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Bile acid


DATA No : BBA0094 INFORMANT : Takashi Iida

NAME : 3b,7a,12a-Trihydroxy-5a-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:236-238degC, (Me ester; mp, 200-202degC)(Ref. 0033/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +25.2pm1deg (C=0.68, MeOH)(Ref. 0038/0237)
[a]d-25: +23.2deg (Me ester)(Ref. 0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1705(C=O), 3420, 1035(OH)(Ref. 0033)
The spectrum was shown as its Et ester derivative(Ref. 0085)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.79(s), 21-Me 0.99(d), 3a-H 3.53(brm), 7b-H 3.78(m), 12b-H 3.91(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.80(s), 21-Me 0.98(d), 3a-H 3.61(brm), COOMe 3.66(s), 7b-H 3.82(m), 12b-H 3.95(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.6, C-2 31.3, C-3 71.0, C-4 37.7, C-5 37.1, C-6 36.5, C-7 67.7, C-8 39.8, C-9 39.3, C-10 35.1, C-11 28.6, C-12 72.8, C-13 46.5, C-14 42.0, C-15 23.0, C-16 27.3, C-17 47.2, C-18 12.5, C-19 11.0, C-20 35.1, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0011)

MASS SPECTRA:Me ester (20eV) m/z: 404(M-H2O, 4%), 386(M-H2O, 87%), 289(M-H2O-SC, 30%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 12%)(Ref. 0012/0033)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0008]
AUTHOR:Iida, T., and Shinohara, T.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part2. Mono-, Di- and Trisubstituted Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:28 PAGE : 175 -179 (1987)
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[0011]
AUTHOR:Iida, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Carbon-13 Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part II. Mono-, Di- and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:Chem. Phys. Lipids
VOL:45 PAGE : 1 -12 (1987)
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[0012]
AUTHOR:Iida, T., Tamura, T., and Matsumoto, T.
TITLE:Mass Spectra of Mono-, Di-, and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:29 PAGE : 279 -288 (1988)
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[0033]
AUTHOR:Iida, T., Shinohara, T., Momose, T., Tamura, T., Matsumoto, T., Nambara, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites;12. Synthesis of Stereoisomeric 3,7,12-Trihydroxy-5a-cholanic Acids and Related Compounds.
JOURNAL:Synthesis
VOL: PAGE : 998 -1004 (1986)
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[0038]
AUTHOR:Mitra, M. N., and Elliott, W. H.
TITLE:Bile acids. 23. A new direct synthesis of allocholic acid and its 3 beta isomer PubMed ID:5634890
JOURNAL:J Org Chem.
VOL:33 PAGE : 175-181 (1968)
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[0085]
AUTHOR:Anderson, I. G., and Haslewood, G. A.
TITLE:Comparative studiesof 'bile salts'. 15. The natural occurrence and preparation of allocholic acid PubMed ID:14012853
JOURNAL:Biochem J.
VOL:85 PAGE : 236-242 (1962)
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[0237]
AUTHOR:Elliott, W. H. (1971) Allo Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1: Chemistry) (Nair, P. P., and Kritchevsky, D. eds), pp47-93, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.