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Bile acid


DATA No : BBA0088 INFORMANT : Takashi Iida

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

COMMON NAME: Ursocholic Acid
7-Epicholic Acid
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:128.0-131.0degC(Ref. 0031)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +62deg (dioxane)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1704 (C=O), 3448, 1042, 1010, 957 (OH)(Ref. 0031)

NMR SPECTRA:1H-NMR (CDCl3+10%DMSO-d6+D2O; 100MHz) d: 18-Me 0.69(s), 19-Me 0.91(s), 3b- and 7a-H 3.51(brm), 12b-H 3.91(m)(Ref. 0031)
as Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.71(s), 19-Me 0.93(s), 3b- and 7a-H 3.59(brm), COOMe 3.64(s), 12b-H 3.98(m)(Ref. 0005/0031)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.2, C-2 29.1, C-3 71.0 C-4 36.9, C-5 42.6, C-6 36.6, C-7 71.0, C-8 43.5, C-9 31.2, C-10 33.9, C-11 27.7, C-12 72.2, C-13 47.5, C-14 47.2, C-15 26.1, C-16 27.4, C-17 45.7, C-18 12.6, C19 23.4, C-20 34.8, C-21 17.2, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 386(M-2H2O, 15%), 371(M-2H2O-CH3, 3%), 368(M-3H2O, 11%), 353(M-3H2O-CH3, 6%), 289(M-H2O-SC, 74%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 91%), 226(M-3H2O-SC-part of ring D (27), 5%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 623(M-CH3, 1%), 548(M-TMSOH, 3%), 458(M-2TMSOH, 14%), 368(M-3TMSOH, 17%), 433(7%), 343(26%), 253(100%), 73(35%)(Ref. 0007/0049)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected in the feces of human, dog, and rat, in human bile, and in the bile of the rat.(Ref. 0101/0162)
Identified in urine and serum of healthy humans and patients with liver diseases.(Ref. 0145/0150/0151/0187/0203)
Occurred in the bile of patients with gallstones.(Ref. 0172)
Identified in urine of a patients treated with chenodeoxycholate, ursodeoxycholate or rifampicin and those with cirrhosis.(Ref. 0193)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in urine of infants during the first year.(Ref. 0210)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Hill, R. A., Kirk, D. N., Makin, H. L. J., and Murphy, G. M. (1991) Chemical Data, Structures and Bibliographies, in Dictionary of Steroids, Chapman & Hall, London.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0005]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:24 PAGE : 163 -165 (1983)
[TOP]

[0006]
AUTHOR:Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C.
TITLE:Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers.
JOURNAL:Org. Magn. Reson.
VOL:21 PAGE : 305 -309 (1983)
[TOP]

[0007]
AUTHOR:Lawson, A. M., and Setchell, K. D. R. (1988) Mass Spectrometry of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchall, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp 167-267, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0010]
AUTHOR:Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T.
TITLE:High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids.
JOURNAL:Biomed. Mass Spectrom.
VOL:9 PAGE : 473 -476 (1982)
[TOP]

[0031]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. 7. 3,7,12-Trihydroxy-5b-cholanic Acids.
JOURNAL:J. Org. Chem.
VOL:47 PAGE : 2972 -2978 (1982)
[TOP]

[0049]
AUTHOR:Batta, A. K., Aggarwal, S. K., Salen, G., and Shefer, S.
TITLE:Selective reduction of oxo bile acids: synthesis of 3 beta-, 7 beta-, and 12 beta-hydroxy bile acids PubMed ID:1940629
JOURNAL:J Lipid Res.
VOL:32 PAGE : 977-983 (1991)
[TOP]

[0101]
AUTHOR:Matschiner, J. T. (1971) Naturally Occurring Bile Acids and Alcohols and their Origins. In The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1 : Chemistry) (Nair, P. P., and Krichevsky, D. eds), pp. 11-46, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0145]
AUTHOR:Amuro, Y., Hayashi, E., Endo, T., Higashino, K., and Kishimoto, S.
TITLE:Unusual trihydroxylated bile acids in urine of patients with liver cirrhosis PubMed ID:6825311
JOURNAL:Clin Chim Acta.
VOL:127 PAGE : 61-67 (1983)
[TOP]

[0150]
AUTHOR:Alme, B., Bremmelgaard, A., Sjovall, J., and Thomassen, P.
TITLE:Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry PubMed ID:864325
JOURNAL:J Lipid Res.
VOL:18 PAGE : 339-362 (1977)
[TOP]

[0151]
AUTHOR:Bremmelgaard, A., and Sjovall, J.
TITLE:Bile acid profiles in urine of patients with liver diseases PubMed ID:118027
JOURNAL:Eur J Clin Invest.
VOL:9 PAGE : 341-348 (1979)
[TOP]

[0162]
AUTHOR:Eneroth, P., Gordon, B., and Sjovall, J.
TITLE:Characterization of trisubstituted cholanoic acids in human feces PubMed ID:5965294
JOURNAL:J Lipid Res.
VOL:7 PAGE : 524-530 (1966)
[TOP]

[0172]
AUTHOR:Howard, P. J., Gleeson, D., Murphy, G. M., and Dowling, R. H.
TITLE:Ursocholic acid: bile acid and bile lipid dose response and clinical studies in patients with gall stones PubMed ID:2920932
JOURNAL:Gut.
VOL:30 PAGE : 97-103 (1989)
[TOP]

[0187]
AUTHOR:Marschall, H. U., Matern, H., Wietholtz, H., Egestad, B., Matern, S., and Sjovall, J.
TITLE:Bile acid N-acetylglucosaminidation. In vivo and in vitro evidence for a selective conjugation reaction of 7 beta-hydroxylated bile acids in humans PubMed ID:1602004
JOURNAL:J Clin Invest.
VOL:89 PAGE : 1981-1987 (1992)
[TOP]

[0193]
AUTHOR:Nakashima, T., Sano, A., Seto, Y., Nakajima, T., Shima, T., Sakamoto, Y., Okuno, T., Kashima, K., and Hasegawa, T.
TITLE:Unusual trihydroxy bile acids in the urine of patients treated with chenodeoxycholate, ursodeoxycholate or rifampicin and those with cirrhosis PubMed ID:2307404
JOURNAL:Hepatology.
VOL:11 PAGE : 255-260 (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]

[0203]
AUTHOR:Summerfield, J. A., Billing, B. H., and Shackleton, C. H.
TITLE:Identification of bile acids in the serum and urine in cholestasis. Evidence for 6alpha-hydroxylation of bile acids in man PubMed ID:938463
JOURNAL:Biochem J.
VOL:154 PAGE : 507-516 (1976)
[TOP]

[0210]
AUTHOR:Wahlen, E., and Strandvik, B.
TITLE:Effects of different formula feeds on the developmental pattern of urinary bile acid excretion in infants PubMed ID:8126625
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:18 PAGE : 9-19 (1994)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.