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Bile acid


DATA No : BBA0120 INFORMANT : Takashi Iida

NAME : 3a,6b,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O6 MOL.WT (average) : 424.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:154-157degC(Ref. 0034)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-26: +36.3deg (C=0.52, MeOH)(Ref. 0181)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1748, 1703(C=O), 3538, 1014, 986, 952 (OH)(Ref. 0034)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.70(s), 21-Me 1.00(d), 19-Me 1.06(s), 3b-H 3.39(brm), 6a- and 7b-H 3.66(m), 12b-H 3.92(m)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.72(s), 19-Me 1.06(s), 21-Me 0.98(d), 3b-H 3.49(brm), COOMe 3.67(s), 6a-H 3.70(m), 7b-H 75(m), 12b-H 4.00(m)(Ref. 0034/0035)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.82, C-2 29.68, C-3 71.40, C-4 36.08, C-5 47.45, C-6 76.02, C-7 72.99, C-8 34.98, C-9 26.51, C-10 34.56, C-11 27.96, C-12 73.31, C-13 46.42, C-14 41.13, C-15 23.28, C-16 27.63, C-17 47.07, C-18 12.51, C-19 24.78, C-20 35.39, C-21 17.36, C-22 31.01, C-23 31.16, C-24 175.09, C-25 51.65(Ref. 0034/0035/0141)

MASS SPECTRA:Me ester (70eV) m/z: 420(M-H2O, 6%), 402(M-2H2O, 33%), 384(M-3H2O, 24%), 366(M-4H2O, 4%), 305(M-H2O-SC, 23%), 287(M-2H2O-SC, 50%), 269(M-3H2O-SC, 46%), 251(M-4H2O-SC, 15%)(Ref. 0034)
Me-TMS ether (70eV) m/z: 636(M-TMSOH, 24%), 546(M-2TMSOH, 85%), 531(M-2TMSOH-CH3, 9%), 456(M-3TMSOH, 72%), 441(M-3TMSOH-CH3, 28%), 431(M-2TMSOH-SC, 30%),365(M-4TMSOH-H, 36%), 341(M-3TMSOH-SC, 100%), 251(M-4TMSOH-SC, 51%)(Ref. 0061)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in amniotic fluid and urine from adult patients with cholestatic liver disease.(Ref. 0061/0141)
Hydroxyation metabolite of cholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0034]
AUTHOR:Iida, T., Komatsubara, I., Yoda, S., Goto, J., Nambara, T., and Chang, F. C.
TITLE:Potential bile acid metabolites. 16. Synthesis of stereoisomeric 3 alpha,6,7,12 alpha-tetrahydroxy-5 beta-cholanoic acids PubMed ID:2089743
JOURNAL:Steroids.
VOL:55 PAGE : 530-539 (1990)
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[0035]
AUTHOR:Iida, T., Chang, F. C., Mushiake, K., Goto, J., and Nambara, T.
TITLE:Complete 1H and 13C Resonance Assignments of Stereoisomeric 3a,6,7,12a-Tetrahydroxycholanoic Acids by Two-Dimensional Shift-Correlated NMR
JOURNAL:Mage. Reson. Chem.
VOL:31 PAGE : 645 -651 (1993)
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[0061]
AUTHOR:Yoshii, M., Kihira, K., Shoda, J., Osuga, T., and Hoshita, T.
TITLE:Identification of 3,6,7,12-tetrahydroxy-5 beta-cholan-24-oic acids in human biologic fluids PubMed ID:2075618
JOURNAL:Steroids.
VOL:55 PAGE : 512-515 (1990)
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[0141]
AUTHOR:Back, P., Fritz, H., and Populoh, C.
TITLE:The isolation of tetrahydroxy bile acids as methyl esters from human urine and their characterization by 1H- and 13C-nuclear magnetic resonance spectroscopy PubMed ID:6329940
JOURNAL:Hoppe Seylers Z Physiol Chem.
VOL:365 PAGE : 479-484 (1984)
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[0153]
AUTHOR:Bremmelgaard, A., and Sjovall, J.
TITLE:Hydroxylation of cholic, chenodeoxycholic, and deoxycholic acids in patients with intrahepatic cholestasis PubMed ID:7462803
JOURNAL:J Lipid Res.
VOL:21 PAGE : 1072-1081 (1980)
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[0181]
AUTHOR:Kurosawa, T., Mahara, R., Nittono, H., and Tohma, M.
TITLE:Synthesis of 6-hydroxylated bile acids and identification of 3 alpha,6 alpha,7 alpha,12 alpha-tetrahydroxy-5 beta-cholan-24-oic acid in human meconium and neonatal urine PubMed ID:2743505
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:37 PAGE : 557-559 (1989)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.