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Bile acid


DATA No : BBA0114 INFORMANT : Takashi Iida

NAME : 1b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O6 MOL.WT (average) : 424.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:288-290degC(Ref. 0016)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:Me ester 1H-NMR (pyridine-d5; 90MHz) d: 18-Me 0.81(s), 19-Me 1.40(s), 1a-, 7b- and 12b-H 4.03-4.38(m), 3b-H 4.48-4.86(m)(Ref. 0016)
Me ester 13C-NMR (CD3OD; 100.6MHz) d: C-1 74.1, C-2 38.0, C-3 67.3, C-4 40.0, C-5 37.0, C-6 35.5, C7 68.8, C-8 41.3, C-9 29.5, C-10 40.3, C-11 29.6, C-12 73.8, C-13 47.3, C-14 42.9, C-15 24.3, C-16 28.5, C-17 48.0, C-18 13.0, C-19 17.9, C-20 36.8, C-21 17.6, C-22 32.2, C-23 31.8, C-24 176.4(Ref. 0004/0141)

MASS SPECTRA:Me-TMS ether (70eV) m/z: 636(M-2TMSOH), 456(M-3TMSOH, 17%), 366(M-4TMSOH, 18%), 251(M-4TMSOH-SC, 11%), 217(100%)(Ref. 0007/0016)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected in human meconium.(Ref. 0016)
Isolated from human urine, serum, faeces, and meconium of patients suffering intrahepatic cholestasis.(Ref. 0141)
Identified in human meconium. : stereochemistry of hydroxyl groups is unidentified.(Ref. 0148/0149/0176/0186/0200/0201)
A hydroxyation metabolite of deoxycholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Fetal bile acid in urine, meconium, and feces.(Ref. 0180)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Detected in serum and urine from healthy human adults.(Ref. 0189)
Fetal bile acid identified in a dried blood disc, meconium and urine.(Ref. 0190)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Excreted in urine of healthy newborn.(Ref. 0194/0210)
Isolated from human fetal gallbladder bile.(Ref. 0198)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in urine of newborns.(Ref. 0245)
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 : - ()
[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 : - ()
[TOP]

[0016]
AUTHOR:Tohma, M., Mahara, R., Takeshita, H., Kurosawa, T., and Ikegawa, S.
TITLE:Synthesis of the 1 beta-hydroxylated bile acids, unusual bile acids in human biological fluids PubMed ID:3769090
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:34 PAGE : 2890-2899 (1986)
[TOP]

[0141]
AUTHOR:Back, P., Fritz, H., and Populoh, C.
TITLE:The isolation of tetrahydroxy bile acids as methyl esters from human urine and their characterization by 1H- and 13C-nuclear magnetic resonance spectroscopy PubMed ID:6329940
JOURNAL:Hoppe Seylers Z Physiol Chem.
VOL:365 PAGE : 479-484 (1984)
[TOP]

[0148]
AUTHOR:Back, P., and Walter, K.
TITLE:Developmental pattern of bile acid metabolism as revealed by bile acid analysis of meconium PubMed ID:7353753
JOURNAL:Gastroenterology.
VOL:78 PAGE : 671-676 (1980)
[TOP]

[0149]
AUTHOR:Batta, A. K., Arora, R., Salen, G., Tint, G. S., Eskreis, D., and Katz, S.
TITLE:Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment PubMed ID:2621422
JOURNAL:J Lipid Res.
VOL:30 PAGE : 1953-1962 (1989)
[TOP]

[0153]
AUTHOR:Bremmelgaard, A., and Sjovall, J.
TITLE:Hydroxylation of cholic, chenodeoxycholic, and deoxycholic acids in patients with intrahepatic cholestasis PubMed ID:7462803
JOURNAL:J Lipid Res.
VOL:21 PAGE : 1072-1081 (1980)
[TOP]

[0176]
AUTHOR:Jonsson, G., Hedenborg, G., Wisen, O., and Norman, A.
TITLE:Presence of bile acid metabolites in serum, urine, and faeces in cirrhosis PubMed ID:1411266
JOURNAL:Scand J Clin Lab Invest.
VOL:52 PAGE : 555-564 (1992)
[TOP]

[0180]
AUTHOR:Kimura, A., Yamakawa, R., Ushijima, K., Fujisawa, T., Kuriya, N., Kato, H., Inokuchi, T., Mahara, R., Kurosawa, T., and Tohma, M.
TITLE:Fetal bile acid metabolism during infancy: analysis of 1 beta-hydroxylated bile acids in urine, meconium and feces PubMed ID:7927221
JOURNAL:Hepatology.
VOL:20 PAGE : 819-824 (1994)
[TOP]

[0186]
AUTHOR:Mahara, R., Takeshita, H., Kurosawa, T., Ikegawa, S., and Tohma, M.
TITLE:Detemination of 1b-Hydroxylated Bile Acids and Related Compounds in Human Biological Fluids by Gas Chromatography-Mass Spectrometry.
JOURNAL:Anal. Sci.
VOL:3 PAGE : 449 -459 (1987)
[TOP]

[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)
[TOP]

[0189]
AUTHOR:Miyara, T., Shindo, N., Tohma, M., and Murayama, K.
TITLE:Capillary gas chromatography/negative ion chemical ionization mass spectrometry for the quantification of bile acids including 1 beta-hydroxylated and unsaturated bile acids in serum and urine PubMed ID:2350598
JOURNAL:Biomed Chromatogr.
VOL:4 PAGE : 56-60 (1990)
[TOP]

[0190]
AUTHOR:Murai, T., Mahara, R., Kurosawa, T., Kimura, A., and Tohma, M.
TITLE:Determination of fetal bile acids in biological fluids from neonates by gas chromatography-negative ion chemical ionization mass spectrometry PubMed ID:9140754
JOURNAL:J Chromatogr B Biomed Sci Appl.
VOL:691 PAGE : 13-22 (1997)
[TOP]

[0192]
AUTHOR:Nakagawa, M., and Setchell, K. D.
TITLE:Bile acid metabolism in early life: studies of amniotic fluid PubMed ID:2373959
JOURNAL:J Lipid Res.
VOL:31 PAGE : 1089-1098 (1990)
[TOP]

[0194]
AUTHOR:Obinata, K., Nittono, H., Yabuta, K., Mahara, R., and Tohma, M.
TITLE:1 beta-hydroxylated bile acids in the urine of healthy neonates PubMed ID:1403443
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:15 PAGE : 1-5 (1992)
[TOP]

[0198]
AUTHOR:Setchell, K. D., Dumaswala, R., Colombo, C., and Ronchi, M.
TITLE:Hepatic bile acid metabolism during early development revealed from the analysis of human fetal gallbladder bile PubMed ID:3182806
JOURNAL:J Biol Chem.
VOL:263 PAGE : 16637-16644 (1988)
[TOP]

[0199]
AUTHOR:Shoda, J., Mahara, R., Osuga, T., Tohma, M., Ohnishi, S., Miyazaki, H., Tanaka, N., and Matsuzaki, Y.
TITLE:Similarity of unusual bile acids in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases PubMed ID:3411245
JOURNAL:J Lipid Res.
VOL:29 PAGE : 847-858 (1988)
[TOP]

[0200]
AUTHOR:Shoda, J., Osuga, T., Mahara, R., Tohma, M., Matsuura, K., Tanaka, N., Matsuzaki, Y., and Miyazaki, H.
TITLE:Altered metabolism of bile acids in cholestasis: determination of 1 beta- and 6 alpha-hydroxylated metabolites PubMed ID:2745625
JOURNAL:J Chromatogr.
VOL:488 PAGE : 315-328 (1989)
[TOP]

[0201]
AUTHOR:Shoda, J., Tanaka, N., Osuga, T., Matsuura, K., and Miyazaki, H.
TITLE:Altered bile acid metabolism in liver disease: concurrent occurrence of C-1 and C-6 hydroxylated bile acid metabolites and their preferential excretion into urine PubMed ID:2324645
JOURNAL:J Lipid Res.
VOL:31 PAGE : 249-259 (1990)
[TOP]

[0202]
AUTHOR:Strandvik, B., Wahlen, E., and Wikstrom, S. A.
TITLE:The urinary bile acid excretion in healthy premature and full-term infants during the neonatal period PubMed ID:8171265
JOURNAL:Scand J Clin Lab Invest.
VOL:54 PAGE : 1-10 (1994)
[TOP]

[0210]
AUTHOR:Wahlen, E., and Strandvik, B.
TITLE:Effects of different formula feeds on the developmental pattern of urinary bile acid excretion in infants PubMed ID:8126625
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:18 PAGE : 9-19 (1994)
[TOP]

[0245]
AUTHOR:Ikegawa, S., Yoshimura, T., Ito, K., Kurosawa, T., and Thoma, M.
TITLE:Simultaneous Fluorometric Determination of Conjugated Fetal Bile Acids in Urine of Newborns by High-Perfomance Liquid Chromatoguraphy.
JOURNAL:Anal. Sci.
VOL:11 PAGE : 91 -96 (1995)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.