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All data
(total 7079)
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(total 7079)
| Id | Image | COMMON NAME | NAME | DATA No | Lipid class | INFORMANT | SYMBOL | FORMULA | MOL.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 POINT | BOILING POINT | DENSITY | REFRACTIVE INDEX | OPTICAL ROTATION | SOLUBILITY | UV SPECTRA | IR SPECTRA | NMR SPECTRA | MASS SPECTRA | OTHER SPECTRA | |||||||||||||||||||
| 1 |  | typical bacterial ornithine-containing lipid | a-N-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-L-ornithine << Ref. 0001/0003/0005/0011>> | ALA0001 | Lipoamino acid | Youko Kawai | OL , Orn-lipid | C37H72O5N2 | 624.978 | Download ChemDraw structure data | Hemagglutinating-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  C | [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) | |||||||||
| 2 |  | Ornithine-containing lipid of Flavobacterium | a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-L-ornithine | ALA0002 | Lipoamino acid | Youko Kawai | C37H72O5N2 | 624.978 | Download ChemDraw structure data | Macrophage 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) | ||||||||||||||
| 3 |  | OH-type ornithine-containing lipid of Flavovacterium | a-N-[3-(2-hydroxyisopentadecanoyloxy)isoheptadecanoyl]-ornithine | ALA0003 | Lipoamino acid | Youko Kawai | C37H72O6N2 | 640.977 | Download ChemDraw structure data | Macrophage 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) | ||||||||||||||
| 4 |  | Flavolipin, Ser-Gly-lipid, Ser-Gly-containing lipid | a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-glycyl-serine | ALA0004 | Lipoamino acid | Youko Kawai | C37H69O7N2 | 653.953 | Download ChemDraw structure data | Macrophage 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 | ALA0005 | Lipoamino acid | Youko Kawai | C40H76O6N2 | 681.041 | Download 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. | |||||||||||||||||
| 6 |  | Ursocholanic Acid | 5b-Cholan-24-oic Acid | BBA0001 | Bile Acid | Takashi Iida | C24H40O2 | 360.573 | Download ChemDraw structure data | 164C, (Me ester; mp, 86C)<< Ref. 0001/0002>> | [a]14D: +21.74 (CHCl3)<< Ref. 0001/0002>> [a]D: +23.2 (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: - () | |||||||||||||
| 7 |  | Allocholanic Acid | 5a-Cholan-24-oic Acid | BBA0002 | Bile Acid | Takashi Iida | C24H40O2 | 360.573 | Download ChemDraw structure data | 170C, (Me ester; mp, 91C)<< Ref. 0001/0002/0237>> | [a]14D: +21.74 (CHCl3)<< Ref. 0001/0002/0237>> [a]D: +22.1 (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: - () | ||||||||||||||
| 8 |  | Lithocholic Acid | 3a-Hydroxy-5b-cholan-24-oic Acid | BBA0003 | Bile Acid | Takashi Iida | C24H40O3 | 376.573 | Download ChemDraw structure data | 186C<< Ref. 0001>> 130-132 C (Me ester)<< Ref. 0040>> | [a] : +33.7 (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) | |||||||||||||
| 9 |  | Isolithocholic Acid | 3b-Hydroxy-5b-cholan-24-oic Acid | BBA0004 | Bile Acid | Takashi Iida | C24H40O3 | 376.573 | Download ChemDraw structure data | 176-176.5, (Me ester; mp, 117.1-118C)<< Ref. 0001>> | [a]D: +32 (CHCl3), [a]D: +21.3 (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) | ||||||||||||||
| 10 |  | Allolithocholic Acid | 3a-Hydroxy-5a-cholan-24-oic Acid | BBA0005 | Bile Acid | Takashi Iida | C24H40O3 | 376.573 | Download ChemDraw structure data | 204-208C, (Me ester; mp, 160-161C)<< Ref. 0001/0237>> | [a] : +26.0, [a]: +22.5 1 (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 | BBA0006 | Bile Acid | Takashi Iida | C24H40O3 | 376.573 | Download ChemDraw structure data | 208-211C<< Ref. 0042/0237>> 164-165 C (Me ester)<< Ref. 0001/0002/0237>> | [a]D: +33.3 (C=0.12, EtOH)<< Ref. 0042/0237>> [a]  : +21 (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 | BBA0007 | Bile Acid | Takashi Iida | C24H40O3 | 376.573 | Download ChemDraw structure data | 226-228C<< Ref. 0019>> | [a]D: +10 (C=0.9, dioxane)<< Ref. 0001>> [a]D: +5 (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 | BBA0008 | Bile Acid | Takashi Iida | C24H40O3 | 376.573 | Download ChemDraw structure data | 221-222C<< Ref. 0074>> 112-114 C (Me ester)<< Ref. 0043>> | [a]D: +52 (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 | BBA0009 | Bile Acid | Takashi Iida | C24H40O3 | 376.573 | Download ChemDraw structure data | 246-248C<< 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 | BBA0010 | Bile Acid | Takashi Iida | C24H40O3 | 376.573 | Download ChemDraw structure data | 227-230C, (Me ester; mp, 87-90C)<< 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- | ||||||||||||||||||
![[Table 0001]](image/ALA0001FT0001.gif){kind=link}
![[Table 0003]](image/ALA0001FT0003.gif){kind=link}
![[Table 0002]](image/ALA0001FT0002.gif){kind=link}
![[Table 0004]](image/ALA0001FT0004.gif){kind=link}
![[Spectrum 0001]](image/ALA0001SP0001.gif){kind=link}
![[Spectrum 0002]](image/ALA0001SP0002.gif){kind=link}
![[Spectrum 0003]](image/ALA0001SP0003.gif){kind=link}
![[Spectrum 0004]](image/ALA0001SP0004.gif){kind=link}
![[Chromatogram 0001]](image/ALA0001CH0001.gif){kind=link}
![[Chromatogram 0002]](image/ALA0001CH0002.gif){kind=link}
![[Table 0006]](image/ALA0002FT0006.gif){kind=link}
![[Table 0007/FT0008]](image/ALA0002FT0007/FT0008.gif){kind=link}
![[Table 0009]](image/ALA0002FT0009.gif){kind=link}
![[Table 0010]](image/ALA0002FT0010.gif){kind=link}
![[Spectrum 0005]](image/ALA0002SP0005.gif){kind=link}
![[Spectrum 0006]](image/ALA0002SP0006.gif){kind=link}
![[Chromatogram 0003]](image/ALA0002CH0003.gif){kind=link}
![[Table 0005]](image/ALA0002FT0005.gif){kind=link}
![[Spectrum 0007]](image/ALA0003SP0007.gif){kind=link}
![[Spectrum 0008]](image/ALA0003SP0008.gif){kind=link}
![[Chromatogram 0001]](image/ALA0003CH0001.gif){kind=link}
![[Table 0011]](image/ALA0004FT0011.gif){kind=link}
![[Spectrum 0009]](image/ALA0004SP0009.gif){kind=link}
![[Spectrum 0012]](image/ALA0004SP0012.gif){kind=link}
![[Spectrum 0010]](image/ALA0004SP0010.gif){kind=link}
![[Spectrum 0011]](image/ALA0004SP0011.gif){kind=link}
![[Chromatogram 0003]](image/ALA0004CH0003.gif){kind=link}
![[Spectrum 0013]](image/ALA0005SP0013.gif){kind=link}
![[Spectrum 0014]](image/ALA0005SP0014.gif){kind=link}
![[Spectrum 0015]](image/ALA0005SP0015.gif){kind=link}
![[Chromatogram 0001]](image/ALA0005CH0001.gif){kind=link}