7,10-DIHYDROXY-8(E)-OCTADECANOIC ACID - STEREOCHEMISTRY AND A NOVEL DERIVATIVE, 7,10-DIHYDROXYOCTADECANOIC ACID

被引:16
作者
KNOTHE, G
BAGBY, MO
PETERSON, RE
HOU, CT
机构
[1] Oil Chemical Research, National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, Peoria, 61604, IL
[2] Bioactive Constituents Research, National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, Peoria, 61604, IL
关键词
ABSOLUTE CONFIGURATION; CIRCULAR DICHROISM; 7,10-DIHYDROXY-8(E)-OCTADECENOIC ACID; 7,10-DIHYDROXYOCTADECANOIC ACID; DIIMIDE; HYDRAZINE; HYDROGENATION; SPECIFIC OPTICAL ROTATION;
D O I
10.1007/BF02636070
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
7,10-Dihydroxy-8(E)-octadecenoic acid (obtained by bioconversion of oleic acid with the bacterial strain PR3) was hydrogenated with hydrazine hydrate under air in ethanolic solution to give a novel compound, 7,10-dihydroxyoctadecanoic acid. The absolute configuration of both compounds was determined with the aid of circular dichroism to be R,R. A different purification method for 7,10-dihydroxy-8(E)-octadecenoic acid is described.
引用
收藏
页码:367 / 371
页数:5
相关论文
共 29 条
[1]   OPTICAL ROTATORY DISPERSION AND ABOSLUTE CONFIGURATION OF SOME LONG-CHAIN HYDROXY ACIDS [J].
APPLEWHITE, TH ;
BINDER, RG ;
GAFFIELD, W .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (04) :1173-+
[2]  
APPLEWHITE TH, 1965, J CHEM SOC CHEM COMM, P255
[3]  
Bagby M, 1989, FATS FUTURE, P301
[4]   INFLUENCE OF ALLYLIC OXYGEN ON PI-]PI] CD OF CERTAIN CHROMOPHORES [J].
BEECHAM, AF .
TETRAHEDRON, 1971, 27 (21) :5207-&
[5]   A USEFUL MODEL OF OPTICAL ACTIVITY .1. OPEN CHAIN COMPOUNDS [J].
BREWSTER, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) :5475-5483
[6]   CHEMICAL IONIZATION MASS SPECTROMETRY .12. ALCOHOLS [J].
FIELD, FH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (09) :2672-&
[7]   OXIDATIVE ACETOXYLATION OF METHYL OLEATE WITH PALLADIUM CATALYSTS [J].
FRANKEL, EN ;
ROHWEDDER, WK ;
NEFF, WE ;
WEISLEDER, D .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (22) :3247-3253
[8]   PRODUCTION OF A NEW COMPOUND, 7,10-DIHYDROXY-8-(E)-OCTADECENOIC ACID FROM OLEIC-ACID BY PSEUDOMONAS SP PR3 [J].
HOU, CT ;
BAGBY, MO .
JOURNAL OF INDUSTRIAL MICROBIOLOGY, 1991, 7 (02) :123-129
[9]   A NOVEL COMPOUND, 7,10-DIHYDROXY-8(E)-OCTADECENOIC ACID FROM OLEIC-ACID BY BIOCONVERSION [J].
HOU, CT ;
BAGBY, MO ;
PLATTNER, RD ;
KORITALA, S .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1991, 68 (02) :99-101
[10]  
HOU CT, 1991, 82ND ANN M AM OIL CH