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Bile acid


DATA No : BBA0060 INFORMANT : Takashi Iida

NAME : 3a,4b,7a-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:131-133degC, (Me ester; mp, 128-130degC)(Ref. 0017)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1707(C=O), 3420, 1016, 975(OH)(Ref. 0017)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.92(s), 3b-H 3.20(brm), 7b-H 3.81(m), 4a-H 4.10(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.64(s), 19-Me 0.92(s), 21-Me 0.90(d), 3b-H 3.25(brm), COOMe 3.64(s), 7b-H 3.87(m), 4a-H 4.12(dd, J, 10.6, 9.0)(Ref. 0017)
13C-NMR (CDCl3; 22.53MHz) d: C-1 34.6, C-2 28.1, C-3 75.9, C-4 75.5, C-5 47.9, C-6 27.5, C-7 68.5, C-8 39.2, C-9 34.9, C-10 37.1, C-11 20.7, C-12 39.6, C-13 42.7, C-14 50.5, C-15 23.6, C-16 28.1, C-17 55.9, C-18 11.8, C-19 22.9, C-20 35.3, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0017)

MASS SPECTRA:Me ester (60eV) m/z: 404(M-H2O, 25%), 386(M-2H2O, 100%), 368(M-3H2O, 14%), 289(M-H2O-SC, 15%), 271(M-2H2O-SC, 24%), 253(M-3H2O-SC, 2%), 244(M-H2O-SC-part of ring D (27), 3%), 229(M-2H2O-SC-ring D (42), 4%), 127(23%)(Ref. 0017)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from human gallbladder bile.(Ref. 0159/0198)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0163/0188)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Identified in urine of newborns.(Ref. 0245)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0017]
AUTHOR:Iida, T., Momose, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. XV. Synthesis of 4 beta-hydroxylated bile acids; unique bile acids in human fetal bile PubMed ID:2632079
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:37 PAGE : 3323-3329 (1989)
[TOP]

[0159]
AUTHOR:Dumaswala, R., Setchell, K. D., Zimmer-Nechemias, L., Iida, T., Goto, J., and Nambara, T.
TITLE:Identification of 3 alpha,4 beta,7 alpha-trihydroxy-5 beta-cholanoic acid in human bile: reflection of a new pathway in bile acid metabolism in humans PubMed ID:2794778
JOURNAL:J Lipid Res.
VOL:30 PAGE : 847-856 (1989)
[TOP]

[0163]
AUTHOR:Goto, J., Hasegawa, K., Nambara, T., and Iida, T.
TITLE:Studies on steroids. CCLIV. Gas chromatographic-mass spectrometric determination of 4- and 6-hydroxylated bile acids in human urine with negative ion chemical ionization detection PubMed ID:1629271
JOURNAL:J Chromatogr.
VOL:574 PAGE : 1-7 (1992)
[TOP]

[0188]
AUTHOR:Meng, L. J., Reyes, H., Palma, J., Hernandez, I., Ribalta, J., and Sjovall, J.
TITLE:Effects of ursodeoxycholic acid on conjugated bile acids and progesterone metabolites in serum and urine of patients with intrahepatic cholestasis of pregnancy PubMed ID:9453429
JOURNAL:J Hepatol.
VOL:27 PAGE : 1029-1040 (1997)
[TOP]

[0192]
AUTHOR:Nakagawa, M., and Setchell, K. D.
TITLE:Bile acid metabolism in early life: studies of amniotic fluid PubMed ID:2373959
JOURNAL:J Lipid Res.
VOL:31 PAGE : 1089-1098 (1990)
[TOP]

[0198]
AUTHOR:Setchell, K. D., Dumaswala, R., Colombo, C., and Ronchi, M.
TITLE:Hepatic bile acid metabolism during early development revealed from the analysis of human fetal gallbladder bile PubMed ID:3182806
JOURNAL:J Biol Chem.
VOL:263 PAGE : 16637-16644 (1988)
[TOP]

[0245]
AUTHOR:Ikegawa, S., Yoshimura, T., Ito, K., Kurosawa, T., and Thoma, M.
TITLE:Simultaneous Fluorometric Determination of Conjugated Fetal Bile Acids in Urine of Newborns by High-Perfomance Liquid Chromatoguraphy.
JOURNAL:Anal. Sci.
VOL:11 PAGE : 91 -96 (1995)
[TOP]

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