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Bile acid


DATA No : BBA0100 INFORMANT : Takashi Iida

NAME : (22R)-3a,7a,22-Trihydroxy-5b-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:141-142degC(Ref. 0050)
110-112degC (Et ester-3,7-diacetate)(Ref. 0264)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +1.0deg (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: 0.69 (3H, s, 18-CH3), 0.97 (3H, s, 19-CH3), 1.17 (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 36.5, C-2 31.4, C-3 72.9, C-4 40.6, C-5 43.1, C-6 35.9, C-7 69.1, C-8 40.8, C-9 34.0, C-10 36.1, C-11 21.7, C-12 40.8, C-13 43.9, C-14 51.2, C-15 24.7, C-16 28.4, C-17 54.6, C-18 12.1, C-19 23.4, C-20 43.1, C-21 12.8, C-22 71.2, C-23 36.5(Ref. 0004/0050)
Et ester-3,7-diacetate 1H-NMR (CD3OD) d: 18-Me 0.72(s), 19-Me 0.92(s), 21-Me 0.97(d), 3b-H 3.20-3.50(brm), 7b-H 3.70-3.85(m), 22-H 4.00-4.30(brm), 3-,7- and 22-OH and24-COOH 4.76(s)(Ref. 0264)
Et ester-3,7-diacetate 1H-NMR (CDCl3) d: 18-Me 0.67(s), 19-Me 0.90(s), CH2CH3 1.23(t, J, 6.0), 7a-OCOMe 1.94(s), 3a-OCOMe 1.97(s), 23-H2 2.13-2.33(m), 22-OH 2.50(brs), 22-H 3.83-4.17(m), CH2CH3 4.02(q, J, 6.0), 3b-H 4.20-4.60(brm), 7b-H 4.60-4.77(m)(Ref. 0264)

MASS SPECTRA:Me ester Hi-MS, m/z: M+, 422.3002 (CALCD. FOR C25H42O5=422.3030); M-H2O, 404.2945 (CALCD. FOR C25H40O4=404.2925); M-2H2O, 386.2729 (CALCD. FOR C25H38O3=386.2818)(Ref. 0050)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

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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[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.