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Steroid


DATA No : SST0008 INFORMANT : Hideaki Nishino

NAME : Cholesta-5,24-dien-3b-ol

COMMON NAME: Desmosterol / 24-Dehydrocholesterol / Desmesterol
SYMBOL:
FORMULA: C27H44O1 MOL.WT (average) : 384.638


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BIOLOGICAL ACTIVITY
One of precursors to cholesterol in animals. (Ref. 0056/0057/0058)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:120.5-121.0degC (methanol) (Ref. 0057) 117-118degC. (Ref. 0059) 120-122degC (Ref. 0060)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]/D=-37.9deg, [a]27/D=-40.2 (c=1 in chloroform) (Ref. 0057)

DENSITY:

SOLUBILITY:Sol in ether, benzene, chloroform, ethanol. (Ref. 0061)
SPECTRAL DATA
UV SPECTRA: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)

IR SPECTRA:1125, 1012, 900 cm-1 (THP ether) (Ref. 0057/0058/0060)

NMR SPECTRA: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)

MASS SPECTRA: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)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Rat skin (Ref. 0056) Chick embryo (Ref. 0057) Red algae (Rhodophyceae) (Ref. 0058) Barnacle (Ref. 0059)
CHEMICAL SYNTHESIS
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)
METABOLISM

GENETIC INFORMATION
Possibly excess accumulation relates to lethal multiple malformations. (Ref. 0064)
NOTE
Conversion to cholesterol in vivo. (Ref. 0056)
REFERENCES
[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.
VOL:232 PAGE : 347-359 (1958)
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[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.
VOL:220 PAGE : 415-430 (1956)
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[0058]
AUTHOR:Idler, D. R., Saito, A., and Wiseman, P.
TITLE:Sterols in red algae (Rhodophyceae) PubMed ID:5643148
JOURNAL:Steroids.
VOL:11 PAGE : 465-473 (1968)
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[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.
VOL:79 PAGE : 6473 -6475 (1957)
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[0060]
AUTHOR:Dasgupta, S. K., Crump, D. R., and Gut, M.
TITLE:New preparation of desmosterol PubMed ID:4853344
JOURNAL:J Org Chem.
VOL:39 PAGE : 1658-1662 (1974)
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[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:
VOL: PAGE : - ()
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[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.
VOL:43 PAGE : 2284 -2285 (1978)
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[0063]
AUTHOR:Koreeda,M., Tanaka,Y., and Schwartz,A.
TITLE:Stereochemically Controlled Synthesis of Steroid Side Chains: Synthesis of Desmosterol.
JOURNAL:J.Org.Chem.
VOL:45 PAGE : 1172 -1174 (1980)
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[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.
VOL:75 PAGE : 145-152 (1998)
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