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Steroid


DATA No : SST9128 INFORMANT : Etsuko Yasugi

NAME : (22E,24R)-24-methyl-5a-cholesta-7,22-dien-3b-ol

COMMON NAME: 5,6-dihydroergosterol
SYMBOL:
FORMULA: C28H46O1 MOL.WT (average) : 398.664


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:174-175degC (Ref. 9155), acetate 185-187degC (Ref. 9219)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:-21deg (Ref. 9155), acetate -23.4deg (Ref. 9213)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:free : 968, 1660, 3020, 3040, 3610cm-1 (Ref. 9217)

NMR SPECTRA:free:1H-NMR(CDCl3): 3-CH=3.60(M), 7-CH=5.15(M), 18-CH3=0.54(S), 19-CH3=0.80(S), 21-CH3=1.02(D), 22-CH AND 23-CH=5.18(M), 26-CH3=0.84(D), 27-CH3=0.82(D), 28-CH3=0.91(D) (Ref. 9149)

MASS SPECTRA:free : 397[M+](16%),383(6%),355(12%),300(10%),299(7%),271(100%),255(26%),246(20%),231(10%),229(16%),213(12%) (Ref. 9123) acetate: 440[M+](53%),425(14%),397(10%),380(10%),365(10%),342(23%), 315(34%),313(100%),299(10%),288(30%),273(10%),25

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
yeast (Ref. 9103), Cleodendron plants(Ref. 9117), Cucurbitaceae plants (Ref. 9151), Porifera Axinella cannabina (Ref. 9149), Haliclona flavescens (Ref. 9220) , chlorella: chlorella vulgaris (Ref. 9219), C.ellipsoidea metabolite (Ref. 9217), Basidiomycetes (Astraeus hygrometricus) (Ref. 9221)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[9103]
AUTHOR:Brooks,C.J.W. (1970) Steroids: Sterols and Bile Acids, in Rodd's Chemistry of Carbon Compounds (Coffey,S. ed) pp1 - 196, Elsevier Publishing Co., Amsterdam
TITLE:
JOURNAL:
VOL: PAGE : 1 -196 (1970)
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[9117]
AUTHOR:Akihisa, T., Matsubara, Y., Ghosh, P., Thakur, S., Tamura, T., and Matsumoto, T.
TITLE:Sterols of some Clerodendrum species (Verbenaceae): occurrence of the 24 alpha- and 24 beta-epimers of 24-ethylsterols lacking a delta 25-bond PubMed ID:2799860
JOURNAL:Steroids.
VOL:53 PAGE : 625-638 (1989)
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[9123]
AUTHOR:Jeong, T. M., Ito, T., Tamura, T., and Matsumoto, T.
TITLE:Sterols from a species of Pichia, a n-alkane-utilizing yeast PubMed ID:1154452
JOURNAL:Steroids.
VOL:25 PAGE : 741-751 (1975)
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[9149]
AUTHOR:Itoh,T., Sica,D., and Djerassi,C.
TITLE:Minor and Trace Sterols in Marine Invertebrates. Part 35. Isolation and Structure Elucidation of Seventy-Four Sterols from the Sponge Axinella Cannabina.
JOURNAL:J. Chem. Soc., Perkin Trans. I
VOL: PAGE : 147 -153 (1983)
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[9151]
AUTHOR:Akihisa,T., Thakur,S., Rosenstein,F.U., and Matsumoto,T.
TITLE:Sterols of Cucurbitaceae: the Configuration at C-24 of 24-Alkyl-D5-,D7- and D8-Sterols.
JOURNAL:Lipids
VOL:21 PAGE : 39 -47 (1986)
[TOP]

[9155]
AUTHOR:Akihisa,T., Kojima,S., Yokota,T., and Tamura,T.
TITLE:24-Methylene-25-Methylcholesterol and Both C-24 Epimers of 24-Ethyl-22-Dehydrocholesterol in a Freshwater Green Alga Hydrodictyon Reticulatum.
JOURNAL:Phytochemistry
VOL:30 PAGE : 3621 -3624 (1991)
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[9213]
AUTHOR:Kobayashi,M., Tsuru,R., Todo,K., and Mitsuhashi,H.
TITLE:Marine Sterols-II. Asterosterol, a New C26 Sterol from Asterias Amurensis Lutken.
JOURNAL:Tetrahedron
VOL:29 PAGE : 1193 -1196 (1973)
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[9217]
AUTHOR:Dickson,L.G., Patterson,G.W., Cohen,C.F., and Dutky,S.R.
TITLE:Two Novel Sterols from Inhibited Chlorella Ellipsoidea.
JOURNAL:Phytochemistry
VOL:11 PAGE : 3473 -3477 (1972)
[TOP]

[9219]
AUTHOR:Akihisa,T., Hori,T., Suzuki,H., Sakoh,T., Yokota,T., and Tamura,T.
TITLE:24b-Methyl-5a-Cholest-9(11)-en-3b-ol,Two 24b-Alkyl-D5,7,9(11)-Sterols and Other 24b-Alkylsterols from Chlorella Vulgaris.
JOURNAL:Phytochemistry
VOL:31 PAGE : 1769 -1772 (1992)
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[9220]
AUTHOR:Zielinski, J., Milkova, T., Popov, S., Marekov, N., and Djerassi, C.
TITLE:Minor and trace sterols in marine invertebrates. Isolation and structure elucidation of 24-methyl-5 alpha-cholesta-7,9(11), 24(28)-trien-3 beta-ol, the first naturally occurring delta 7,9(11) unsaturated marine sterol PubMed ID:7157438
JOURNAL:Steroids.
VOL:39 PAGE : 675-680 (1982)
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[9221]
AUTHOR:Takaishi,Y., Murakami,Y., Ohashi,T., Nakano,K., Murakami,K., and Tomimatsu,T.
TITLE:Three Triterpenes from Astraeus Hygrometricus.
JOURNAL:Phytochemistry
VOL:26 PAGE : 2341 -2344 (1987)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.