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Bile acid


DATA No : BBA0092 INFORMANT : Takashi Iida

NAME : 3a,7a,12a-Trihydroxy-5a-cholan-24-oic Acid

COMMON NAME: Allocholic Acid
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:254-257degC, (Me ester; mp, 228-230degC)(Ref. 0024/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +27.8pm0.1deg (C=0.75, MeOH)(Ref. 0038/0237)
[a]d-25: +26.7deg (C=0.84, MeOH) (Me ester)(Ref. 0001/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1709 (C=O), 3400, 1031, 1011 (OH)(Ref. 0024)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.66(s), 19-Me 0.74(s), 21-Me 0.98(d), 7b-H 3.71(m), 12b-H 3.86(m), 3b-H 3.95(m)(Ref. 0024)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.77(s), 21-Me 0.98(d), COOMe 3.66(s), 7b-H 3.83(m), 12b-H 3.95(m), 3b-H 4.05(m)(Ref. 0008/0024)
>Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 31.9, C-2 28.8, C-3 66.3, C-4 35.5, C-5 31.5, C-6 36.3, C-7 67.9, C-8 39.8, C-9 39.2, C-10 35.8, C-11 28.1, C-12 72.8, C-13 46.4, C-14 42.1, C-15 23.0, C-16 27.3, C-17 47.1, C-18 12.5, C-19 9.9, C-20 35.1, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.6, C-25 51.3(Ref. 0011)

MASS SPECTRA:Me ester (70eV) m/z: 404(M-H2O, 1%), 386(M-2H2O, 69%), 371(M-2H2O-CH3, 8%), 289(M-H2O-SC, 15%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 19%)(Ref. 0012/0024/0033)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from many animal sources such as fishes, birds, penguins, sturgeons, and mammals.(Ref. 0001/0085/0101)
Identified in lizards, snakes, birds, and rabbits.(Ref. 0100)
Identified in urine, feces, and meconium of healthy humans and patients with liver diseases.(Ref. 0145/0148/0150/0151/0162)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Isolated from the leopard seal, Hydrurga leptonyx, and the California sealion, Zalophus californianus.(Ref. 0168)
Detected in the bile of germ-free domestic fowl.(Ref. 0169)
A metabolite of 5a-cholestan-3b-ol in the rat.(Ref. 0177)
Isolated from bile of patients with cerebrotendinous xanthomatosis.(Ref. 0178)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
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)
A biotransformation product of 7a-hydroxycholesterol in the hen.(Ref. 0214)
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.
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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.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0008]
AUTHOR:Iida, T., and Shinohara, T.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part2. Mono-, Di- and Trisubstituted Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:28 PAGE : 175 -179 (1987)
[TOP]

[0011]
AUTHOR:Iida, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Carbon-13 Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part II. Mono-, Di- and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:Chem. Phys. Lipids
VOL:45 PAGE : 1 -12 (1987)
[TOP]

[0012]
AUTHOR:Iida, T., Tamura, T., and Matsumoto, T.
TITLE:Mass Spectra of Mono-, Di-, and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:29 PAGE : 279 -288 (1988)
[TOP]

[0024]
AUTHOR:Iida, T., Nishida, S., Chang, F. C., Niwa, T., Goto, J., and Nambara, T.
TITLE:Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids.
JOURNAL:Chem. Pharm. Bull
VOL:41 PAGE : 763 -765 (1993)
[TOP]

[0033]
AUTHOR:Iida, T., Shinohara, T., Momose, T., Tamura, T., Matsumoto, T., Nambara, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites;12. Synthesis of Stereoisomeric 3,7,12-Trihydroxy-5a-cholanic Acids and Related Compounds.
JOURNAL:Synthesis
VOL: PAGE : 998 -1004 (1986)
[TOP]

[0038]
AUTHOR:Mitra, M. N., and Elliott, W. H.
TITLE:Bile acids. 23. A new direct synthesis of allocholic acid and its 3 beta isomer PubMed ID:5634890
JOURNAL:J Org Chem.
VOL:33 PAGE : 175-181 (1968)
[TOP]

[0085]
AUTHOR:Anderson, I. G., and Haslewood, G. A.
TITLE:Comparative studiesof 'bile salts'. 15. The natural occurrence and preparation of allocholic acid PubMed ID:14012853
JOURNAL:Biochem J.
VOL:85 PAGE : 236-242 (1962)
[TOP]

[0100]
AUTHOR:Haselwood, G. A. D. (1978) The Biological Importance of Bile Salts, in Frontiers of Biology (Vol. 47) (Neuberger, A., and Tatum, E. L. eds), North-Holland Publishing Co., Amsterdam.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[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.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0145]
AUTHOR:Amuro, Y., Hayashi, E., Endo, T., Higashino, K., and Kishimoto, S.
TITLE:Unusual trihydroxylated bile acids in urine of patients with liver cirrhosis PubMed ID:6825311
JOURNAL:Clin Chim Acta.
VOL:127 PAGE : 61-67 (1983)
[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]

[0150]
AUTHOR:Alme, B., Bremmelgaard, A., Sjovall, J., and Thomassen, P.
TITLE:Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry PubMed ID:864325
JOURNAL:J Lipid Res.
VOL:18 PAGE : 339-362 (1977)
[TOP]

[0151]
AUTHOR:Bremmelgaard, A., and Sjovall, J.
TITLE:Bile acid profiles in urine of patients with liver diseases PubMed ID:118027
JOURNAL:Eur J Clin Invest.
VOL:9 PAGE : 341-348 (1979)
[TOP]

[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)
[TOP]

[0162]
AUTHOR:Eneroth, P., Gordon, B., and Sjovall, J.
TITLE:Characterization of trisubstituted cholanoic acids in human feces PubMed ID:5965294
JOURNAL:J Lipid Res.
VOL:7 PAGE : 524-530 (1966)
[TOP]

[0168]
AUTHOR:Haslewood, G. A.
TITLE:Comparative studies of 'bile salts'. 13. Bile acids of the leopard seal, Hydrurga leptonyx, and of two snakes of the genus Bitis PubMed ID:13712142
JOURNAL:Biochem J.
VOL:78 PAGE : 352-359 (1961)
[TOP]

[0169]
AUTHOR:Haslewood, G. A.
TITLE:Bile salts of germ-free domestic fowl and pigs PubMed ID:5128663
JOURNAL:Biochem J.
VOL:123 PAGE : 15-18 (1971)
[TOP]

[0177]
AUTHOR:Karavolas, H. J., Elliott, W. H., Hsia, S. L., Doisy, E. A., Jr., Matschiner, J. T., Thayer, S. A., and Doisy, E. A.
TITLE:Bile Acids. Xxii. Allocholic Acid, A Metabolite Of 5-Alpha-Cholestan-3-Bet-A-Ol In The Rat PubMed ID:14285492
JOURNAL:J Biol Chem.
VOL:240 PAGE : 1568-1572 (1965)
[TOP]

[0178]
AUTHOR:Kihira, K., Shimazu, K., Kuwabara, M., Yoshii, M., Takeuchi, H., Nakano, I., Ozawa, S., Onuki, M., Hatta, Y., and Hoshita, T.
TITLE:Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis PubMed ID:3660436
JOURNAL:Steroids.
VOL:48 PAGE : 109-119 (1986)
[TOP]

[0191]
AUTHOR:Nakagawa, M., Colombo, C., and Setchell, K. D.
TITLE:Comprehensive study of the biliary bile acid composition of patients with cystic fibrosis and associated liver disease before and after UDCA administration PubMed ID:2391071
JOURNAL:Hepatology.
VOL:12 PAGE : 322-334 (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]

[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]

[0214]
AUTHOR:Yamasaki, H., and Yamasaki, K.
TITLE:In vivo conversion of 7 -hydroxycholesterol- 14 C to 3, 7 -dihydroxychol-5-enoic- 14 C and -4-enoic- 14 C acids as well as to allocholic- 14 C acid in the hen PubMed ID:5015369
JOURNAL:J Biochem (Tokyo).
VOL:71 PAGE : 77-83 (1972)
[TOP]

[0237]
AUTHOR:Elliott, W. H. (1971) Allo Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1: Chemistry) (Nair, P. P., and Kritchevsky, D. eds), pp47-93, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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