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Bile acid


DATA No : BBA0032 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:167.5-172.5degC(Ref. 0020)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:lmaxmm: 5.92 (C=O), 9.34, 10.25 (OH)(Ref. 0003/0020)
Me ester: nmaxmm: 9.33, 9.70, 9.87, 10.22(Ref. 0003)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.89(s), 21-Me 0.91(d), 3b-H 3.4(brm), 7b-H 3.79 (m)(Ref. 0005/0021)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.2, C-2 30.5, C-3 71.7, C-4 39.6, C-5 41.5, C-6 34.7, C-7 68.2, C-8 39.3, C-9 32.7, C-10 35.0, C-11 20.5, C-12 39.6, C-13 42.5, C-14 50.3, C-15 23.5, C-16 28.0, C-17 55.7, C-18 11.7, C-19 22.7, C-20 35.2, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 20%), 373(M-H2O-CH3, 11%), 370(M-2H2O, 100%), 355(M-2H2O-CH3, 61%), 273(M-H2O-SC, 57%), 264(M-SC-27, 22%), 255(M-2H2O-SC, 90%), 249(M-SC-ring D (42), 10%), 246(M-H2O-SC-part of ring D (27), 34%), 228(M-2H2O-SC-27, 57%), 213(M-2H2O-SC-42, 77%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Cholagogic agent used for dissolution of gallstones.(Ref. 0001/0101)
Simplest and common primary bile acid. Occurred in human bile and bile of many other vertebrates.(Ref. 0100/0101/0102)
Identified in urine and feces of healthy humans and patients with liver diseases.(Ref. 0150/0151/0161)
Identified in plasma of patients with bacterial overgrowth in the small intestine.(Ref. 0256)
CHEMICAL SYNTHESIS
Perpared from hyodeoxycholic acid.(Ref. 0084)
Perpared from androstenedione.(Ref. 0262)
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:
VOL: PAGE : - ()
[TOP]

[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]

[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)
[TOP]

[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 : - ()
[TOP]

[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 : - ()
[TOP]

[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]

[0020]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. 3. A New Route to Chenodeoxycholic Acid.
JOURNAL:J. Org. Chem.
VOL:46 PAGE : 2786 -2788 (1981)
[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]

[0084]
AUTHOR:Zhou, W-S., Wang Z-Q., and Jiang B.
TITLE:Stereocontrolled Conversion of Hyodeoxycholic Acid into Chenodeoxycholic Acid and Ursodeoxycholic Acid.
JOURNAL:J. Chem. Soc. Perkin Trans. 1.
VOL: PAGE : 1 -3 (1990)
[TOP]

[0100]
AUTHOR:Haselwood, G. A. D. (1978) The Biological Importance of Bile Salts, in Frontiers of Biology (Vol. 47) (Neuberger, A., and Tatum, E. L. eds), North-Holland Publishing Co., Amsterdam.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[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]

[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]

[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]

[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)
[TOP]

[0262]
AUTHOR:Wovkulich, P. M., Batcho, A. D., and Uskokovic, M. R.
TITLE:Stereosective Introduction of Steroid Side Chains. Synthesis of Chenodeoxycholic Acid.
JOURNAL:Helv. Chim. Acta.
VOL:67 PAGE : 612 -615 (1984)
[TOP]

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