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Bile acid


DATA No : BBA0118 INFORMANT : Takashi Iida

NAME : 3a,6a,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:158-161degC(Ref. 0034)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-26: +23.3deg (C=0.47, MeOH)(Ref. 0181)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1710(C=O), 3419, 1040 (OH)(Ref. 0034)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.88(s), 21-Me 0.99(d), 3b-H 3.42(brm), 6b-H 3.77(brm), 7b-H 3.77(m), 12b-H 3.91(m)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.67(s), 19-Me 0.89(s), 21-Me 0.98(d), 3b-H 3.41(brm), COOMe 3.66(s), 6b-H 3.81(m), 7b-H 3.85(m), 12b-H 3.96(m)(Ref. 0034/0035)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.64, C-2 29.86, C-3 71.70, C-4 32.22, C-5 47.79, C-6 69.99, C-7 72.04, C-8 38.62, C-9 26.22, C-10 35.71, C-11 28.16, C-12 72.98, C-13 46.56, C-14 41.61, C-15 23.20, C-16 27.57, C-17 47.03, C-18 12.49, C-19 22.78, C-20 35.38, C-21 17.33, C-22 30.95, C-23 31.15, C-24 174.92, C-25 51.58(Ref. 0034/0035/0141)

MASS SPECTRA:Me ester (70eV) m/z: 438(M+, 1%), 420(M-H2O, 3%), 402(M-2H2O, 25%), 384(M-3H2O, 52%), 366(M-4H2O, 10%), 305(M-H2O-SC, 35%), 287(M-2H2O-SC, 31%), 269(M-3H2O-SC, 70%), 251(M-4H2O-SC, 24%)(Ref. 0034)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in amniotic fluid, serum, faeces, and urine from adult patients with cholestatic liver disease.(Ref. 0061/0141/0163/0176/0200)
A hydroxyation metabolite of cholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in human meconium and neonatal urine.(Ref. 0181)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Fetal bile acid identified in a dried blood disc, meconium and urine.(Ref. 0190)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Identified in urine, bile, portal and peripheral renous sera, and liver specimens from subjects with liver diseases (cholestasis, liver cirrhosis, chronic hepatitis, acute hepatitis).(Ref. 0201)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in urine of infants during the first year.(Ref. 0210)
Identified in urine of newborns.(Ref. 0245)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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]

[0034]
AUTHOR:Iida, T., Komatsubara, I., Yoda, S., Goto, J., Nambara, T., and Chang, F. C.
TITLE:Potential bile acid metabolites. 16. Synthesis of stereoisomeric 3 alpha,6,7,12 alpha-tetrahydroxy-5 beta-cholanoic acids PubMed ID:2089743
JOURNAL:Steroids.
VOL:55 PAGE : 530-539 (1990)
[TOP]

[0035]
AUTHOR:Iida, T., Chang, F. C., Mushiake, K., Goto, J., and Nambara, T.
TITLE:Complete 1H and 13C Resonance Assignments of Stereoisomeric 3a,6,7,12a-Tetrahydroxycholanoic Acids by Two-Dimensional Shift-Correlated NMR
JOURNAL:Mage. Reson. Chem.
VOL:31 PAGE : 645 -651 (1993)
[TOP]

[0061]
AUTHOR:Yoshii, M., Kihira, K., Shoda, J., Osuga, T., and Hoshita, T.
TITLE:Identification of 3,6,7,12-tetrahydroxy-5 beta-cholan-24-oic acids in human biologic fluids PubMed ID:2075618
JOURNAL:Steroids.
VOL:55 PAGE : 512-515 (1990)
[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]

[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)
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[0155]
AUTHOR:Clayton, P. T., Muller, D. P. R., and Lawson, A. M.
TITLE:The Bile Acids Composition of Gastric Contents from Neonates with High Intestinal Obstruction. PubMed ID:7150258
JOURNAL:Biochem. J.
VOL:206 PAGE : 489 -498 (1982)
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[0163]
AUTHOR:Goto, J., Hasegawa, K., Nambara, T., and Iida, T.
TITLE:Studies on steroids. CCLIV. Gas chromatographic-mass spectrometric determination of 4- and 6-hydroxylated bile acids in human urine with negative ion chemical ionization detection PubMed ID:1629271
JOURNAL:J Chromatogr.
VOL:574 PAGE : 1-7 (1992)
[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)
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[0181]
AUTHOR:Kurosawa, T., Mahara, R., Nittono, H., and Tohma, M.
TITLE:Synthesis of 6-hydroxylated bile acids and identification of 3 alpha,6 alpha,7 alpha,12 alpha-tetrahydroxy-5 beta-cholan-24-oic acid in human meconium and neonatal urine PubMed ID:2743505
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:37 PAGE : 557-559 (1989)
[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]

[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]

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