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Bile acid


DATA No : BBA0247 INFORMANT : Takashi Iida

NAME : 3a,5b,7b-Trihydroxycholan-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:148-149degC (Me ester-3,7-diacetate)(Ref. 0228)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester-3,7-diacetate: nmaxcm-1: 1027, 1366, 1729, 2874, 2910, 2935, 3600(Ref. 0228)

NMR SPECTRA:Me ester-3,7-diacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.68(s), 21-Me 0.92(d), 19-Me 0.94(s), 3a- and 7b-OCOMe 1.99 and 2.02(each s), 23-H 2.23(m), 23'-H 2.35(m), COOMe 3.67(s), 7a-H 4.64(td, J, 11.0, 5.5), 3b-H 5.06(m)(Ref. 0228)
Me ester-3,7-diacetate 13C-NMR (CDCl3; 125MHz) d: C-1 29.0, C-2 25.8, C-3 70.6, C-4 39.0, C-5 74.4, C-6 41.9, C-7 73.9, C-8 39.2, C-9 41.3, C-10 39.0, C-11 21.2, C-12 39.6, C-13 43.3, C-14 55.3, C-15 25.5, C-16 28.3, C-17 54.9, C-18 11.9, C-19 16.1, C-20 35.1, C-21 18.2, C-22 30.9, C-23 30.8, C-24 174.8, C-25 51.4(Ref. 0228)

MASS SPECTRA:Me-TMS ether m/z: 638(M+), 623(M-15), 548(M-TMSOH), 533(M-15-TMSOH), 458(M-2TMSOH), 443(M-15-2TMSOH), 368(M-3TMSOH), 353(M-15-3TMSOH), 343(ABCD-skeleton+TMSOH), 253(ABCD-skeleton), 493, 403, 331, 289, 229(Ref. 0124/0188)
Me ester-3,7-diacetate m/z: 428(5%), 386(53%), 368(63%), 353(16%), 332(100%), 331(17%), 313(27%), 271(78%), 253(63%), 226(10%), 211(16%)(Ref. 0228)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
A biotransformation product of ursodeoxycholic acid in the isolated perfused rat liver.(Ref. 0183)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0124]
AUTHOR:Koopman, B. J., Wolthers, B. G., van der Molen, J. C., Nagel, G. T., and Kruizinga, W.
TITLE:Abnormal urinary bile acids in a patient suffering from cerebrotendinous xanthomatosis during oral administration of ursodeoxycholic acid PubMed ID:3801500
JOURNAL:Biochim Biophys Acta.
VOL:917 PAGE : 238-246 (1987)
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[0183]
AUTHOR:Lake, J. R., Renner, E. L., Scharschmidt, B. F., Cragoe, E. J., Jr., Hagey, L. R., Lambert, K. J., Gurantz, D., and Hofmann, A. F.
TITLE:Inhibition of Na+/H+ exchange in the rat is associated with decreased ursodeoxycholate hypercholeresis, decreased secretion of unconjugated urodeoxycholate, and increased ursodeoxycholate glucuronidation PubMed ID:2455672
JOURNAL:Gastroenterology.
VOL:95 PAGE : 454-463 (1988)
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[0188]
AUTHOR:Meng, L. J., Reyes, H., Palma, J., Hernandez, I., Ribalta, J., and Sjovall, J.
TITLE:Effects of ursodeoxycholic acid on conjugated bile acids and progesterone metabolites in serum and urine of patients with intrahepatic cholestasis of pregnancy PubMed ID:9453429
JOURNAL:J Hepatol.
VOL:27 PAGE : 1029-1040 (1997)
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[0228]
AUTHOR:Cerr$`e$, C., Hofmann, A. F., and Schteingart, C. D.
TITLE:Oxyfunctionalization of (5b)-Bile Acids by Dimethyldioxrane: Hydroxylation at C-5, C-14, and C-17.
JOURNAL:Tetrahedron
VOL:53 PAGE : 435 -446 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.