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Steroid


DATA No : SST9127 INFORMANT : Etsuko Yasugi

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

COMMON NAME: stellasterol
SYMBOL:
FORMULA: C28H46O1 MOL.WT (average) : 398.664


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:159-160degC (Ref. 9155), acetate 181-182degC (Ref. 9213)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:+18deg(Ref. 9155), acetate +6.4deg (Ref. 9213)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:free = 970, 3300-3400cm-1 (Ref. 9214) acetate = 967, 1663cm-1 (Ref. 9213)

NMR SPECTRA:free:1H-NMR(CDCl3): 3-CH=3.60(M), 7-CH=5.16(M), 18-CH3=0.54(S), 19-CH3=0.80(S), 21-CH3=1.01(D), 22-CH AND 23-CH=5.16(M), 26-CH3=0.84(D), 27-CH3=0.82(D), 28-CH3=0.91(D) (Ref. 9149)

MASS SPECTRA:free : 398[M+](22%),383(8%),365(1%),355(3%),300(13%),299(10%),271(100%),255(34%),246(25%),231(13%),229(20%),213(17%) (Ref. 9149) acetate : 440[M+](47%),425(16%),397(9%),380(6%),365(11%),342(21%),337(7%),313(100%),288(25%),273(7%),255(64%),253(1

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Porifera Axinella cannabina (Ref. 9149), Asteroidea :Asterias amurensis (Ref. 9213), A.rubens (spatial arrangement at C-24 unknown) (Ref. 9216), Cucurbitaceae plants(Ref. 9151/9215)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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)
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[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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[9214]
AUTHOR:Anastasia,M., and Fiecchi,A.
TITLE:Stereospecific Synthesis of the Marine Sterol Stellasterol,(22e,24s)-5a-Ergosta-7,22-Dien-3b-ol.
JOURNAL:J. Org. Chem.
VOL:46 PAGE : 1726 -1728 (1981)
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[9215]
AUTHOR:Matsumoto,T., Shigemoto,T., and Itoh,T.
TITLE:(22E,24S)-5a-Ergosta-7,22-Dien-3b-ol from the Seeds of Cucumis Sativus.
JOURNAL:Phytochemistry
VOL:22 PAGE : 1300 -1301 (1983)
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[9216]
AUTHOR:Smith, A. G., Rubinstein, I., and Goad, L. J.
TITLE:The sterols of the echinoderm Asterias rubens PubMed ID:4772271
JOURNAL:Biochem J.
VOL:135 PAGE : 443-455 (1973)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.