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Bile acid


DATA No : BBA0101 INFORMANT : Takashi Iida

NAME : (22S)-3a,7a,22-Trihydroxy-5b-cholan-24-oic Acid

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:247-250degC(Ref. 0050)
143-145degC (Et ester-3,7-diacetate)(Ref. 0264)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +2.4deg (C=1.3, MeOH)(Ref. 0050)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 3400 (OH), 1720 (COOH)(Ref. 0050)
Et ester-3,7-diacetate: nmaxcm-1: 1730 (C=O), 3530 (OH)(Ref. 0264)

NMR SPECTRA:1H-NMR (Pyridine-d5) d: 0.74 (3H, s, 18-CH3), 0.96 (3H, s, 19-CH3), 1.16 (3H, d, J=6Hz, 21-CH3), 3.4-4.4 (3H, m, 3b-, 7b- and 22-CH-OH)(Ref. 0050)
13C-NMR (CD3OD) d: C-1 36.6, C-2 31.5, C-3 73.0, C-4 40.6, C-5 43.2, C-6 36.0, C-7 69.2, C-8 40.9, C-9 34.1, C-10 36.2, C-11 21.8, C-12 41.2, C-13 43.5, C-14 51.4, C-15 24.7, C-16 28.7, C-17 53.8, C-18 12.1, C-19 23.4, C-20 42.0, C-21 12.4, C-22 70.9, C-23 41.5(Ref. 0004/0050)
Et ester-3,7-diacetate 1H-NMR (CD3OD) d: 18-Me 0.68(s), 19-Me 0.92(s), 21-Me 0.95(d), 3b-H 3.17-3.50(brm), 7b-H 3.68-3.87(m), 22-H 3.97-4.27(m), 3-,7- and 22-OH and24-COOH 4.57(s)(Ref. 0264)
Et ester-3,7-diacetate 1H-NMR (CDCl3) d: 18-Me 0.63(s), 19-Me 0.90(s), CH2CH3 1.21(t, J, 6.0), 3a- and 7a-OCOMe 1.94(s), 23-H2 2.13-2.67(m), 22-OH 2.50(s), 22-H 3.83-4.10(m), CH2CH3 3.95(q, J, 6.0), 3b-H 4.14-4.57(brm), 7b-H 4.57-4.73(m)(Ref. 0264)

MASS SPECTRA:Me ester Hi-MS m/z: M+, 422.3070 (CALCD.FOR C25H42O5=422.3030); M-H2O, 404.2944 (CALCD.FOR C25H40O4=404.2925) ; M-2H2O, 386.2858 (CALCD.FOR C25H38O3=386.2818)(Ref. 0050)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from the bile of a marine teleost, Parapristipoma trilineatum, and fresh water fishes, Polypterus senegalus and Mormyrus caballus.(Ref. 0050/0051)
Isolated from seals, sealions and a walrus ; stereochemistry of a hydroxyl group at C-23 is unidentified.(Ref. 0100)
Primary bile acid in bony fish.(Ref. 0102)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0004]
AUTHOR:Barnes, S., and Kirk, D. N. (1988) Nuclear Magnetic Resonance Spectroscopy of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchell, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp65-136, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0050]
AUTHOR:Kihira, K., Morioka, Y., and Hoshita, T.
TITLE:Synthesis of (22R and 22S)-3a,7a,22-Trihydroxy-5b-cholan-24-oic. Acids and Structure of Haemulcholic Acid, A Unique Bile Acid Isolated from Fish Bile. PubMed ID:7320628
JOURNAL:J. Lipid Res.
VOL:22 PAGE : 1181 -1187 (1981)
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[0051]
AUTHOR:Hoshita, T., Hirofugi, S., and Kazono, T.
TITLE:Sterobile Acids and Bile Alcohols. LXXXVII. Isolation of a New Bile Acid, Haemulcholic Acid from the Bile of Parapristipoma trilineatum. PubMed ID:6048964
JOURNAL:J. Biochem.
VOL:61 PAGE : 136 -141 (1967)
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[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:
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[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:
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[0264]
AUTHOR:Pellicciari, R., Natalini, B., Cecchetti, S., and Fringuelli, R.
TITLE:Reduction of a-Diazo-b-Hydroxy Esters to b-Hdroxy Esters: Application in One of Two Convergent Syntheses of a (22S)-22-Hydroxy Bile Acid from Fish Bile and its (22R)-Epimer.
JOURNAL:J. Chem. Soc. Perkin Trans.
VOL:1 PAGE : 493 -497 (1985)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.