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Steroid
(total 479)
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(total 479)
| Id | Image | COMMON NAME | NAME | DATA No | Lipid class | INFORMANT | SYMBOL | FORMULA | MOL.WT(average) | Download cdx file / Mol format file | BIOOGICAL ACTIVITY | PHYSICAL AND CHEMICAL PROPERTIES | SPECTRAL DATA | CHROMATOGRAM DATA | SOURCE | CHEMICAL SYNTHESIS | METABOLISM | GENETIC INFORMATION | NOTE | REFERENCES | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| MELTING POINT | BOILING POINT | DENSITY | REFRACTIVE INDEX | OPTICAL ROTATION | SOLUBILITY | UV SPECTRA | IR SPECTRA | NMR SPECTRA | MASS SPECTRA | OTHER SPECTRA | |||||||||||||||||||
| 1 |  | Allocholesterol / Coprostenol / 4:5-Coprosten-3-ol | Cholest-4-en-3b-ol | SST0001 | Steroid | Hideaki Nishino | C27H46O1 | 386.654 | Download ChemDraw structure data | 132 (ether-methanol) << Ref. 0002>> | [a]23/D=+43.7 (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>> | << Ref.0001 >> AUTHOR: Windaus,A. TITLE: Umlagerung des Cholesterins JOURNAL: Justus Liebigs Ann Chem. VOLUME: 453 PAGE: 101 -112 (1927) << Ref.0002 >> AUTHOR: Schoenheimer,R., and Evans,Jr.,E.A. TITLE: Allocholesterol and Epiallocholesterol JOURNAL: J.Biol.Chem. VOLUME: 114 PAGE: 567 -582 (1936) << Ref.0003 >> AUTHOR: Stoll,W. TITLE: Untersuchungen an Sterinen 5. Über das Allocholesterin und Seinen Nachweis. JOURNAL: Z.Physiol.Chem. VOLUME: 246 PAGE: 10 -12 (1937) << Ref.0004 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp45-45, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () | ||||||||||||||
| 2 |  | Androsterone / Cis-androsterone / 3a-Hydroxy-17-androstanone / Androstan-3(a)-ol-17-one / 3(a)-Hydroxyetioallocholan-17-one / 3-Epihydroxyetioallocholan-17-one | 3a-Hydroxy-5a-androstan-17-one | SST0002 | Steroid | Hideaki Nishino | C19H30O2 | 290.440 | Download ChemDraw structure data | Androgenic activity. Sex determination in fetus. Maintenance of genitalia functions. << Ref. 0005/0006>> | 185-185.5 C << Ref. 0006>> | [a]15/D=+87.8 1.5, [a]15/5461=+107.31.5 (c=1.5379 in dioxan) << Ref. 0006>> | Sol in most organic solvents. Barely sol in water. << Ref. 0007>> | max. 292.51.0 nm, min. 232.52.5 nm (ethanol) << Ref. 0008>> | Isolation from male urine. << Ref. 0005/0006>> | Synthesis from cholesterol. << Ref. 0009/0010>> | Not precipitated by digitonin. << Ref. 0007>> | << Ref.0005 >> AUTHOR: Butenandt,A., and Tscherning,K. TITLE: Über Androsteron, ein Krystallisiertes Männliches Sexualhormon. I Isolierung und Reindarstellung aus Männerharn JOURNAL: Z.Physol.Chem. VOLUME: 229 PAGE: 167 -184 (1934) << Ref.0006 >> AUTHOR: von Euw,J., and Reichstein,T. TITLE: Über Bestandteile der NebennierenRinde und Verwandte Stoffe. 56. Mitteilung. Substanz V und Konfigurations-Bestimmungen in der C21O5-Gruppe JOURNAL: Helv.Chim.Acta VOLUME: 25 PAGE: 988 -1022 (1942) << Ref.0007 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp101-101, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0008 >> AUTHOR: Hogness,T.R., Sidwell,Jr.,A.R., and Zscheile,Jr.,F.P. TITLE: The Absorption Spectra of Compounds Related to the Sterols JOURNAL: J.Biol.Chem. VOLUME: 120 PAGE: 239 -256 (1937) << Ref.0009 >> AUTHOR: Ruzicka,L., Goldberg,M.W., and Brügger,H. TITLE: Zur Kenntnis der Sexualhormone I. Über die Gewinnung von 3-Chlor- und 3-Oxy-Ätio-Allocholanon-(17). Synthese einer Verbindung von den Eigenschaften des Testikelhormons JOURNAL: Helv.Chim.Acta VOLUME: 17 PAGE: 1389 -1394 (1934) << Ref.0010 >> AUTHOR: Marker,R.E. TITLE: Androsterone JOURNAL: J.Am.Chem.Soc. VOLUME: 57 PAGE: 1755 -1756 (1935) | |||||||||||
| 3 |  | Bufotalin | 16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide / 3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide 16-acetate | SST0003 | Steroid | Hideaki Nishino | C26H36O6 | 444.560 | Download ChemDraw structure data | Cardiotoxic steroid. Applied for Chinese medicine named Senso as cardiotonic agent. << Ref. 0011/0012/0013/0014/0015/0016>> | 269-272 C (3-acetate), 233 C (free) << Ref. 0013>> | [a]20/D=+5.4 (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>> | << Ref.0011 >> AUTHOR: Faust,E.S. TITLE: Ueber Bufonin und Bufotalin, die Wirksamen Bestandtheile des Krötenhautdüsecretes JOURNAL: Arch.Exp.Pathol.Pharmakol. VOLUME: 47 PAGE: 278 -310 (1902) << Ref.0012 >> AUTHOR: Faust,E.S. TITLE: Weitere Beiträge zur Kenntniss der Wirksamen Bestandtheile des Krötenhautdrüsensecretes. JOURNAL: Arch.Exp.Pathol.Pharmakol. VOLUME: 49 PAGE: 1 -6 (1902) << Ref.0013 >> AUTHOR: Wieland,H., and Weil,F.J. TITLE: Über das Krötengift. JOURNAL: Ber. VOLUME: 46 PAGE: 3315 -3327 (1913) << Ref.0014 >> AUTHOR: Wieland,H., Hesse,G., and Hüttel,R. TITLE: Zur Kenntnis der Krötengiftstoffe. IX. Weiteres zur Konstitutionsfrage. JOURNAL: Justus Liebigs Ann Chem. VOLUME: 524 PAGE: 203 -222 (1936) << Ref.0015 >> AUTHOR: Meyer,K. TITLE: Über Herzaktive Krötengifte (Bufogenine). 5. Mitteilung. Konstitution des Bufotalins. JOURNAL: Helv.Chim.Acta VOLUME: 32 PAGE: 1993 -2003 (1949) << Ref.0016 >> AUTHOR: Pettit,G.R., Brown,P., Bruschweiler,F., and Houghton,L.E. TITLE: Structure of the Bufadienolide Bufotalin JOURNAL: J.Chem.Soc.,Chem.Commun. VOLUME: 1970 PAGE: 1566 -1567 (1970) << Ref.0017 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp224-224, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0018 >> AUTHOR: Kamano, Y., Pettit, G. R., and Inoue, M. TITLE: Bufadienolides. 29. Synthetic routes to bufotalin PubMed ID:4412262 JOURNAL: J Org Chem. VOLUME: 39 PAGE: 3007-3013(1974) | ||||||||||
| 4 |  | Chlorogenin | 5a-Spirostan-3b,6a-diol | SST0004 | Steroid | Hideaki Nishino | C27H44O4 | 432.636 | Download ChemDraw structure data | Saponin useful as fish poisons. << Ref. 0025>> | 273-276C, 154-155C (diacetate) << Ref. 0023>> | [a]24/546 = -52 (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>> | << Ref.0019 >> AUTHOR: Marker,R.E., and Rohrmann,E. TITLE: Sterols. LVIII. The Position of the Nuclear Hydroxyl Groups in Chlorogenin. JOURNAL: J.Am.Chem.Soc. VOLUME: 61 PAGE: 946 -949 (1939) << Ref.0023 >> AUTHOR: Marker,R.E., Turner,D.L., and Ulshafer,P.R. TITLE: Sterols. CXI. Sapogenins. XL. The Conversion of Chlorogenin to Tigogenin. JOURNAL: J.Am.Chem.Soc. VOLUME: 62 PAGE: 3009 -3010 (1940) << Ref.0024 >> AUTHOR: Chakravarty,A.K., Dhar,T.K., and Pakrashi,S.C. TITLE: Hispigenin, a Novel 22bo-Spirostane from Solanum Hispidum JOURNAL: Tetrahedron Lett. VOLUME: 1978 PAGE: 3875 -3878 (1978) << Ref.0025 >> AUTHOR: Liang,P., and Noller,C.R. TITLE: Saponins and Sapogenins. III. The Sapogenins Obtained from Chlorogalum Pomeridianum JOURNAL: J.Am.Chem.Soc. VOLUME: 57 PAGE: 525 -527 (1935) | |||||||||||
| 5 |  | Cholestanol / b-Cholestanol | Dihydroxycholesterol / 3b-Hydroxycholestan / 5a-Cholestan-3b-ol | SST0005 | Steroid | Hideaki Nishino | C27H48O1 | 388.669 | Download ChemDraw structure data | Accumulation within the nervous system in cerebrotendinous xanthomatosis patients. << Ref. 0031>> | 141.5-142C << Ref. 0026>> | [a] 22/D=+28.8 << 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>> | << Ref.0026 >> AUTHOR: Willstätter,R., and Mayer,E.W. TITLE: Reduktion Mit Platin und Wasserstoff. II. Über Dihydrocholesterin. JOURNAL: Ber. VOLUME: 41 PAGE: 2199 -2203 (1908) << Ref.0027 >> AUTHOR: Ellis,G.W., and Gardner,J.A. TITLE: On b-Cholestanol, Some of Its Derivatives and Oxidation Products. JOURNAL: Biochem.J. VOLUME: 12 PAGE: 72 -80 (1918) << Ref.0028 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp341-341, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0029 >> AUTHOR: Tori,K., Komeno,T., and Nakagawa,T. TITLE: Nuclear Magnetic Resonance Studies on Steroids. III. Steroidal Epoxides and Episulfides JOURNAL: J.Org.Chem. VOLUME: 29 PAGE: 1136 -1141 (1964) << Ref.0030 >> AUTHOR: Rosenfeld, R. S. TITLE: Analysis of sterol extracts for cholestanol PubMed ID:5323673 JOURNAL: Anal Biochem. VOLUME: 12 PAGE: 483-487(1965) << Ref.0031 >> AUTHOR: Menkes, J. H., Schimschock, J. R., and Swanson, P. D. TITLE: Cerebrotendinous xanthomatosis. The storage of cholestanol within the nervous system PubMed ID:5676919 JOURNAL: Arch Neurol. VOLUME: 19 PAGE: 47-53(1968) | |||||||||||
| 6 |  | Coprostenol / 3b-Cholestanol / Stercorin | 5b-Cholestan-3b-ol | SST0006 | Steroid | Hideaki Nishino | C27H48O1 | 388.669 | Download ChemDraw structure data | 101C (methanol) << Ref. 0035>> | [a]18/D=+28 (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>> | << Ref.0002 >> AUTHOR: Schoenheimer,R., and Evans,Jr.,E.A. TITLE: Allocholesterol and Epiallocholesterol JOURNAL: J.Biol.Chem. VOLUME: 114 PAGE: 567 -582 (1936) << Ref.0032 >> AUTHOR: Bondzynski,S.T., and Humnicki,V. TITLE: Ueber das Schicksal des Cholesterins im Thierischen Organismus JOURNAL: Z.Physiol.Chem. VOLUME: 22 PAGE: 396 -410 (1896) << Ref.0033 >> AUTHOR: Wells, W. W., Coleman, D. L., and Baumann, C. A. TITLE: Intestinal sterols. I. Delta7-cholestenol and 7-dehydrocholesterol in feces PubMed ID:13259659 JOURNAL: Arch Biochem Biophys. VOLUME: 57 PAGE: 437-444(1955) << Ref.0034 >> AUTHOR: Samuel,P., Urivetzky,M., and Kaley,G. TITLE: Separation and Radioassay of Fecal Cholesterol and Coprosterol Using Thin-Layer Chromatography. JOURNAL: J.Chromatog. VOLUME: 14 PAGE: 508 -509 (1964) << Ref.0035 >> AUTHOR: Ruzicka,L., Brüngger,H., Eichenberger,E., and Meyer,J. TITLE: Polyterpene und Polyterpenoide XCI. Zur Präparativen Hersterins und Epi-Dihydro-Cholesterins. Beitrag zur Kenntnis der Räumlichen Lage der Hydroxylgruppe bei den Sterinen. JOURNAL: Helv.Chim.Acta. VOLUME: 17 PAGE: 1407 -1416 (1934) << Ref.0036 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp394-394, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0037 >> AUTHOR: Shoppee,C.W., and Summers,H.R. TITLE: Steroids and the Walden Inversion. Part VI. Reduction of Cholest-5-en-3-one with Lithium Alminum Hydride JOURNAL: J.Chem.Soc. VOLUME: 1950 PAGE: 687 -689 (1950) << Ref.0038 >> AUTHOR: Ruzicka,L., Furter,M., and Goldberg,M.W. TITLE: Über Steroide und Sexualhormone (42. Mitteilung) Zur Stereo Chemie Epimerer Steroider Alkohole Mit Einem Hydroxyl in den Stellungen 3 Odor 17. JOURNAL: Helv.Chim.Acta VOLUME: 21 PAGE: 498 -514 (1938) << Ref.0039 >> AUTHOR: Shoppee,C.W., Agashe, B.D., and Summers,G.H.R. TITLE: Steroids. Part XIII. Catalytic Hydrogenation of 3a- and 3b-Substituted D4-Steroids. JOURNAL: J.Chem.Soc. VOLUME: 1957 PAGE: 3107 -3112 (1957) << Ref.0040 >> AUTHOR: Dart,M.C., and Henbest,H.B. TITLE: Aspects of Stereochemistry. Part XV. Catalytic Hydrogenation of Cyclic Allylic Alcohols in the Presence of Sodium Nitrite. JOURNAL: J.Chem.Soc. VOLUME: 1960 PAGE: 3563 -3570 (1960) << Ref.0041 >> AUTHOR: Rosenfeld,R.S., and Gallagher,T.F. TITLE: Further Studies of the Biotransformation of Cholesterol to Coprostanol. JOURNAL: Steroids VOLUME: 4 PAGE: 515 -520 (1964) | ||||||||||||
| 7 |  | 7-Dehydrocholesterol / Provitamin D3 | Cholesta-5,7-dien-3b-ol | SST0007 | Steroid | Hideaki Nishino | 7-DHC | C27H44O1 | 384.638 | Download ChemDraw structure data | Immediate precursor to cholesterol. << Ref. 0051/0052>> | 149-150C << Ref. 0043>> | [a]20/D=-122.5(benzene), -113.6(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>> | << Ref.0008 >> AUTHOR: Hogness,T.R., Sidwell,Jr.,A.R., and Zscheile,Jr.,F.P. TITLE: The Absorption Spectra of Compounds Related to the Sterols JOURNAL: J.Biol.Chem. VOLUME: 120 PAGE: 239 -256 (1937) << Ref.0042 >> AUTHOR: Windaus,A., Lettre,H., and Schenck,Fr. TITLE: Über das 7-Dehydro-Cholesterin JOURNAL: Justus Liebigs Ann Chem. VOLUME: 520 PAGE: 98 -106 (1935) << Ref.0043 >> AUTHOR: Boer,A.G., Reerink,E.H., van Wijk,A., and van Niekerk,J. TITLE: A Naturally Occurring Chicken Provitamin-D. JOURNAL: Proc.Acad.Sci.Amsterdam VOLUME: 39 PAGE: 622 -632 (1936) << Ref.0045 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp2857-2858, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0046 >> AUTHOR: Loofbourow,J.R. TITLE: Physical Methods for Identification and Assay of Vitamins and Hormones. JOURNAL: Vitamins and Hormones VOLUME: 1 PAGE: 109 -155 (1943) << Ref.0047 >> AUTHOR: Deuel,Jr.,H.T.(1951) Distribution, Properties, and Chemistry of the Provitamins D and Vitamins D in the Lipids Their Chemistry and Biochemistry I (Deuel,Jr.,H.J., eds.), pp739-792, Interscience Publishers, New York TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0048 >> AUTHOR: Windaus,A., and Bock,F. TITLE: Über das Provitamin aus dem Sterin der Schweinschwarte. JOURNAL: Z.Physiol.Chem. VOLUME: 245 PAGE: 168 -170 (1937) << Ref.0049 >> AUTHOR: Bock,F., and Wetter,F. TITLE: Über die bei Einigen Avertebraten Vorkommenden Antirachitishen Provitamine JOURNAL: Z.Physiol.Chem. VOLUME: 256 PAGE: 33 -41 (1938) << Ref.0050 >> AUTHOR: Windaus,A. TITLE: The Antirachitic Provitamins in the Animal Kingdom JOURNAL: Nachr.Ges.Wiss.Göttingen, Math.-Physk.Klasse, Fachgruppe III VOLUME: 1 PAGE: 185 -192 (1936) << Ref.0051 >> AUTHOR: Windaus,A., Schenck,Fr., and von Werder,F. TITLE: Über das Antirachitisch Wirksame Bestrahlungsprodukt aus 7-Dehydro-Cholesterin. JOURNAL: Z.Physiol.Chem. VOLUME: 241 PAGE: 100 -103 (1936) << Ref.0052 >> AUTHOR: Windaus,A., Deppe,N., and Wunderlich,W. TITLE: Über Einige Bestrahlungsprodukte aus 7-Dehydro-Cholesterin. JOURNAL: Justus Liebigs Ann Chem. VOLUME: 533 PAGE: 118 -127 (1938) << Ref.0053 >> AUTHOR: Buisman,J.A.K., Stevens,W., and von der Vliet,J. TITLE: Investigations on Sterols. I. A New Synthesis of 7-Dehydrocholesterol (Provitamin D). JOURNAL: Rec.Trav.Chim. VOLUME: 66 PAGE: 83 -92 (1947) << Ref.0054 >> AUTHOR: Confalone,P.N., Kulesha,I.D., and Uskokovic,M.R. TITLE: A New Synthesis of 7-Dehydrocholesterols. JOURNAL: J.Org.Chem. VOLUME: 46 PAGE: 1030 -1032 (1981) << Ref.0055 >> AUTHOR: Salen, G., Shefer, S., Batta, A. K., Tint, G. S., Xu, G., Honda, A., Irons, M., and Elias, E. R. TITLE: Abnormal cholesterol biosynthesis in the Smith-Lemli-Opitz syndrome PubMed ID:8808751 JOURNAL: J Lipid Res. VOLUME: 37 PAGE: 1169-1180(1996) | ||||||||
| 8 |  | Desmosterol / 24-Dehydrocholesterol / Desmesterol | Cholesta-5,24-dien-3b-ol | SST0008 | Steroid | Hideaki Nishino | C27H44O1 | 384.638 | Download ChemDraw structure data | One of precursors to cholesterol in animals. << Ref. 0056/0057/0058>> | 120.5-121.0C (methanol) << Ref. 0057>> 117-118C. << Ref. 0059>> 120-122C << Ref. 0060>> | [a]/D=-37.9, [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), (7 10-7 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>> | << Ref.0056 >> AUTHOR: Stokes, W. M., Hickey, F. C., and Fish, W. A. TITLE: Sterol metabolism. I. The occurrence of desmosterol (24-dehydrocholesterol) in rat skin and its conversion in vivo to cholesterol PubMed ID:13549424 JOURNAL: J Biol Chem. VOLUME: 232 PAGE: 347-359(1958) << Ref.0057 >> AUTHOR: Stokes, W. M., Fish, W. A., and Hickey, F. C. TITLE: Metabolism of cholesterol in the chick embryo. II. Isolation and chemical nature of two companion sterols PubMed ID:13319360 JOURNAL: J Biol Chem. VOLUME: 220 PAGE: 415-430(1956) << Ref.0058 >> AUTHOR: Idler, D. R., Saito, A., and Wiseman, P. TITLE: Sterols in red algae (Rhodophyceae) PubMed ID:5643148 JOURNAL: Steroids. VOLUME: 11 PAGE: 465-473(1968) << Ref.0059 >> AUTHOR: Fargerlund,U.H.M., and Idler,D.R. TITLE: Marine Sterols. IV. 24-Dehydrocholesterol: Isolation from a Barnacle and Synthesis by the Wittig Reaction. JOURNAL: J.Am.Chem.Soc. VOLUME: 79 PAGE: 6473 -6475 (1957) << Ref.0060 >> AUTHOR: Dasgupta, S. K., Crump, D. R., and Gut, M. TITLE: New preparation of desmosterol PubMed ID:4853344 JOURNAL: J Org Chem. VOLUME: 39 PAGE: 1658-1662(1974) << Ref.0061 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp460-460, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0062 >> AUTHOR: Apfel,M.A. TITLE: A New Synthesis for D24-Sterols: Preparation of Cholesta-5,24-Dien-3b-Ol (Desmosterol). JOURNAL: J.Org.Chem. VOLUME: 43 PAGE: 2284 -2285 (1978) << Ref.0063 >> AUTHOR: Koreeda,M., Tanaka,Y., and Schwartz,A. TITLE: Stereochemically Controlled Synthesis of Steroid Side Chains: Synthesis of Desmosterol. JOURNAL: J.Org.Chem. VOLUME: 45 PAGE: 1172 -1174 (1980) << Ref.0064 >> AUTHOR: FitzPatrick, D. R., Keeling, J. W., Evans, M. J., Kan, A. E., Bell, J. E., Porteous, M. E., Mills, K., Winter, R. M., and Clayton, P. T. TITLE: Clinical phenotype of desmosterolosis PubMed ID:9450875 JOURNAL: Am J Med Genet. VOLUME: 75 PAGE: 145-152(1998) | |||||||
| 9 |  | a-Ecdysone | 2,3,14,22,25-Pentahydroxycholest-7-en-6-one | SST0009 | Steroid | Hideaki Nishino | C27H44O6 | 464.635 | Download ChemDraw structure data | Molting hormone of insects. << Ref. 0065/0066/0068/0069/0075>> | 238-239C << Ref. 0067/0068>> | [a]20/578 = +62 << 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-190): 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>> | << Ref.0065 >> AUTHOR: Karlson, P., Hoffmeister, H., Hummel, H., Hocks, P., and Spiteller, G. TITLE: [On the chemistry of ecdysone. VI. Reactions of ecdysone molecules] PubMed ID:5849855 JOURNAL: Chem Ber. VOLUME: 98 PAGE: 2394-2402(1965) << Ref.0066 >> AUTHOR: Huber, R., and Hoppe, W. TITLE: [On the chemistry of ecdysone. VII. Analysis of the crystal and molecular structure of the molting hormone in insects, ecdysone, using the automized folding molecule method] PubMed ID:5849856 JOURNAL: Chem Ber. VOLUME: 98 PAGE: 2403-2424(1965) << Ref.0067 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp547-547, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0068 >> AUTHOR: Mori,H., Shibata,K., Tsuneda,K., and Sawai,M. TITLE: Synthesis of Ecdysone. JOURNAL: Chem.Pharm.Bull. VOLUME: 16 PAGE: 563 -566 (1968) << Ref.0069 >> AUTHOR: Kaplanis, J. N., Thompson, M. J., Robbins, W. E., and Bryce, B. M. TITLE: Insect hormones: alpha ecdysone and 20-hydroxyecdysone in bracken fern PubMed ID:6037858 JOURNAL: Science. VOLUME: 157 PAGE: 1436-1438(1967) << Ref.0070 >> AUTHOR: Siddall, J. B., Marshall, J. P., Bowers, A., Cross, A. D., Edwards, J. A., and Fried, J. H. TITLE: Synthetic studies on insect hormones. I. Synthesis of the tetracyclic nucleus of ecdysone PubMed ID:5900550 JOURNAL: J Am Chem Soc. VOLUME: 88 PAGE: 379-380(1966) << Ref.0071 >> AUTHOR: Kerb, U., Schulz, G., Hocks, P., Wiechert, R., Furlenmeier, A., Furst, A., Langemann, A., and Waldvogel, G. TITLE: [On the synthesis of ecdysone. IV. On insect hormones. The synthesis of the natural skin shedding hormone] PubMed ID:5924992 JOURNAL: Helv Chim Acta. VOLUME: 49 PAGE: 1601-1606(1966) << Ref.0072 >> AUTHOR: Butenandt,A., and Karlson,P. TITLE: Über die Isolierung eines Metamorphose-Hormons der Insekten in Kristallisierter Form. JOURNAL: Z.Natureforsch VOLUME: 9 PAGE: 389 -391 (1954) << Ref.0073 >> AUTHOR: Heinrich, G., and Hoffmeister, H. TITLE: [Ecdysone as companion substance of ecdysterone in Polypodium vulgare L] PubMed ID:6077902 JOURNAL: Experientia. VOLUME: 23 PAGE: 995-(1967) << Ref.0074 >> AUTHOR: Iddall, J. B., Cross, A. D., and Fried, J. H. TITLE: Steroids. CCXCII. Synthetic studies on insect hormones. II. The synthesis of ecdysone PubMed ID:5902567 JOURNAL: J Am Chem Soc. VOLUME: 88 PAGE: 862-863(1966) << Ref.0075 >> AUTHOR: Ashburner, M. TITLE: Chromosomal action of ecdysone PubMed ID:6250033 JOURNAL: Nature. VOLUME: 285 PAGE: 435-436(1980) | |||||||||
| 10 |  | b-Ecdysone / 20-Hydroxyecdysone / Ecdysterone / Crustecdysone / Isoinokosterone | 2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one | SST0010 | Steroid | Hideaki Nishino | C27H44O7 | 480.634 | Download ChemDraw structure data | Molting and metamorphosis hormone for Insecta and Crustacea. Much potent than a-ecdysone. << Ref. 0077>> | 240-242C (methanol-ethylacetate) << Ref. 0079>> | [a]28/D = +63(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>> | << Ref.0067 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp547-547, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0076 >> AUTHOR: Dammeier, B., and Hoppe, W. TITLE: [The crystal and molecular structure analysis of the insectmoulting hormone 20-hydroxyecdysone (Ecdysterone)] PubMed ID:5154405 JOURNAL: Chem Ber. VOLUME: 104 PAGE: 1660-1673(1971) << Ref.0077 >> AUTHOR: Hocks,P., and Wiechert,R. TITLE: 20-Hydroxy-Ecdyson, Isoliert aus Insekten. JOURNAL: Tetrahedron Lett. VOLUME: 1966 PAGE: 2989 -2993 (1966) << Ref.0078 >> AUTHOR: Hampshire,F., and Horn,D.H.S. TITLE: Structure of Crustecdysone, a Crustacean Moulting Hormone. JOURNAL: J.Chem.Soc., Chem Commun. VOLUME: 1966 PAGE: 37 -38 (1966) << Ref.0079 >> AUTHOR: Hüppi,G., and Siddall,J.B. TITLE: Steroids. CCCXXXIII. Synthetic Studies on Insect Hormones. V. The Synthesis of Crustecdysone (20-Hydroxyecdysone). JOURNAL: J.Am.Chem.Soc. VOLUME: 89 PAGE: 6790 -6792 (1967) << Ref.0080 >> AUTHOR: Takemoto,T., Ogawa,S., and Nishimoto,N. TITLE: Isolation of the Moulting Hormones of Insects from Achyranthis Radix. JOURNAL: Yakugaku Zasshi VOLUME: 87 PAGE: 325 -327 (1967) << Ref.0081 >> AUTHOR: Galbraith,M.N., and Horn,D.H.S. TITLE: An Insect-Moulting Hormone from a Plant. JOURNAL: J.Chem.Soc., Chem.Commun. VOLUME: 1966 PAGE: 905 -906 (1966) << Ref.0082 >> AUTHOR: Horn, D. H., Fabbri, S., Hampshire, F., and Lowe, M. E. TITLE: Isolation of crustecdysone (20R-hydroxyecdysone) from a crayfish (Jasus lalandei H. Milne-Edwards) PubMed ID:5685865 JOURNAL: Biochem J. VOLUME: 109 PAGE: 399-406(1968) << Ref.0083 >> AUTHOR: Kerb,U., Wiechert,R., Furlenmeier,A., and Fürst,A. TITLE: Über eine Synthese des Crustecdysons (20-Hydroxyecdyson). JOURNAL: Tetrahedron Lett. VOLUME: 1968 PAGE: 4277 -4280 (1968) << Ref.0084 >> AUTHOR: Mori, H., and Shibata, K. TITLE: Synthesis of ecdysterone PubMed ID:5347599 JOURNAL: Chem Pharm Bull (Tokyo). VOLUME: 17 PAGE: 1970-1973(1969) << Ref.0085 >> AUTHOR: Kametani,T., Tsubuki,M., and Nemoto,H. TITLE: A Stereocontrolled Total Synthesis of 2b,3b,20b-Triacetoxy-5a-Pregnan-6-One. A Total Synthesis of 20-Hydroxyecdysone. JOURNAL: Tetrahedron Lett. VOLUME: 21 PAGE: 4855 -4856 (1980) | ||||||||
| 11 |  | Equilin | 3-Hydroxyestra-1,2,5(10),7-tetraen-17-one / 1,3,5,7-Estratetraen-3-ol-17-one | SST0011 | Steroid | Hideaki Nishino | C18H20O2 | 268.350 | Download ChemDraw structure data | Weaker than estron, stronger than estriol. << Ref. 0091>> Clinically available because of mild estrogenic hormone activity. << Ref. 0093>> | 237-239C << Ref. 0087>> 238-240C << Ref. 0088>> 237-240C << Ref. 0089>> | [a]15/D=+308 (dioxane) << Ref. 0088>> [a]25/D=+304(dioxane) << Ref. 0087>> [a]/D=+295(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>> | << Ref.0087 >> AUTHOR: Pearlman,W.H., and Wintersteiner,O. TITLE: Estrogens with Oxygen in Ring B I. 7-Ketoestrone and 7-Hydroxyestrone. JOURNAL: J.Biol.Chem. VOLUME: 130 PAGE: 35 -45 (1939) << Ref.0088 >> AUTHOR: Girard,A., Sandulesco,G., Fridenson,A., and Rutgers,J.-J. TITLE: Sur Une Nouvelle Hormone Sexuelle Cristallisee. JOURNAL: Compt.rend. VOLUME: 195 PAGE: 981 -984 (1932) << Ref.0089 >> AUTHOR: Zderic,J.A., Bowers,A., Carpio,H., and Djerassi,C. TITLE: Steroids. XCVI. The Synthesis of Equilin. JOURNAL: J.Am.Chem.Soc. VOLUME: 80 PAGE: 2596 -2597 (1958) << Ref.0090 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp570-570, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0091 >> AUTHOR: Cartland,G.F., and Meyer,R.K. TITLE: A Study of Equilin Prepared from Pregnant Mare Urine. JOURNAL: J.Biol.Chem. VOLUME: 112 PAGE: 9 -14 (1935) << Ref.0092 >> AUTHOR: Bagri,J.F., Morand,P.F., Wiesner,K., and Gaudry,R. TITLE: A Simple Synthesis of Equilin. JOURNAL: Tetrahedron Lett. VOLUME: 1964 PAGE: 387 -389 (1964) << Ref.0093 >> AUTHOR: Stein,R.P., Buzby,Jr.,G.C., and Smith,H. TITLE: A New Total Synthesis of Equilin. JOURNAL: Tetrahedron Lett. VOLUME: 1966 PAGE: 5015 -5020 (1966) << Ref.0094 >> AUTHOR: Stein, R. P., Buzby, G. C., Jr., and Smith, H. TITLE: Totally synthetic steroid hormones. XX. Novel total syntheses of equilin and equilenin PubMed ID:5433528 JOURNAL: Tetrahedron. VOLUME: 26 PAGE: 1917-1933(1970) << Ref.0095 >> AUTHOR: Bailey,E.J., Gale,A., Phillipps,G.H., Siddons,P.T., and Smith,G. TITLE: Syntheses of Equilenin, Equilin, and 17b-Hydroxyoestr-4-En-3-One. JOURNAL: J.Chem.Soc., Chem.Commun. VOLUME: 1967 PAGE: 1253 -1254 (1967) << Ref.0096 >> AUTHOR: Marshall,D.J., and Deghenghi,R. TITLE: A New Direct Synthesis of Equilin from Equilenin. Potassium-Ammonia Reduction of Some Non-Conjugated Double Bonds. JOURNAL: Can.J.Chem. VOLUME: 47 PAGE: 3127 -3131 (1969) | ||||||||||||
| 12 |  | Ergosterol / Ergosterin / Provitamin D2 | Ergosta-5,7,22-trien-3b-ol | SST0012 | Steroid | Hideaki Nishino | C28H44O1 | 396.648 | Download ChemDraw structure data | Antirachitic activity as 1,25-dihydroxyergocalciferol. << Ref. 0102>> | 168C (alcohol) << Ref. 0098>> | bp0.01 = 250C << Ref. 0098>> | [a] 20/D=-135 (c=1.2 in chloroform), [a] 20/546=-171(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>> | << Ref.0008 >> AUTHOR: Hogness,T.R., Sidwell,Jr.,A.R., and Zscheile,Jr.,F.P. TITLE: The Absorption Spectra of Compounds Related to the Sterols JOURNAL: J.Biol.Chem. VOLUME: 120 PAGE: 239 -256 (1937) << Ref.0046 >> AUTHOR: Loofbourow,J.R. TITLE: Physical Methods for Identification and Assay of Vitamins and Hormones. JOURNAL: Vitamins and Hormones VOLUME: 1 PAGE: 109 -155 (1943) << Ref.0050 >> AUTHOR: Windaus,A. TITLE: The Antirachitic Provitamins in the Animal Kingdom JOURNAL: Nachr.Ges.Wiss.Göttingen, Math.-Physk.Klasse, Fachgruppe III VOLUME: 1 PAGE: 185 -192 (1936) << Ref.0097 >> AUTHOR: Chung,C.K. TITLE: Über die Konstitution des Ergosterins. JOURNAL: Justus Liebigs Ann Chem. VOLUME: 500 PAGE: 270 -280 (1933) << Ref.0098 >> AUTHOR: Bills,C.E., and Honeywell,E.M. TITLE: Antiricketic Substances. VIII. Studies on Highly Purified Ergosteroles and Its Esters. JOURNAL: J.Biol.Chem. VOLUME: 80 PAGE: 15 -23 (1928) << Ref.0099 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp574-574, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0100 >> AUTHOR: Bills,C.E. TITLE: Physiology of the Sterols, Including Vitamin D. JOURNAL: Physiol.Rev. VOLUME: 15 PAGE: 1 -97 (1935) << Ref.0101 >> AUTHOR: Tanret,C. TITLE: Ergosterol and Fongisterol. JOURNAL: Ann.Chim.Phys. VOLUME: 15 PAGE: 313 -330 (1908) << Ref.0102 >> AUTHOR: Bekemeier, H., and Benad, A. TITLE: [On the annual rhythm of the efficacy of antirachitic and toxic doses of vitamin D] PubMed ID:5321600 JOURNAL: Int Z Vitaminforsch. VOLUME: 35 PAGE: 247-257(1965) | ||||||||||
| 13 |  | 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 | Estra-1,3,5(10)-triene-3b,17b-diol | SST0013 | Steroid | Hideaki Nishino | C18H24O2 | 272.382 | Download ChemDraw structure data | Most potent estrogenic activity. << Ref. 0103>> | 173-179C << Ref. 0104>> | [a]25/D= from +76 to +83(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>> | << Ref.0103 >> AUTHOR: Maccorquodale,D.W., Thayer,S.A., and Doisy,E.A. TITLE: The Isolation of the Principal Estrogenic Substance of Liquor Folliculi. JOURNAL: J.Biol.Chem. VOLUME: 115 PAGE: 435 -448 (1936) << Ref.0104 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp583-583, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0105 >> AUTHOR: Sober,H.A., (1968) Section F Steroids in Handbook of Biochemistery Selected Data for Molecular Biology (Sober,H.A., eds.) ppF11-F11, The Chemical Rubber, Cleveland TITLE: JOURNAL: VOLUME: PAGE: - () << Ref.0106 >> AUTHOR: Eder,U., Gibian,H., Haffer,G., Neef,G., Sauer,G., and Wiechert,R. TITLE: Total Synthesis of Optically Active Steroids, XIV Synthesis of Estradiol. JOURNAL: Chem.Ber. | ||||||||||