Back to HOME

Bile acid


DATA No : BBA0085 INFORMANT : Takashi Iida

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

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


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:200.0-201.5degC(Ref. 0032)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +30.5deg (EtOH), [a]D: +14.0deg (Me ester)(Ref. 0032)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmax cm-1: 1724 (ester C=O)(Ref. 0032)

NMR SPECTRA:1H-NMR (CD3COCD3+D2O) d: 18-Me 0.71(s), 19-Me 0.91(s), 3b- and 12a-H 3.40(brm)(Ref. 0005/0032)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.72(s), 19-Me 0.90(s), 3b- and 12a-H 3.40(brm), COOMe 3.54(s), 7b-H 3.86(m)(Ref. 0032)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.8, C-2 30.6, C-3 71.4 C-4 39.3, C-5 41.2, C-6 35.2, C-7 67.7, C-8 38.0, C-9 32.0, C-10 34.8, C-11 29.3, C-12 78.9, C-13 47.5, C-14 47.2, C-15 26.1, C-16 23.7, C-17 57.0, C-18 7.6, C-19 22.5, C-20 32.5, C-21 20.9, C-22 32.1, C-23 30.8, C-24 174.7, C-25 51.3(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 402(M-H2O, 2%), 386(M-2H2O, 13%), 371(M-2H2O-CH3, 4%), 368(M-3H2O, 5%), 353(M-3H2O-CH3, 2%), 289(M-H2O-SC, 9%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 36%), 226(M-3H2O-SC-part of ring D (27), 3%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 623(M-CH3, 7%), 548(M-TMSOH, 1%), 458(M-2TMSOH, 48%), 368(M-3TMSOH, 25%), 343(76%), 253(100%), 73(50%)(Ref. 0007/0049)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in urine specimens from healthy humans.(Ref. 0212)
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)
[TOP]

[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)
[TOP]

[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 : - ()
[TOP]

[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)
[TOP]

[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)
[TOP]

[0049]
AUTHOR:Batta, A. K., Aggarwal, S. K., Salen, G., and Shefer, S.
TITLE:Selective reduction of oxo bile acids: synthesis of 3 beta-, 7 beta-, and 12 beta-hydroxy bile acids PubMed ID:1940629
JOURNAL:J Lipid Res.
VOL:32 PAGE : 977-983 (1991)
[TOP]

[0212]
AUTHOR:Yamaga, N., Ikebuchi, J., Kohara, H., Ogura, Y., and Yamada, K.
TITLE:Analysis of bile acids in urine specimens from healthy humans: determination of several bile acids with beta-hydroxyl and carbonyl groups PubMed ID:8743575
JOURNAL:J Biochem (Tokyo).
VOL:119 PAGE : 725-730 (1996)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.