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Bile acid


DATA No : BBA0051 INFORMANT : Takashi Iida

NAME : 7b,12a-Dihydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:174.5-176.0degC, (Me ester; mp, 131-132degC)(Ref. 0026)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1689 (C=O), 3356, 1026, 1015, 943 (OH)(Ref. 0026)

NMR SPECTRA:1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 0.67(s), 19-Me 0.90(s), 7a- 3.49(brm), 12b-H 3.88(m)(Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d : 18-Me 0.70(s), 19-Me 0.93(s), 7a- 3.57(brm), COOMe 3.63(s), 12b-H 3.98(m)(Ref. 0026)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.2, C-2 20.7, C-3 26.8, C-4 27.8, C-5 43.9, C-6 36.8, C-7 71.1, C-8 43.7, C-9 31.9, C-10 34.1, C-11 28.7, C-12 72.2, C-13 47.1, C-14 47.2, C-15 26.2, C-16 27.6, C-17 45.7, C-18 12.6, C-19 23.8, C-20 34.8, C-21 17.1, C-22 30.8, C-23 30.8, C-24 174.4, C-25 51.2(Ref. 0006)

MASS SPECTRA:m/z: 374(M-H2O, 3.6%), 356(M-2H2O, 24.5%), 273(M-H2O-SC, 77.5%), 255(M-2H2O-SC, 100.0%)(Ref. 0027)
Me ester (70eV) m/z: 370(M-2H2O, 16%), 273(M-H2O-SC, 56%), 255(M-2H2O-SC, 100%)(Ref. 0010)
Me ester-DMES ether m/z: 578(M+, 0.2%), 563(M-CH3, 4.0%), 549(M-29, 100.0%), 370(M-2DMESOH, 34.7%), 255(M-2DMESOH-SC, 56.4%)(Ref. 0027)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0006]
AUTHOR:Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C.
TITLE:Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers.
JOURNAL:Org. Magn. Reson.
VOL:21 PAGE : 305 -309 (1983)
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[0010]
AUTHOR:Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T.
TITLE:High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids.
JOURNAL:Biomed. Mass Spectrom.
VOL:9 PAGE : 473 -476 (1982)
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[0026]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. 8. 7,12-Dihydroxy- and 7b-Hydroxy-5b-cholanic Acids.
JOURNAL:J. Org. Chem.
VOL:48 PAGE : 1194 -1197 (1983)
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[0027]
AUTHOR:Arimoto, K., Adachi, K., and Yamaga, N.
TITLE:7 beta,12 beta-Dihydroxy-5 beta-cholan-24-oic acid as an internal standard for quantitative determination of bile acids by gas chromatography PubMed ID:7157435
JOURNAL:Steroids.
VOL:39 PAGE : 631-641 (1982)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.