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Bile acid


DATA No : BBA0020 INFORMANT : Takashi Iida

NAME : 1b,3a-Dihydroxy-5b-cholan-24-oic Acid

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:274-278degC, (Me ester; mp, 203-205degC)(Ref. 0016)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +47.5deg (C=0.80, CHCl3) (Me ester)(Ref. 0016)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 3300, 3200, 1680(Ref. 0016)

NMR SPECTRA:1H-NMR (Pyridin-d5; 90MHz) d: 18-Me 0.62(s), 19-Me 1.28(s), 1a-H 4.12-4.28(m), 3b-H 4.61-4.99(m)(Ref. 0016)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 1.04(s), COOMe 3.65(s), 1a-H 3.90(t, J, 3.0), 3b-H 3.83-4.17(m)(Ref. 0016)

MASS SPECTRA:Me-TMS ether (70eV) m/z: 535(M-15), 460(M-TMSOH, 10%), 370(M-2TMSOH, 3%), 217 (100%), 147(5%) (Ref. 0016)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
A metabolite of lithocholic acid in human fetal liver.(Ref. 0164)
Detected in serum and urine from healthy human adults.(Ref. 0189)
Excreted in urine of healthy newborn.(Ref. 0194)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0016]
AUTHOR:Tohma, M., Mahara, R., Takeshita, H., Kurosawa, T., and Ikegawa, S.
TITLE:Synthesis of the 1 beta-hydroxylated bile acids, unusual bile acids in human biological fluids PubMed ID:3769090
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:34 PAGE : 2890-2899 (1986)
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[0164]
AUTHOR:Gustafsson, J., Anderson, S., and Sjovall, J.
TITLE:Bile acid metabolism during development: metabolism of lithocholic acid in human fetal liver PubMed ID:3797138
JOURNAL:Pediatr Res.
VOL:21 PAGE : 99-103 (1987)
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[0189]
AUTHOR:Miyara, T., Shindo, N., Tohma, M., and Murayama, K.
TITLE:Capillary gas chromatography/negative ion chemical ionization mass spectrometry for the quantification of bile acids including 1 beta-hydroxylated and unsaturated bile acids in serum and urine PubMed ID:2350598
JOURNAL:Biomed Chromatogr.
VOL:4 PAGE : 56-60 (1990)
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[0194]
AUTHOR:Obinata, K., Nittono, H., Yabuta, K., Mahara, R., and Tohma, M.
TITLE:1 beta-hydroxylated bile acids in the urine of healthy neonates PubMed ID:1403443
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:15 PAGE : 1-5 (1992)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.