Back to HOME

Bile acid


DATA No : BBA0116 INFORMANT : Takashi Iida

NAME : 3a,4b,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid

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


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:150-152degC, (Me ester; mp, 146-148degC)(Ref. 0017)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1703(C=O), 3396, 1028(OH)(Ref. 0017)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 19-Me 0.91(s), 21-Me 0.99(d), 3b-H 3.20(brm), 7b- and 12b-H 3.85(m), 4a-H 4.13(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.65(s), 19-Me 0.90(s), 21-Me 0.95(d), 3b-H 3.25(brm), COOMe 3.64(s), 7b-H 3.88(m), 12b-H 3.94(t, J, 2.8), 4a-H 4.12(dd, J, 10.7, 9.1)(Ref. 0017)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.6, C-2 28.1, C-3 76.0, C-4 75.3, C-5 47.9, C-6 27.5, C-7 68.5, C-8 39.2, C-9 28.1, C-10 36.8, C-11 28.1, C-12 73.0, C-13 46.4, C-14 41.6, C-15 23.1, C-16 27.5, C-17 47.0, C-18 12.4, C-19 22.5, C-20 35.2, C-21 17.3, C-22 31.0, C-23 31.0, C-24 174.7, C-25 51.4(Ref. 0017)

MASS SPECTRA:Me ester (60eV) m/z: 420(M-H2O, 4%), 402(M-2H2O, 21%), 384(M-3H2O, 25%), 287(M-2H2O-SC, 35%), 269(M-3H2O-SC, 100%), 260(M-2H2O-SC-part of ring D (27), 12%), 242(M-3H2O-SC-27, 32%), 127(25%)(Ref. 0017)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from feces from healthy newborn infants.(Ref. 0159)
Identified in human urine.(Ref. 0163)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
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]

[0202]
AUTHOR:Strandvik, B., Wahlen, E., and Wikstrom, S. A.
TITLE:The urinary bile acid excretion in healthy premature and full-term infants during the neonatal period PubMed ID:8171265
JOURNAL:Scand J Clin Lab Invest.
VOL:54 PAGE : 1-10 (1994)
[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.