Bile acid
DATA No : BBA0032
INFORMANT : Takashi Iida
NAME : 3
a,7
a-Dihydroxy-5
b-cholan-24-oic Acid
| COMMON NAME | : | Chenodeoxycholic Acid |
| SYMBOL | : | |
| FORMULA | : | C24H40O4 MOL.WT (average) : 392.572 |
| PHYSICAL AND CHEMICAL PROPERTIES |
| MELTING POINT | : | 167.5-172.5 C(Ref. 0020) |
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| BOILING POINT | : | |
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| REFRACTIVE INDEX | : | |
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| OPTICAL ROTATION | : | |
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| DENSITY | : | |
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| SOLUBILITY | : | |
| UV SPECTRA | : | |
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| 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)
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| 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)
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| OTHER SPECTRA | : |
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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)
[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 : - () |
[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) |
[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) |
[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) |
[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 : - () |
[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 : - () |
[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) |
[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) |
[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) |
[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) |
[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 : - () |
[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 : - () |
[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 : - () |
[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) |
[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) |
[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) |
[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) |
[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) |
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