3- Hydroxymyristic acid

Using PTLC six major fractions of lipids (phospholipids, free sterols, free fatty acids, triacylglycerols, methyl esters, and sterol esters) were separated from the skin lipids of chicken to smdy the penetration responses of Schistosoma cercaria and Austrobilharzia variglandis [79a]. To determine the structure of nontoxic lipids in lipopolysaccharides of Salmonella typhimurium, monophosphoryl lipids were separated from these lipids using PTLC. The separated fractions were used in FAB-MS to determine [3-hydroxymyristic acid, lauric acid, and 3-hydroxymyristic acids [79b]. 

Results of chemical analysis showed that the glucosamine and total fatty acid contents of the KDO depleted, toxic lipid A and the nontoxic lipid A were essentially the same but that the nontoxic lipid A was significantly lower in the phosphorus content (Table V). The molar ratio of glucosamine phosphorus fatty acids was 2 2 4 for the toxic lipid A and 2 1 4 for the nontoxic lipid A. The relative molar distribution of normal fatty acids (lauric, myristic, and palmitic acids) and the 3-hydroxymyristic acid did not indicate a correlation between the content of these components and toxicity. The nontoxic lipid A possessed as high a tumor regression activity when combined with CWS as did the purified... 

The polysaccharide moiety of the lipopolysaccharide of Schizothrix calcicola contains 2-amino-2-deoxy-D-glucose, D-galactose, D-glucose, D-mannose, D-xylose, and L-rhamnose. In contrast to many enterobacterial lipopoly-saccharides, the major fatty acid component has been identified as 3-hydroxy-palmitic acid and not 3-hydroxymyristic acid. 

Ratios calculated as the total percentage of 16 1 plus 18 1 divided by the total percentage of 14 0 plus 16 0, Hydroxymyristic acid was omitted from this calculation. 

Tridecylic acid has been prepared by the malonic ester synthesis from undecyl iodide,1 by the oxidation of a-hydroxymyristic acid in acetone with potassium permanganate,2 by the action of dodecyl bromide on potassium cyanide and subsequent hydrolysis,3 and from undecyl iodide and ethyl cyanoacetate.4 The present method is an adaptation of that of Ruzicka, Stoll, and Schinz.3... 

Convolvulinolic acid = (115)-hydroxytetradecanoic acid = 11-hydroxymyristic acid Ipolearic acid = (35,115)-dihydroxyhexadecanoic acid = 3,11-dihydroxypalmitic acid Ipurolic acid = (35,11 -dihydroxytetradecanoic acid = 3,11-dihydroxymyristic acid Jalapinolic acid = (115)-(+)-hydroxyhexadecanoic acid = 11-hydroxypalmitic acid Operculinolic acid = 3,12-dihydroxyhexadecanoic acid = 3,12-dihydroxypalmitic acid Turpetholic acid A = 3,12-dihydroxypentadecanoic acid Turpetholic acid B = 4,12-dihydroxypentadecanoic acid... 

The (S)-enantiomer was predominantly hydroxylated to the diastereoisomer three-12,13-dihydroxymyristic acid (80% (12J ,13R)-12,13-dihydroxymyristic add and 20% (12J ,13S)-12,13-dihydroxymyristic acid). When (i )-13-hydroxymyristic acid was used as substrate in a similar reaction system, mainly erythro-12,13-dihydroxymyrisitic add (85% (12S,13i )-12,13-dihydroxymyristic add and 15% (12R,13J )-12,13-dihydroxymyristic acid) was generated (Scheme 5.19) [82]. 

---