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Bile acid


DATA No : BBA0034 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:204.0-206.0degC, (Me ester; mp, 156.5-158.5degC)(Ref. 0021)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +7deg (MeOH)(Ref. 0073)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1715 (C=O), 1071, 1034, 1003, 982 (OH)(Ref. 0021)

NMR SPECTRA:Me ester 1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 0.67(s), 19-Me 0.94(s),7b-H 3.87(m), 3a-H 4.07(m)(Ref. 0005/0021)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.8, C-2 27.7, C-3 66.7, C-4 36.6, C-5 35.9, C-6 35.5, C-7 68.5, C-8 39.3, C-9 32.0, C-10 34.2, C-11 20.8, C-12 39.6, C-13 42.6, C-14 50.4, C-15 23.6, C-16 28.0, C-17 55.7, C-18 11.7, C-19 23.1, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.4(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 100%), 373(M-H2O-CH3, 37%), 370(M-2H2O, 31%), 357(M-H2O-CH3, 13%), 355(M-2H2O-CH3, 25%), 273(M-H2O-SC, 100%), 264(M-SC-part of ring D (27), 27%), 255(M-2H2O-SC, 23%), 249(M-SC-ring D (42), 30%), 246(M-H2O-SC-27, 55%), 228(M-2H2O-SC-27, 30%), 213(M-2H2O-SC-42, 61%)(Ref. 0009/0010)
Me-TMS ether (70eV) m/z: 460(M-TMSOH, 0.2%), 370(M-2TMSOH, 100%), 355(24%), 255(21%), 73(13%)(Ref. 0007/0049)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected as a trace component of human feces.(Ref. 0101/0161)
Identified in urine and serum of healthy humans and patients with liver diseases.(Ref. 0150/0151/0203/0212)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
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)
Identified in plasma of patients with bacterial overgrowth in the small intestine.(Ref. 0256)
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)
[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 : - ()
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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)
[TOP]

[0021]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. 6. Stereoisomeric 3,7-Dihydroxy-5b-cholanic Acids.
JOURNAL:J. Org. Chem.
VOL:47 PAGE : 2966 -2972 (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]

[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)
[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)
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[0155]
AUTHOR:Clayton, P. T., Muller, D. P. R., and Lawson, A. M.
TITLE:The Bile Acids Composition of Gastric Contents from Neonates with High Intestinal Obstruction. PubMed ID:7150258
JOURNAL:Biochem. J.
VOL:206 PAGE : 489 -498 (1982)
[TOP]

[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)
[TOP]

[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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[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)
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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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[0212]
AUTHOR:Yamaga, N., Ikebuchi, J., Kohara, H., Ogura, Y., and Yamada, K.
TITLE:Analysis of bile acids in urine specimens from healthy humans: determination of several bile acids with beta-hydroxyl and carbonyl groups PubMed ID:8743575
JOURNAL:J Biochem (Tokyo).
VOL:119 PAGE : 725-730 (1996)
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[0256]
AUTHOR:Setchell, K. D., Harrison, D. L., Gilbert, J. M., and Mupthy, G. M.
TITLE:Serum unconjugated bile acids: qualitative and quantitative profiles in ileal resection and bacterial overgrowth PubMed ID:4064336
JOURNAL:Clin Chim Acta.
VOL:152 PAGE : 297-306 (1985)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.