CONFIGURATION ANALYSIS OF UNSATURATED HYDROXY FATTY-ACIDS

被引:6
作者
SONNET, PE
DUDLEY, RL
OSMAN, S
PFEFFER, PE
SCHWARTZ, D
机构
[1] US Department of Agriculture, ARS, Eastern Regional Research Center, Philadelphia, PA 19118
来源
JOURNAL OF CHROMATOGRAPHY | 1991年 / 586卷 / 02期
关键词
D O I
10.1016/0021-9673(91)85129-4
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Stereoisomers of methyl ricinoleate, methyl isoricinoleate, and related methyl esters of bis-homoallylic hydroxy fatty acids were reacted with (R)- and (S)-alpha-naphthylethyl isocyanate to form diastereomeric carbamates that separated well on silica gel high-performance liquid chromatography. Proton nuclear magnetic resonance shifts of the carbomethoxymethyl protons were used to assign configuration to the alcohol component of the carbamate derivative. Combining high-performance liquid chromatography with proton nuclear magnetic resonance spectroscopy may allow one to determine the configuration of naturally occurring hydroxy fatty acids as well as to determine configurational purity.
引用
收藏
页码:255 / 258
页数:4
相关论文
共 10 条
[1]  
CORNELIS PA, 1979, BIOCHIM BIOPHYS ACTA, V574, P103
[2]   THERMAL-BEHAVIOR OF PROSPECTIVE HYDROXY ACID GREASE THICKENERS [J].
HAGEMANN, JW ;
ROTHFUS, JA .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1991, 68 (03) :139-143
[3]  
MORI K, 1978, TETRAHEDRON LETT, P4127
[4]   BIOCHEMICAL RESOLUTION OF RACEMIC TERPENES .8. ENZYMIC RESOLUTION OF (+/-)-ACYCLIC ALCOHOLS VIA ASYMMETRIC HYDROLYSIS OF CORRESPONDING ACETATES BY MICROORGANISMS [J].
ORITANI, T ;
YAMASHITA, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1980, 44 (10) :2407-2411
[5]   BROAD-SPECTRUM METHODS FOR RESOLUTION OF OPTICAL ISOMERS - DISCUSSION OF REASONS UNDERLYING CHROMATOGRAPHIC SEPARABILITY OF SOME DIASTEREOMERIC CARBAMATES [J].
PIRKLE, WH ;
HAUSKE, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (11) :1839-1844
[6]   NEW SOURCES OF 9-D-HYDROXY-CIS-12-OCTADECENOIC ACID [J].
POWELL, RG ;
KLEIMAN, R ;
SMITH, CR .
LIPIDS, 1969, 4 (06) :450-&
[7]  
SCHWARTZ DA, UNPUB
[8]  
SMITH CR, 1970, TOPICS LIPID CHEM, V1, P320
[9]   SYNTHESIS AND CHARACTERIZATION OF ENANTIOMERS OF 5-METHYLOCTANOIC AND 6-METHYLOCTANOIC ACIDS [J].
SONNET, PE ;
GAZZILLO, JA ;
DUDLEY, RL ;
BOSWELL, RT .
CHEMISTRY AND PHYSICS OF LIPIDS, 1990, 54 (3-4) :205-214
[10]  
SOUTER RW, 1987, CHROMATOGRAPHIC SEPA, pCH2