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Bile acid


DATA No : BBA0006 INFORMANT : Takashi Iida

NAME : 3b-Hydroxy-5a-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O3 MOL.WT (average) : 376.573


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:208-211degC(Ref. 0042/0237)
164-165degC (Me ester)(Ref. 0001/0002/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +33.3deg (C=0.12, EtOH)(Ref. 0042/0237)
[a]d-22: +21deg (CHCl3) (Me ester)(Ref. 0001/0002/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1705 (C=O)(Ref. 0042)
Me ester: nmaxcm-1: 3494, 1712, 1297, 1051, 1002, 952, 893(Ref. 0013)

NMR SPECTRA:1H-NMR (CDCl3-CH3OH) d: 18-Me 0.69 (s), 19-Me 0.81 (s), 21-Me 0.95 (d), 3a-H 3.20-3.75 (m)(Ref. 0042)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.80(s), 21-Me 0.91(d), 3a-H 3.57(brm)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.9, C-2 31.3, C-3 71.0, C-4 38.0, C-5 44.7, C-6 28.6, C-7 31.9, C-8 35.4, C-9 54.2, C-10 35.2, C-11 21.1, C-12 39.9, C-13 42.5, C-14 56.3, C-15 24.0, C-16 27.9, C-17 55.8, C-18 11.9, C-19 12.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.2(Ref. 0011)

MASS SPECTRA:Me ester (70eV) m/z: 390(M+1, 56%), 375(M-CH3, 27%), 372(M-H2O, 40%), 357(M-H2O-CH3, 37%), 341(M-H2O-31, 16%), 257(M-H2O-SC, 6%),248(M-SC-part of ring D (27), 37%), 233(M-SC-ring D (42), 100%), 230(M-H2O-SC-27, 17%), 215(M-H2O-SC-42, 99%), 159(13%), 149(27%), 147(32%)(Ref. 0009/0012)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from the marine invertebrate Ptilosarcus gurneyi (sea pen).(Ref. 0096)
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:
VOL: PAGE : - ()
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[0002]
AUTHOR:Brooks, C. J. W. (1970) Bile Acids (Chapter 15: Steroids; Sterols and Bile Acids), in Rodd's Chemistry of Carbon Compounds (Vol. II, Part D) (Coffey, S. ed), pp 168-196, Elsevier Publishing Co., Amsterdam.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[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 : - ()
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[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)
[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]

[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)
[TOP]

[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)
[TOP]

[0013]
AUTHOR:Mitra, M. N., and Elliott, W. H.
TITLE:Bile acids. XXIV. Raney nickel in the preparation of allocholanic acids PubMed ID:5742844
JOURNAL:J Org Chem.
VOL:33 PAGE : 2814-2818 (1968)
[TOP]

[0042]
AUTHOR:Fukumoto, K., Suzuki, K., Nemoto, H., Kametani, T., and Furuyama, H.
TITLE:An Efficient Synthesis of Cholanic Acids from 20-Ketopregnanes.
JOURNAL:Tetrahedron
VOL:38 PAGE : 3701 -3704 (1982)
[TOP]

[0096]
AUTHOR:Vanderah, D. J., and Djerassi, C.
TITLE:Marine Natural Products. Synthesis of Four Naturally Occurring 20b-H Cholanic Acid Derivatives.
JOURNAL:J. Org. Chem.
VOL:43 PAGE : 1442 -1448 (1978)
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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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