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Bile acid


DATA No : BBA0064 INFORMANT : Takashi Iida

NAME : 3a,6a,7a-Trihydroxy-5b-cholan-24-oic Acid

COMMON NAME: Hyocholic Acid
g-Muricholic Acid
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:188-189degC, (Me ester; mp, 83-85degC)(Ref. 0001)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-21: +5.5deg (C=1.7, EtOH)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1718 (C=O), 3430, 1050 (OH)(Ref. 0029)

NMR SPECTRA:1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.90(s), 21-Me 0.93(d), 3b-H 3.39(brm), 6b- and 7b-H 3.82(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz ) d: 18-Me 0.66(s), 19-Me 0.90(s), 21-Me 0.93(d), 3b-H 3.42-3.48brm), COOMe 3.67(s), 6b- and 7b-H 3.85(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.5, C-2 30.4, C-3 71.7, C-4 32.6, C-5 47.8, C-6 71.9, C-7 69.6, C-8 38.6, C-9 32.5, C-10 35.9, C-11 20.5, C-12 39.5, C-13 42.7, C-14 50.1, C-15 23.0, C-16 28.1, C-17 55.8, C-18 11.7, C-19 23.5, C-20 35.3, C-21 18.2, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0029)

MASS SPECTRA:Me ester (70eV) m/z: 422(M+, 16%), 404(M-H2O, 24%), 386(M-2H2O, 23%)(Ref. 0029)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
A primary bile acid in pigs.(Ref. 0101/0102/0167/0215)
Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in urine and serum of healthy humans and patients with malabsorption.(Ref. 0143)
Identified in urine of patients with liver cirrhosis.(Ref. 0145/0149/0150/0151/0163/0176/0189/0200)
Identified in human meconium.(Ref. 0148)
A hydroxylation metabolites of chenodeoxycholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Detected in the bile of germ-free domestic fowl.(Ref. 0169)
Isolated from serum, urine and duodenal fluid of a child with intrahepatic cholestasis.(Ref. 0173)
A fetal bile acid in urine, meconium, and feces.(Ref. 0180/0181/0194)
A fetal bile acid identified in a dried blood disc, meconium and urine.(Ref. 0190)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Identified in urine of a patients treated with chenodeoxycholate, ursodeoxycholate or rifampicin and those with cirrhosis.(Ref. 0193)
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)
Identified in urine, bile, portal and peripheral venous 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 the serum and urine in cholestasis.(Ref. 0203)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
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
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[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.
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[0029]
AUTHOR:Iida, T., Momose, T., Tamura, T., Matsumoto, T., Chang, F. C., Goto, J., and Nambara, T.
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[0101]
AUTHOR:Matschiner, J. T. (1971) Naturally Occurring Bile Acids and Alcohols and their Origins. In The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1 : Chemistry) (Nair, P. P., and Krichevsky, D. eds), pp. 11-46, Plenum Press, New York.
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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.
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[0124]
AUTHOR:Koopman, B. J., Wolthers, B. G., van der Molen, J. C., Nagel, G. T., and Kruizinga, W.
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[0143]
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[0145]
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[0149]
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[0150]
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[0151]
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[0153]
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VOL:21 PAGE : 1072-1081 (1980)
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[0155]
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VOL:206 PAGE : 489 -498 (1982)
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[0163]
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JOURNAL:J Chromatogr.
VOL:574 PAGE : 1-7 (1992)
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[0167]
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VOL:62 PAGE : 637-645 (1956)
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[0169]
AUTHOR:Haslewood, G. A.
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VOL:123 PAGE : 15-18 (1971)
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[0173]
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VOL:38 PAGE : 1118 - (1979)
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[0176]
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[0180]
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VOL:20 PAGE : 819-824 (1994)
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[0181]
AUTHOR:Kurosawa, T., Mahara, R., Nittono, H., and Tohma, M.
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VOL:37 PAGE : 557-559 (1989)
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[0189]
AUTHOR:Miyara, T., Shindo, N., Tohma, M., and Murayama, K.
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VOL:4 PAGE : 56-60 (1990)
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[0190]
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[0191]
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VOL:12 PAGE : 322-334 (1990)
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[0192]
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VOL:31 PAGE : 1089-1098 (1990)
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[0193]
AUTHOR:Nakashima, T., Sano, A., Seto, Y., Nakajima, T., Shima, T., Sakamoto, Y., Okuno, T., Kashima, K., and Hasegawa, T.
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JOURNAL:Hepatology.
VOL:11 PAGE : 255-260 (1990)
[TOP]

[0194]
AUTHOR:Obinata, K., Nittono, H., Yabuta, K., Mahara, R., and Tohma, M.
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VOL:15 PAGE : 1-5 (1992)
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[0198]
AUTHOR:Setchell, K. D., Dumaswala, R., Colombo, C., and Ronchi, M.
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VOL:263 PAGE : 16637-16644 (1988)
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[0199]
AUTHOR:Shoda, J., Mahara, R., Osuga, T., Tohma, M., Ohnishi, S., Miyazaki, H., Tanaka, N., and Matsuzaki, Y.
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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.
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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]

[0203]
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VOL:154 PAGE : 507-516 (1976)
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[0206]
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VOL:9 PAGE : 425-432 (1979)
[TOP]

[0210]
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VOL:18 PAGE : 9-19 (1994)
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[0215]
AUTHOR:Hsia, S. L. (1971) Hyocholic Acid and Muricholic Acid, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1 : Chemistry) (Nair, P. P. and Krichevsky, D., eds), pp95-120, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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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)
[TOP]

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