ON THE SYNTHESES OF BRANCHED SATURATED FATTY-ACIDS

被引:7
作者
GRONOWITZ, S [1 ]
KLINGSTEDT, T [1 ]
SVENSSON, L [1 ]
HANSSON, U [1 ]
机构
[1] KARLSHAMNS AB,S-37482 KARLSHAMN,SWEDEN
关键词
D O I
10.1007/BF02537496
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In order to investigate the relation between the structure of mono-branched saturated fatty acids and their physical properties, a three-factor central composite design war, constructed. For this purpose sixteen different fatty acids were prepared. The synthetic strategy was to use, if possible, a few common starting materials for the preparation of most of the acids. Thus alkylation and hydrolysis of oxazolines were used for the preparation of 2-butylhexanoic acid, 2-methyloctadecanoic acid, 2-hexadecyloctadecanoic acid and 2-pentyloctadecanoic acid. A number of acids were prepared from thiophene derivatives followed by desulfurization with Raney-Nickel alloy under alkaline conditions. Thus, starting from 3-ethylthiophene, 4-ethyl-2-thiophenecarboxylic acid and 4-ethyl-2-methyl-5-thiophenecarboxylic acid were prepared, which upon desulfurization gave the desired 4-methylhexanoic acid. From 3-bromo-2-methylthiophene, 3-ethyl-2-methyl-5-thiophenecarboxylic acid was prepared via 3-acetyl-2-methylthiophene and 3-ethyl-2-methylthiophene. Desulfurization gave 4-ethylhexanoic acid. Another approach started with 2-acylthiophenes, which were reacted with Grignard reagent to yield the appropriate olefins. By metalation and reaction with carbon dioxide, these were transformed to the corresponding 2-thiophenecarboxylic acids. Upon desulfurization, the desired fatty acids were obtained. In this way 6-propyldecanoic acid, 6-hexyldodecanoic acid, 6-methyldodecanoic acid and 6-pentylpentadecanoic acid were prepared. The remaining four acids were prepared from some of the branched acids described above through Kolbe reactions of dioic acids. Thus 16-methyloctadecanoic acid and 10-methyl-dodecanoic acid were obtained from 4-methylhexanoic acid, 16-ethyloctadecanoic acid from 4-ethylhexanoic acid and 9-pentyloctadecanoic acid from 6-pentylpentadecanoic acid.
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页码:889 / 897
页数:9
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[41]   METABOLISM OF SATURATED FATTY-ACIDS BY PARAMECIUM-TETRAURELIA [J].
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[42]   THE EFFECTS OF SATURATED FATTY-ACIDS ON ENDOTHELIAL-CELLS [J].
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LYNGMO, V ;
NORDOY, A .
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[43]   SATURATED FATTY-ACIDS IN SOILS FROM COFFEE PLANTATIONS [J].
HASLER, R ;
WANNER, H .
PLANT AND SOIL, 1977, 48 (02) :397-408
[44]   ATHEROGENIC EFFECT OF TRANS AND SATURATED FATTY-ACIDS IN RABBITS [J].
GOTTENBOS, JJ ;
VLES, RO .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1980, 57 (02) :A123-A123
[45]   COMPARED PHYSIOLOGY - SATURATED FATTY-ACIDS AND CHOLESTEROLEMIA IN RUMINANTS [J].
FERRANDO, R .
BULLETIN DE L ACADEMIE NATIONALE DE MEDECINE, 1991, 175 (06) :881-884
[46]   COMBINATION THERAPY USING SATURATED AND CYCLOPROPENE FATTY-ACIDS [J].
FERMOR, B ;
HABIB, NA ;
MILLER, J ;
MASTERS, JRW ;
WOOD, CB ;
WILLIAMSON, RCN .
ANTICANCER RESEARCH, 1988, 8 (05) :1119-1119
[47]   PROPERTIES OF PURE SODIUM SOAPS OF SATURATED FATTY-ACIDS [J].
SHETH, GN ;
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JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1982, 59 (07) :860-862
[48]   MIXED MONOLAYERS OF SIMPLE SATURATED AND UNSATURATED FATTY-ACIDS [J].
FEHER, AI ;
COLLINS, FD ;
HEALY, TW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (03) :511-519
[49]   PLASMA-CHOLESTEROL RESPONSIVENESS TO SATURATED FATTY-ACIDS [J].
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[50]   INHIBITORY-ACTION OF SATURATED FATTY-ACIDS AND THEIR DERIVATIVES [J].
ANDO, T ;
TSUKAMOTO, Y .
PHYTOCHEMISTRY, 1981, 20 (09) :2143-2144