Back to HOME

All data

(total 7079)


Download Data as Excel
Download All Images
Download All ChemDraw structure data
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
1typical bacterial ornithine-containing lipid a-N-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-L-ornithine << Ref. 0001/0003/0005/0011>> ALA0001Lipoamino acidYouko KawaiOL , Orn-lipid C37H72O5N2 624.978Download ChemDraw structure dataHemagglutinating-activity , minimum hemagglutinating concentration on human erythrocyte is 1 mg/ml. [Table 0001] << Ref. 0001/0003>> , Hemolitic activity of O-deacylated OL, [Table 0003] << Ref. 0001>>, Inhibition of hemagglutination [Table 0002] << Ref. 0001>>, Macrophage activation , PGE2 and IL-1- inducing activities, nontoxic (nonlethality, and non TNF-inducing activity) << Ref. 0009/0011>>, the structure of the OL is similar to the structure of lipid A of bacterial LPS [Table 0004]. 155-156 degC [a]D25 +1.8 Soluble in chloroform/methanol (2:1) [Spectrum 0001] Ester linkage (1730 cm-1), Secondary amide linkage (1640 and 1540 cm-1)<< Ref. 0001>> << Ref. 0005>> [Spectrum 0002] OL of B. pertussis, Trimethylsilyl OL, Molecular ion 606 (M-90, loss of trimethylsilyl) , [Spectrum 0003] OL of B. pertussis, Trimethylsilyl O-deacylated OL, Molecular ion 425 ( M-105, loss of trimethylsilyl and methyl), [Spectrum 0004] OL of P. fluorescens, two Molecular ions , 623 (typical OL) and 651 (Orn-3-OH 18:1-16:0 plus Orn-3-OH 16:0-18:1) << Ref. 0001/0003/0005>> [Chromatogram 0001] TLC pattern of neutral solvent extractable lipid of B. pertussis . the OL is located just below of phosphatidylethanolamine << Ref. 0002>>. [Chromatogram 0002] TLC pattern of neutral solvent extractable lipid of Pseudomonas << Ref. 0005>> distributed in various bacteria such as Bordetella pertussis, B. parapertussis, B. bronchisepticum , Pseudomonas fluorescens, P. aeruginosa, P. stuteri, P. cepacia, Achromobacter xylosoxidans, Serratia marcescens and Rhodopseudomonas spheroides. << Ref. 0001/0005/0011/0012>> Synthesis of the ornithine containing lipid are described in the litarature << Ref. 0011>> << Ref.0001 >> AUTHOR: Kawai, Y., and Yano, I. TITLE: Ornithine-containing lipid of Bordetella pertussis, a new type of hemagglutinin PubMed ID:6315433 JOURNAL: Eur J Biochem. VOLUME: 136 PAGE: 531-538(1983)
<< Ref.0002 >> AUTHOR: Kawai, Y. TITLE: Characteristic cellular fatty acid composition and an ornithine-containing lipid as a new type of hemagglutinin in Bordetella pertussis PubMed ID:2872110 JOURNAL: Dev Biol Stand. VOLUME: 61 PAGE: 249-254(1985)
<< Ref.0003 >> AUTHOR: Kawai, Y., Moribayashi, A., and Yano, I. TITLE: Ornithine-containing lipid of Bordetella pertussis that carries hemagglutinating activity PubMed ID:6290456 JOURNAL: J Bacteriol. VOLUME: 152 PAGE: 907-910(1982)
<< Ref.0005 >> AUTHOR: Kawai, Y., Yano, I., Kaneda, K., and Yabuuchi, E. TITLE: Ornithine-containing lipids of some Pseudomonas species PubMed ID:3409887 JOURNAL: Eur J Biochem. VOLUME: 175 PAGE: 633-641(1988)
<< Ref.0009 >> AUTHOR: Kawai, Y., Takasuka, N., Akagawa, K., and Naito, S. TITLE: Hypothermic response of mice to ornithine-containing lipids and to endotoxin PubMed ID:8675313 JOURNAL: Infect Immun. VOLUME: 64 PAGE: 2101-2105(1996)
<< Ref.0011 >> AUTHOR: Kawai, Y., Nakagawa, Y., Matuyama, T., Akagawa, K., Itagawa, K., Fukase, K., Kusumoto, S., Nishijima, M., and Yano, I. TITLE: A typical bacterial ornithine-containing lipid Nalpha-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-ornithine is a strong stimulant for macrophages and a useful adjuvant PubMed ID:10030549 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 23 PAGE: 67-73(1999)
<< Ref.0012 >> AUTHOR: Miyazaki, Y., Oka, S., Hara-Hotta, H., and Yano, I. TITLE: Stimulation and inhibition of polymorphonuclear leukocytes phagocytosis by lipoamino acids isolated from Serratia marcescens PubMed ID:8388762 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 6 PAGE: 265-271(1993)
2Ornithine-containing lipid of Flavobacterium a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-L-ornithine ALA0002Lipoamino acidYouko Kawai C37H72O5N2 624.978Download ChemDraw structure dataMacrophage activation by the OL was studied. TNF-inducing activity was very low [Table 0006]. Prostaglandin (PGE2)- and interleukin (IL)-1-inducing avtivities were strong. [Table 0007/FT0008] << Ref. 0006/0009>>. B-lymphocyte mitogenicity was strong [Table 0009] << Ref. 0007>>. LPS antagonist activity [Table 0010] << Ref. 0008>>. Preadministration of the OL protects mice from the endotoxin lethality. [Spectrum 0005] Esterlinkage 1730 cm -1, Secondary amide linkage 1640 and 1540 -1. [Spectrum 0006] Molecular ion 625. [Chromatogram 0003] TLC of free lipids of Flavobacterium meningosepticum. Two OLs and Ser-containing lipid are detected. These OLs containing branched fatty acids are very rare. This type of the OLs are found Flavobacterium meningosepticum, F. indologenes << Ref. 0004>>, and Cytophaga johnsonae << Ref. 0013>>. [Table 0005] Structures of the lipid A of LPS and the OLs are similar in amide and ester linkages of the fatty acids. << Ref.0004 >> AUTHOR: Kawai, Y., Yano, I., and Kaneda, K. TITLE: Various kinds of lipoamino acids including a novel serine-containing lipid in an opportunistic pathogen Flavobacterium. Their structures and biological activities on erythrocytes PubMed ID:3123236 JOURNAL: Eur J Biochem. VOLUME: 171 PAGE: 73-80(1988)
<< Ref.0006 >> AUTHOR: Kawai, Y., and Akagawa, K. TITLE: Macrophage activation by an ornithine-containing lipid or a serine-containing lipid PubMed ID:2499544 JOURNAL: Infect Immun. VOLUME: 57 PAGE: 2086-2091(1989)
<< Ref.0007 >> AUTHOR: Kawai, Y., Kamoshita, K., and Akagawa, K. TITLE: B-lymphocyte mitogenicity and adjuvanticity of an ornithine-containing lipid or a serine-containing lipid PubMed ID:1778427 JOURNAL: FEMS Microbiol Lett. VOLUME: 67 PAGE: 127-129(1991)
<< Ref.0008 >> AUTHOR: Kawai, Y., Kaneda, K., Morisawa, Y., and Akagawa, K. TITLE: Protection of mice from lethal endotoxemia by use of an ornithine-containing lipid or a serine-containing lipid PubMed ID:1906840 JOURNAL: Infect Immun. VOLUME: 59 PAGE: 2560-2566(1991)
<< Ref.0009 >> AUTHOR: Kawai, Y., Takasuka, N., Akagawa, K., and Naito, S. TITLE: Hypothermic response of mice to ornithine-containing lipids and to endotoxin PubMed ID:8675313 JOURNAL: Infect Immun. VOLUME: 64 PAGE: 2101-2105(1996)
<< Ref.0013 >> AUTHOR: Pitta, T. P., Leadbetter, E. R., and Godchaux, W., 3rd TITLE: Increase of ornithine amino lipid content in a sulfonolipid-deficient mutant of Cytophaga johnsonae PubMed ID:2914878 JOURNAL: J Bacteriol. VOLUME: 171 PAGE: 952-957(1989)
3OH-type ornithine-containing lipid of Flavovacterium a-N-[3-(2-hydroxyisopentadecanoyloxy)isoheptadecanoyl]-ornithine ALA0003Lipoamino acidYouko Kawai C37H72O6N2 640.977Download ChemDraw structure dataMacrophage activation was very weak << Ref. 0011>> Ester and secondary amide linkages [Spectrum 0007] [Spectrum 0008] Molecular ion 641 Flavobacterium meningosepticum << Ref. 0004>> [Chromatogram 0001](Data No. 0002) << Ref.0004 >> AUTHOR: Kawai, Y., Yano, I., and Kaneda, K. TITLE: Various kinds of lipoamino acids including a novel serine-containing lipid in an opportunistic pathogen Flavobacterium. Their structures and biological activities on erythrocytes PubMed ID:3123236 JOURNAL: Eur J Biochem. VOLUME: 171 PAGE: 73-80(1988)
<< Ref.0011 >> AUTHOR: Kawai, Y., Nakagawa, Y., Matuyama, T., Akagawa, K., Itagawa, K., Fukase, K., Kusumoto, S., Nishijima, M., and Yano, I. TITLE: A typical bacterial ornithine-containing lipid Nalpha-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-ornithine is a strong stimulant for macrophages and a useful adjuvant PubMed ID:10030549 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 23 PAGE: 67-73(1999)
4Flavolipin, Ser-Gly-lipid, Ser-Gly-containing lipid a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-glycyl-serine ALA0004Lipoamino acidYouko Kawai C37H69O7N2 653.953Download ChemDraw structure dataMacrophage activation was observed << Ref. 0006>>. PGE2- and IL-1-inducing activities were strong. The structure is similar to the OL [Table 0011]. [Spectrum 0009]Ester-linkage 1730 and secondary amide linkage, << Ref. 0004>> [Spectrum 0012]The spectra of Flavolipin and the synthetic Flavolipin was identical. << Ref. 0010>> [Spectrum 0010] Negative FAB mass. Flavolipin and [Spectrum 0011]Synthetic Flavolipin. These spectra was identical. Positive FAB mass ( Molecular ion 654) << Ref. 0010>> [Chromatogram 0003] TLC of the free lipid of Flavobacterium Ser-Gly-lipid is vary rare. It is found only in Flavobacterium. << Ref. 0004>> << Ref.0004 >> AUTHOR: Kawai, Y., Yano, I., and Kaneda, K. TITLE: Various kinds of lipoamino acids including a novel serine-containing lipid in an opportunistic pathogen Flavobacterium. Their structures and biological activities on erythrocytes PubMed ID:3123236 JOURNAL: Eur J Biochem. VOLUME: 171 PAGE: 73-80(1988)
<< Ref.0006 >> AUTHOR: Kawai, Y., and Akagawa, K. TITLE: Macrophage activation by an ornithine-containing lipid or a serine-containing lipid PubMed ID:2499544 JOURNAL: Infect Immun. VOLUME: 57 PAGE: 2086-2091(1989)
<< Ref.0010 >> AUTHOR: Shiozaki, M., Deguchi, N., Mochizuki, T., Wakabayashi, T., Ishikawa, T., Haruyama, H., Kawai, Y., and Nishijima, M. TITLE: Revised structure and synthesis of Flavolipin. JOURNAL: Tetra hedron VOLUME: 54 PAGE: 11861 -11876 (1998)
5 a-N-[3-(2-hydroxynonadecacyclopropanoyloxy)hexadecanoyl]-ornithine ALA0005Lipoamino acidYouko Kawai C40H76O6N2 681.041Download ChemDraw structure data [Spectrum 0013] Ester and secondary amide linkages were detected. [Spectrum 0014]Molecular ion was detected. a-N-[3-(2-hydroxyoctadecenoyloxy)hexadecanoyl-ornithine was found with the OL. [Spectrum 0015] 2-hydroxynonadecacyclopropanoic acid and 2-hydroxyoctadecenoic acid [Chromatogram 0001] The OL was located lower position than that of the typical bacterial OLs. This OL was found in Pseudomonas cepacia.
6Ursocholanic 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: - ()
7Allocholanic 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: - ()
8Lithocholic 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)
9Isolithocholic 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)
10Allolithocholic 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: - ()
11 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: - ()
12 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)
13 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)
14 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)
15 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-