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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
FORMULA: C24H40O4 MOL.WT (average) : 392.572

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



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



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)


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)




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)

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)

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.
VOL: PAGE : - ()

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.
VOL: PAGE : - ()

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)

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)

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)

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)

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.
VOL: PAGE : - ()

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)

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)

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)

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)

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
VOL:12 PAGE : 322-334 (1990)

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)

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)

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)

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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