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Bile Acid

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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
1
Ursocholanic Acid 5b-Cholan-24-oic Acid BBA0001Bile AcidTakashi Iida C24H40O2 360.573Download ChemDraw structure data 164degC, (Me ester; mp, 86degC)<< Ref. 0001/0002>> [a]14D: +21.74deg (CHCl3)<< Ref. 0001/0002>>
[a]D: +23.2deg (dioxane) (Me ester)<< Ref. 0001>>
nmaxm: 9.68, 10.58<< Ref. 0003>>
Me ester: nmaxm: 9.65, 9.88, 10.60<< Ref. 0003>>
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 21-Me 0.90(d), 19-Me 0.91(s)<< Ref. 0004/0005>>
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.2, C-3 26.9, C-4 27.4, C-5 43.6, C-6 27.1, C-7 26.4, C-8 35.7, C-9 40.4, C-10 35.2, C-11 20.7, C-12 40.2, C-13 42.6, C-14 56.5, C-15 24.1, C-16 28.0, C-17 55.8, C-18 11.9, C-19 24.1, C-20 35.2, C-21 18.1, C-22 30.8, C-23 30.8, C-24 174.2, C-25 51.1<< Ref. 0004/0006>>
Me ester (22eV) m/z: 374(M+), 359(M-CH3, 100%), 343(M-CH3O, 2%), 325(M-CH3O-H2O, 5%), 317(4%), 278(M-ring A, 5%), 264(M-ring A and C-6, 12%), 259(M-SC, 1%), 257(M-SC-2H, 1%), 249(M-ring A and C-6-CH3, 1%), 232(ABC ion, 15%), 217(ABC-ring ion, 100%), 203(11%)<< Ref. 0039>>
The spectrum (70eV) was shown as the Me-ester derivative<< Ref. 0007>>
Isolated from the embryo of the jequirity bean, Abrus precatorius.<< Ref. 0001>>
Detected as a trace component of human feces.<< Ref. 0101>>
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0002 >> AUTHOR: Brooks, C. J. W. (1970) Bile Acids (Chapter 15: Steroids; Sterols and Bile Acids), in Rodd's Chemistry of Carbon Compounds (Vol. II, Part D) (Coffey, S. ed), pp 168-196, Elsevier Publishing Co., Amsterdam. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0003 >> AUTHOR: Levin, S. J., and Johnston, C. G. TITLE: Infrared Correlations in the Bile Acid Series JOURNAL: Talanta. VOLUME: 8 PAGE: 871 -879 (1961)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0005 >> AUTHOR: Iida, T., and Chang, F. C. TITLE: Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives JOURNAL: J. Coll. Engin. Nihon Univ. (A) VOLUME: 24 PAGE: 163 -165 (1983)
<< Ref.0006 >> AUTHOR: Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C. TITLE: Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers. JOURNAL: Org. Magn. Reson. VOLUME: 21 PAGE: 305 -309 (1983)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0039 >> AUTHOR: Lee, S. P., Lester, R., and Pyrek, J. S. TITLE: Vulpecholic acid (1 alpha, 3 alpha, 7 alpha-trihydroxy-5 beta-cholan-24-oic acid): a novel bile acid of a marsupial, Trichosurus vulpecula (Lesson) PubMed ID:3559398 JOURNAL: J Lipid Res. VOLUME: 28 PAGE: 19-31(1987)
<< Ref.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: VOLUME: PAGE: - ()
2
Allocholanic Acid 5a-Cholan-24-oic Acid BBA0002Bile AcidTakashi Iida C24H40O2 360.573Download ChemDraw structure data 170degC, (Me ester; mp, 91degC)<< Ref. 0001/0002/0237>> [a]14D: +21.74deg (CHCl3)<< Ref. 0001/0002/0237>>
[a]D: +22.1deg (Me ester)<< Ref. 0237>>
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 19-Me 0.77(s), 21-Me 0.90(d)<< Ref. 0008>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d : C-1 38.6, C-2 22.1, C-3 26.7, C-4 29.0, C-5 46.9, C-6 29.0, C-7 32.0, C-8 35.4, C-9 54.7, C-10 36.1, C-11 20.7, C-12 40.0, C-13 42.5, C-14 56.5, C-15 24.0, C-16 28.0, C-17 55.8, C-18 11.9, C-19 12.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.2<< Ref. 0011>>
The spectrum (70eV) was shown as the Me-ester derivative<< Ref. 0007>> Detected in the biliary bile from alligator mississippiensis.<< Ref. 0209>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.0002 >> AUTHOR: Brooks, C. J. W. (1970) Bile Acids (Chapter 15: Steroids; Sterols and Bile Acids), in Rodd's Chemistry of Carbon Compounds (Vol. II, Part D) (Coffey, S. ed), pp 168-196, Elsevier Publishing Co., Amsterdam. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.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) VOLUME: 28 PAGE: 175 -179 (1987)
<< Ref.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 VOLUME: 45 PAGE: 1 -12 (1987)
<< Ref.0209 >> AUTHOR: Tint, G. S., Dayal, B., Batta, A. K., Shefer, S., Joanen, T., McNease, L., and Salen, G. TITLE: Biliary Bile Acids, Bile Alchols, and Sterols of Alligator mississippiensis. PubMed ID:7354247 JOURNAL: J. Lipid Res. VOLUME: 21 PAGE: 110 -117 (1980)
<< Ref.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: VOLUME: PAGE: - ()
3
Lithocholic Acid 3a-Hydroxy-5b-cholan-24-oic Acid BBA0003Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 186degC<< Ref. 0001>>
130-132degC (Me ester)<< Ref. 0040>>
[a]d-20: +33.7deg (C=1.5, MeOH)<< Ref. 0001>> nmaxm: 9.72, 10.60<< Ref. 0003>>
Me ester: nmaxcm-1: 1721 (C=O), 3610 (OH), 1106, 1010, 725<< Ref. 0040>>
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 19-Me 0.88(s), 21-Me 0.88(d), 3b-H 3.5(brm)<< Ref. 0005>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.0, C-2 30.1, C-3 71.0, C-4 36.0, C-5 41.8, C-6 26.9, C-7 26.2, C-8 35.5, C-9 40.1, C-10 34.2, C-11 20.5, C-12 39.9, C-13 42.4, C-14 56.2, C-15 23.9, C-16 27.8, C-17 55.6, C-18 11.7, C-19 23.1, C-20 35.1, C-21 17.9, C-22 30.7, C-23 30.7, C-24 174.2, C-25 51.0<< Ref. 0006>>
Me ester (70eV) m/z: 372(M-H2O, 78%), 357(M-H2O-CH3, 17%), 257(M-H2O-SC, 23%), 248(M-SC-part of ring D (27), 10%), 230(M-H2O-SC-27, 29%), 217(M-173, 42%), 215(M-H2O-SC-ring D (42), 100%)<< Ref. 0009/0010>>
The spectrum (70eV) was shown as the Me-TMS derivative<< Ref. 0007>>
Occurred in ox, moneky, rabbit, and pig bile.<< Ref. 0001/0101>>
Identified in human blood and feces.<< Ref. 0101>>
Bacterial 7-dehydroxylation product of chenodeoxycholic acid and ursodeoxycholic acid.<< Ref. 0102>>
Identified in urine of healthy humans and patients with liver diseases.<< Ref. 0150/0151>>
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0003 >> AUTHOR: Levin, S. J., and Johnston, C. G. TITLE: Infrared Correlations in the Bile Acid Series JOURNAL: Talanta. VOLUME: 8 PAGE: 871 -879 (1961)
<< Ref.0005 >> AUTHOR: Iida, T., and Chang, F. C. TITLE: Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives JOURNAL: J. Coll. Engin. Nihon Univ. (A) VOLUME: 24 PAGE: 163 -165 (1983)
<< Ref.0006 >> AUTHOR: Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C. TITLE: Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers. JOURNAL: Org. Magn. Reson. VOLUME: 21 PAGE: 305 -309 (1983)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0009 >> AUTHOR: Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0010 >> AUTHOR: Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T. TITLE: High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids. JOURNAL: Biomed. Mass Spectrom. VOLUME: 9 PAGE: 473 -476 (1982)
<< Ref.0040 >> AUTHOR: Baker, J. F., and Blickenstaff, R. T. TITLE: Intramolecular catalysis. VIII. Effects on the acetylation of the 7alpha-hydroxyl group of steroids. A H nuclear magnetic resonance rate method PubMed ID:1142040 JOURNAL: J Org Chem. VOLUME: 40 PAGE: 1579-1586(1975)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.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. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.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. VOLUME: 18 PAGE: 339-362(1977)
<< Ref.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. VOLUME: 9 PAGE: 341-348(1979)
4
Isolithocholic Acid 3b-Hydroxy-5b-cholan-24-oic Acid BBA0004Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 176-176.5deg, (Me ester; mp, 117.1-118degC)<< Ref. 0001>> [a]D: +32deg (CHCl3), [a]D: +21.3deg (CHCl3) (Me ester)<< Ref. 0001>> Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 21-Me 0.91(d), 19-Me 0.95(s), 3a-H 4.06(m)<< Ref. 0004/0005>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.8, C-2 27.8, C-3 66.7, C-4 33.4, C-5 36.3, C-6 26.5, C-7 26.1, C-8 35.5, C-9 39.6, C-10 34.9, C-11 20.9, C-12 40.2, C-13 42.6, C-14 56.4, C-15 24.0, C-16 28.0, C-17 55.8, C-18 11.9, C-19 23.7, C-20 35.2, C-21 18.1, C-22 30.8, C-23 30.8, C-24 174.4, C-25 51.2<< Ref. 0006>>
Me ester (70eV) m/z: 390(M+1, 35%), 375(M-CH3, 18%), 372(M-H2O, 55%), 358(M-MeOH, 11%), 357(M-H2O-CH3, 35%), 248(M-SC-part of ring D (27), 27%), 233(M-SC-ring D (42), 62%), 230(M-H2O-SC-27, 11%), 217(M-173, 26%), 215(M-H2O-SC-42, 100%)<< Ref. 0009/0010>>
The spectrum (70eV) was shown as the Me-TMS derivative<< Ref. 0007>>
Constituent of the bile of man, ox, rabbit, and hog.<< Ref. 0001>>
Identified in human of feces.<< Ref. 0101/0161>>
Excreted in urine of healthy premature and full-term infants.<< Ref. 0202>>
Identified in feces of patients with cororectal cancer or polyps.<< Ref. 0243>>
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0005 >> AUTHOR: Iida, T., and Chang, F. C. TITLE: Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives JOURNAL: J. Coll. Engin. Nihon Univ. (A) VOLUME: 24 PAGE: 163 -165 (1983)
<< Ref.0006 >> AUTHOR: Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C. TITLE: Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers. JOURNAL: Org. Magn. Reson. VOLUME: 21 PAGE: 305 -309 (1983)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0009 >> AUTHOR: Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0010 >> AUTHOR: Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T. TITLE: High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids. JOURNAL: Biomed. Mass Spectrom. VOLUME: 9 PAGE: 473 -476 (1982)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0161 >> AUTHOR: Eneroth, P., Gordon, B., Ryhage, R., and Sjovall, J. TITLE: Identification of mono- and dihydroxy bile acids in human feces by gas-liquid chromatography and mass spectrometry PubMed ID:5966634 JOURNAL: J Lipid Res. VOLUME: 7 PAGE: 511-523(1966)
<< Ref.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. VOLUME: 54 PAGE: 1-10(1994)
<< Ref.0243 >> AUTHOR: Imray, C. H., Radley, S., Davis, A., Barker, G., Hendrickse, C. W., Donovan, I. A., Lawson, A. M., Baker, P. R., and Neoptolemos, J. P. TITLE: Faecal unconjugated bile acids in patients with colorectal cancer or polyps PubMed ID:1427378 JOURNAL: Gut. VOLUME: 33 PAGE: 1239-1245(1992)
5
Allolithocholic Acid 3a-Hydroxy-5a-cholan-24-oic Acid BBA0005Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 204-208degC, (Me ester; mp, 160-161degC)<< Ref. 0001/0237>> [a]d-26: +26.0deg, [a]d-26: +22.5pm1deg (C=0.85, CHCl3) (Me ester)<< Ref. 0001/0237>> Me ester: nmaxcm-1: 3225, 1736, 1275, 1034, 1002, 956, 894<< Ref. 0013>> Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.77(s), 21-Me 0.91(d), 3b-H 4.00(m)<< Ref. 0008>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.1, C-2 28.9, C-3 66.3, C-4 35.8, C-5 39.0, C-6 28.5, C-7 31.9, C-8 35.4, C-9 54.2, C-10 35.9, C-11 20.7, C-12 39.9, C-13 42.5, C-14 56.4, C-15 24.0, C-16 28.0, C-17 55.8, C-18 12.0, C-19 11.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.3<< Ref. 0011>>
Me ester (20eV) m/z: 390(M+1, 61%), 375(M-CH3, 16%), 372(M-H2O, 85%), 357(M-H2O-CH3, 27%), 249(M-141, 14%), 248(M-SC-part of ring D (27), 57%), 233(M-SC-ring D (42), 90%), 230(M-H2O-SC-27, 15%), 217(M-173, 40%), 215(M-H2O-SC-42, 100%)<< Ref. 0012>> Isolated from human faceces.<< Ref. 0001>>
Identified in urine of healthy humans and patients with liver diseases.<< Ref. 0150/0151>>
Isolated from urine of infants with biliary atresia.<< Ref. 0185>>
Identified in biliary bile of patients with cystic fibrosis.<< Ref. 0191>>
Constituent of a urinary bile acid in late prenancy and in recurrent cholestasis of pregnancy.<< Ref. 0206>>
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.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) VOLUME: 28 PAGE: 175 -179 (1987)
<< Ref.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 VOLUME: 45 PAGE: 1 -12 (1987)
<< Ref.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) VOLUME: 29 PAGE: 279 -288 (1988)
<< Ref.0013 >> AUTHOR: Mitra, M. N., and Elliott, W. H. TITLE: Bile acids. XXIV. Raney nickel in the preparation of allocholanic acids PubMed ID:5742844 JOURNAL: J Org Chem. VOLUME: 33 PAGE: 2814-2818(1968)
<< Ref.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. VOLUME: 18 PAGE: 339-362(1977)
<< Ref.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. VOLUME: 9 PAGE: 341-348(1979)
<< Ref.0185 >> AUTHOR: Makino, I., Sjovall, J., Norman, A., and Strandvik, B. TITLE: Excretion of 3beta-hydroxy-5-cholenoic and 3a-hydroxy-5a-cholanoic acids in urine of infants with biliary atresia PubMed ID:11945837 JOURNAL: FEBS Lett. VOLUME: 15 PAGE: 161-164(1971)
<< Ref.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. VOLUME: 12 PAGE: 322-334(1990)
<< Ref.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. VOLUME: 9 PAGE: 425-432(1979)
<< Ref.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: VOLUME: PAGE: - ()
6
3b-Hydroxy-5a-cholan-24-oic Acid BBA0006Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 208-211degC<< Ref. 0042/0237>>
164-165degC (Me ester)<< Ref. 0001/0002/0237>>
[a]D: +33.3deg (C=0.12, EtOH)<< Ref. 0042/0237>>
[a]d-22: +21deg (CHCl3) (Me ester)<< Ref. 0001/0002/0237>>
nmaxcm-1: 1705 (C=O)<< Ref. 0042>>
Me ester: nmaxcm-1: 3494, 1712, 1297, 1051, 1002, 952, 893<< Ref. 0013>>
1H-NMR (CDCl3-CH3OH) d: 18-Me 0.69 (s), 19-Me 0.81 (s), 21-Me 0.95 (d), 3a-H 3.20-3.75 (m)<< Ref. 0042>>
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.80(s), 21-Me 0.91(d), 3a-H 3.57(brm)<< Ref. 0008>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.9, C-2 31.3, C-3 71.0, C-4 38.0, C-5 44.7, C-6 28.6, C-7 31.9, C-8 35.4, C-9 54.2, C-10 35.2, C-11 21.1, C-12 39.9, C-13 42.5, C-14 56.3, C-15 24.0, C-16 27.9, C-17 55.8, C-18 11.9, C-19 12.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.2<< Ref. 0011>>
Me ester (70eV) m/z: 390(M+1, 56%), 375(M-CH3, 27%), 372(M-H2O, 40%), 357(M-H2O-CH3, 37%), 341(M-H2O-31, 16%), 257(M-H2O-SC, 6%),248(M-SC-part of ring D (27), 37%), 233(M-SC-ring D (42), 100%), 230(M-H2O-SC-27, 17%), 215(M-H2O-SC-42, 99%), 159(13%), 149(27%), 147(32%)<< Ref. 0009/0012>>
The spectrum (70eV) was shown as the Me-TMS derivative<< Ref. 0007>>
Isolated from the marine invertebrate Ptilosarcus gurneyi (sea pen).<< Ref. 0096>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.0002 >> AUTHOR: Brooks, C. J. W. (1970) Bile Acids (Chapter 15: Steroids; Sterols and Bile Acids), in Rodd's Chemistry of Carbon Compounds (Vol. II, Part D) (Coffey, S. ed), pp 168-196, Elsevier Publishing Co., Amsterdam. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.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) VOLUME: 28 PAGE: 175 -179 (1987)
<< Ref.0009 >> AUTHOR: Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.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 VOLUME: 45 PAGE: 1 -12 (1987)
<< Ref.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) VOLUME: 29 PAGE: 279 -288 (1988)
<< Ref.0013 >> AUTHOR: Mitra, M. N., and Elliott, W. H. TITLE: Bile acids. XXIV. Raney nickel in the preparation of allocholanic acids PubMed ID:5742844 JOURNAL: J Org Chem. VOLUME: 33 PAGE: 2814-2818(1968)
<< Ref.0042 >> AUTHOR: Fukumoto, K., Suzuki, K., Nemoto, H., Kametani, T., and Furuyama, H. TITLE: An Efficient Synthesis of Cholanic Acids from 20-Ketopregnanes. JOURNAL: Tetrahedron VOLUME: 38 PAGE: 3701 -3704 (1982)
<< Ref.0096 >> AUTHOR: Vanderah, D. J., and Djerassi, C. TITLE: Marine Natural Products. Synthesis of Four Naturally Occurring 20b-H Cholanic Acid Derivatives. JOURNAL: J. Org. Chem. VOLUME: 43 PAGE: 1442 -1448 (1978)
<< Ref.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: VOLUME: PAGE: - ()
7
6a-Hydroxy-5b-cholan-24-oic Acid BBA0007Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 226-228degC<< Ref. 0019>> [a]D: +10deg (C=0.9, dioxane)<< Ref. 0001>>
[a]D: +5deg (CHCl3) (Me ester)<< Ref. 0043>>
nmaxcm-1: 1703 (C=O), 3348, 1022, 992 (OH)<< Ref. 0019>> 1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.64(s), 19-Me 0.90(s), 21-Me 0.92(d), 6b-H 4.01(brm)<< Ref. 0019>> Me ester (70eV) m/z: 390(M+1, 2%), 375(M-CH3, 1%), 372(M-H2O, 100%), 357(M-H2O-CH3, 36%), 341(M-H2O-31, 11%), 257(M-H2O-SC, 15%), 249(7%), 248(M-SC-part of ring D, 15%), 233(M-SC-ring D (42), 8%), 231(9%), 230(M-H2O-SC-27, 25%), 217(21%), 215(M-H2O-SC-42, 67%), 159(8%), 149(30%), 147(24%)<< Ref. 0009>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.0009 >> AUTHOR: Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0019 >> AUTHOR: Iida, T., Tamaru, T., Chang, F. C., Niwa, T., Goto, J., and Nambara, T. TITLE: Potential bile acid metabolites. 20. A new synthetic route to stereoisomeric 3,6-dihydroxy- and 6-hydroxy-5 alpha-cholanoic acids PubMed ID:8212086 JOURNAL: Steroids. VOLUME: 58 PAGE: 362-369(1993)
<< Ref.0043 >> AUTHOR: Jones, D. N., and Summers, G.H.R. TITLE: Reduction of 5b-Methyl-3- and -6-oxo-19-nor-5b-cholest-9(10)-enes by Metal Hydrides. JOURNAL: J. Chem. Soc. VOLUME: PAGE: 2594 -2597 (1959)
8
6b-Hydroxy-5b-cholan-24-oic Acid BBA0008Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 221-222degC<< Ref. 0074>>
112-114degC (Me ester)<< Ref. 0043>>
[a]D: +52deg (C=0.4, CHCl3) (Me ester)<< Ref. 0043>> << Ref.0043 >> AUTHOR: Jones, D. N., and Summers, G.H.R. TITLE: Reduction of 5b-Methyl-3- and -6-oxo-19-nor-5b-cholest-9(10)-enes by Metal Hydrides. JOURNAL: J. Chem. Soc. VOLUME: PAGE: 2594 -2597 (1959)
<< Ref.0074 >> AUTHOR: Hoehn, W. M., Linsk, J., and Moffett, R. B. TITLE: 3-Keto-6(b)-hydroxycholanic Acid and 3(a)-Hydroxy-6-ketocholanic Acid. JOURNAL: J. Am. Chem. Soc. VOLUME: 68 PAGE: 1855 -1857 (1946)
9
6a-Hydroxy-5a-cholan-24-oic Acid BBA0009Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 246-248degC<< Ref. 0019>> nmaxcm-1: 1711 (C=O), 3383, 1034, 1004 (OH)<< Ref. 0019>> 1H-NMR (CDCl3+40%DMSO-d6; 90MHz) d: 18-Me 0.64(s), 19-Me 0.76(s), 21-Me 0.90(d), 6b-H 3.30(brm)<< Ref. 0019>>
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.618(s), 19-Me 0.754(s), 21-Me 0.882(d, 7.0), 6b-H 3.345(ddd, J, 5.0, 11.0, 15.5), COOMe 3.630(s)<< Ref. 0019>>
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 38.94, C-2 21.85, C-3 26.26, C-4 22.85, C-5 53.84, C-6 70.22, C-7 41.66, C-8 34.27, C-9 54.22, C-10 37.02, C-11 20.79, C-12 39.93, C-13 42.69, C-14 56.43, C-15 24.19, C-16 28.11, C-17 55.91, C-18 12.11, C-19 13.40, C-20 35.42, C-21 18.33, C-22 31.06, C-23 31.12, C-24 174.81, C-25 51.53<< Ref. 0019>>
The spectrum (70eV) was shown as the Me-TMS derivative<< Ref. 0007>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.0019 >> AUTHOR: Iida, T., Tamaru, T., Chang, F. C., Niwa, T., Goto, J., and Nambara, T. TITLE: Potential bile acid metabolites. 20. A new synthetic route to stereoisomeric 3,6-dihydroxy- and 6-hydroxy-5 alpha-cholanoic acids PubMed ID:8212086 JOURNAL: Steroids. VOLUME: 58 PAGE: 362-369(1993)
10
6b-Hydroxy-5a-cholan-24-oic Acid BBA0010Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 227-230degC, (Me ester; mp, 87-90degC)<< Ref. 0019>> nmaxcm-1: 1708 (C=O), 3390, 1022, 1004 (OH)<< Ref. 0019>> 1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 21-Me 0.93(d), 19-Me 1.00(s), 6a-H 3.72(m)<< Ref. 0019>>
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.655(s), 21-Me 0.888(d, 6.5), 19-Me 0.974(s), COOMe 3.632(s), 6a-H 3.743(dd, J, 3.5, 6.5)<< Ref. 0019>>
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 40.46, C-2 22.17, C-3 27.13, C-4 26.10, C-5 49.70, C-6 72.55, C-7 39.55, C-8 30.27, C-9 54.64, C-10 36.26, C-11 20.68, C-12 40.05, C-13 42.78, C-14 56.37, C-15 24.22, C-16 28.16, C-17 55.99, C-18 12.19, C-19 15.81, C-20 35.45, C-21 18.36, C-22 31.09, C-23 31.15, C-24 174.84, C-25 51.53<< Ref. 0019>>
<< Ref.0019 >> AUTHOR: Iida, T., Tamaru, T., Chang, F. C., Niwa, T., Goto, J., and Nambara, T. TITLE: Potential bile acid metabolites. 20. A new synthetic route to stereoisomeric 3,6-dihydroxy- and 6-hydroxy-5 alpha-cholanoic acids PubMed ID:8212086 JOURNAL: Steroids. VOLUME: 58 PAGE: 362-369(1993)
11
7a-Hydroxy-5b-cholan-24-oic Acid BBA0011Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 96-99degC<< Ref. 0001>>
80-81degC (Me ester)<< Ref. 0040>>
[a]d-22: +7deg (CHCl3)<< Ref. 0001>>
[a]d-20: +6pm2deg (C=1.5) (Me ester)<< Ref. 0132>>
nmaxm: 9.70, 9.91, 10.22, 10.59<< Ref. 0003>>
Me ester: nmaxcm-1: 1724 (C=O), 3584 (OH), 1106<< Ref. 0040>>
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.91(s), COOMe 3.68(s), 7b-H 3.86(br)<< Ref. 0040>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.4, C-2 21.1, C-3 27.5, C-4 30.2, C-5 43.7, C-6 35.5, C-7 68.1, C-8 39.2, C-9 32.6, C-10 35.0, C-11 20.3, C-12 39.4, C-13 42.3, C-14 50.1, C-15 23.3, C-16 27.8, C-17 55.5, C-18 11.4, C-19 23.3, C-20 35.0, C-21 17.9, C-22 30.6, C-23 30.6, C-24 174.1, C-25 51.0<< Ref. 0006>>
Me ester (70eV) m/z: 372(M-H2O, 100%), 358(M-MeOH, 10%), 357(M-H2O-CH3, 40%), 276(M-114, 16%), 257(M-H2O-SC, 70%), 230(M-H2O-SC-part of ring D (27), 31%), 217(M-173, 13%), 215(M-H2O-SC-ring D (42), 61%)<< Ref. 0009/0010>>
The spectrum (70eV) was shown as the Me-TMS derivative<< Ref. 0007>>
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0003 >> AUTHOR: Levin, S. J., and Johnston, C. G. TITLE: Infrared Correlations in the Bile Acid Series JOURNAL: Talanta. VOLUME: 8 PAGE: 871 -879 (1961)
<< Ref.0006 >> AUTHOR: Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C. TITLE: Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers. JOURNAL: Org. Magn. Reson. VOLUME: 21 PAGE: 305 -309 (1983)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0009 >> AUTHOR: Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0010 >> AUTHOR: Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T. TITLE: High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids. JOURNAL: Biomed. Mass Spectrom. VOLUME: 9 PAGE: 473 -476 (1982)
<< Ref.0040 >> AUTHOR: Baker, J. F., and Blickenstaff, R. T. TITLE: Intramolecular catalysis. VIII. Effects on the acetylation of the 7alpha-hydroxyl group of steroids. A H nuclear magnetic resonance rate method PubMed ID:1142040 JOURNAL: J Org Chem. VOLUME: 40 PAGE: 1579-1586(1975)
<< Ref.0132 >> AUTHOR: Kagan, H. B., and Jacques, J. TITLE: Acides Biliaires Comportant des Hydroxyles en Position 6 et 7. JOURNAL: Bull. Soc. Chim. Fr. VOLUME: PAGE: 871 -878 (1960)
12
7b-Hydroxy-5b-cholan-24-oic Acid BBA0012Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 131-133.5degC, (Me ester; mp, 89.0-90.5degC)<< Ref. 0026>> Me ester: nmaxcm-1: 1695 (C=O), 3401, 1015, 990 (OH)<< Ref. 0026>> 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.68(s), 19-Me 0.93(s), 7a-H 3.58(brm)<< Ref. 0026>>
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.64(s), 19-Me 0.99(s), 7a-H 3.60(brm), COOMe 3.68(s)<< Ref. 0026>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.4, C-2 21.0, C-3 26.7, C-4 28.4, C-5 44.0, C-6 37.1, C-7 71.2, C-8 43.6, C-9 39.1, C-10 34.7, C-11 20.9, C-12 40.1, C-13 43.6, C-14 55.7, C-15 26.9, C-16 27.9, C-17 54.8, C-18 12.0, C-19 24.1, C-20 35.1, C-21 18.2, C-22 30.8, C-23 30.8, C-24 174.3, C-25 51.2<< Ref. 0006>>
Me ester (70eV) m/z: 390(M+1, 16%), 372(M-H2O, 100%), 358(M-MeOH, 11%), 357(M-H2O-CH3, 34%), 276(M-114, 16%), 257(M-H2O-SC, 64%), 233(M-SC-ring D (42), 15%), 230(M-H2O-SC-part of ring D (27), 33%), 217(M-173, 45%), 215(M-H2O-SC-42, 37%)<< Ref. 0009/0010>>
The spectrum (70eV) was shown as the Me-TMS derivative<< Ref. 0007>>
Detected as a trace component of human stool.<< Ref. 0101>>
Detected in human feces.<< Ref. 0219>>
<< Ref.0006 >> AUTHOR: Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C. TITLE: Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers. JOURNAL: Org. Magn. Reson. VOLUME: 21 PAGE: 305 -309 (1983)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0009 >> AUTHOR: Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0010 >> AUTHOR: Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T. TITLE: High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids. JOURNAL: Biomed. Mass Spectrom. VOLUME: 9 PAGE: 473 -476 (1982)
<< Ref.0026 >> AUTHOR: Iida, T., and Chang, F. C. TITLE: Potential Bile Acid Metabolites. 8. 7,12-Dihydroxy- and 7b-Hydroxy-5b-cholanic Acids. JOURNAL: J. Org. Chem. VOLUME: 48 PAGE: 1194 -1197 (1983)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0219 >> AUTHOR: Hayakawa, S. TITLE: Intestinal Bacteria and Bile Acids. JOURNAL: Saishin Igaku. VOLUME: 37 PAGE: 1920 -1927 (1982)
13
7a-Hydroxy-5a-cholan-24-oic Acid BBA0013Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 155-156degC, (Me ester; mp, 105-106degC)<< Ref. 0038/0237>> [a]d-25: -1.0pm0.5deg (C=1.0, MeOH)<< Ref. 0038/0237>>
[a]d-25: +2deg (C=0.95, MeOH) (Me ester)<< Ref. 0001/0237>>
nmax cm-1: 3279, 1701, 1255, 1236, 1212, 1096, 1029, 1014, 993, 959, 888, 778<< Ref. 0038>> Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.78(s), 21-Me 0.92(d), 7b-H 3.80(m)<< Ref. 0008>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 38.6, C-2 22.2, C-3 26.8, C-4 28.8, C-5 39.4, C-6 37.1, C-7 68.1, C-8 39.8, C-9 46.6, C-10 36.5, C-11 20.8, C-12 39.9, C-13 42.9, C-14 50.9, C-15 23.7, C-16 28.0, C-17 56.2, C-18 11.9, C-19 11.1, C-20 35.4, C-21 18.4, C-22 31.2, C-23 31.2, C-24 174.2, C-25 51.0<< Ref. 0011>>
Me ester (20eV) m/z: 390(M+1, 7%), 372(M-H2O, 100%), 357(M-H2O-CH3, 22%), 257(M-H2O-SC, 76%), 249(M-141, 11%), 248(M-SC-part of ring D (27), 28%), 233(M-SC-ring D (42), 30%), 230(M-H2O-SC-27, 69%), 217(M-173, 24%), 215(M-H2O-SC-42, 31%)<< Ref. 0009/0012>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.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) VOLUME: 28 PAGE: 175 -179 (1987)
<< Ref.0009 >> AUTHOR: Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.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 VOLUME: 45 PAGE: 1 -12 (1987)
<< Ref.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) VOLUME: 29 PAGE: 279 -288 (1988)
<< Ref.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. VOLUME: 33 PAGE: 175-181(1968)
<< Ref.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: VOLUME: PAGE: - ()
14
7b-Hydroxy-5a-cholan-24-oic Acid BBA0014Bile AcidTakashi Iida C24H40O3 376.573Download ChemDraw structure data 90.5-91degC (Me ester)<< Ref. 0041/0237>> Me ester: nmaxcm-1: 3356 (OH), 1742 (COOMe), 1166 (COOMe), 1072 (OH)<< Ref. 0041>> Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.80(s), 21-Me 0.93(d), 7a-H 3.37(m)<< Ref. 0008>>
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 39.0, C-2 22.3, C-3 26.8, C-4 28.9, C-5 44.5, C-6 39.1, C-7 75.4, C-8 44.0, C-9 53.5, C-10 35.3, C-11 21.1, C-12 40.4, C-13 43.9, C-14 56.2, C-15 27.0, C-16 28.6, C-17 55.5, C-18 12.4, C-19 12.4, C-20 35.3, C-21 18.5, C-22 31.3, C-23 31.3, C-24 174.3, C-25 51.1<< Ref. 0011>>
Me ester (20eV) m/z: 390(M+1, 9%), 372(M-H2O, 100%), 358(M-MeOH, 14%), 357(M-H2O-CH3, 32%), 257(M-H2O-SC (115), 58%), 249(M-141, 11%), 248(M-SC-part of ring D (27), 27%), 233(M-SC-ring D (42), 21%), 230(M-H2O-SC-27, 29%), 217(M-173, 42%), 215(M-H2O-SC-42, 26%)<< Ref. 0009/0012>>