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Bile acid


DATA No : BBA0343 INFORMANT : Mizuho Une

NAME : 5b-Cholestane-3a,7a,12a,23-tetrol

COMMON NAME:
SYMBOL:
FORMULA: C27H48O4 MOL.WT (average) : 436.668


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:232-233(23R), 189-191(23S) (Ref. 0369)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D=+52(23R), [a]D=+41(23S)(Ref. 0369)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:cm-1 (KBr) 3400(OH), 1080,1040,980,950,920 (23R), 3340(OH), 1080,1030,980,950,918 (23S) (Ref. 0369)

NMR SPECTRA:1H-NMR(pyridine-d5) 18-CH3=0.89, 26-and 27-CH3=1.00,1.03, 19-CH3=1.01, 21-CH3=1.39, 3b-H=3.70, 7b-H and 23-H=4.10, 12b-H=4.32 :(23R) , 18-CH3=0.88, 26-and 27-CH3=0.95,0.98, 19-CH3=1.00, 21-CH3=1.38, 3b-H=3.70, 7b-H and 23-H=4.10, 12b-H=4.32: (23S) (Ref. 0369)

MASS SPECTRA:m/z 724,667,634,544,454,364,253(base peak),159. (as TMS derivative) (Ref. 0369/0370)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Patient with Cerebrotendinous xanthomatosis; Bile (Ref. 0327/0371), urine (Ref. 0327), feces (Ref. 0327/0370)
CHEMICAL SYNTHESIS
(Ref. 0452)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0327]
AUTHOR:Shimazu,K.,Kuwabara,M.,Yoshii,M.,Kihira,K.,Takeuchi,H.,Nakano,I.,Ozawa,S.,Hatta,Y,and Hoshita,T.
TITLE:Bile alcohol profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. PubMed ID:3700361
JOURNAL:J.Biochem.
VOL:99 PAGE : 477 -483 (1986)
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[0369]
AUTHOR:Kuramoto,T.,Matsumoto,N.,and Hoshita,T.
TITLE:Synthesis of 22- and 23-hydroxylated bile alcohols.
JOURNAL:Chem.Pharm.Bull.
VOL:26 PAGE : 2788 -2792 (1978)
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[0370]
AUTHOR:Yasuhara,M.,Kuramoto,T.,and Hoshita,T.
TITLE:Identification of 5b-cholestane-3a,7a,12a,23b-tetrol, 5b-cholestane-3a,7a,12a,24a-tetrol, and 5b-cholestane-3a,7a,12a,24
JOURNAL:Steroids
VOL:31 PAGE : 333 -345 (1978)
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[0371]
AUTHOR:Hoshita,T.,Yasuhara,M.,Une,M.,Kibe,A.,Itoga,E.,Kito,S.,and Kuramoto,T.
TITLE:Occurrence of bile alcohol glucuronides in bile of patients with Cerebrotendinous xanthomatosis. PubMed ID:7462799
JOURNAL:J. Lipid Res.
VOL:21 PAGE : 1015 -1021 (1980)
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[0452]
AUTHOR:Kihira, K., Kubota, A., and Hoshita, T.
TITLE:Absolute configuration at carbon 23 of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol excreted by patients with cerebrotendinous xanthomatosis PubMed ID:6491531
JOURNAL:J Lipid Res.
VOL:25 PAGE : 871-875 (1984)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.