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Bile acid


DATA No : BBA0043 INFORMANT : Takashi Iida

NAME : 3b,12b-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:204.3-205.6degC, (Me ester; mp, 115.8-116.3degC)(Ref. 0025)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +27.0deg (dioxane)(Ref. 0025)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:lmax mm: 5.84 (COOH), 2.80, 3.00, 9.73, 9.95 (OH)(Ref. 0025)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 19-Me 0.96(s), 21-Me 1.00(d), 12a-H 3.4(brm), 3a-H 4.06(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.5, C-2 27.3, C-3 66.1, C-4 33.0, C-5 35.7, C-6 26.3, C-7 25.5, C-8 33.9, C-9 38.3, C-10 34.5, C-11 29.1, C-12 78.9, C-13 47.5, C-14 54.2, C-15 23.3, C-16 23.6, C-17 57.0, C-18 7.5, C-19 23.3, C-20 32.1, C-21 20.5, C-22 31.8, C-23 31.0, C-24 174.4, C-25 51.0(Ref. 0006)

MASS SPECTRA:Me ether (70eV) m/z: 388(M-H2O, 12%), 273(M-H2O-SC, 92%), 255(M-2H2O-SC, 100%), 213(M-2H2O-SC-ring D (42), 7%)(Ref. 0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected as a trace component of human feces.(Ref. 0101/0161)
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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[0007]
AUTHOR:Lawson, A. M., and Setchell, K. D. R. (1988) Mass Spectrometry of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchall, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp 167-267, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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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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[0025]
AUTHOR:Chang, F. C., Wood, N. F., and Holton, W. G.
TITLE:3 Beta, 12 Beta-Dihydroxycholanic Acid PubMed ID:14325490
JOURNAL:J Org Chem.
VOL:30 PAGE : 1718-1723 (1965)
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[0101]
AUTHOR:Matschiner, J. T. (1971) Naturally Occurring Bile Acids and Alcohols and their Origins. In The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1 : Chemistry) (Nair, P. P., and Krichevsky, D. eds), pp. 11-46, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0161]
AUTHOR:Eneroth, P., Gordon, B., Ryhage, R., and Sjovall, J.
TITLE:Identification of mono- and dihydroxy bile acids in human feces by gas-liquid chromatography and mass spectrometry PubMed ID:5966634
JOURNAL:J Lipid Res.
VOL:7 PAGE : 511-523 (1966)
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