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione / 2-O-b-D-Glucopyranosylcucurbitacin E
Hideaki Nishino
C38H54O13 718.828 Download ChemDraw structure file

158-160degC. (Ref. 0691/0692)
[a]/D=+50deg (c=0.4 in ethanol). (Ref. 0691)
Sol in ethanol, acetone, chloroform. Sparingly sol in ether, water. (Ref. 0691)
UVmax: 234-236nm (loge=4.11). (Ref. 0691)
Like a-elaterin, exhibits 3570, 3450(OH), 1725(Ac), 1685(C:C-CO), 1660, 1625, 1415 (diosphenol)/cm. Others, 1425, 1390, 1370, 1250, 1220, 1120, 1070/cm (Ref. 0692)

Plants. Fruits of Citrullus colocynthis Schred., Cucurbitaceae. (Ref. 0691)

Anti-cancer glycoside. (Ref. 0691/0692)

Glucose is included in sugar residues. (Ref. 0691) The aglycon is a-elaterin (Ref. 0691/0692)
Colpormon / Colpogynon
3,16a-Bis(acetyloxy)estra-1,3,5(10)-trien-17-one / 3,16a-Dihydroxyestrone diacetate / 3,16a-Diacetoxy-D1,3,5-estratrien-17-one
Hideaki Nishino
C22H26O5 370.439 Download ChemDraw structure file
Synthesis from b-hydroxyandrostane-17-one (isoandrosterone). Estriol is yielded by lithium aluminum hydride-treatment. (Ref. 0120)
179-180degC. (Ref. 0120)
[a]28/D=+122deg (chloroform). (Ref. 0120)

[M]/D=+451. (Ref. 0120)

Estrogenic acitivty. (Ref. 0120)

Conessine / Neriine / Roquessine / Wrightine
Hideaki Nishino
C24H40N2 356.588 Download ChemDraw structure file
Total synthesis from an intermediate of coal tar. (Ref. 0698) Stereospecific synthesis (total synthesis of dl-conessine). (Ref. 0699) Synthesis from conan-4-en-3-one. (Ref. 0700)
127-128.5degC (acetone) (Ref. 0698/0699)
[a]20/D=+25.3deg (c=0.7 in anhydrous alcohol) (Ref. 0693)
Slightly sol in water. (Ref. 0693)
798, 826, 1665/cm (Ref. 0695)

Plants. Barks or seeds of Holarrhena anti-dysenterica Wall., Apocynaceae (India), H. africana A. DC., H. congolensis Stapf, H. wulfsbergii Stapf, and H. febrifuga Klotzsch, Apocynaceae. (Ref. 0693/0694)

Anti-amebic. (Ref. 0693/0694)

Coproergostane / Pseudoergostane
Hideaki Nishino
C28H50 386.697 Download ChemDraw structure file
Synthesis from cholanic acid via norcholyl-methyl-ketone. (Ref. 0701)
64degC (acetone). (Ref. 0701)
[a]19/D=+25.3deg (c=2 in chloroform) (Ref. 0701)

Coprostane / Pseudocholestane
Hideaki Nishino
C27H48 372.670 Download ChemDraw structure file
Yielded coprostane (55%) and cholestane (45%) by hydrogenation of cholest-4-ene in the presence of ethanol, platinum, and sodium nitrite. (Ref. 0040) Synthesis by hydrogenation of D6-coprostene. (Ref. 0704) Synthesis by reduction of coprostan-3-one. (Ref. 0705)
72degC (alcohol) (Ref. 0702)
[a]11/D=+25.1deg (c=2 in chloroform) (Ref. 0040)
Sol in ether, chloroform. Sparingly sol in anhydrous alcohol. (Ref. 0702/0703/0040/0704/0705)
Characteristic bands at 900 and 1070/cm. (Ref. 0040)

Corticosterone / Compd B / Reichstein's Substance H / Kendall's Compd B
11b,21-Dihydroxypregn-4-ene-3,20-dione / 4-Pregnene-11b,21-diol-3,20-dione
Hideaki Nishino
C21H30O4 346.460 Download ChemDraw structure file

180-182degC (acetone). (Ref. 0615)
[a]15/D=+223deg (c=1.1 in alc.). (Ref. 0615)
Insol in water. Sol in general organic solvents. (Ref. 0269)
UVmax: 240nm (loge=Ca.4) (Ref. 0615)

Animals. Main biosynthesis site is the zona fasciculata of adrenal cortex. (Ref. 0269)

A glucocorticoid as adrenocortical steroid, same as cortisol and cortisone. However, weaker both in glycogen storage action and anti-inflammatory effect than the other two species. Utilized as a precursor to aldosterone, which is biosynthesized as a strong mineralcorticoid in adrenocortical zona glomerulosa by active 18-hydroxylase. (Ref. 0615)

By conc. sulfate, turned to be orange-yellow colored solution, which emits strong fluorescence. (Ref. 0615)
Cortivazol / MK-650 / H3625 / Altim / Diaster / Dilaster / Idaltim
11b,17,21-Trihydroxy-6,16a-dimethyl-2'-phenyl-2'H-pregna-2,4,6-trieno[3,2-C]pyrazol-20-one 21-acetate / 1,2,3,3A,3B,7,10,10A,10B,11,12,12A-Dodecahydro-1,11-dihydroxy-2,5,10A,12A-tetramethyl-7-phenylcyclopenta[7,8]phenanthro[2,3-C]pyrazol-1-ylhydroxymethylketoneacetate / 6,16a-dimethyl-11b,17a, 21-trihydroxy-2'-phenyl[3,2-C]pyrazolo-4,6-pregnadien-20-one 21-acetate
Hideaki Nishino
C32H38O5N2 530.655 Download ChemDraw structure file
Obtained by hydrolysis of 2-hydroxymethylene-17a,20,20,21-bismethylenedioxy-6,16a-dimethyl-4,6-pregnadiene-11b-ol-3-one. (Ref. 0706)
160-165degC and 229-230degC (double m.p.). (Ref. 0706)
[a]23/D=+14deg (chloroform). (Ref. 0706)
UVmax (methanol): 283, 315nm (e=15,700, 19,000). (Ref. 0706)

Glucocorticoid action. Anti-inflammatory effect. In systemic granuloma, cortivazol, 551 (oral ingestion to male Holtzman rats (Ca.125g) every day for a week) when 9a-fluoro-16a-methyl-1,4,6-pregnatriene-11b,17a,21-triol-3,20-dione21-acetate (D6-dexamethasone), 150. 75-Times higher activity to human rheumatoid arthritis pain than hydrocortisone. No reports on sodium retention activity. (Ref. 0706)

3a,17a,20a,21-tetrahydroxypregnan-11-one / 3a,17a,20a,21-pregnanetetrol-11-one
Hideaki Nishino
C21H34O5 366.492 Download ChemDraw structure file
Synthesis from pregnane-3a,17a-diol-11,20-dione as a starting material. (Ref. 0708) Synthesis by treatment of D20-allopregnene-3b,20-diol diacetate with perbenzoic acid, and
208-209degC (acetone). (Ref. 0707)
[a]25/D=+44deg (c=0.5 in ethanol), [a]28/D=+34.2deg (ethanol). (Ref. 0707)

Extraction from crude oxidation product in silica gel chromatography. (Ref. 0709) Animals. Adrenal cortex. Human urine after injection of cortisone, hydrocortisone, ACTH. (Ref. 0707)

Cucurbitacin A
Hideaki Nishino
C32H46O9 574.702 Download ChemDraw structure file

207-208degC (ethyl acetate) (Ref. 0710)
[a]27/D=+97.3deg (c=1.04 in ethanol) (Ref. 0710)
UVmax (ethanol): 229, 290nm (loge=4.03, loge=2.26), inflexion: 330-350nm (loge=1.81-1.64). (Ref. 0710)
Free hydroxyl group (nmax 3448/cm). (Ref. 0711), 5.85m (isolated keto-group, carbonyl of the acetyl group), 5.92m, 6.14m (carbonyl and double bond of ab-unsaturated keto group). (Ref. 0710)

M (X-ray method), 587pm16. (Ref. 0711)

Plants. Fruits of Cucurbitaceae cucumis Myriocarpus, C. Leptodermis. (Ref. 0710)

Bitter taste component of Cucurbitaceae. Minimum lethal dose (M.L.D), 0.7mg/kg rabbit (i.v.). (Ref. 0710)

Neutral, included one acetyl group. (Ref. 0710)
Cucurbitacin C
Hideaki Nishino
C32H48O8 560.719 Download ChemDraw structure file

207-207.5degC (ethyl acetate) (Ref. 0710)
[a]27/D=+95.2deg (c=1.03 in ethanol). (Ref. 0710)
UVmax (ethanol): 231, 298nm (e=11,100, 11,131). (Ref. 0712)
nmax 1731, 1256 (OAc), 1689, 1631 (CO-C:C)/cm. (Ref. 0712)

M (X-ray method), 577pm12. (Ref. 0712)

Plants. Fruits of Cucurbitaceae cucumis Sativus var. Hanzil. (Ref. 0710/0712)

Bitter taste component in Cucurbitaceae. (Ref. 0710) Bitter taste component in most greenhouse cucumber. (Ref. 0712) Medicinal, cytostatic, and toxic. (Ref. 0713)

Neutral, included one acetyl group. (Ref. 0710) Four methyl groups. (Ref. 0713)
Cucurbitacin B
25-(Acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-trione / 1,2-Dihydro-a-elaterin
Hideaki Nishino
C32H46O8 558.703 Download ChemDraw structure file

184-186.5degC (absolute alcohol). (Ref. 0714), 180-182degC (Ref. 0710), 178-179degC. (Ref. 0715)
[a]25/D=+88deg (c=1.55 in ethanol). (Ref. 0714) [a]25/D=+87.5deg (c=1.554 in 96% ethanol). <0710>> [a]25/D=+87deg(c=0.89 in abs. ethanol). (Ref. 0715)
lmax, mm(E1%/1cm): 229 (Ref. 0211), 290(3.4) in neutral solution, 312(95) in alkaline solution.(Ref. 0714), gmax 228mm (loge=4.02), marked inflection between 270 and 290mm, 280mm (loge=2.32) (Ref. 0715)
Strong absorption maxima at 2.92, 5.82, 5.92, 6.17m (Ref. 0715)

Plants. Isolation from fruits of Cucurbitaceae (Cucumis africanus, Lagenaria leucantha) by modified method of rimington. (Ref. 0710) Roots of Echinocystis fabacea (man-root, man-in-the-ground, or wild cucumber vine). (Ref. 0715)

Toxic. (M.L.D.(eel), 0.5mg/kg). (Ref. 0710) Bitter taste component of Cucurbitaceae. (Ref. 0714) Make a decoction of the roots to utilize for fishing, suicide, or killing old, weak, or sick people by California Indians. When using as a drug, extract from seeds or roots was supplied for rheumatoid arthritis or venereal disease. Strong diarrheal activity in the roots. Utilization of the roots for making Stoughton's Bitters in California. (Ref. 0715)

X-ray crystallography. Reduction of Tollens reagent. Positive in Molish reaction. Positive in acetic acid test. Red-colored when solving in acetic acid containing sulfate. In Liebermann- and Liebermann-Burchard tests, burgundy-colored by reacted with hydrogen bromide in acetic acid, purple-colored by reacted with antimony pentachloride in chloroform. Negative in ferric chloride and legal test. Zerevitionv determinations: 0.824 and 0.824%H. (Ref. 0715) Interrelationships in Cucurbitacins B, D (Elatericin A), E (a-elaterin), I (Elatericin B). (Ref. 0717) Stereochemistry of cucurbitacins. (Ref. 0719)
Cucurbitacin D / Elatericin A
Hideaki Nishino
C30H46O7 518.682 Download ChemDraw structure file

151-153degC (ethylacetate+benzene), 151-152degC (Ref. 0710)
[a]/D=+48deg (c=1.5 in chloroform) (Ref. 0719) [a]/D=+52deg (in ethanol) (Ref. 0714) [a]/D=+46deg (in CHF.) (Ref. 0716)
lmax, mm (E1%/1cm): 230(230) in neutral solution, 314(108) in alkaline solution. (Ref. 0714), lmax:232mm (e=9,000) (Ref. 0716)
nmax: 3425, 1689, 1626, 1377, 1088, 1058, 983/cm (Ref. 0716)

Plants. Isolated as crystals from bitter ornamental gourd of Cucurbitaceae (several species of Cucurbita pepo). Yield is 0.005%, only trace amount. (Ref. 0710) Roots of Cucumis hirsutus. (Ref. 0714) Ecballium elaterium L. (Ref. 0716)

Bitter taste component. Anti-tumor activity. (Ref. 0716)

No color reaction in the presence of ferric chloride in ethanol. (Ref. 0716) Interrelationship in Cucurbitacins B, D (Elatericin A), E (a-elaterin), I (Elatericin B). (Ref. 0717) Stereochemistry of Cucurbitacins. (Ref. 0719)
Cucurbitacin F
Hideaki Nishino
C30H44O7 516.666 Download ChemDraw structure file

244-245degC (chloroform) (Ref. 0714)
[a]/D=+38deg (c=1.2 in ethanol) (Ref. 0714)
lmax, mm (E1%/1cm): 232(228), 300(2.7) in neutral solution, unchanged in alkaline solution (Ref. 0714)
nmax (in KBr): 1690, 1629/cm ab-unsaturated ketone group), 1700/cm (isolated ketone group) (Ref. 0718)

Plants. Purification by insolubility in chloroform from leaves of Cucurbitaceae (Cucumis angolensis). (Ref. 0714) Leaves of Cucumis dinteri Cogn. (Ref. 0718)

Bitter taste component. (Ref. 0718)

Revision as C30H46O7. No color reaction by tetrazolium blue. Direct relationship between Cucurbitacin D and F because reduction of Dihydrocucurbitacin D by sodium borohydride results in Dihydrocucurbitacin F. (Ref. 0718)
Cucurbitacin I / Elatericin B
2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione / 1,2-Dehydroelatericin A.
Hideaki Nishino
C30H42O7 514.650 Download ChemDraw structure file

148-148.5degC (Ref. 0714), 148-149degC (Ref. 0716)
[a]/D=-52deg (c=1.56 in chloroform) (Ref. 0716)
Sol in dil. alkali, ethylacetate, chloroform, benzene. (Ref. 0716)
UVmax (ethanol): 234, 266nm (e=11,000, 6,850) (Ref. 0716), lmax, mm (E1%/1cm): 234(246), 269(158) in neutral solution, 232(251), 314(104) in alkaline solution (Ref. 0714)
nmax: 3410, 1685, 1660, 1629, 1606, 1413, 1090, 1005/cm (Ref. 0716)

Complete separation from Cucurbitacin D in developing solvent of ethylacetate:benzene (1:1) or chloroform:benzene (1:1) in paper chromatography. Not clearly separated in a developing solvent consisted of only chloroform. Strong color-reaction by treatment with ferric chloride in ethanol. (Ref. 0714)
Plants. Fruits of Ecballium elaterium (L.) A. Rich., Cucurbitaceae. (Ref. 0720) Crude foams of Citrullus ecirrhosus. (Ref. 0716)

Diarrheal agent. Anti-tumor activity. (Ref. 0716)

Five methyl groups bound to quaternary atoms of tetracyclic nucleus. (Ref. 0713) Stereochemistry (Ref. 0719)
Cucurbitacin E / a-Elaterin
Hideaki Nishino
C32H44O8 556.687 Download ChemDraw structure file

232-233degC (Ref. 0720), 234.5degC (Ref. 0714)
[a]/D=-62deg (chloroform) (Ref. 0714), [a]/D=-59deg (c=0.7 in CHF.) (Ref. 0720)
Slightly sol in alcohol. Insol in water. Sol in petroleum ether, chloroform.
Strong peak at 234mm (e=11,700), shoulder at 267mm (e=8,350) (Ref. 0720)
mmax: 3450, 1723, 1683, 1660, 1627, 1412, 1370, 1130, 1090, 990/cm (Ref. 0720)

Plants. Fruits of Ecballium elaterium (L.) A. Rich., Cucurbitaceae (squirting cucumber). (Ref. 0720)

The fruit juice, called Elaterium, had been used as a strong diarrheal agent from ancient times. Recorded in The British Pharmacopeia. Very strong anti-tumor activity to mouse sarcoma-37 transplanted in the muscle by intraperitoneal injection together with b-elaterin. No significant anti-tumor activity by the dermenchysis of Cucurbitacin E only. (Ref. 0720)

Upon addition of NaOH, disappear shoulder (267mm) in ultraviolet region, new peak appeared at 318mm (e= 5,000). This bathochromic shift is reversed by addition of acid. Strong color-reaction by treatment with ferric chloride in ethanol. (Ref. 0720) Five methyl groups bound to quaternary atoms of tetracyclic nucleus. (Ref. 0713) Stereochemistry. (Ref. 0719)
Cucurbitacin G
Hideaki Nishino
C30H46O8 534.681 Download ChemDraw structure file

149-150degC (Ref. 0714)
[a]/D=+84deg (c=1.5 in chloroform). (Ref. 0714)
Sol in chloroform, benzene. (Ref. 0714)
lmax., mm (E1%/1cm): 282(4.2) in neutral solution, 314(99) in alkaline solution.(Ref. 0714)

Have ever been found along with Dihydrocucurbitacin D because of the same m.p. and very similar IR spectra. However, completely separated each other in paper chromatography. (Ref. 0714)
Plants. Roots of Cucumis hirsutus Sond., Cucurbitaceae.(Ref. 0714)

Bitter taste component. (Ref. 0714)

Cucurbitacin H
Hideaki Nishino
C30H46O8 534.681 Download ChemDraw structure file

[a]/D=+57deg (c=1.5 in chloroform). (Ref. 0714)

Amorphous. Unable to crystallize by rechromatography using acid-washed alumina or formamide-impregnated paper. (Ref. 0714)
Plants. Bitter taste component in roots of Cucumis hirsutus. (Ref. 0714)

Bitter taste component. (Ref. 0714)

Cucurbitacin J
Hideaki Nishino
C30H44O8 532.666 Download ChemDraw structure file

200-202degC (ethyl acetate) (Ref. 0721), 196-198degC. (Ref. 0714)
[a]/D=-36deg (c=1.0 in chloroform). (Ref. 0721)
lmax, 270mm (e=8,700 in ethanol), 313 mm (e=6,300 in 0.1N KOH in 50% ethanol). (Ref. 0721) lmax., (E1%/1cm): 270(157) in neutral solution, 314(104) in alkaline solution (Ref. 0714)
nmax: 1695, 1664/cm (Ref. 0721)

Separated from Cucurbitacin D in paper chromatography using chloroform:benzene (1:1) as a developing solvent. Not separated using ethylacetate:benzene. (Ref. 0714)
Plants. Isolation from enzyme-degradated materials of crude foams of Citrullus ecirrhosus Sond. (Colocynthis ecirrhosus Chakrav.), Cucurbitaceae. (Ref. 0714) Isolation from Iberis amara, Cruciferae. Preparation by alkali-treatment of Cucurbitacin I. (Ref. 0721)

Bitter taste component .(Ref. 0714)

Different only atomic orientation of hydroxyl group at C24 between Cucurbitacin J and K, each other. (Ref. 0721)
Cucurbitacin K
Hideaki Nishino
C30H44O8 532.666 Download ChemDraw structure file

Indefine. (Ref. 0721) 137-141degC (Ref. 0714)
[a]/D=-74deg (c=1.0 in chloroform) (Ref. 0721)
lmax, 270mm (e=8,000 in ethanol), 312 mm (e=5,900 in 0.1N KOH in 50% ethanol) (Ref. 0721), lmax, 269mm (E1%/1cm 148) in neutral solution, 314mm (E1%/1cm 104) in alkaline solution (Ref. 0714)
nmax: 1695, 1664/cm. (Ref. 0721)

Plants. Isolation from enzyme-hydrolyzate of crude foams of Citrullus ecirrhosus Sond.(Colocynthis ecirrhosus Chakrav.), Cucurbitaceae. (Ref. 0714) Isolation from Iberis amara, Cruciferae. (Ref. 0721)

Bitter taste component. (Ref. 0714)

Different only atomic orientation of hydroxyl group at C24 between Cucurbitacin J and K, each other. (Ref. 0721)
Cucurbitacin L
2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5-diene-3,11,22-trione / 23,24-Dihydrocucurbitacin L
Hideaki Nishino
C30H44O7 516.666 Download ChemDraw structure file

About 140degC. (Ref. 0721) 122-127degC. (Ref. 0714)
[a]/D=-49deg (c=1.0 in chloroform). (Ref. 0721) [a]28/D=-41deg (c,1.3% in ethanol). (Ref. 0714) [a]22/D=-42pm2deg (c=1.0 in ethanol). (Ref. 0419)
lmax, 270mm (e=8,050 in ethanol), 313 mm (e=5,850 in 0.1N KOH in 50% ethanol) (Ref. 0721); lmax, mm(E1%/1cm); 270(164), 314(119)(Ref. 0714); lmax (loge)=270mm (3.75) in neutral, 309mm (3.64) in alkaline. (Ref. 0419)
nmax: 1695, 1661/cm. (Ref. 0721); (chloroform): 3605, 3450, 2972, 1688, 1660/cm (Ref. 0419)

Plants. Roots of Citrullus ecirrhosus Sond.(Colocynthis ecirrhosus Chakrav.), Cucurbitaceae (Ref. 0721)

Bitter taste component. (Ref. 0714)

Identical with 23,24-dihydrocucurbitacin I. (Ref. 0721)
Cyclobuxine / Alkaloid A.
Hideaki Nishino
C25H42ON2 386.614 Download ChemDraw structure file

246-247degC (Ref. 0723), 245-247degC. (Ref. 0724)
[a]23/D=+98deg (chloroform). (Ref. 0724)
lmax: 6.09, 11.20m (terminal methylene). (Ref. 0724)
5.20, 5.43 (2H, doublets, Jle1C.1S.; terminal methylene), 5.92 (1H, octuplet, J'S3,7,9.5C./S.; CH2CHOH-CH), 7.53 and 7.57 (6H, two NCH3), 8.87 and 9.03 (6H, two tertiary CH3), 8.92 (3H, doublet, J6 C./S.; one sec. CH3) and 9.72 and 9.95J (2H, doublets, J4C./S.; cyclopropyl methylene). (Ref. 0724)

Extract from Buxus sempervirens L., Buxaceae. (Ref. 0722/0724)

Application as a drug for therapy of various diseases, such as malaria, venerealdisease from ancient times. Also effective as an anti-tuberculosis. (Ref. 0724)

Determination of stereochemistry. (Ref. 0725)
Danazol / Win 17.757 / Danol
17a-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol / 17a-Pregn-4-en-20-yno[2,3-d]isoxazol-17-ol / 1-Ethynyl-2,3,3A,3B,4,5,10,10A,10B,11,12,12A-dodecahydro-10A,12A-dimethyl-1H-cyclopenta[7,8]phenanthro-[3,2-D]-isoxazol-1-ol / 17a-Etynyl-17b-hydroxy-4-androsteno[2,3-D]isoxazole
Hideaki Nishino
C22H27O2N 337.455 Download ChemDraw structure file
Preparation by reaction of 2-hydroxymethylene-3-ketosteroid and hydroxylamine. (Ref. 0726)
224.4-226.8degC (Ref. 0726)
[a]25/D=+7.5deg (ethanol) [a]25/D=+21.9deg (chloroform) (Ref. 0726)
UVmax (ethanol): 286nm (e=11,300) (Ref. 0726)

Suppressor to prehypphysis function (gonadal inhibitor) (inhibition of gonadotropin-release in normal human). Inhibition of synthesis of androgen in Leydig cell. (Ref. 0727) Similar effect also in albino rats, rats, mice, rabbits to human. (Ref. 0419) Espacially effective in therapy of precocious pubery, endometriosis, virginal breast hypertrophy, chronic cystic mastitis. (Ref. 0728)

Dehydroepiandrosterone / Dehydroisoandrosterone / Trans-Dehydroandrosterone / 17-Hormoforin / Diandron / Psicosterone / 17-Chetouis
3b-Hydroxyandrost-5-en-17-one / D5-Androsten-3b-ol-17-one
Hideaki Nishino
C19H28O2 288.424 Download ChemDraw structure file
Praparation by degradation of g-sitosterol, which can be isolated from soya beans. (Ref. 0734) Preparation from cholesterol. (Ref. 0730/0209/0731)
140-141degC, 152-153degC (biphase). (Ref. 0209)
[a]18/D=+10.9deg (c=0.4 in alc.). (Ref. 0734)
Sol in benzene, alcohol ether. Slightly sol in chloroform, petroleum ether. (Ref. 0209)

Animals. Isolation from male urine. (Ref. 0005/0729) Dehydroandrosterone is isolated as an epimer from male urine. (Ref. 0731)

Androgen activity. (Ref. 0005/0729)

Ppt with digitonin. (Ref. 0730/0209/0731/0732/0733)
Deoxyxorticosterone / 21-Hydroxyprogesterone / Desoxycorticosterone / 11-Deoxycorticosterone / Cortexone / Desoxycortone / Kendall's Desoxy Compound B / Reichstein's Substance Q
21-Hydroxypregn-4-ene-3,20-dione / 4-Pregnen-21-ol-3,20-dione
Hideaki Nishino
C21H30O3 330.461 Download ChemDraw structure file
Preparation of D4-3-keto-21-acetoxy-pregnen-20-on. (Ref. 0615) Preparation from pregnen-(4)-ol-(20)-on-(3)-al-(21). (Ref. 0735)
141-142degC (ether). (Ref. 0615/0188)
[a]22/D=+178deg (c=1.5 in alcohol). (Ref. 0188)
Sol in alcohol, acetone. (Ref. 0188)
UVmax 240nm (loge=Ca, 4). (Ref. 0615)

Animals. Adrenal glands. (Ref. 0615) Isolation from water beetle, Dytiscus marginalis. (Ref. 0736)

Action as an adrenocortical steroid (Salt-regulating). (Ref. 0615)

4a,9-Epoxycevane-3b,4,6a,7a,14,15a,16b,20-octol 6,7-Diacetate 15-(2-methylbutanoate) / Protoverine 6,7-diacetate 15-(2-methylbutyrate) / Protoverine 6,7-diacetate 15(L)-2'-methylbutyrate
Hideaki Nishino
C36H55O12N 693.821 Download ChemDraw structure file

232-233degC (Ref. 0737)
[a]26/D=-46deg (c=0.95 in pyridine) (Ref. 0737)

Plants. Synthesis. Preparation from treatment of protoveratrine B with periodate, followed by alkalization with ammonium hydroxide. protoveratrine is an alkaloid isolated from Veratrum album. Later identified as a mixture of A- and B-forms. (Ref. 0737)

Insecticide. Also applicable to the therapy for hypertension. (Ref. 0737)

Protoveratrine A / Pro-Amid / Protalba
4a,9-Epoxycevane-3b,4,6a,7a,14,15a,16b,20-octol-6,7-diacetate 3(S)-(2-hydroxy-2-methylbutanoate) / 15(R)-(2-Methylbutanoate)-protoverine 3-(d)-2'-Hydroxy-2'-methylbutyrate 6,7-diacetate 15-(L)-2'-methylbutyrate
Hideaki Nishino
C41H63O14N 793.937 Download ChemDraw structure file

267-269degC (dec.). (Ref. 0742), 273-275degC (Ref. 0737)
[a]25/D=-40.5deg (c=1 in pyridine), [a]25/D=-10.5deg (c=1 in chloroform). (Ref. 0742)
Sol in chloroform, pyridine, hot alcohol. Insol in water, petroleum ether. (Ref. 0742)

Plant family such as Veratrum. Alkaloid extracted from rhizome of Veratrum album L., Liliaceae. (Ref. 0737/0738/0739/0742/0743) Also isolated from Veratrum viride. (Ref. 0740/0741)

Application as an antihypertensive. Somewhat bitter, induces a sneezing. (Ref. 0737)

Structure determination of protoveratrine A and B. (Ref. 0737) Protoveratrine is a mixture of two alkaloids, which share very similar structure. However, hydrolysis yields one different product. (Ref. 0742/0743) In hydrolysis by p-touenesulfonic acid, yields 1.88 mol acetic acid, 0.92 mol 2-methylbutyric acid, 0.93 mol 2-hydroxy-2-methylbutyric acid. (Ref. 0742)
Protoveratriene B / Veratetrine / Neoprotoveratrine
4a,9-Epoxycevane-3b,4,6a,7a,14,15a,16b,20-octol-6,7-diacetate 3(S)-(2,3-dihydroxy-2-methylbutanoate)15(R)-(2-methylbutanoate) / Protoverine3-(d)-thred-2',3'-dihydroxy-2'-methylbutyrate 6,7-diacetate 15-(L)-2'-methylbutyrate
Hideaki Nishino
C41H63O15N 809.937 Download ChemDraw structure file

268-270degC (Ref. 0742), 267-269degC (Ref. 0737)
[a]25/D=-37deg (pyridine), [a]25/D=-3.5deg (chloroform) (Ref. 0742)
Sol in chloroform, pyridine, hot alcohol. Insol in water, petroleum ether. (Ref. 0742)

Plant family such as Veratrum. Alkaloid extracted from rhizome of Veratrum album L., Liliaceae. (Ref. 0738/0739/0742/0743/0737) Also isolated from Veratrum viride. (Ref. 0740/0741)

Application as an antihypertensive. Somewhat bitter, induces a sneezing. (Ref. 0737)

Structure determination of protoveratrine A and B. (Ref. 0737) Protoveratrine is a mixture of two alkaloids, which share very similar structure. However, hydrolysis yields one different product. (Ref. 0742) Proportion to protoveratrine A, diverse in each root and rhizome, from 0.36 to 0.58. (Ref. 0742) Hydrolysis yields 2 mol acetic acid, 1 mol (-)a-methyl-butylic acid, and 1 mol (+)a-methyl-a,b-dioxy-butylic acid. (Ref. 0743)
Descinolone / 21-Deoxytriamcinolone
9-Fluoro-11b,16a,17-trihydroxypregna-1,4-diene-3,20-dione / 9a-Fluoro-1,4-pregnadiene-11b,16a,17a-triol-3,20-dione
Hideaki Nishino
C21H27O5F 378.434 Download ChemDraw structure file

286-287degC (Ref. 0744), 298-300degC (Ref. 0745)
[a]25/D=+53.3deg (c=0.41 in methanol), [a]25/D=+36.8deg (c=1.09 in pyridine). (Ref. 0745) [a]25/D=+62deg (c=0.52, methanol), [a]25/D=+41.5deg (c=1.09, pyridine). (Ref. 0744)
Sol in methanol, ethyl acetate. (Ref. 0744)
UVmax (methanol): 238nm (e=15,700). (Ref. 0745); lmax: 238mm (e=15,100). (Ref. 0744)
nmax: 3509, 3401, 1709, 1667, 1618, 1603/cm (Ref. 0744); lmax: 2.85, 2.93, 5.86, 6.01, 6.19, 6.25, 9.34m (Ref. 0745)

Preparation by microbiological dehydrogenation: 1 % innoculation of Nocardia corallina (ATCC 999) cultured for 8 h in beef extract, yeast extract, peptone, and cerelose medium. Add 9a-fluoro-11b,16a,17a-trihydroxy-4-pregnene-3,20-dione solubilized in methanol and further culture at 28degC for 17 h. Extract the content into ethyl acetate for purification. (Ref. 0744)

In glucocorticoid activity (rat liver glycogen analysis), 4-times higher than hydrocortisone. No sodium retention activity. (Ref. 0744)

Preparation of the acetate, 16a-acetoxy 9a-fluoro-11b,17a-dihydroxy-1,4-pregnadiene-3,20-dione by overnight treatment in acetic anhydride-pyridine. m.p. 242-244deg, [a]25/D=+27.3deg (c=0.768, methanol), lmax 239mm (e=16,200): nmax 3509, 3413, 1736, 1695, 1672, 1629, 1250/cm. The isopropylidene derivative, 9aFluoro-11b-hydroxy-16a,17a-isopropylidenedioxy-1,4-pregnadiene-3,20-dione: m.p. 307deg, [a]25/D=+102 (c=0.975), lmax 238mm (e=15,500), nmax 3333, 1712, 1667, 1626, 1176, 1059/cm. (Ref. 0744)
Deslanoside / Deacetyllanatoslde C / Desacetyllanatoside C / Desacetyldigilanide C / Purpureaglycoside C / Cedilanid-D / Desace / Desaci / Lanimerck (ampuls)
(3b,5b,12b)-3-[(O-b-D-glucopyranosyl-(1 to 4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1 to 4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1 to 4)-2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide
Hideaki Nishino
C47H74O19 943.079 Download ChemDraw structure file

[a]20/D=+12deg (c=1.084 in 75% alc.). (Ref. 0746/0747)
Sol in 5000 parts water, 200 parts methanol, 2500 parts ethanol. Sparingly sol in chloroform. Insol in ether. (Ref. 0746/0747)

Plants. Preparation by treatment of digilanide C, extracted from the leaves of Digitalis lanata Ehrh., Scrophulariaceae with Ca(OH)2. (Ref. 0746/0747)

Cardiotonic action. (Ref. 0746/0747)

The aglycon is digoxigenin. (Ref. 0746/0747)
Desonide / Prednacinolone / D-2083 / Steroderm / Tridesilon
11,21-Dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione / 11b,16a,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone / 16a-Hydroxyprednisolone-16a,17-acetonide; 11b,21-Dihydroxy-16a,17-isopropylidenedioxy-1,4-pregna-diene-3,20-dione / 16a-Hydroxy-D1-hydrocortisone-16a,17a-acetonide / 16a,17a-Isopropylidenedioxyprednisolone
Hideaki Nishino
C24H32O6 416.507 Download ChemDraw structure file
Non-halogenated steroid prepared from 16a-hydroxyprednisolone by boiling in acetone containing HCl. (Ref. 0748) Synthesis method utilizing microbiological hydroxylation. (Ref. 0752)
274-275degC (methanol), 263-266degC (ethyl acetate-petr. ether) (Ref. 0748/0752)
[a]25/D=+123deg (c=0.5 in DMF) (Ref. 0752), [a]25/D=+122deg (methanol). (Ref. 0748)
UVmax: 242nm (E1%/1cm 356). (Ref. 0752); lmax: 242mm (e=15,800). (Ref. 0748)
nmax: 3401,1709, 1661, 1616, 1603, (inflection), 1087, 1053/cm. (Ref. 0748)

The acetonide form exerts stronger glucocorticoid activity than parent free steroids. Can make the synthetic non-halogenated corticoids much stronger: in thymus involution and liver glycogen, the acetonide shows 17-times, 13-times stronger activities, respectively (in adrenalectomized immature male rat). One of most synthetic corticoids, one of most active compounds. LD50, 2.4-times higher than prednisolone. Anti-inflammatory action. (Ref. 0748/0749/0750)

Improved recovery by perchloric acid method. (Ref. 0748) Relationship between structure and activity in adrenocorticoids. (Ref. 0751)
Desoximetasone / A41-304 / R-2113 / HOE304 / Esperson / Topicorte / Topiderm / Topisolon
9-Fluoro-11b,21-dihydroxy-16a-methylpregna-1,4-diene-3,20-diene-3,20-dione / 9a-Fluoro-16a-methyl-17-desoxyprednisolone / 9a-Fluoro-16a-methyl-D1-corticosterone
Hideaki Nishino
C22H29O4F4 433.457 Download ChemDraw structure file
Preparation from 3a-hydroxy-11,20-dioxo-16a-methyl-pregnane or 3a-acetoxy-20-oxo-16a-methyl-5b,D9(11)-pregnene. (Ref. 0753)
217degC (ethyl acetate) (Ref. 0753)
[a]/D=+109deg (chloroform) (Ref. 0753)
Sol in alcohol, acetone, chloroform, ethylacetate (hot). Slightly sol in ether, benzene. Insol in water, dil. acid, alkaline solution. (Ref. 0753)
UVmax: 238nm (e=15,750). (Ref. 0753)
39.8(C-1), 63.5(C-2), 7.2(C-3), 68.2(C-4), 25.6(C-5), 162.1(C-6), 165.3(C-7), 159.0(C-8), 91.3(C-9), 14.45(C-10), 122.0(C-11), 149.5(C-12), 147.8(C-13), 144,3(C-14), 159.6(C-15), 162.1(C-16), 125.3(C-17), 176.4(C-18), 169.7(C-19), -17.4(C20), 123.3(C-21), 170.7(C-16Me) (Ref. 0753)

Corticoid exerting anti-inflammatory action in application to peripheral skin. Analysis by modified cotton pellet granuloma method. (Ref. 0753) Can make the anti-inflammatory action and thymolytic activity much stronger by 9a-fluoro substitution than 16a-methyl-D1-corticosterone. Potassium diuresis, sodium diuresis. much lower inhibitiory effect to growth than prednisolone and dexamethasone when compared with a dose of same anti-inflammatory action. (Ref. 0754/0755)

Cortexolone / 17-Hydroxydesoxycorticosterone / Reichstein's Substance S / 11-Desoxycortisone
17,21-Dihydroxypregn-4-ene-3,20-dione / 4-Pregnene-17a,21-diol-3,20-dione / 17-(1-Keto-2-hydroxyethyl)-4-androsten-17a-ol-3-one / 11-Desoxy-17-hydroxycorticosterone
Hideaki Nishino
C21H30O4 346.460 Download ChemDraw structure file
Preparation from 4-pregnene-17a,20,21-triol-3-one 21-monoacetate. (Ref. 0272) Preparation from 3a-formoxy-17a-hydroxypregnan-20-one. (Ref. 0759). Preparation from 16,17-oxido-5-pregnen-3b-ol-20-one acetate. (Ref. 0760) Praparation from 5-pregnen-3b-ol-20-one. (Ref. 0761)
207-209degC (Ref. 0757)
Very sparingly sol in water, ether. Sol in acetone, methanol, alcohol. (Ref. 0757)
UVmax: 240nm (loge=4.23). (Ref. 0757)

The acetate, C23H32O5, m.p. 237.2-240.2deg, [a]24/D=+116deg (acetone), UVmax 242nm (E1%/1cm 448) (Ref. 0758) The monoacetate (pregnene-4-diol-17(b),21-dione-3,20-monoacetate-21), C23H32O5, m.p. 235-238deg (formation of sinter at 232deg), [a]/D=+118pm4deg (c=0.7), lmax=242mm (e=14,700). Strongly and rapidly reduces silver nitrate-ammoniacal solution. Characteristic scarlet-color reaction in conc. sulfate. (Ref. 0272)
Dexamethasone / Hexadecadrol / Calonat / Decasone / Decacortin / Deronil / Decadron / Fluormone / Dekacort / Dexa-cortisyl / Millicorten / Fortecortin / Anaflogistico / Spoloven / Luxazone / Dectancyl / Dexameth / Dexasone / Dexinoral / Gammacorten / Dextelan / Policort / Dexacortal / Deseronil / Corson / Dergramin / Hexadrol / Deltafluorene / Oradexon / Dexa-cortidelt / Aeroseb-D / Dexinolon / Decaderm / Dexafarma / Cortisumman / Dexasine / Loverine / Maxidex / Dexa-Scheroson
9-Fuloro-11b,17,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione / 9a-Fluoro-16a-methylprednisolone / 16a-Methyl-9a-fluoro-1,4-pregnadiene-11b,17a,21-triol-3,20-dione / 16a-Methyl-9a-fluoro-prednisolone / 1-Dehydro-16a-methyl-9a-fluorohydrocortisone / 16a-methyl-9a-fluoro-D1-hydrocortisone
Hideaki Nishino
C22H29O5F 392.461 Download ChemDraw structure file
Synthesis of the 21-acetate from 16a-methylhydrocortisone acetate as the starting material. (Ref. 0762) Synthesis of the 21-acetate from 16a-methylpregnenolone as the starting material. (Ref. 0763)
229-231degC as the 21-acetate. (Ref. 0763), 215-221degC as the 21-acetate. (Ref. 0762)
[a]/D=+77.6deg. (Ref. 0763) [a]/=+73deg as the 21-acetate. (Ref. 0762)
Sol in water (10 mg/100 ml at 25deg). Sol in acetone, ethanol, chloroform. (Ref. 0762)
As the 21-acetate, lmax: 239mm (e=14,900); as the 21-acetate, lmax: 239mm (e=14,500). (Ref. 0762)

Most active steroid in glucocorticoid activity (Liver glycogen activity in rat), systemic granuloma activity (in intact Holzman rat), and anti-inflammatory action (in human). Negative in sodium retention (rats), less than 1 (human). (Ref. 0762) The eosinopenic activity is 4 to 6-times higher than prednisone and prednisolone in mouse, dog, and human. In granuloma pouch test, 6.5-times higher than prednisolone acetate. In thymus involution (rats) and nitrogen excretion (dogs), 25-times higher than prednisolone acetate and prednison. (Ref. 0762/0763)

Dichlorisone / Diloderm / Disoderm
9,11b-Dichloro-17,21-dihydroxy-pregna-1,4-diene-3,20-dione / 9a,11b-Dichloro-1,4-pregnadi-ene-17a,20-diol-3,21-dione / 9a,11b-Dichloroanalog of prednisolone
Hideaki Nishino
C21H26O4Cl2 413.334 Download ChemDraw structure file
Preparation by halogenation of 1,4,9(11)-pregnatriene-17a,21-diol-3,20-dione-21-acetate. (Ref. 0764)
238-241degC (Ref. 0764)
[a]20/D=+134deg (pyridine) (Ref. 0764)
UVmax (methanol): 237nm (e=15,400) (Ref. 0764)
lNujol/max: 3.0, 5.86, 6.04, 6.22, 6.25m (Ref. 0764)

[M]/D=+737 (dioxane) (Ref. 0764)

Antipruritic in peripheral tissues. In granuloma pouch test, strong anti-inflammatory agent. (Ref. 0764)

Hideaki Nishino
C28H40O7 488.613 Download ChemDraw structure file

155-183degC (unclear melting range). (Ref. 0766)
[a]20/D=-176deg (Ref. 0765/0768) [a]14/D=-223pm4deg (c=2.3 in chloroform) (Ref. 0766)
Sol in chloroform. Slightly so in ether, acetone, ethylacetate, carbon tetrachloride. Inso in water. (Ref. 0765/0766)
UVmax (ethanol): 309nm (loge=1.94), 310nm(loge=2.00) (Ref. 0768)
(chloroform) 3585(OH), 1735(C=O), 1712(C=O), 1655(C=C), 1095, 1060, 1032(C-O-C), 891, 872, 853(CO-C-O-C) (Ref. 0768)

Optical rotatory dispersion: in methanol, [M]-13,650deg (335 mm, through), +11, 100deg (292.5 mm, peak) (Ref. 0768)

Isolation from the leaves of Digitalis purpurea L., Scrophulariaceae. (Ref. 0765)

Upon hydrolysis, separates into diginigenin (C21H28O4) and diginose (C7H14O4). (Ref. 0766) Synthesis of the aglycon, diginigenin. (Ref. 0766/0770/0771)
Digitalin / Digitalinum Verum / Digitalinum True / Schmiedeberg's Diginorgin
Hideaki Nishino
C36H56O14 712.821 Download ChemDraw structure file

240-243deg (methanol+water). (Ref. 0774), 244deg (Ref. 0774/0775), 241-244deg. (Ref. 0776)
[a]20/D=-1.1pm3deg (c=0.894 in methanol). (Ref. 0774) [a]26/D=+1.5pm1.2deg (1.73% in chloroform). (Ref. 0775)
Slightly sol in water, chloroform, ether. Sol in alcohol. (Ref. 0772/0773/0774/0775/0776)

Paper chromatography: Rf 0.00 (Ref. 0775)
Plants. Isolation from seeds of Digitalis purpurea L., Scrophulariaceae, roots of Adenium honghel A. DC., Apocynaceae. (Ref. 0772/0773/0774/0775)

Cardiotonic action. (Ref. 0772/0776) Toxicity: cat method, 1.206mg/kg; pigeon method, 1.24mg/kg, 1.30mg/kg. (Ref. 0775)

In Keller-Kiliani reaction, pink color in sulfate layer, no color in acetic acid layer. (Ref. 0775)
Digitonin / Digitin
Hideaki Nishino
C56H92O29 1229.312 Download ChemDraw structure file

244-285degC (Ref. 0778), 227-240degC (Ref. 0777)
[a]20/D=-40deg (pyridine, c=2.6) (Ref. 0778)
Sol in anhydrous alcohol (1g/57ml), 95% alcohol (1 g/220 ml). Inso in water. Also inso in chloroform, ether. (Ref. 0777/0778)

Isolation from seeds of Digitalis purpurea L., Scrophulariaceae. (Ref. 0777)

Application to quantification of cholesterol in plasma, bile acid, and tissues. (Ref. 0778)

Dimethisterone / Secrosteron
17b-Hydroxy-6a-methyl-17-(1-propynyl)androst-4-en-3-one / 6a-Methyl-17-(1-propynyl)testosterone / 6a,21-Dimethyl-17b-hydroxy-17a-pregn-4-en-20-yn-3-one / 6a,21-Dimethylethisterone / 17a-Ethynyl-6a,21-dimethyltestosterone / 17a-Ethynyl-17-hydroxy-6a,21-dimethylandrost-4-en-3-one
Hideaki Nishino
C23H32O2 340.499 Download ChemDraw structure file
Synthesis from 17a-ethynyl-17b-hydroxy-derivatives of androstane. (Ref. 0779)
99-102degC (Ref. 0779)
[a]24/D=+12deg (c=1.0) (Ref. 0779)
Insol in water. Sol in ethanol. Slightly sol in acetone, chloroform. (Ref. 0779)
UVmax: 241nm (loge=4.16) (Ref. 0779)

Progestin activity. (Ref. 0779)

Dromostanolone Propionate / Drostanolone propionate / Drolban / Emdisterone / Masterid / Masteril / Masterone / Permastril
2a-Methyl-17b-(1-oxopropoxy)-5a-androstan-3-one / 17b-Hydroxy-2a-methyl-androstan-3-one propionate / 2a-Methylandrostan-17b-ol-3-one propionate / 2a-Methyldihydrotestosterone propionate
Hideaki Nishino
C23H36O3 360.530 Download ChemDraw structure file
Synthesis by hydrogenation of 2-hydroxymethylene-3-ketoandrostanes. (Ref. 0780)
126-130degC (Ref. 0780)
[a]/D=+24deg (Ref. 0780)

Anti-tumor drug. (Ref. 0780)

Dydrogesterone / Duphaston / Gestatron / Prodel / Retrone
9b,10a-Pregna-4,6-diene-3,20-dione / 10a-Pregna-4,6-diene-3,20-dione / 6-Dehydro-retro-progesterone / 10a-Isopregnenone
Hideaki Nishino
C21H28O2 312.446 Download ChemDraw structure file
Synthesis from lumisterol2 as a starting material. (Ref. 0781) Synthesis by UV-irradiation to pregna-5,7-dien-3b-ol-20-one, which yields 9b,10a compound, Oppenauer oxidation and isomerization of 9b-Pregna-5,7-dien-3a-ol-20-one. (Ref. 0782)
169-170degC (acetone+hexane). (Ref. 0781)
[a]25/D=-484.5deg (chloroform). (Ref. 0782)
UVmax: 286nm (e=26,400). (Ref. 0781)
nmax, 888, 1574, 1617, 1656, 1695/cm. (Ref. 0781)

High progestin activity to a same degree as 9b,10a-pregn-4-ene-3,20-dione (oral ingestion). Strong elevation of progestin activity in 6-dehydro-progesterone (pregna-4,6-diene-3,20-dione) by introduction of double bond to C6-C7 of progesterone (pregn-4-ene-3,20-dione). (Ref. 0781)

Echujin / Echugin
Hideaki Nishino
C42H66O17 842.963 Download ChemDraw structure file

165-172deg (acetate) (Ref. 0785)
[a]20/D=-6.5deg (c=0.964 in methanol) [a]24/D=-9.8deg (c=0.969 in water) (Ref. 0785)
Sol in water, alcohol. Insol in benzene, chloroform, ether, petroleum ether. (Ref. 0783/0784/0785)

Plants. Derived from arrow poison isolated from milk sap extracted Adenium boehmianum Schinz, Apocynaceae and A. lugardii N. E. Br., Apcynaceae. (Ref. 0783/0784)

Toxic glycoside. LD50 i.v. in cats: 0.3mg/kg (Ref. 0520)

Enoxolone / Uralenic acid / Biosone
3b-Hydroxy-11-oxo-20b-olean-12-en-29-oic acid / 3b-Hydroxy-11-oxoolean-12-en-30-oic acid / 18b-Glycyrrhetinic acid
Hideaki Nishino
C30H46O4 470.684 Download ChemDraw structure file

296deg (alcohol+petr. ether). (Ref. 0786/0787/0788)
[a]21/D=+86deg (alc.), [a]20/D=+145.5deg (dioxane), [a]20/D=+163deg (chloroform). (Ref. 0786/0787)
Sol in chloroform, dioxane, alcohol, pyridine, acetic acid. Insol in petroleum ether. (Ref. 0786/0787)

Plants. Roots of licorice. (Ref. 0789)
Metabolism. (Ref. 0790)

Stereochemistry. (Ref. 0788)
Epiandrosterone / Isoandrosterone
3b-Hydroxy-5a-androstan-17-one / 3b-Hydroxy-17-androstanone / 3b-Androstanol-17-one / 3b-Hydroxyetioallocholan-17-one
Hideaki Nishino
C19H30O2 290.440 Download ChemDraw structure file
Synthesis method. (Ref. 0791/0792/0793)
dl-Form: 161-162degC, d-form: 174.5degC (ethyl acetate+petr. ether) (Ref. 0791/0792/0793)
d-form: [a]20/D=+88deg (methanol). (Ref. 0791/0792/0793)
d-form: Insol in water. Sol in organic solvents. (Ref. 0791/0792/0793)

Animals. The trace amount is present in healthy human urine.(Ref. 0793)

Androgen activity, weaker than androsterone. (Ref. 0793)

d-Form: ppt with digitonin. (Ref. 0791)
5a-Cholestan-3a-ol; 3a-Hydroxycholestane; e-Cholestanol
Hideaki Nishino
C27H48O 388.669 Download ChemDraw structure file
Preparation from cholestanone. (Ref. 0035/0366) Synthesis from cholesterol via a-cholestyl chloride. (Ref. 0794)
185-186degC (alcohol). (Ref. 0794), 182-184degC. (Ref. 0366)
[a]20/D=+32.2deg (c=2.0 in chloroform). (Ref. 0366)
Lower solubility than cholestanol. (Ref. 0794)

Not ppt with digitonin. Epicholestanyl acetate, m.p. 92-94deg (Ref. 0366)
Estra-5,7,9-triene-3a,17a-diol / 5(10),6,8-Estratriene-3a,17a-diol / 5,7,9-Estratriene-3a,17a-diol
Hideaki Nishino
C18H24O2 272.382 Download ChemDraw structure file
Preparation by reduction of equilenin. (Ref. 0795)
172degC (also reported 181deg or 191-193degC) (Ref. 0795)
[a]20/D=+68deg (c=0.9 in alcohol) (Ref. 0795)
Very sol in pyridine. (Ref. 0795)

Equilin glycol / 7,8-Dihydroxyestrone
3,7,8-Trihydroxyestra-1,3,5(10)-triene-17-one / 1,3,5-Estratrien-17-one-3,7,8-triol
Hideaki Nishino
C18H22O4 302.365 Download ChemDraw structure file
Preparation from equilin extracted from pregnant mares. (Ref. 0087)
Polymorphous crystals I, 210-216degC; orthorhombic sphenoidal II, 253-254deg. (Ref. 0087)
I, [a]23/D=+135deg (0.39% in dioxane); II, [a]23/D=+139deg (c=0.33 in dioxane). (Ref. 0087)
II, Sol in water. Slightly sol in organic solvents. (Ref. 0087)

Estrogen activity. (Ref. 0087)

Two preparations with high melting point and low melting point. However they are proved to be identical compound by acetylation: shift of m.p. to 211-212degC, [a]26/D= +90deg and +92deg (in alcohol), respectively. Dehydrogenation of equilin glycol yields 7-ketoestrone, which turns to be 7-hydroxy-estrone by reduction. (Ref. 0087)
Hideaki Nishino
C28H50 386.697 Download ChemDraw structure file
Synthesis from allocholanic acid. (Ref. 0796)
85degC (ether+methanol). (Ref. 0796)
[a]20/D=+17deg (c=2 in chloroform). (Ref. 0796)

Hideaki Nishino
C28H50O 402.696 Download ChemDraw structure file
Preparation by hydrogenation of ergosta-14,22-dien-7-one. (Ref. 0797)
144-145degC (Ref. 0797)
[a]20/D=+15.9deg (c=1.8 in chloroform). (Ref. 0797)

Ppt with digitonin. (Ref. 0797)
Hideaki Nishino
C28H48O 400.680 Download ChemDraw structure file
Preparation by hydrogenation of ergosterol acetate with acetic acid. (Ref. 0798) Preparation from 22-dihydro ergosterol. (Ref. 0799)
130-131degC (methanol) (Ref. 0798/0799)
[a]16/D=+11deg (c=0.9 in methanol), [a]/546=-10.2deg (c=1 in methanol) (Ref. 0798/0799)

Ppt with digitonin. (Ref. 0798/0799)
Hideaki Nishino
C28H48O 400.680 Download ChemDraw structure file
a-Preparation by treatment of ergostenol with HCl-gas in chloroform. (Ref. 0800)
141degC (alcohol). (Ref. 0800)
[a]20/D=+21.2deg (c=0.9 in chloroform) (Ref. 0800)

Ergost-7-en-3b-ol / 3b-Hydroxergost-7-ene
Hideaki Nishino
C28H48O 400.680 Download ChemDraw structure file
Preparation from 22,23-dihydroergosterol. (Ref. 0801) Preparation from ergosterol. (Ref. 0802) High recovery by hydrogenation of 3b-acetoxyergosta-7,22-dien using Raney nickel catalyst. (Ref. 0803)
146degC (isopropanol) (Ref. 0802)

Escigenin / Aescigenin
Hideaki Nishino
C30H48O5 488.699 Download ChemDraw structure file

317-318deg (alcohol). (Ref. 0806/0807/0808/0809)
[a]20/D=+46deg (c=1.52 in abs. ethanol) [a]19.5/D=+45pm2deg (c=1.60 in pyridine) (Ref. 0806/0807/0808/0809)
UVmax (anhydrous alcohol): 275nm (loge=1.58) (Ref. 0804)

Had ever been regarded as an aglykon of escin. (Ref. 0804/0805/0806)
Escin / Aescin / Aescusan / Reparil
Hideaki Nishino
Download ChemDraw structure file

a-Escin: 225-227degC (Ref. 0805), 222-223deg (Ref. 0805)
a-Escin: [a]25/D=-13.5deg (c=5 in methanol), b-escin: [a]27/D=-23.7deg (c=5 in abs. methanol) (Ref. 0805)
a-Escin can be sol in water. (Ref. 0805) b-Escin cannot be sol in water. (Ref. 0815/0805)

Plants. Saponin produced in seeds of Aesculus hippocastanum L., Hippocastanaceae horse chestnut tree.(Ref. 0810)

a-Escin, LD50 in mice, rats, guinea pigs: 320, 720, 475 mg/kg orally; 3.2, 5.4, 15.2 mg/kg i.v. hemolytic index; 1:20,000. b-Escin, hemolytic index; 1:40,000. LD50 in mice, rats, guinea pigs: 134, 400, 188mg/kg orally; 1.4, 2.0, 7.2mg/kg i.v., respectively. (Ref. 0816)

Ppt with cholesterol. Escin can be separated into two isomers, a-escin and b-escin, because of different properties in melting point, optical rotation, hemolytic index, solubility in water. (Ref. 0805) Escin had ever been regarded as an glycoside from aescigenin (C30H48O5). Isolation and purification by chromatography. (Ref. 0811/0812/0813) Escin is a mixture of two major Glycosides. The aglycon is protoescigenin, which is acylated at C-22 with acetic acid. The sugar parts are composed of Glucuronic acid and two D-Glucose molecules. The difference in two main glycosides is based on acylated compound at C-21, angelic acid or tiglic acid. Hydroxyl group at C-3 is linled to D-glucuronic acid, which is connected to 2 molecules of D-glucose at 2, 4-positions. One of D-glucose molecules is often substituted with D-xylose or D-galactose. (Ref. 0814/0815)
Estranediol B / 3,17-Dihydroxyestrane / Octahydrofollicular Hormone / Octahydroestrone / Hexahydrodesoxyestriol / Hexahydroestradiol
Hideaki Nishino
C18H30O2 278.430 Download ChemDraw structure file
Preparation along with stereoisomer by hydrogenation of estrone. The diacetate, C22H34O4, crystallization from methanol. M.p.160deg (Ref. 0818)
210-211degC (benzene+petr. ether) (Ref. 0817), 204-205degC (Ref. 0818)
[a]20/D=+7.8deg (13mg in 2ml abs. alc.) (Ref. 0818) [a]22/D=+7.2deg (Ref. 0817)

Animals. Presence in urine of non-pregnant women. Formed by non-enzymic reduction of estrone. (Ref. 0818)

Estrogenic hormone (Ref. 0818)

5,6,8-Estratrien-3b-ol-17-one / 5,7,9-Estratrien-3b-ol-17-one
Hideaki Nishino
C18H22O2 270.366 Download ChemDraw structure file

138-139.5degC (Ref. 0420)
[a]27/D=+59pm3deg (1.19% in ethanol) (Ref. 0420)
Insol in water. Sol in alcohol, ether, other organic solvents. (Ref. 0420)
UVmax: 269.5, 278mm (e=345,240), shoulder at 278mm. UVmin: 249, 276mm (e=95,233) (Ref. 0420)

Animals. Urine of pregnant mares. Pure praparation weighing about 160mg was obtained from 10,000 gallon of urine. (Ref. 0420)

Ring B is benzenoid, not ring A, so bond isomer of estrone. Not ppt with digitonin. The oxime, C18H23NO2, m.p. 195-197deg (dec.). The acetate, C18H21O(OCOCH3), m.p.158deg. The benzoate, C25H26O3, m.p.196-198deg. Strong positive in the Liebermann-Burchard reaction and Salkowski reaction. The latter reaction is reversible like ergosterol. Negative in Rosenhelm test. Deep yellow color reaction by tetranitromethane. (Ref. 0420)
Ethylestrenol / Orabolin / Durabolin-O / Orgaboral / Maxibolin / Orgabolin (Obsolete)
19-Nor-17a-pregn-4-en-17-ol / 17a-Ethylestr-4-en-17b-ol / 17a-Ethyl-17b-hydroxy-4-estrene / 17b-Hydroxy-17a-ethyl-19-nor-4-androstene
Hideaki Nishino
C20H32O 288.467 Download ChemDraw structure file
Synthesis from 19-nortestosterone as a starting material. (Ref. 0819)
76-78degC (Ref. 0819)
[a]/D=+31deg (chloroform) (Ref. 0819)

Anabolic action. Strong progestational agent, at least same activity as already known D4-3-ketones. (Ref. 0819)

Fludrocortisone / 9a-Fluorohydrocortisone / 9a-Fluorocortisol / Fluodrocortisone / Fluohydrisone / Fluohydrocortisone / Alflorone / Astonin-H / F-Cortef / Florinef / Fludrocortone
9-Fluoro-11b,17,21-trihydroxypregn-4-ene-3,20-dione / 9a-Fluoro-17-hydroxycorticosterone
Hideaki Nishino
C21H29O5F 380.450 Download ChemDraw structure file
Preparation from 4-pregnen-9b,11b-oxido-17a,21-diol-3,20-dione 21-acetate. Preparation from 9a-fluorohydrocortisone acetate by deacetylation with sodium methylate. (Ref. 0820)
260-262degC (dec.). (Ref. 0820)
[a]23/D=+139deg (c=0.55 in 95% ethanol). (Ref. 0820)
Sol in water. (Ref. 0820)
UVmax (ethanol): 239nm (e=17,600). (Ref. 0820)
lNujol/max 3.0m(OH), 5.84m(20-carbonyl), 6.07m, 6.20m(D4-3-ketone) (Ref. 0820)

Anti-inflammatory effect. Application to domestic animals as as adrenocortical steroid. (Ref. 0820)

Several times increase in glucocorticoid activity by halogenation. (Ref. 0820)
Flumedroxone acetate / WG537 / Demigran
17-(Acetyloxy)-6a-(trifluoromethyl)pregn-4-ene-3,20-dione / 17-Hydroxy-6a-(trifluoromethyl)pregn-4-ene-3,20-dione acetate / 17-Acetoxy-6a-(trifluoromethyl)progesterone / 17-Hydroxy-6a-(trifluoromethyl)progesterone acetate / 6a-(Trifluoromethyl)-17-hydroxyprogesterone acetate
Hideaki Nishino
C24H31O4F3 440.496 Download ChemDraw structure file
Preparation by UV-irradiation of 17a-acetoxyprogesterone-3-ethyl enol ether in trifluoroiodomethane-pyridine, followed by hydrolysis of the product, 6-trifluoromethyl-17a-acetoxypregesterone-3-ethyl enol ether. (Ref. 0821)
206-207degC (Ref. 0821)
[a]20/D=+30deg (Ref. 0821)
UVmax (ethanol): 234nm(e=15,600) (Ref. 0821)

Oral progestational activity (Clauberg assay, modified by McPhail) is 1 to 2 when relative activity of 6a-methyl-17a-acetoxyprogesterone is 1. (Ref. 0821)

Remarkable increase in oral progestational activity by introduction of a-fluorine, chlorine, or bromine to C-6 of 17a-acetoxyprogesterone. (Ref. 0821)
Flumethasone / 6a-Fluorodexamethasone / Aniprime / Cortexilar / Flucort / Methagon
6a,9-Difluoro-11b,17a,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione / 6a,9a-Difluoro-16a-methylprednisolone
Hideaki Nishino
C22H28O5F2 410.452 Download ChemDraw structure file
Preparation by dehydration of 6a-fluoro-16a-methyl Substance S in mesyl chloride and pyridine-dimethylformamide. (Ref. 0822)
The 21-acetate (C24H30F2O6), 260-264degC (acetone+hexane). (Ref. 0822/0823)
The 21-acetate: [a]/D=+91deg (Ref. 0822/0823).
The 21-acetate UVmax (ethanol): 237nm (loge=4.16) (Ref. 0822/0823)
lKBr/max 5.73, 5.80, 6.03, 6.23m (Ref. 0822/0823)

Glucocorticoid, anti-inflammatory action, application to domestic animals as an adrenocortical steroid. Promotion of sodium ion excretion. (Ref. 0822) The strongest anti-inflammatory effect among 6a-fluoro-16a-methylcorticoids: hydrocortisone, 1; 6a-fluoro-16a-methylprednisolone acetate, 60; 6a,9a-difluoro-16a-methylhydrocortisone acetate, 65; 6a,9a-difluoro-16a-methylprednisolone acetate, 300. High effect on patients suffering from rheumatoid arthritis according to clinical test in Mexico and USA. (Ref. 0823)

Four substitutions, D1-double bond, 6a-fluorine, 9a-fluorine, and 16a-methylgroup increase anti-inflammatory effect, respectively. (Ref. 0822)
Fluocinolone acetonide / Dermalar / Jellin / Localyn / Fluovitef / Fluocinil / Synamol / Synsac / Synandone / Synalar
6a,9-Difluoro-11b,21-dihydroxy-16a,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione / 6a,9a-Difluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone / 6a,9a-Difluoro-16a-hydroxyprednisolone 16,17-acetonide / 6a,9a-Difluoro-16a,17a-isopropylidenedioxy-1,4-pregnadiene-3,20-dione
Hideaki Nishino
C24H30O6F2 452.488 Download ChemDraw structure file
Praparation by acetate-treatment of 6a,9a-difluoro-16a-hydroxyprednisolone, which is synthesized from available 16a,17a-oxido-D5-pregnene-3b,21-diol-20-one 21-acetate. (Ref. 0824)
265-266degC (acetone+hexane). (Ref. 0824)
[a]/D=+95deg (chloroform). (Ref. 0824)
UVmax: 238nm (loge=4.21). (Ref. 0824)
Observation of IR spectra. (Ref. 0825)

Glucocorticoid activity. High anti-inflammatory action (no sodium retention). Application to domestic animals as an adrenocortical steroid in peripheral tissues. Anti-inflammatory action; 100-times higher than hydrocortisone. High suppressor effect on allergy reactions like rheumatoid arthritis and asthma in clinical trial. (Ref. 0824)

Fluocortolone / Ultralan Oral
6a-Fluoro-11b,21-dihydroxy-16a-methylpregna-1,4-diene-3,20-dione / 6a-Fluoro-16a-methyl-1-dehydrocorticosterone / 6a-Fluoro-16a-methyl-D1,4-pregnadiene-11b,21-diol-3,20-dione
Hideaki Nishino
C22H29O4F 376.462 Download ChemDraw structure file
Synthesis by substrate-structure-directed specific 11b-hydroxylation in Curvularia lunata. (Ref. 0827)
188-190.5degC. (Ref. 0826)
[a]20/D=+100deg (dioxane). (Ref. 0826)
295 in water (37deg), 120 in ethanol (20deg), 440 in toluene (20deg) (mg/ml). (Ref. 0826)
UVmax (methanol): 242nm (e=16,300). (Ref. 0826), e242=15,900. (Ref. 0827)

Metabolism after i.v. injection, oral ingestion. Isolation as fluocortolone-21-carbonic acid in soluble form from urine. (Ref. 0830) No influence on nitrogen balance. Inhibitory effect on removal of 17-ketosteroids, 17-hydroxy-corticosteroids into urine by 50%, 55-65%, respectively (human, 20 to 60mg/day). (Ref. 0831)
Glucocorticoid activity: 3 to 10 times higher than hydrocortisone acetate (ED50, 0.003 to 0.01 (mg/animal/day) in mouse gluconeogenesis). In granuloma pouch, ED50: 0.0005 (0.0002 to 0.001) (topical), 0.02 (0.01 to 0.04) (subcutaneous), 0.02 (0.01-0.03) (oral) (mg/animal/day). Thymolytic activity, 17 times higher than hydrocortisone acetate (ED50, 0.006 (0.003 to 0.013) mg/animal/day), Promotion of sodium-potassium excretion. (Ref. 0826/0828) Less suppressor effect to Cortisol secretion by 10mg Fluocortolone than by 45mg STC407 (6-dehydro-16-methylene-hydrocortisone). (Ref. 0829)

Fluoxymesterone / Androsterolo / Androfluorene / Androfluorone / Fluotestin / Halotestin / Oratestin / Oratestryl / Testoral / Ultandren.
9-Fluoro-11b,17b-dihydroxy-17-methylandrost-4-en-3-one / 11b,17b-Dihydroxy-9a-fluoro-17a-methyl-4-androsten-3-one / 9a-Fluoro-11b-hydroxy-17a-methyltestosterone
Hideaki Nishino
C20H29O3F 336.441 Download ChemDraw structure file
Synthesis by utilization of reaction with Grignard reagent from 11b-hydroxy-4-androstene-3,17-dione. (Ref. 0832)
270degC (dec.) (Ref. 0832)
[a]/D=+109deg (ethanol) (Ref. 0832)
UVmax (methanol): 240nm(e=16,700) (Ref. 0832)

Strong androgen activity. Anabolic activity, androgenic activity; ;20.0, 9.5 in fluoxymesterone; 1, 1 in 17-methyltestosterone (oral ingestion). (Ref. 0832)

Reaction of fluoxymesterone with chromium trioxide in acetic acid yields 17b-hydroxy-9a-fluoro-17-methyl-4-androstene-3,11-dione (m.p. 213-220deg (dec.), [a]/d=+144deg (chloroform), C20H27O3F, anabolic activity, androgenic activity; 22, 8.5; 1, 1 in 17-methyltestosterone, respectively. Stronger anabolic activity than fluoxymesterone. (Ref. 0832)
Fluperolone acetate / P-1742 / ALAcortril / Methral
17(S9-[2-(Acetyloxy)-1-oxo-propyl]-9-fluoro-11b,17a-dihydroxyandrosta-1,4-dien-3-one / 9-Fluoro-11b,17a-dihydroxy-17(S)-lactoylandrosta-1,4-diene-3-one 17b-acetate / 9a-Fluoro-11b,17a,21-trihydroxy-21-methylpregna-1,4-diene-3,20-dione 21-acetate / 17b-[2-Acetoxypropionyl]-9a-fluoro-11b,17-dihydroxyandrosta-1,4-dien-3-one / 21-Methyl-9a-fluoroprednisolone acetate / 9a-Fluoro-21-methyl-1,4-pregnadiene-11b,17a,21B-triol-3,20-dione 21-acetate
Hideaki Nishino
C24H31O6F 434.498 Download ChemDraw structure file
Synthesis via 9a-fluorine substitution by raction of prednisolone 21-aldehyde with diazomethane. (Ref. 0833) Synthesis of 21aF-hydroxy-21-methylcorticoid, one of C-21-selective and stereospecific dihydroderivatives by reduction of 20, 21-diketones in yeasts. (Ref. 0834)
215-253degC (Ref. 0833)
[a]/D=+87deg (Ref. 0833)
UVmax: 239nm (e=15,350) (Ref. 0833)

No electrolyte-regulating activity, raises only slight natriuresis in adrenalectomized rats. In granuloma pouch test, one sixth anti-inflammatory effect of 9a-fluoroprednisolone acetate. Through 21-methyl substitution, can remove completely the strong sodium retention activity from 9a-fluoroprednisolone molecules and leaves anti-inflammatory effect. (Ref. 0833)

Synthesized several C21 epimers. (Ref. 0833) Among six species of topical steroids as medicine, in vasoconstrictor test, 10 (3 to 35) when with fluocinolone acetnide is 100, in rank third, in subcutaneous thymolytic test, 21(11 to 27) in mice (rank second) and 16 in rats (rank third) when with betamethasone alcohol is 100. (Ref. 0835)
Fluprednidene acetate / Fluprednylidene 21-acetate / StL 1106 / Etacortin / Decoderm sine Gentamycin
21-(Acetyloxy)-9-fluoro-11b,17-dihydroxy-16-methylenepregna-1,4-diene-3,20-dione / 9a-Fluoro-11b,17,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione 21-acetate / 9a-Fluoro-16-methylene-D1,4-pregnadiene-11b,17,21-triol-3,20-dione 21-acetate / 16-Methylene-9a-fluoroprednisolone 21-acetate / 9a-Fluoro-16-methyleneprednisolone 21-acetate
Hideaki Nishino
C24H29O6F 432.482 Download ChemDraw structure file
Synthesis by reaction of 3a,17a-dihydroxy-16-methylenepregnane-11,20-dione with bromine in chloroform. (Ref. 0836) Synthesis from 16-methyl-16-dehydropregnenolone acetate as the starting material. (Ref. 0838)
231-234degC. (Ref. 0836/0837)
[a]/D=+87deg (chloroform). (Ref. 0836/0837), [a]/D=+32degC (dioxane). (Ref. 0838)
UVmax (methanol): 238nm(e=15,700). (Ref. 0836/0837), lmax=239mm(e=15,900. (Ref. 0838)
lchloroform/max 2.73, 2.85-2.90, 5.73, 5.76, 5.99, 6.10, 6.18, 11.2m. (Ref. 0836/0837)
t4.74, 4.94 (C-16=CH2).

Anti-inflammatory medicine (topical). (Ref. 0838)

Flurogestone acetate / Flugestone acetate / Chronogest / SC-9880 / Cronolone / Synchronate
17-(Acetyloxy)-9-fluoro-11b-hydroxypregn-4-ene-3,20-dione / 9-Fluoro-11b,17-dihydroxypregn-4-ene-3,20-dione-17-acetate / 17a-Acetoxy-9a-fluoro-11b-hydroxyprogesterone / 9-Fluoro-11b,17-dihydroxyprogesterone 17-acetate
Hideaki Nishino
C23H31O5F 406.488 Download ChemDraw structure file
Synthesis by reaction of 16,17a-epoxy-4,9(11)-pregnadiene-3,20-dione with hydriodic acid in acetic acid. (Ref. 0839)
266-269degC (benzen+petr. ether or ethyl acetate+petr. ether) (Ref. 0839)
[a]20/D=+77.6deg (in chloroform) (Ref. 0839)
UVmax (methanol): 238nm(e=17,500) (Ref. 0839)

Progestin activity. Application to regulation of the estrus (mating time) in domestic animals as a progestational agent. In Clauberg assay, oral ingestion, 25-times higher activity than subcutaneous progesterone. Compared with oral progesterone, 2500-times higher activity, 25-times higher than norlutin, 5-times higher than 6a-methyl-17a-acetoxy-progesterone. (Ref. 0839)

Formocortal / FI 6341 / fluoroforymlon / Cortocin-F / Cutisterol / Deflamene / Fluderma
21-(Acetyloxy)-3-(2-chloroethoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-20-oxopregna-3,5-diene-6-carboxaldehyde / 3-(2-Chloroethoxy)-9-fluoro-11b,16a,17,21-tetrahydroxy-20-oxopregna-3,5-diene-6-carboxaldehyde,cyclic 16,17-acetal with acetone,21-acetate / 3-(2-Chloroethoxy)-6-formyl-9a-fluoropregna-3,5-diene-11b,16a,17,21-tetrol-20-one 21-acetate 16a,17a-acetonide / 3-(2-Chloroethoxy)-9a-fluoro-6-formyl-11b,21-dihydroxy-16a,17a-isopropylidenedioxypregna-3,5-dien-20-one
Hideaki Nishino
C29H38O8FCl 569.058 Download ChemDraw structure file
Synthesis from 9a-fluoro-cortisone-21-acetate 3-cycloethyleneketal as the starting material. (Ref. 0840)
180-182degC (ether-petroleum ether). (Ref. 0840)
[a]20/D=+26deg(chloroform). (Ref. 0840)
UVmax (ethanol): 216, 324nm (e=12,100, 17,100). (Ref. 0840)

Glucocorticoid action. In granuloma pouch assay, ED50; topical, 0.001mg; oral, 0.105mg. Relative potency (F-acetate, 1); in granuloma pouch assay, 680 in topical, 36 in oral, s.c., 23; cotton pellets, 6.5 in topiocal; hepatic glycogen, 130; inhibition of total plasmatic corticosterone (FOH=1), 29. (Ref. 0840)

The 21-pentanoate, m.p.103-105deg, lmax=216, 323nm (e=10,200, 11,700), [a]/D=+32deg (Ref. 0840)
Formyldienolone / Esiclene
11a,17b-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehyde / 2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-diol-3-one / 2-Formyl-11a-hydroxy-D1-methyltestosterone
Hideaki Nishino
C21H28O4 344.445 Download ChemDraw structure file
Synthesis from 17a-methylandrosta-1,4-dien-11a,17b-diol-3-one as the starting material. (Ref. 0841) Synthesis from 17a-methylandrost-4-ene-17b-hydroxy-3,11-dione as the starting material. (Ref. 0842)
209-212degC (ethyl acetate) (Ref. 0842)
[a]25/D=-105deg (chloroform) (Ref. 0842)
Sol in water. (Ref. 0842)

Method for synthesis of tritium-labeled formyldienolone and the metabolism. In oral ingestion, the blood concentration reached the maximum at 2 h and slowly decreased for the course of 22 h. Highest radioactivity in liver. Detected as little as 4% in urine. Recovered 42% in feces. (Ref. 0842)
Anabolic steroid action. (Ref. 0841)

D:A-Friedooleanan-3-one / friedelan-3-one
Hideaki Nishino
C30H50O 426.717 Download ChemDraw structure file

261-265degC (Ref. 0844)
[a]/D=-27.8deg (chloroform) (Ref. 0846) [a]14/D=-22deg (c=0.812) (Ref. 0844)
Sol in chloroform (1 g/8.6 ml), 99% alcohol (1 g/264 ml). (Ref. 0844)

Plants. Main triterpene in corc, extraction in alcohol. (Ref. 0843) Extraction from Ceratopetalum apetalum D. Don, Cunoniaceae. This tree is also called coachwood, which is distributed in rain forest in New South Wales (Australia). Identical to the compound obtained from cork.(Ref. 0843/0844)

Stereochemistry. Evidence for ketone-group at C-3, determination of friedolin structure. (Ref. 0845/0846)
Ergosta-6,8,22-trien-3b-ol / D6:7,8:9,:22:23-Ergostatriene-3-ol
Hideaki Nishino
C28H44O 396.648 Download ChemDraw structure file

147.5degC (alcohol+ether+ethyl acetate) (Ref. 0848)
[a]15/D=-21.9deg (chloroform) (Ref. 0848)
e 283mm = 9980 (Ref. 0848)

Bacteria, molds. Purification from sterol crystal of Penicillium chrysogenum. (Ref. 0848)
Investigation on the biosynthetic pathway of fungisterol. (Ref. 0851)

The acetate, m.p.158.5deg, [a]15/D=-15.7deg. (Ref. 0848) Determination of structure by the properties of fungisterol derivatives. (Ref. 0849) Confirmation of the structure by oxidation of fungisterol, isomerization by HCl. (Ref. 0850)
Hideaki Nishino
C22H38ON2 346.550 Download ChemDraw structure file

194-195degC (methanol) (Ref. 0852)
[a]/D=+49deg (c=1 in chloroform) (Ref. 0852)

Plants. Barks of Funtumia latifolia Stapf., Apocynaceae. (Ref. 0852)

Gestonorone caproate / Gestronol caproate / SH 582 / Depostat
17-Hydroxy-17-norpregn-4-ene-3,20-dione hexanoate / 17a-Hydroxy-19-norprogesterone caproate / 17-Hydroxyestr-4-ene-3-one hexanoate
Hideaki Nishino
C26H38O4 414.578 Download ChemDraw structure file
Synthesis from pregnadienolone or pregnadienolone-3-acetate as the starting material. Can obtain biologically active compounds from the product through successive several reactions. Can remove 19-methyl group by aromatization of D1,4-3-Keto-compound or intramolecular odidation. (Ref. 0853)
123-124degC (Ref. 0853)
[a]/D=+13deg (chloroform) (Ref. 0853)
UVmax: 239nm (e=17,540) (Ref. 0853)

Effect on excretion of estrogen, 17-ketosteroids, 17-hydroxycorticosteroids, pregnanetriol into urine by intramuscular injection. (Ref. 0853)
Application to therapy for prostate hypertrophy. (Ref. 0854)

F-gitonin / Gitogenin b-Lycotetraoside
O-b-D-Glucopyranosyl-(1-2glc1)-O-b-D-xylopyranosyl-(1-3glc1)-O-b-D-glucopyranosyl-(1-4)-O-b-D-galactopyranosyl 25D,5a-spirostane-2a,3b-diol (gitogenin b-lycotetraoside)
Hideaki Nishino
C50H82O23 1051.172 Download ChemDraw structure file

252-255degC (decomp.) (Ref. 0855), 251-255degC (dec.) (Ref. 0856)
[a]25/D=-58.5deg (c=0.53 in pyridine) (Ref. 0855) [a]28/D=-66deg (c=0.50 in pyridine) (Ref. 0856)
nmax: 862, 898, 924, and 982/cm (intensity 898ge924) (Ref. 0856)

Purification in TLC. C50H82O23-2H2O (gitogenin+3timeshexose+pentose, dihydrate), D-glucose, D-galactose, D-xylose = 2.1:1.0:1.0. The aglycon can be crystallized in MeOH, m.p. 275-278deg, identical with gitogenin. (Ref. 0855/0315)
Plants. Saponin extracted from leaves of Digitalis purpurea L., Scrophulariaceae. (Ref. 0855)

Application as a cardiotonic medicine. (Ref. 0855)

Gitoxin / Anhydrogitalin / Bigitalin / Pseudodigitoxin
Hideaki Nishino
C41H64O14 780.938 Download ChemDraw structure file

285degC (decomp.) (Ref. 0859), 278degC (hot stage) (Ref. 0860)
[a]24/D=+5pm1deg (1% in pyridine) (Ref. 0860) [a]20/5461=-3.5deg (c=1.02 in pyridine, [a]20/Hg=[a]20/5461) (Ref. 0859)
Insol in chloroform, ethylacetate, acetone. Sol in mixture of chloroform with alcohol or pyridine, dil. alcohol. (Ref. 0859)
lmax = 219mm (E1%/1cm=191) (Ref. 0860)

Plants. Extraction as anhydrogitalin from foxglove, Digitalis purpurea L., D. lanata Ehrh., Scrophulariaceae. (Ref. 0857) Extraction from D. purpurea as a name, Digitalinum cristallisatum. (Ref. 0858) Glycoside extracted as gitoxin from Digitalis lanta. (Ref. 0859)

Application as a cardiotonic medicine. In cats, average lethal dose is 0.443pm0.014mg. (digitoxin, 0.375pm0.015 mg, so gitoxin possesses 83% toxicity of digitoxin) (Ref. 0860)

In acid hydrolysis, yielded 1 mol gitoxigenin and 3 mol digitoxose. (Ref. 0861/0862)
Gypsogenin / Githagenin / Albasapogenin / Gypsophilasapogenin
3b-Hydroxy-23-oxooleann-12-en-28-oic acid
Hideaki Nishino
C30H46O4 470.684 Download ChemDraw structure file

274-276degC (methanol) (Ref. 0864), 286-287degC (Ref. 0863)
[a]/D=+91deg (alc.) (Ref. 0864) [a]180/D (alcohol) =+77.3deg (Ref. 0863)
sol in hot water, ether. (Ref. 0865)

Plants. Isolation as a githagonin from Corncockle, Agrostemma githago (L.) Scop., Caryophyllaceae. (Ref. 0863) Isolation as a gypsogenin from soapwort, Gypsophila oldhamiana, Caryophyllaceae. (Ref. 0864) Isolation from Fuller's herb, Saponaria officinalis L. (Ref. 0865)

Cardiotonic glycoside. (Ref. 0863/0864/0865)

Gypsogenin is identical to githagenin. The acetate, sintering 173deg, m.p. 188-189deg, [a]/D=+79deg (c=6.70 in chloroform). The methyl ester of the acetate, m.p. 191deg, [a]/D=+80deg (c=1.318 in chloroform) (Ref. 0865)
Halcinonide / SQ-18,566 / Halciderm / Halog
21-Chloro-9-fluoro11b-hydroxy-16a,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione / 21-Chloro-9-fluoro-11b,16a,17-trihydroxypregn-4-ene-3,20-dione cyclic 16,17-acetal with acetone / 21-Chloro-9a-fluoro-11b-hydroxy-16a,17a-isopropylidenedioxy-4-pregn-ene-3,20-dione / 9a-Fluoro-21-chloro-11b,16a,17a-trihydroxypregn-4-ene-3,20-dione 16,17-acetonide.
Hideaki Nishino
C24H32O5FCl 454.959 Download ChemDraw structure file
Synthesis from 21-chloro-9a-fluoro-11b,16a,17a-trihydroxy-4-pregnene-3,20-dione as a starting material. (Ref. 0866)
264-265degC (acetone-petr. ether) (Ref. 0866)
[a]25/D=+155deg (chloroform) (Ref. 0866)
Sol in acetone, ethylacetate, petroleum ether. (Ref. 0866)
UVmax (methanol): 238 nm (e=16,400) (Ref. 0866)
nmax: 3425, 1725, 1660, 1620, 860/cm (Ref. 0866)

Application as a topical anti-inflammatory medicine. In thymus involution assay, it has been resolved that the introduction of chloride to C21 make the activity increased, and D4-form exerts higher effect than D1,4-form. No introduction of sodium retention activity in Salt-loaded adrenalectomized rats. (Ref. 0866) Rank as topical anti-inflammatory agent in vasocontrictor assay and stripped-skin assay: equivalent to those of betamethasone valerate (9a-fluoro-11b,17a-21-trihydroxy-16bmethylpregna-1,4-diene-3,20-dione 17-valerate) and SQ15,361 (9a-fluoro-21-chloro-11b,16a,17a-trihydroxypregna-1,4-diene 3,20-dione,16,17-acetonide), and higher activities than SQ20,589 (21-chloro-11b,16a,17a-trihydroxypregna-1,4-diene 3,20-dione,16,17-acetonide) and SQ20,811 (21-chloro-11b,16a,17a-trihydroxypregn-4-ene-3,20-dione,16,17-acetonide). (Ref. 0867)

Haloprogesterone / Prohalone
17-Bromo-6a-fluoropregn-4-ene-3,20-dione / 17a-Bromo-6a-fluoroprogesterone / 6a-Fluoro-17a-bromoprogesterone
Hideaki Nishino
C21H28O2FBr 411.348 Download ChemDraw structure file
Synthesis from 17a-bromo-D5-pregnen-3b-ol 20-one as a starting material. (Ref. 0868) Synthesis from pregnenolone acetate. (Ref. 0869) Remarkable progestin activity. (Ref. 0869)
180-181degC (dil. acetone) (Ref. 0868), 169-170degC (decomp.) (Ref. 0869)
[a]24/D=+12.1deg (c=2.46 in carbon tetrachloride) (Ref. 0868/0869)
Sol in acetone, glacial acetic acid. (Ref. 0868)
UVmax (ethanol): 236nm (loge=4.20) (Ref. 0868) lEtOH/max: 236-237mm (loge=4.2) (Ref. 0869)
nKBr/max: 1621, 1680, (D4-3-ketone doublet), 1704 (20-ketone)/cm (Ref. 0869)

[M]/D=+50deg (Ref. 0869)

First derivative of 6.17-dihalogenated progesterone. (Ref. 0869)
Hederagenin / Caulosapogenin / Melanthigenin
3b-23-Dihydroxyolean-12-en-28-oic acid
Hideaki Nishino
C30H48O4 472.700 Download ChemDraw structure file

332-334degC (alc.) (Ref. 0875)
[a]20/D=+81deg (c=0.7 in pyridine). (Ref. 0875)
Sol in pyridine. Also sol in a mixture of chloroform and alcohol. Slowly sol in alcohol. Insol in water. Sol in dil. alcoholic NaOH. Insol in alkali solution. (Ref. 0872)
emax: 2860 at 210 mm. (Ref. 0874)

Plants. Glycoside isolated from petals of Polyscias nodosa or Hedera helix. (Ref. 0870) Glycoside extracted from aril of fruit seed of Ackee (Blighia sapida Koenig). (Ref. 0872) Isolation as acid Sapogenin, Melanthigenin, yielded by hydrolysis of alcohol extract of delipidated seed of Nigella sativa L. (Ranunculaceae). (Ref. 0873) Isolation as Caulosapogenin by hydrolysis of aqueous-ethanolic solution of a saponin, Caulosaponin, from bloom stalks of Clematis vitalba Linn, (Ranunculaceae), Caulophyllum thalictroides, Linn, Michaux (Berberidaceae). (Ref. 0874)

Aglycon of saponin inducing hemolysis of rabbit blood. (Ref. 0872)

Identical compound to Melanthigenin. (Ref. 0873) Identical compound to Caulosapogenin. (Ref. 0874)
a-Hederin / Helixin (the saponin)
Hideaki Nishino
C41H66O12 750.956 Download ChemDraw structure file

256-257degC (Ref. 0876/0877), 256-259degC (Ref. 0879)
[a]20/D=+14.5deg (c=0.92 in methanol) (Ref. 0879)

Plants. Extraction from petals of Polyscias nodosa Forst. or ivy leaves (Hedera helix L., Araliaceae). (Ref. 0870/0876)

Hemolytic index, 1:150000; LD50 (rat), 4.5mg/kg; Preventive activity to edema. 1.1mg/kg. (Ref. 0879)

Yielded 1 mol a-hederagenin, 1 mol D-arabinose, 1 mol D-rhamnose by hydrolysis. (Ref. 0877/0878)
Hellebrin / Hellebrigenin / Glucorhamnoside
Hideaki Nishino
C36H52O15 724.789 Download ChemDraw structure file

283-284degC (hot methanol) (Ref. 0880)
[a]20/D=-23.4pm0.2deg (50% methanol) (Ref. 0880)
Sol in dil. alcohol. Slightly sol in water. Insol in ether. (Ref. 0880)
lmax = 300 mm (logE1%/1cm=1.96) (Ref. 0880)

Plants. Glycoside extracted from rhizome of Helleborus niger L., Ranunculaceae. (Ref. 0880) 0.30-1.5% Hellebrin included in the rhizome of Helleborus viridis, H. odorus, H. multifidus, H. dumetorum subsp. atrorubens, H. purpurascens, H. cyclophyllus, and H. bocconei subsp. siculus. Trace amount of Hellebrin in the rhizome of H. orientalis. No hellebrin in H. foetidus, H. lividus subsp. corsicus, H. niger (several samples investigated), H. vesicarius. (Ref. 0881)

Application as a cardiotonic agent. (Ref. 0880/0881)

3b-(Dimethylamino)con-5-enin-12b-ol / 12b-Hydroxyconessine
Hideaki Nishino
C24H40ON2 372.587 Download ChemDraw structure file

197-198degC (acetic acid or ethyl acetate) (Ref. 0882), 190-193degC (Ref. 0883), 198.5-199deg (Ref. 0884)
[a]24/D=-7deg (chloroform) (Ref. 0882), [a]24/D=+9deg (alcohol), [a]24/D=-4pm3deg (chloroform) (Ref. 0883)
Insol in water. Sol in alcohol, chloroform. Slightly sol in ether, acetone, ethylacetate. (Ref. 0882)

[M]/D=+24deg (ethanol) (Ref. 0883)

Plants. Extraction from leaves and barks of Holarrhena congolensis Stapf, Apocynaceae. (Ref. 0882)

The hydrobromide, C24H38N2O, 2HBr, Molecular mass 532.3. [a]/D=+11deg or +12.1deg (anhydrous salt) (Ref. 0882) Evidence for identification to 12b-hydroxy-5a-pregnane prepared from hydrolysis of hecogonin as a hydroxy 5a-pregnane through Hofmann reaction and Emde reaction. Confirmation of holarrhenin structure as 12b-hydroxyconessin. (Ref. 0884)
Hydrallostane / Allodihydrohydrocortisone / Allodihydro F
11b,17a,21-Trihydroxy-5a-pregnane-3,20-dione / 11b,17a,21-Trihydroxyallopregnane-3,20-dione / Allopregnane-11b,17a,21-triol-3,20-dione; 4,5a-Dihydrocortisol / 5a-Dihydrohydrocortisone
Hideaki Nishino
C21H32O5 364.476 Download ChemDraw structure file
Synthesis from 17a-hydroxycorticosterone acetate as a 21-acetate: m.p. 210-212deg, [a]20/D=69deg (chloroform). (Ref. 0886) Synthesis from bismethylenedioxyhydrocortisone. Reichstein's Substance C (also can be synthesized from 3a,11b,17a,21-tetrahydroxyallopregnane-20-one and the 3b-isomer). (Ref. 0887)
234-240degC (dec.) (Ref. 0887), 219-224degC (Ref. 0885)
[a]25/D=+83deg (acetone) (Ref. 0887)
Insol in water. Sol in methanol, acetone, chloroform. (Ref. 0887)
nKBr/max: 3640, 2400, 1705 (broad)/cm (Ref. 0887)

Animals. Extraction from adrenal glands of bovine and swine. (Ref. 0885)

Hydrocortisone / Cortisol / Ala-Cort / Cremesone / Cobadex / Cort-dome / Cortef / Cortifoam / Cortril / Dome cort / Efcorbin / Efcorlin / EF-cortelan / Efcortelin / Reichstein's Substance M / Scheroson F / Sigmacort / Texacort / Demacort / Proctocort / Epicort / Ficortril / Genacort (Lotion) / Hidro-colisona / HVB / Hydro-adreson / Hydrocortisyl / Hydrocortone / Lubricort / Meusicort
11b,17,21-Trihydroxypregn-4-ene-3,20-dione-4-pregnene-11b,17a,21-triol-3,20-dione / 17-Hydroxycorticosterone
Hideaki Nishino
C21H30O5 362.460 Download ChemDraw structure file

217-220degC (anhydrous ethanol or isopropanol) commercial sample 212-213deg (Ref. 0888), 207-210degC. (Ref. 0295)
[a]22/D=+167deg (abs. ethanol), commercial sample [a]22/D=+163deg (c=0.5 in methanol) (Ref. 0295)
Sol in water (0.28 mg/ml, 25deg), ethanol (15.0 mg/ml), methanol (6.2 mg/ml), acetone (9.3 mg/ml), chloroform (1.6 mg/ml), propyleneglycol (12.7 mg/ml), ether (about 0.35 mg/ml). (Ref. 0295)
UVmax: 242nm (E1%/1cm=445) (Ref. 0889)
Complete identification in IR spectra. (Ref. 0892)

Animals. Isolation from adrenal glands. (Ref. 0295/0888) Found in urine of Cushing's syndrome accompanied with severe diabetes. (Ref. 0889) Extraction from blood in adrenal glands of dogs dosed with ACTH. (Ref. 0890) Conversion from cholesterol in adrenal glands. (Ref. 0893) Synthesis from 11-oxygenation of 11-desoxy-17-hydroxycorticosterone in Streptomyces fradiae. (Ref. 0894)

Glucocorticoid action. Application to domestic animals as adrenocortical steroid, glucocorticoid. Also applied as a topical anti-inflammatory medicine. (Ref. 0295/0888/0889/0890/0006/0891/0892/0893)

Determination of stereochemical structure. (Ref. 0006/0891) Synthesis as 21-acetate from 20-cyano-17-pregnene-21-ol-3,11-dione as a starting material: m.p. 218.5-220.5deg, [a]25/D=+150.7deg (0.5 acetone), lmax (methanol) 2420A, E1%/1cm 371, not depressed mixed m.p. by authentic sample.
Hydroxydione sodium / Hydroxydione succinate / Presuren / Viadril
21-(3-Carboxy-1-oxopropoxy)-5b-pregnane-3,20-dione sodium salt / 21-Hydroxypregnane-3,20-dione sodium hemisuccinate
Hideaki Nishino
C25H35O6Na 454.532 Download ChemDraw structure file
Synthesis as a sodium salt by Palladium-reduction and acetic anhydride-treatment of deoxycorticosterone. (Ref. 0895)
195-197degC (free acid) (Ref. 0895)
[a]20/D=+95deg (in chloroform, free acid) (Ref. 0895)
Sol in water. Also sol in mild alkaline buffer, acetone, chloroform. (Ref. 0895)
UVmax: 280nm (e=93.2) (Ref. 0895)

Soluble steroid applied to human, mouse, rat, cat, dog, and monkey as an anesthetic. AD50 21.5mg/kg, LD50 250mg/kg, TI(LD50/AD50) 11.5. More excellent than thiopental sodium (TI, 4) (i.v. injection). (Ref. 0895)

17-Hydroxy-16-methylene-D6-progesterone / 17-Hydroxy-16-methylenepregna-4,6-diene-3,20-dione / 6-Dehydro-17a-hydroxy-16-methyleneprogesterone
Hideaki Nishino
C22H28O3 340.456 Download ChemDraw structure file
Synthesis from 3b-acetoxy-16b-methyl-16a,17b-oxido-D5-pregnen-20-one as a starting material. (Ref. 0896)
196.5-197degC (methanol) (Ref. 0896)
[a]20/D=-72.5pm1deg (Ref. 0896)
Sol in benzene, caproic acid anhydride. (Ref. 0896)
UVmax: 283nm (loge=4.51) (Ref. 0896)
881, 1597, 1630, 1658, 1672 (D4,6-3-ketone), 1705 (H-bridge), 1724(20-CO), 3480(assoc,OH), 3610(free OH)/cm (Ref. 0896)

Application as an oral progestogen. (Ref. 0896)

17a-Hydroxyprogesterone 3-cyclopentyl enol ether / 3-(Cyclopentyloxy)-17-hydroxypregna-3,5-dien-20-one
Hideaki Nishino
C26H38O3 398.578 Download ChemDraw structure file
Synthesis as 17a-acetate. (Ref. 0897)
184.5-186.5degC (Ref. 0897)
[a]/D=-115deg (dioxane) (Ref. 0897)

Application as progestin. (Ref. 0897)

17a-Acetoxyprogesterone 3-cyclopentylenol ether, Gestovis, solid, m.p. 137-138deg, [a]/D=-147deg (dioxane) (Ref. 0897)
8-Isoestrone / 8a-Estrone / 8-Epiestrone
3-Hydroxy-8a-estra-1,3,5(10)-trien-17-one / D1.3.5-8-Epiestratrien-3-ol-17-one
Hideaki Nishino
C18H22O2 270.366 Download ChemDraw structure file
Preparation from isoestrone-benzoate. (Ref. 0086) Synthesis from condensation product prepared from carbinol and 2-methylcyclopenthane-1,3-dione as a starting material. (Ref. 0898)
dl-form: 254-255deg (methanol) (Ref. 0385), 247degC (Ref. 0086), 255-252degC (from acetate). (Ref. 0898)
[a]20/D=+94deg (dioxane) (Ref. 0086)

The methylester, m.p. 149-152deg, the benzoate, m.p. 197-198deg (Ref. 0385)
Hideaki Nishino
C27H39O3N 425.603 Download ChemDraw structure file
Synthesis from 3b-acetoxy-5a-etiojirv-12(13)-en-17-one as a starting material. (Ref. 0910)
243.5-244.5degC (methanol+water) (Ref. 0902), 238degC (Ref. 0906), 240-241degC (Ref. 0899)
[a]/D=-147deg (ethanol) (Ref. 0906), [a]19/D=-150deg (ethanol) (Ref. 0899), [a]20/D=-167.6deg (chloroform) (Ref. 0902)
UVmax: 250nm(e=15,000), 360nm(e=60) (Ref. 0904), l/252(14,000), 360(70). (Ref. 0906)
NMR spectra of degradated products. (Ref. 0909)

Plants. Sneeze alkaloid isolated from the roots of white hellebore, Veratrum grandiflorum (Maxim.) Loes F., V. album L., V. viride Sol., Liliaceae. (Ref. 0899/0900/0901/0902/0903/0904)

Moved to sneeze. (Ref. 0899)

Evidence for no normal steroidal skeleton in jervine by degradation into perhydrobenzfluorene derivatives. (Ref. 0905). Revised structure along with veratramine. (Ref. 0907/0908)
11-Ketoprogesterone / 11-Oxoprogesterone / U-1258 / Ketogestin
Hideaki Nishino
C21H28O3 328.445 Download ChemDraw structure file
Synthesis by reaction of corticosteron (11b,21-dihydroxypregn-4-ene-3,20-dione) with CH3C6H4SO2Cl in pyridine. (Ref. 0911)
172-174degC (Ref. 0911)
[a]/D=+238.5pm8deg (c=0.8889 in acetone) (Ref. 0911)
Insol in water. Sol in acetone, chloroform. (Ref. 0911)

Utilization to ketosis. (Ref. 0911)

N,N,N',N'-Tetramethylpregn-5-ene-3b,20a-diamine / 3b,20a-Bis(dimethylamino)-5-pregnene
Hideaki Nishino
C25H44N2 372.630 Download ChemDraw structure file

140-141degC (acetone) (Ref. 0913)
[a]20/D=-37deg (c=1.9), -36deg (c=1.112 in chloroform), [a]22/D=-17deg (c=1.050 in methanol) (Ref. 0913)

Plants. Extraction from barks of Holarrhena antidysenterica Wall., Apocynaceae. (Ref. 0912/0914)

Perhaps identical compound to sarcodinine extracted from Saracococa pruniformis Lindl., Euphorbiaceae. (Ref. 0913)
Hideaki Nishino
C25H44O2N2 404.629 Download ChemDraw structure file

218.5-221.5degC (acetone) (Ref. 0912)
[a]20/D=-4pm2deg (chloroform), +5pm2deg (c=0.001 anhydrous ethanol) (Ref. 0912)
Very sol in chloroform, methanol, ethanol, pyridine. Sparingly sol in hot acetone. Insol in ethylacetate, benzene, petroleum ether, water. (Ref. 0912)
Me2Na+C-3:J=7.71; MeNa+C-18/C-20:J=7.80 (Ref. 0915)
m+/e 71(79%), 84(100%), 156(19%), 324(24%), 389(22%; m+/e-CH3), 404(16%) (Ref. 0915)

Lupeol / Monogynol B / b-Viscol / Fagarasterol
Hideaki Nishino
C30H50O 426.717 Download ChemDraw structure file

215degC (alcohol or acetone) (Ref. 0916)
[a]20/D=+27.2deg (c=4.8 in chloroform) (Ref. 0638), [a]/D=+29deg (c=1.088) (Ref. 0917)
Sol in ether, benzene, petroleum ether, alcohol. Insol in water, dil. acid, alkali. (Ref. 0916/0917)

Mainly from plants. Cocoon of Bombyx mori. Plant terpene abundantly present in seed shells of Lupin, chicle, fig trees, and latex of rubber trees. (Ref. 0916) Isolation from Melodinus monogynus Roxb. as monogynol B. (Ref. 0918)

b-Viscol is identical to lupeol. (Ref. 0917) Monogynol B is identical to lupeol. (Ref. 0918) Total synthesis. (Ref. 0922)
Lynestrenol / 3-Desoxynorlutin / Ethinylestrenol / Exlutona / Exlutena / Orgametril / Orgametil
19-Nor-17a-pregn-4-en-20-yn-17-ol / 17a-Ethinyl-17b-hydroxyestr-4-ene / 17a-Ethynylestr-4-en-17b-ol / 17a-Ethynyl-19-nor-androst-4-en-17b-ol
Hideaki Nishino
C20H28O 284.436 Download ChemDraw structure file
Preparation method. (Ref. 0819)
158-160degC (Ref. 0819)
[a]/D=-13deg (chloroform) (Ref. 0819)

Metabolism in human. Excreted 16% in the day of dose, additional 24% excreted in 4 days, which is somewhat delayed than norethisterone. Found 3% in plasma as a conjugated form after 24 h. The half-life is 30 min. in plasma as a free form. Lynestrenol cannot be detected in urine. (Ref. 0923) Excreted 31.2 to 57.6% in 5 days after administration to human irrespective of oral or i.v. Biological half-life was 26.5 h. About 10% of metabolite in urine was excreted as a sulfate-conjugated form. Rapidly disappeared from plasma than norethisterone. (Ref. 0924)
Progestin. Oral contraceptive when taken along with mestranol. (Ref. 0819)

Medrogestone / AY62022 / Colpro / Colprone / Prothil
6,17-Dimethylpregna-4,6-diene-3,20-dione / 6,17a-Dimethyl-6-dehydroprogesterone
Hideaki Nishino
C23H32O2 340.499 Download ChemDraw structure file
Synthesis by alkylation of 16-dehydro-20-keto-pregnanes in reducing condition. (Ref. 0927) Synthesis from 3b-hydroxy-17a-methyl-5a,6a-epoxyetianic acid methyl ester as a starting material. (Ref. 0926)
144-146degC (ether). (Ref. 0926)
[a]23/D=+79deg (c=1 in chloroform) (Ref. 0926)
UVmax: 288mm (e=25,000), 289mm (e=24,900) (Ref. 0926)

Progestin activity. Same activity as 6a-methyl-17-acetoxyprogesterone in oral administration. No androgen activity. Clauberg test (relative potency): subcutaneous, 5 (progesterone=1); oral, 10 (norethindrone=1). (Ref. 0925) Progesterone exerts no effect in oral administartion, but the 6,17-substituents do. (Ref. 0926)

17-Hydroxy-6a-methylpregn-4-ene-3,20-dione / 17a-Hydroxy-6a-methylprogesterone / 6a-Methyl-17a-hydroxyprogesterone / 6a-Methyl-4-pregnen-17a-ol-3,20-dione
Hideaki Nishino
C22H32O3 344.488 Download ChemDraw structure file
Synthesis from 17a-hydroxyprogesterone bisethylene acetal as a starting material. (Ref. 0928)
220-223.5degC (chloroform) (Ref. 0928)
[a]25/D=+75deg (chloroform) (Ref. 0928)
UVmax (ethanol): 241nm (e=16,150) (Ref. 0928)

6a-Methyl-17a-hydroxyprogesterone and the acetate are the strongest progestational agents of the known compound. Application for regulation of the estruation (mating season) in domestic animals. (Ref. 0928)

The 17-acetate: m.p. 205-209deg, [a]/D=+56deg, lmax 240mm (am 15,950). (Ref. 0928)
Medrysone / Hydroxymesterone / U-8471 / HMS / Spectramedryn
11b-Hydroxy-6a-methylpregn-4-ene-3,20-dione / 11b-Hydroxy-6a-methylprogesterone / 6a-Methyl-11b-hydroxyprogesterone
Hideaki Nishino
C22H32O3 344.488 Download ChemDraw structure file
Synthesis. (Ref. 0930)
155-158degC (Ref. 0930)
[a]/D=+189deg (in chloroform) (Ref. 0930)

Application to therapy for the inflammatory in eyes as a glucocorticoid. Never increases intraocular pressure. Never brings about the reactivation of herpetic keratitis. (Ref. 0929)

Megestrol acetate / Megace / Niagestin / Ovaban
17a-Hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate / 17a-Acetoxy-6-methylpregna-4,6-diene-3,20-dione / 6-Dehydro-6-methyl-17a-acetoxy-progesterone / 6-Methyl-D4,6-pregnadien-17a-ol-3,20-dione acetate
Hideaki Nishino
C24H32O4 384.508 Download ChemDraw structure file
Synthesis from D5-pregnene-3b-17a-diol-20-one acetate as a starting material. (Ref. 0931)
218-220degC (Ref. 0931)
[a]/D=+11deg (Ref. 0931)
Water (37deg) 2mg/ml, plasma (37deg) 24mg/ml (Ref. 0931)
lmax 289mm (e=24,000) (Ref. 0931)
lKBr/max 1580, 1625, 1660, 1710, 1730/cm (Ref. 0931)

Metabolism in woman orally administered. Excreted 66.4% into urine and19.8% into feces in 7 days. (Ref. 0933) A factor regulating steroid diffusion through dimethylpolysiloxane membrane. (Ref. 0934)
Utilize as a mixture for anti-tumor medicine or oral contraceptive. Application to the progestational action, the regulation of estruation (mating season) in domestic animals. Compared with 19-nor-17a-ethynyl testosterone (norlutin) as the standard, more than 2 to 3-times higher than progestational potency (Clauberg assay, oral route) in animal experiments. (Ref. 0931) Dimethylpolysiloxane implant is the most effective application. Same activity in 1/6 to 1/25 dose as other medicine. (Ref. 0932)

Meprednisone / Betapred / Betapar / Deltacortene beta / Betalone / Deltisona B
17,21-Dihydroxy-16b-methylpregna-1,4-diene-3,11,20-trione / 16b-Methylprednisone
Hideaki Nishino
C22H28O5 372.455 Download ChemDraw structure file
Preparation by hydrolysis of 16b-methylprednisone acetate (m.p. 230-233deg, [a]CHF/D=+216deg, lMeOH/max= 238mm (15,100)) in potassium-bicarbonate-aqueous methanol. (Ref. 0633) Preparation by hydrolysis of 16b-methylprednisone 21-acetate in potassium bicarbonate. (Ref. 0935/0635) Synthesis from 5a-pregn-16-en-3b-ol-11,20-dione acetate. (Ref. 0936)
200-205degC (Ref. 0936), 195-200degC (Ref. 0633/0635), 204-210degC (Ref. 0935)
[a]/D=+200deg (dioxane) (Ref. 0936) [a]CHF/D=+205deg (Ref. 0633/0635) [a]/D=+190.2deg (Ref. 0935)
UVmax (methanol) 239nm (E1%/1cm 416) (Ref. 0936); lMeOH/max 238mm (e=14,900) (Ref. 0633); lMeOH/max 238mm (e=14,700) (Ref. 0935)
lCHF/max 2.90, 1625, 5.82, 6.00, 6.14, 6.19, 11.21m (Ref. 0635)

Glucocorticoid. High anti-inflammatory action. No salt retention in animal experiments and clinical application. (Ref. 0633/0935) In rats, 16b-methyl cortical steroids (hydrocortisone=1) compound, liver glycogen, systematic granulo A ; cortisone, 0.4, 2; hydrocortisone, 0.6, 4; prednisone, 1, 26; prednisolone, 1.5, 23; 9a-fluorohydrocortisone, 8.5, 23; 9a-fluoroprednisolone, 11, 70. They all exert no sodium retention activity in adrenalectomized rats. Except 16b-methyl forms of cortisone, hydrocortisone, and 9a-fluorohydrocortisone, show equivalent metabolic activity and anti-inflammatory action in human. (Ref. 0635) The 21-acetate possesses the same activity. (Ref. 0936)

Mestanolone / Androstalone (Roussel)
17b-Hydroxy-17-methyl-5a-androstan-3-one / 17b-Hydroxy-17a-methyl-3-androstanone / 17a-Methyl-androstan-17b-ol-3-one / 17a-Methylandrostan-3-on-17b-ol
Hideaki Nishino
C20H32O2 304.467 Download ChemDraw structure file
Yielded by oxidation of 17-methyl-3,17-androstanediol. (Ref. 0444)
192-193deg (ethyl acetate) (Ref. 0444)
Insol in water. Sol in acetone, alcohol, ether, ethylacetate. (Ref. 0444)

Androgenic activity. (Ref. 0444)

Mestranol / Norquen / Ovastol
3-Methoxy-19-nor-17a-pregna-1,3,5(10)-trien-20-yn-17-ol / 17a-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17b-ol / 17a-Ethynylestradiol 3-methylether
Hideaki Nishino
C21H26O2 310.430 Download ChemDraw structure file

150-151degC (methanol or acetone) (Ref. 0937)

Estrogenic activity, administered as an oral contraceptive in a combination. (Ref. 0937)

Methenolone / Metenolone
17b-Hydroxy-1b-methyl-5a-androst-1-en-3-one / 1-Methyl-D1-androsten-17b-ol-3-one
Hideaki Nishino
C20H30O2 302.451 Download ChemDraw structure file
Synthesis from D2'-pyrazolino-4',3':1,2-androstanol-(17b)-on-(3) (Ref. 0938)
149.5-152degC (isopropyl ether) (Ref. 0938)
[a]/D=+58.9deg. (Ref. 0938)

Anabolic action. (Ref. 0938)

6a-Methylprednisolone / Artisone-Wyeth / Medrate / Medrol / Medrone / Metastab / Metrisone / Promacortin / Suprametil / Urbason
11b,17a,21-Trihydroxy-6a-methyl-1,4-pregnadiene-3,20-dione / 1-Dehydro-6a-methylhydrocortisone / D1-6a-Methylhydrocortisone / 6a-Methyl-11b,17a,21-triol-1,4-pregnadiene-3,20-dione
Hideaki Nishino
C22H30O5 374.471 Download ChemDraw structure file
Synthesis form the 3,20-bis ethylene ketal converted from 11a-acetoxyprogesterone. (Ref. 0939) Synthesis after protection of 6-ketone by Grignard addition. (Ref. 0940)
228-237degC (Ref. 0939), 229-234degC (Ref. 0940)
[a]20/D=+83deg (dioxane) (Ref. 0939), [a]/D=+94deg (c=0.5 dioxane) (Ref. 0940)
UVmax (95% ethanol): 243nm (aM=14,875) (Ref. 0939); lmax: 244mm (E=14,500) (Ref. 0940)
lNujol/max: 5.83, 6.01, 6.19, SH.6.21m. (Ref. 0940)

Glucocorticoid action. Stronger than hydrocortisone. (Ref. 0939)

The 21-acetate, m.p. 205-208deg; [a]/D=+101deg, (dioxane), l 95% alc./max 243Mm, am=14,825 (Ref. 0939)
17-Methyltestosterone / Anertan (Tabl) / Glosso-Sterandryl / Homandren (Tebl) / Malestrone (Tebl) / Metandren / Neo-Hombreol M / Nu-Man / Orchisterone-M / Oreton-M / Perandren (Lozenges) / Synadrotabs / Testhormona / Testosid (Tabl) / Testovviron (Tabl)
17b-Hydroxy-17-methylandrost-4-en-3-one / 17a-Methyl-D4-androsten-17b-ol-3-one
Hideaki Nishino
C20H30O2 302.451 Download ChemDraw structure file
Synthesis from 17-methyl-D5,6-androstendiol-(3,17). (Ref. 0941)
161.5-164.5degC (Ref. 0941)
[a]/D=+76.4deg (alcohol) (Ref. 0941)
Sol in alcohol, methanol, ether, other organic solvents. Slightly sol in vegetable oils. Insol in water. (Ref. 0941)

Androgen activity. (Ref. 0941)

RP12,222 / Pandrocine / Penmestrol
17a-Methyltestosterone 3-cyclopentyl enol ether / 3-(Cyclopentyloxy)-17-methylandrosta-3,5-dien-17b-ol
Hideaki Nishino
C25H38O2 370.568 Download ChemDraw structure file
Preparation by enol esterification of 17-methyltestosterone. (Ref. 0897)
148-152degC (Ref. 0897)
[a]/D=-150deg (in dioxane) (Ref. 0897)

Myotropic, androgen action. Weaker in non-oral administration, reversely stronger in oral-administration (stronger 5-times more than 17a-methyltestosterone). Anti-breast cancer action (effective even by subcutaneous ingection). (Ref. 0897)

Methyltrienolone / R1881
17b-Hydroxy-17-methylestra-4,9,11-trien-3-one / 17b-Hydroxy-17-methyl-19-norandrosta-4,9,11-trien-3-one / 17a-Methyl-4,9,11-estratrien-17b-ol-3-one
Hideaki Nishino
C19H24O2 284.393 Download ChemDraw structure file
Synthesis from 3-chloro-4,5-seco 5-oxo 17-benzoxy 19-nor-androsta 2,9-diene as a starting material. (Ref. 0942)
170degC (diisopropyl ether) (Ref. 0942)
[a]20/D=-58.7deg (c=0.5 in ethanol) (Ref. 0942)

Anabolic action. (Ref. 0942)

17b-Hydroxyestr-4-en-3-one / 17b-Hydroxy-4-estren-3-one / 4-Estren-17b-ol-3-one / 17b-Hydroxy-19-nor-4-androsten-3-one
Hideaki Nishino
C18H26O2 274.398 Download ChemDraw structure file
Synthesis from alkyl ester of estradiol. (Ref. 0943) Synthesis form estrone. (Ref. 0944)
112degC and124degC, mixed m.p.123.6-124.5degC (Ref. 0944)
[a]22/D=+55pm0.6deg (c=0.93 in chloroform) (Ref. 0944)
Sol in alcohol, ether, chloroform. (Ref. 0944)
UVmax (ethanol): 240.5mm (e=17,000), 307-310mm (Ref. 0944)
lCS2/max 2.77m(OH), 6.02m (conj, C'=0) (Ref. 0944)

M/D=+151deg (Ref. 0944)

Anabolic action. (Ref. 0943/0944)

Nandrolone p-hexyloxyphenylpropionate / Nortestosterone-hexoxyphenylpropionate / Anador / Anadur
17b-[3-[4-(Hexyloxy)phenyl]-1-oxopropoxy]estr-4-en-3-one / 17b-Hydroxyestr-4-en-3-one p-(hexyloxy)hydrocinnamate / 17b-Hydroxyestr-4-en-3-one p-hexyloxyphenylpropionate / 17b-Hydroxy-19-norandrost-4-en-3-one p-hexyloxyphenyl propionate / 19-Nortestosterone-3-(p-hexyloxyphenyl)propionate
Hideaki Nishino
C33H46O4 506.716 Download ChemDraw structure file
Synthesis started by solubilization of testosterone and p-hexoxyhydrocinnamoyl anhydride in pyridine. (Ref. 0945)
53-55degC (Ref. 0945)
[a]/D=+45deg (c=1.0 in dioxane) (Ref. 0945)

Anabolic action. Improvement in the strength and duration by esterification. The improvement is dependent on the length of p-alkoxy group. (Ref. 0945)

Hideaki Nishino
C29H42O9 534.638 Download ChemDraw structure file

206-208degC (methanol+ethyl acetate) (Ref. 0947)
Sol in water, alcohol. (Ref. 0947)
lmax 217, 274mm (Ref. 0947)

Plants. Obtained by purification from extract of leaves of Nerium oleander L., Apocynaceae. (Ref. 0946)

Cardiotonic glycoside. (Ref. 0947)

Neriantin is a steroidal glycoside consisting of Neriantogenin and glucose. (Ref. 0947)
Norbolethone / WY-3475 / Genabol
DL-13-Ethyl-17-hydroxy-18,19-di-nor-17a-pregn-4-en-3-one / DL-13b,17a-Diethyl-17b-hydroxygon-4-en-3-one
Hideaki Nishino
C21H32O2 316.478 Download ChemDraw structure file
Synthesis from (pm)-13b-alkylgon-4-ene. (Ref. 0948)
144-145degC (alcohol) (Ref. 0948)
UVmax: 241nm (e=16,500) (Ref. 0948)