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Bile acid


DATA No : BBA0024 INFORMANT : Takashi Iida

NAME : 3a,6a-Dihydroxy-5b-cholan-24-oic Acid

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:197-198degC(Ref. 0045)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +8deg (MeOH)(Ref. 0045)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxm: 9.72(Ref. 0003)
Me ester: nmaxm: 9.73(Ref. 0003)

NMR SPECTRA:Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.5, C-2 30.2, C-3 71.5, C-4 29.2, C-5 48.4, C-6 67.9, C-7 34.8, C-8 34.8, C-9 39.8, C-10 35.9, C-11 20.7, C-12 39.8, C-13 42.8, C-14 56.61, C-15 24.1, C-16 28.0, C-17 55.9, C-18 11.9, C-19 23.4, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0018)

MASS SPECTRA:Me ester (70eV) m/z: 406(M+1, 1%), 388(M-H2O, 100%), 373(M-H2O-CH3, 29%), 370(M-H2O, 96%), 357(M-H2O-31, 8%), 355(M-2H2O-CH3, 27%), 273(M-H2O-SC, 23%), 255(M-2H2O-SC, 61%), 249(M-SC-ring D (42), 11%), 246(M-H2O-SC-part of ring D (27), 31%), 228(M-2H2O-SC-27, 29%), 213(M-2H2O-SC-42, 80%)(Ref. 0009)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from pig bile.(Ref. 0001)
Occurred in plasma, liver, bile, and feces of rat.(Ref. 0101)
Bacterial 7-dehydroxylation product of hyodeoxycholic acid; a hepatic hydroxylation product of 7-oxolithocholic acid.(Ref. 0102)
Identified in urine of a patients with malabsorption.(Ref. 0143)
Identified in human meconium.(Ref. 0148)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Metabolite of lithocholic acid in human fetal liver.(Ref. 0164)
Detected in the bile of germ-free domestic fowl.(Ref. 0169)
Isolated from human fetal gallbladder bile.(Ref. 0198)
Identified in the serum and urine in cholestasis.(Ref. 0203)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
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:
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[0003]
AUTHOR:Levin, S. J., and Johnston, C. G.
TITLE:Infrared Correlations in the Bile Acid Series
JOURNAL:Talanta.
VOL:8 PAGE : 871 -879 (1961)
[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:
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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:
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[TOP]

[0018]
AUTHOR:Iida, T., Momose, T., Tamura, T., Matsumoto, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. 13. Improved routes to 3 beta, 6 beta- and 3 beta, 6 alpha-dihydroxy-5 beta-cholanoic acids PubMed ID:3367086
JOURNAL:J Lipid Res.
VOL:29 PAGE : 165-171 (1988)
[TOP]

[0045]
AUTHOR:Moffett, R.B., and Hoehn, W.M.
TITLE:Configuration of the C6 Hydroxyl Group in Hyodesoxycholic Acid.
JOURNAL:J. Am. Chem. Soc.
VOL:69 PAGE : 1995 -1996 (1947)
[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]

[0102]
AUTHOR:Hofmann, A. F., Schteingart, C. D., and Hagey, L. R. (1995) Species Differences in Bile Acid Metabolism, in Bile Acids in Liver Diseases (Paumgartner, G., and Beuers, U. eds), pp 3-30, Kluwer Academic Publishers, Dordrecht.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0143]
AUTHOR:Alme, B., Norden, A., and Sjovall, J.
TITLE:Glucuronides of unconjugated 6-hydroxylated bile acids in urine of a patient with malabsorption PubMed ID:668117
JOURNAL:Clin Chim Acta.
VOL:86 PAGE : 251-259 (1978)
[TOP]

[0148]
AUTHOR:Back, P., and Walter, K.
TITLE:Developmental pattern of bile acid metabolism as revealed by bile acid analysis of meconium PubMed ID:7353753
JOURNAL:Gastroenterology.
VOL:78 PAGE : 671-676 (1980)
[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]

[0164]
AUTHOR:Gustafsson, J., Anderson, S., and Sjovall, J.
TITLE:Bile acid metabolism during development: metabolism of lithocholic acid in human fetal liver PubMed ID:3797138
JOURNAL:Pediatr Res.
VOL:21 PAGE : 99-103 (1987)
[TOP]

[0169]
AUTHOR:Haslewood, G. A.
TITLE:Bile salts of germ-free domestic fowl and pigs PubMed ID:5128663
JOURNAL:Biochem J.
VOL:123 PAGE : 15-18 (1971)
[TOP]

[0198]
AUTHOR:Setchell, K. D., Dumaswala, R., Colombo, C., and Ronchi, M.
TITLE:Hepatic bile acid metabolism during early development revealed from the analysis of human fetal gallbladder bile PubMed ID:3182806
JOURNAL:J Biol Chem.
VOL:263 PAGE : 16637-16644 (1988)
[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]

[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)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.