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Bile acid


DATA No : BBA0080 INFORMANT : Takashi Iida

NAME : 3a,6a,12a-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:135-137degC(Ref. 0030)
154-155degC (Me ester-3,6-diacetate)(Ref. 0001)
150-151degC (Me ester-3,6,12-triacetate)(Ref. 0217)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +18deg (dioxane)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1709 (C=O), 3401, 1037 (OH)(Ref. 0030)

NMR SPECTRA:1H-NMR (CDCl3; 90MHz) d: 18-Me 0.67(s), 19-Me 0.89(s), 21-Me 0.99(d), 3b-H 3.58(brm), 6b- and 12b-H 4.03(m and brm)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 500MHz)d: 18-Me 0.666(s), 19-Me 0.890(s), 21-Me 0.967(d), 3b-H 3.583(brm), COOMe 3.663(s), 12b-H 3.977(m), 4b-H 4.007(brm)(Ref. 0030)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.66, C-2 30.08, C-3 71.53, C-4 29.18, C-5 48.53, C-6 68.08, C-7 34.81, C-8 35.10, C-9 32.97, C-10 35.60, C-11 28.62, C-12 72.95, C-13 46.69, C-14 47.87, C-15 23.81, C-16 27.51, C-17 47.27, C-18 12.73, C-19 23.28, C-20 35.27, C-21 17.32, C-22 31.18, C-23 30.96, C-24 174.85, C-25 51.59(Ref. 0030)

MASS SPECTRA:Me ester (70eV) m/z: 404(M-H2O, 7%), 386(M-2H2O, 81%), 368(M-3H2O, 23%), 289(M-H2O-SC, 20%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 67%)(Ref. 0030)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from urine of healthy subjects, a patient with malabsorption and a patient with moderate cholestasis of pregnancy.(Ref. 0001/0143/0144)
A hydroxyation metabolite of deoxycholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Bile acid of human fetus in early gestation.(Ref. 0156)
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)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Hill, R. A., Kirk, D. N., Makin, H. L. J., and Murphy, G. M. (1991) Chemical Data, Structures and Bibliographies, in Dictionary of Steroids, Chapman & Hall, London.
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]

[0030]
AUTHOR:Iida, T., Tamaru, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. XVIII. Synthesis of stereoisomeric 3,6,12 alpha-trihydroxy-5 beta-cholanoic acids PubMed ID:1856610
JOURNAL:J Lipid Res.
VOL:32 PAGE : 649-658 (1991)
[TOP]

[0143]
AUTHOR:Alme, B., Norden, A., and Sjovall, J.
TITLE:Glucuronides of unconjugated 6-hydroxylated bile acids in urine of a patient with malabsorption PubMed ID:668117
JOURNAL:Clin Chim Acta.
VOL:86 PAGE : 251-259 (1978)
[TOP]

[0144]
AUTHOR:Alme, B., and Sjovall, J.
TITLE:Analysis of bile acid glucuronides in urine. Identification of 3 alpha, 6 alpha, 12 alpha-trihydroxy-5 beta-cholanoic acid PubMed ID:7464137
JOURNAL:J Steroid Biochem.
VOL:13 PAGE : 907-916 (1980)
[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]

[0156]
AUTHOR:Colombo, C., Zuliani, G., Ronchi, M., Breidenstein, J., and Setchell, K. D.
TITLE:Biliary bile acid composition of the human fetus in early gestation PubMed ID:3822601
JOURNAL:Pediatr Res.
VOL:21 PAGE : 197-200 (1987)
[TOP]

[0206]
AUTHOR:Thomassen, P. A.
TITLE:Urinary bile acids in late pregnancy and in recurrent cholestasis of pregnancy PubMed ID:119641
JOURNAL:Eur J Clin Invest.
VOL:9 PAGE : 425-432 (1979)
[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]

[0217]
AUTHOR:Takeda, K., and Igarashi, K.
TITLE:Bile Acids and Steroids. XI. Synthesis of 3a,6a,12a-Trihydroxycholanic Acid and its Oxidation Products.
JOURNAL:J. Biochem.
VOL:46 PAGE : 1313 -1322 (1959)
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