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Bile acid


DATA No : BBA0086 INFORMANT : Takashi Iida

NAME : 3b7a,12a-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:196.5-197.0degC, (Me ester; mp, 185.0-187.0degC)(Ref. 0032)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +31deg (MeOH)(Ref. 0073)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1H-NMR (DMSO-d6; 270MHz) d: 18-Me 0.59(s), 19-Me 0.83(s), 21-Me 0.92(d), 7b-H 3.61(q, J=3.0), 3a- and 12b-H (m)(Ref. 0073)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.68(s), 19-Me 0.91(s), COOMe 3.64(s), 7b-H 3.86(m), 3a- and 12b-H 4.01(m)(Ref. 0005/0032)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.8, C-2 27.7, C-3 66.9 C-4 36.6, C-5 35.9, C-6 35.2, C-7 68.5, C-8 39.5, C-9 25.9, C-10 34.3, C-11 28.6, C-12 72.8, C-13 46.6, C-14 41.9, C-15 23.2, C-16 27.4, C-17 47.2, C-18 12.5, C-19 22.9, C-20 35.2, C-21 17.4, C-22 31.1, C-23 30.9, C-24 174.7, C-25 51.4(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 402(M-H2O, 1%), 386(M-2H2O, 50%), 371(M-2H2O-CH3, 8%), 368(M-3H2O, 4%), 353(M-3H2O-CH3, 3%), 289(M-H2O-SC, 8%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 25%), 226(M-3H2O-SC-part of ring D (27), 2%)(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 feces of human and dog.(Ref. 0101/0162)Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
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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[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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[0073]
AUTHOR:Riva, S., Bovara, R., Zetta, L., Pasta, P., Ottolina, G., and Carrea, G.
TITLE:Enzymatic a/b Inversion of C-3 Hydroxyl of Bile Acids and Study of the Effects of Organic Solvents on Reaction Rates.
JOURNAL:J. Org. Chem.
VOL:53 PAGE : 88 -92 (1988)
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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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[0155]
AUTHOR:Clayton, P. T., Muller, D. P. R., and Lawson, A. M.
TITLE:The Bile Acids Composition of Gastric Contents from Neonates with High Intestinal Obstruction. PubMed ID:7150258
JOURNAL:Biochem. J.
VOL:206 PAGE : 489 -498 (1982)
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[0162]
AUTHOR:Eneroth, P., Gordon, B., and Sjovall, J.
TITLE:Characterization of trisubstituted cholanoic acids in human feces PubMed ID:5965294
JOURNAL:J Lipid Res.
VOL:7 PAGE : 524-530 (1966)
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[0191]
AUTHOR:Nakagawa, M., Colombo, C., and Setchell, K. D.
TITLE:Comprehensive study of the biliary bile acid composition of patients with cystic fibrosis and associated liver disease before and after UDCA administration PubMed ID:2391071
JOURNAL:Hepatology.
VOL:12 PAGE : 322-334 (1990)
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