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Bile acid


DATA No : BBA0041 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:172.5-173.6degC(Ref. 0025)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +37.8deg (dioxane)(Ref. 0025)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:lmax mm: 5.86(COOH), 2.82, 2.95, 9.65, 9.82, 10.00 (OH)(Ref. 0025)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 19-Me 0.86(s), 21-Me 0.95(d), 3b- and 12a-H 3.4(brm)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.2, C-2 30.3, C-3 71.1, C-4 35.9, C-5 41.6, C-6 26.9, C-7 25.8, C-8 34.4, C-9 39.3, C-10 34.2, C-11 29.5, C-12 79.1, C-13 47.8, C-14 54.8, C-15 23.5, C-16 24.0, C-17 57.3, C-18 7.8, C-19 23.0, C-20 32.5, C-21 20.7, C-22 32.0, C-23 31.2, C-24 174.6, C-25 51.2(Ref. 0006)

MASS SPECTRA:Me ether (70eV) m/z: 388(M-H2O, 8%), 370(M-2H2O, 13%), 273(M-H2O-SC, 92%), 255(M-2H2O-SC, 100%), 213(M-2H2O-SC-ring D (42), 9%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 538(M-CH3, 8%), 460(M-TMSOH, 4%), 370(M-2TMSOH, 25%), 355(13%), 255(100%), 73(17%)(Ref. 0007/0049)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in human feces.(Ref. 0101/0161)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151/0212)
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)
Identified in feces of patients with cororectal cancer or polyps.(Ref. 0243)
Constituent in the bile of rabbits and hamsters.(Ref. 0257)
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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[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]

[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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[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 : - ()
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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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[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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[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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[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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[0243]
AUTHOR:Imray, C. H., Radley, S., Davis, A., Barker, G., Hendrickse, C. W., Donovan, I. A., Lawson, A. M., Baker, P. R., and Neoptolemos, J. P.
TITLE:Faecal unconjugated bile acids in patients with colorectal cancer or polyps PubMed ID:1427378
JOURNAL:Gut.
VOL:33 PAGE : 1239-1245 (1992)
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[0257]
AUTHOR:Schmassmann, A., Angellotti, M. A., Clerici, C., Hofmann, A. F., Ton-Nu, H. T., Schteingart, C. D., Marcus, S. N., Hagey, L. R., Rossi, S. S., and Aigner, A.
TITLE:Transport, metabolism, and effect of chronic feeding of lagodeoxycholic acid. A new, natural bile acid PubMed ID:2394330
JOURNAL:Gastroenterology.
VOL:99 PAGE : 1092-1104 (1990)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.