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Steroid


DATA No : SST9039 INFORMANT : Etsuko Yasugi

NAME : 5-cholestene-3b,22-diol (22-hydroxycholesterol)

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:

NMR SPECTRA:

MASS SPECTRA:GC-EI-MS(TMS) M/E=546[M], 531[M-CH3], 475[M-(CH2)2CH(CH3)2],173 (Ref. 9095)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
infant feces (Ref. 9095)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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]

[9095]
AUTHOR:Gustafsson, J. A., and Sjovall, J.
TITLE:Identification of 22-, 24- and 26-hydroxycholesterol in the steroid sulphage fraction of faeces from infants PubMed ID:5796137
JOURNAL:Eur J Biochem.
VOL:8 PAGE : 467-472 (1969)
[TOP]

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