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Steroid


DATA No : SST9036 INFORMANT : Etsuko Yasugi

NAME : 5b,6b-epoxycholestan-3b-ol (5b,6b-epoxycholesterol)

COMMON NAME:
SYMBOL:
FORMULA: C27H46O2 MOL.WT (average) : 402.653


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BIOLOGICAL ACTIVITY
biotoxicity of oxidized cholesterol : cytotoxicity (Ref. 9073/9074/9075/9076), angiotoxicity (Ref. 9077), mutagenicity (Ref. 9078/9079/9080), carcinogenicity (Ref. 9081), other effects (Ref. 9082/9083/9084/9085)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:OH group : 3600cm-1 (Ref. 9092/9060)

NMR SPECTRA:

MASS SPECTRA:EI-MS (Ref. 9092) GC-EI-MS(Ref. 9091) GC-EI-MS(TMS) M/E=474[M], 459[M-CH3], 384[M-HOTMS], 366, 351(Ref. 9090)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
auto-oxidation of cholesterol (Ref. 9065/9066/9067/9092), photo-oxidation of egg yolk lipid (Ref. 9060), human serum (Ref. 9089), reaction product of rat liver microsomes and cholesterol (Ref. 9069), In reaction mixture of rat sub-hepatic cells and cholesterol (Ref. 9090), reaction product of bovine liver microsomes and cholesterol
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[9060]
AUTHOR:Chicoye,E., Powrie,W.D., and Fennema,O.
TITLE:Photoxidation of Cholesterol in Spray-Dried Egg Yolk Upon Irradiation.
JOURNAL:J. Food Sci.
VOL:33 PAGE : 581 -587 (1968)
[TOP]

[9065]
AUTHOR:Fioriti, J. A., and Sims, R. J.
TITLE:Autoxidation products from cholesterol PubMed ID:6041381
JOURNAL:J Am Oil Chem Soc.
VOL:44 PAGE : 221-224 (1967)
[TOP]

[9066]
AUTHOR:Maerker,G., and Bunick,F.J.
TITLE:Cholesterol Oxides II. Measurement of the 5,6-Epoxides During Cholesterol Oxidation in Aqueous Disoersions.
JOURNAL:J. Am. Oil Chem. Soc.
VOL:63 PAGE : 771 -777 (1986)
[TOP]

[9067]
AUTHOR:Maerker,G.
TITLE:Cholesterol Autoxidation-Current Status.
JOURNAL:J. Am. Oil Chem. Soc.
VOL:64 PAGE : 388 -392 (1987)
[TOP]

[9069]
AUTHOR:Aringer, L., Eneroth, P., and Nordstrom, L.
TITLE:Side chain hydroxylation of cholesterol, campesterol and beta-sitosterol in rat liver mitochondria PubMed ID:932558
JOURNAL:J Lipid Res.
VOL:17 PAGE : 263-272 (1976)
[TOP]

[9073]
AUTHOR:Peng, S. K., Taylor, C. B., Tham, P., Werthessen, N. T., and Mikkelson, B.
TITLE:Effect of auto-oxidation products from cholesterol on aortic smooth muscle cells: an in vitro study PubMed ID:579964
JOURNAL:Arch Pathol Lab Med.
VOL:102 PAGE : 57-61 (1978)
[TOP]

[9074]
AUTHOR:Baranowski, A., Adams, C. W., High, O. B., and Bowyer, D. B.
TITLE:Connective tissue responses to oxysterols PubMed ID:7066074
JOURNAL:Atherosclerosis.
VOL:41 PAGE : 255-266 (1982)
[TOP]

[9075]
AUTHOR:Hill, J. C., Peng, S. K., Morin, R. J., and Taylor, C. B.
TITLE:Effects of cholesterol autoxidation derivatives on hexose transport in cultured aortic smooth muscle cells PubMed ID:6479295
JOURNAL:Exp Mol Pathol.
VOL:41 PAGE : 249-257 (1984)
[TOP]

[9076]
AUTHOR:Peng, S. K., Taylor, C. B., Hill, J. C., and Morin, R. J.
TITLE:Cholesterol oxidation derivatives and arterial endothelial damage PubMed ID:3986012
JOURNAL:Atherosclerosis.
VOL:54 PAGE : 121-133 (1985)
[TOP]

[9077]
AUTHOR:Tokuyasu, K., Imai, H., Taura, S., Cho, B. H., and Kummerow, F. A.
TITLE:Aortic lesions in nonlaying hens with endogenous hyperlipidemia PubMed ID:6892521
JOURNAL:Arch Pathol Lab Med.
VOL:104 PAGE : 41-45 (1980)
[TOP]

[9078]
AUTHOR:Smith, L. L., Smart, V. B., and Ansari, G. A.
TITLE:Mutagenic cholesterol preparations PubMed ID:386108
JOURNAL:Mutat Res.
VOL:68 PAGE : 23-30 (1979)
[TOP]

[9079]
AUTHOR:Ansari, G. A., Walker, R. D., Smart, V. B., and Smith, L. L.
TITLE:Further investigations of mutagenic cholesterol preparations PubMed ID:7040182
JOURNAL:Food Chem Toxicol.
VOL:20 PAGE : 35-41 (1982)
[TOP]

[9080]
AUTHOR:Sevanian, A., and Peterson, A. R.
TITLE:Cholesterol epoxide is a direct-acting mutagen PubMed ID:6588383
JOURNAL:Proc Natl Acad Sci U S A.
VOL:81 PAGE : 4198-4202 (1984)
[TOP]

[9081]
AUTHOR:Bischoff, F., and Bryson, G.
TITLE:The pharmacodynamics and toxicology of steroids and related compounds PubMed ID:335852
JOURNAL:Adv Lipid Res.
VOL:15 PAGE : 61-157 (1977)
[TOP]

[9082]
AUTHOR:Peng, S. K., Tham, P., Taylor, C. B., and Mikkelson, B.
TITLE:Cytotoxicity of oxidation derivatives of cholesterol on cultured aortic smooth muscle cells and their effect on cholesterol biosynthesis PubMed ID:34998
JOURNAL:Am J Clin Nutr.
VOL:32 PAGE : 1033-1042 (1979)
[TOP]

[9083]
AUTHOR:Parsons, P. G., and Goss, P.
TITLE:Chromosome damage and DNA repair induced in human fibroblasts by UV and cholesterol oxide PubMed ID:708320
JOURNAL:Aust J Exp Biol Med Sci.
VOL:56 PAGE : 287-296 (1978)
[TOP]

[9084]
AUTHOR:Peng, S. K., Taylor, C. B., Mosbach, E. H., Huang, W. Y., Hill, J., and Mikkelson, B.
TITLE:Distribution of 25-hydroxycholesterol in plasma lipoproteins and its role in atherogenesis. A study in squirrel monkeys PubMed ID:7066085
JOURNAL:Atherosclerosis.
VOL:41 PAGE : 395-402 (1982)
[TOP]

[9085]
AUTHOR:Peng, S. K., Hill, J. C., Morin, R. J., and Taylor, C. B.
TITLE:Influence of cholesterol oxidation derivatives on membrane bound enzymes in cultured aortic smooth muscle cells PubMed ID:2994076
JOURNAL:Proc Soc Exp Biol Med.
VOL:180 PAGE : 126-132 (1985)
[TOP]

[9089]
AUTHOR:Gray,M.F., Lawrie,T.D.V., and Brooks,C.J.W.
TITLE:Isolation and Identification of Cholesterol A-Oxide and Other Sterols in Human Serum. PubMed ID:5127479
JOURNAL:Lipids
VOL:6 PAGE : 836 -843 (1971)
[TOP]

[9090]
AUTHOR:Aringer,L., and Eneroth,P.
TITLE:Formation and Metabolism In Vitro of 5,6-Epoxides of Cholesterol and b-Sitosterol. PubMed ID:4152888
JOURNAL:J. Lipid Res.
VOL:15 PAGE : 389 -398 (1974)
[TOP]

[9091]
AUTHOR:Watabe, T., Kanai, M., Isobe, M., and Ozawa, N.
TITLE:The hepatic microsomal biotransformation of delta 5-steroids to 5 alpha, 6 beta-glycols via alpha- and beta-epoxides PubMed ID:7204381
JOURNAL:J Biol Chem.
VOL:256 PAGE : 2900-2907 (1981)
[TOP]

[9092]
AUTHOR:Chicoye,E., Powrie,W.D., and Fennema,O.
TITLE:Isolation and Characterization of Cholesterol -5b,6b-Oxide from an Aerated Aqueous Dispersion of Cholesterol.
JOURNAL:Lipids
VOL:3 PAGE : 335 -339 (1968)
[TOP]

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