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Bile acid


DATA No : BBA0042 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:178.4-180.5degC, (Me ester; mp, 156.5-158.2degC)(Ref. 0025)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +39.0deg (dioxane), +45.6deg (EtOH)(Ref. 0025)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:lmax mm: 5.78, 5.85(COOH), 2.80, 2.92, 9.70 (OH)(Ref. 0025)

NMR SPECTRA:1H-NMR (DMSO-d6; 270MHz) d: 18-Me 0.60(s), 19-Me 0.86(s), 21-Me 0.91(d), 12b-H 3.78(t, J=2.8), 3a-H 3.88(J=3.0)(Ref. 0073)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.94(s), 21-Me 0.95(d), 12b-H 3.91(m), 3a-H 4.04(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.7, C-2 27.6, C-3 66.9, C-4 33.3, C-5 36.4, C-6 26.5, C-7 25.9, C-8 35.7, C-9 32.7, C-10 34.5, C-11 28.8, C-12 73.0, C-13 46.4, C-14 48.3, C-15 23.5, C-16 27.4, C-17 47.2, C-18 12.6, C-19 23.5, C-20 35.0, C-21 17.2, C-22 31.0, C-23 30.8, C-24 174.5, C-25 51.4(Ref. 0006)

MASS SPECTRA:Me ether (70eV) m/z: 388(M-H2O, 8%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 65%), 213(M-2H2O-SC-ring D (42), 7%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected as a trace component of rabbit and human feces.(Ref. 0101/0157/0161)
Identified in urine of healthy humans and patients with liver diseases(Ref. 0150/0151)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Excreted in duodenal bile and urine of diabetic patients.(Ref. 0221)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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)
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[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)
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[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 : - ()
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[0009]
AUTHOR:Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[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)
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[0025]
AUTHOR:Chang, F. C., Wood, N. F., and Holton, W. G.
TITLE:3 Beta, 12 Beta-Dihydroxycholanic Acid PubMed ID:14325490
JOURNAL:J Org Chem.
VOL:30 PAGE : 1718-1723 (1965)
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[0073]
AUTHOR:Riva, S., Bovara, R., Zetta, L., Pasta, P., Ottolina, G., and Carrea, G.
TITLE:Enzymatic a/b Inversion of C-3 Hydroxyl of Bile Acids and Study of the Effects of Organic Solvents on Reaction Rates.
JOURNAL:J. Org. Chem.
VOL:53 PAGE : 88 -92 (1988)
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[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 : - ()
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[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)
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[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)
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[0157]
AUTHOR:Danielsson, H., Eneroth, P., Hellstrom, K., and Sjovall, J.
TITLE:Synthesis of some 3beta-hydroxylated bile acids and the isolation of 3beta, 12alpha-dihydroxy-5beta-cholanic acid from feces PubMed ID:14024950
JOURNAL:J Biol Chem.
VOL:237 PAGE : 3657-3659 (1962)
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[0161]
AUTHOR:Eneroth, P., Gordon, B., Ryhage, R., and Sjovall, J.
TITLE:Identification of mono- and dihydroxy bile acids in human feces by gas-liquid chromatography and mass spectrometry PubMed ID:5966634
JOURNAL:J Lipid Res.
VOL:7 PAGE : 511-523 (1966)
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[0191]
AUTHOR:Nakagawa, M., Colombo, C., and Setchell, K. D.
TITLE:Comprehensive study of the biliary bile acid composition of patients with cystic fibrosis and associated liver disease before and after UDCA administration PubMed ID:2391071
JOURNAL:Hepatology.
VOL:12 PAGE : 322-334 (1990)
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[0206]
AUTHOR:Thomassen, P. A.
TITLE:Urinary bile acids in late pregnancy and in recurrent cholestasis of pregnancy PubMed ID:119641
JOURNAL:Eur J Clin Invest.
VOL:9 PAGE : 425-432 (1979)
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[0221]
AUTHOR:Andersen, E., Karlaganis, G., and Sjovall, J.
TITLE:Altered bile acid profiles in duodenal bile and urine in diabetic subjects PubMed ID:3133222
JOURNAL:Eur J Clin Invest.
VOL:18 PAGE : 166-172 (1988)
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