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Bile acid


DATA No : BBA0087 INFORMANT : Takashi Iida

NAME : 3b,7a,12b-Trihydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:225-226degC(Ref. 0032)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +23.4deg (EtOH), [a]D: +17.0deg (Me ester)(Ref. 0032)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmax cm-1: 1721 (C=O)(Ref. 0032)

NMR SPECTRA:1H-NMR (CD3COCD3+D2O; 100MHz) d: 18-Me 0.73(s), 19-Me 0.95(s), 12a-H 3.43(brm), 7b-H 3.82(m), 3a-H 3.97(m)(Ref. 0032)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.73(s), 19-Me 0.95(s), 12a-H 3.45(brm), COOMe 3.66(s), 7b-H 3.88(m), 3a-H 4.04(m)(Ref. 0005/0032)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.8, C-2 27.7, C-3 66.6 C4 36.5, C-5 35.7, C-6 35.4, C-7 68.2, C-8 38.0, C-9 31.3, C-10 34.4, C-11 29.3, C-12 79.0, C-13 47.6, C-14 48.6, C-15 23.1, C-16 23.8, C-17 57.1, C-18 7.7, C-19 23.0, C-20 32.6, C-21 21.0, C-22 32.1, C-23 31.2, C-24 174.7, C-25 51.4(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 402(M-H2O, 2%), 386(M-2H2O, 11%), 371(M-2H2O-CH3, 4%), 289(M-H2O-SC, 10%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 8%)(Ref. 0010)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0005]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:24 PAGE : 163 -165 (1983)
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[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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[0032]
AUTHOR:Chang, F. C.
TITLE:Potential Bile Acid Metabolites. 2. 3,7,12-Trisubstituted-5b-cholanic Acids.
JOURNAL:J. Org. Chem.
VOL:44 PAGE : 4567 -4572 (1979)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.