Back to HOME

Bile acid


DATA No : BBA0022 INFORMANT : Takashi Iida

NAME : 3a,4b-Dihydroxy-5b--cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:156-158degC, (Me ester; mp, 174-175degC)(Ref. 0017)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1703(C=O), 3456, 1019(OH)(Ref. 0017)

NMR SPECTRA:1H-NMR (CDCl3 ; 90MHz) d: 18-Me 0.65(s), 21-Me 0.93(d), 19-Me 0.96(s), 3b-H 3.41(brm), 4a-H 3.68(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.62(s), 19-Me 0.94(s), 21-Me 0.88(d), COOMe 3.64(s), 3b-H 3.38(brm), 4a-H 3.70(dd, J, 10.7, 9.1)(Ref. 0017)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.6, C-2 27.3, C-3 76.7, C-4 72.7, C-5 48.7, C-6 20.9, C-7 26.0, C-8 35.7, C-9 42.4, C-10 37.0, C-11 20.9, C-12 40.1, C-13 42.7, C-14 56.5, C-15 24.1, C-16 28.1, C-17 56.0, C-18 12.0, C-19 23.5, C-20 35.3, C-21 18.2, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.3(Ref. 0017)

MASS SPECTRA:Me ester (60eV) m/z: 406(M+ 16%), 388 (M-H2O, 100%), 370(M-2H2O, 23%), 264(M-SC-part of ring D (27), 18%), 249(M-SC-ring D (42), 21%), 231(M-SC-42-H2O, 24%), 213(M-SC-42-2H2O, 30%)(Ref. 0017)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Isolated from human fetal gallbladder bile.(Ref. 0198)
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]

[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]

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