Z-13-docosenoic acid

Only a few specific kinds of lipids can be identified on the basis of the characteristic features of the FA profile and the presence of specific biomarkers. For example, oils obtained from the seeds of Brassicaceae, such as rapeseed oil, are characterized by abundant amounts of uncommon FA such as gondoic (Z-11 -eicosenoic) acid and erucic (Z-13-docosenoic) acid and, after ageing their oxidation products. Other examples are reported in Table 7.2 and in Chapter 1. 

AI3-18180 13-Docosenoic acid, (Z)- 13-Docosenoic acid, (13Z)- 13-cis-Docosenoic acid cis-13-Docosenoic acid (Z)-Docos-13-enoic acid EINECS 204-011-3 Erucic acid HSDB 5015 Hystrene 2290 NSC 6814. Major fatty acid in mustard, rapeseed and wallflower seed. Used as a chemical intermediate. Needles mp 33.5 bp = 381, bpi5 = 265 d b 0.860 insoluble in H2O, soluble in EtOH, CCI4, very soluble in Et20, MeOH. 

CigHjjNO, Mr 281.48, mp. 75 -76 °C. O. was first isolated from cerebrospinal fluid of cats that had been deprived of sleep for a longer time. The compound has also been detected in the cerebrospinal fluids of humans and rats. Injections of O. in animals artificially induce sleep ( sleep lipids"). O. is converted in the brain to oleic acid by enzymatic hydrolysis and thus deactivated. Another physiologically active fatty acid amide occurring in cerebrospinal fluid is erucic acid amide [(Z)-13-docosenoic acid amide, C22H43NO, Mr 337.59, mp. 94 °C],... 

Docos-13-enoic acid 13-Docosenoic acid, (Z)- cis-13-Docosenoic acid 5 13 14-Docosenoic acid 5 (13)-cis-Docosenoic acid (Z)-13-Docosenoic acid. See Erucic acid Docosyl docosanoate. See Behenyl behenate Docusate sodium. See Dioctyl sodium sulfosuccinate Dodecafluoropentane. See Perfluoropentane Dodecahydrobisphenol A. See Bisphenol A, hydrogenated Dodecahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanol. 

Although similar in structure to common fatty acids, eru-cic acid (Z-13-docosenoic acid) (66), when fed to rats at as little as 15% of their caloric intake, produced myocarditis (accumulation of lipids in the heart) (Fig. 2.28). Eventually, myocardial fibrosis and other abnormalities were observed. Because rapeseed oil was widely used for margarine production, a breeding program was initiated to produce new varieties in which most or all of the erucic acid is replaced with oleic acid. This new product is called canola oil. High erucic rapeseed oil is still used to prepare lubricants (Simpson and Conner-Ogorzaly, 1986). Both types are cultivated. 

Erucic acid, Z-13-docosenoic acid, d docose-noic acid- CH3-(CH2),-CH = CH-(CH2)n-COOH, M, 338.56, cis-form m.p. 34 C, b.p.jo 254.5 °C, a fatty acid found esterified in the glycerides of many seed oils of the Cruciferae and Tropaeolaceae. It constitutes 40-50 % of the total fatty acids of rapeseed, mustard and wallflower seeds, and 80 % of the fatty acids of nasturtium seeds. 

Caprinat/Decanat) erucic acid, (Z)-13-docosenoic acid... 

Z 11 eicosenoic (gondoic) acid, Z 13 docosenoic (erucic) acid, 11,12 dihydroxyeicosanoic acid, 13,14 dihydroxydocosanoic acid Oils from Brassicaeae seeds [12,44,45]... 

Previously, the strain DS5 bioconversion products from oleic and linoleic acids were identified as 10-ketostearic (23) and 10-hydroxy-12(Z)-octadecenoic acid(24), respectively. It is interesting to find that all unsaturated fatty acids tested are hydrated at the 9,10 positions with the oxygen functionality at C-10 despite their varying degree of unsaturations. DS5 hydratase was not active on saturated fatty acids and other non-9(Z)-unsaturated fatty acids such as elaidic [9(.B)-octadecenoic], arachidonic [5( ),8( ),1 l( ),14( )-eicosatetraenoic], and erucic [13( )-docosenoic] acids (25). From all of the data gathered, it is concluded fliat DS5 hydratase is indeed a C-10 positional-specific enzyme. The fact that elaidic acid was not hydrated indicates that die unsaturation must be in flie cis configuration for DS5 hydratase activity. 

CAS 27640-89-7 EINECS/ELINCS 248-587-4 Synonyms 13-Docosenoic acid, 13-docosenyl ester 13-Docosenyl 13-docosenoate (Z)-Docos-13-enyl (Z)-docos-l 3-enoate... 

CAS 97259-85-3 EINECS/ELINCS 306-449-1 Synonyms 13-Docosenoic acid, isooctadecyl ester Isooctadecyl 13-docosenoate 16-Methyl heptadecyl (Z)-, docos-13-enoate... 

CAS 2752-99-0 EINECS/ELINCS 220-399-7 Synonyms 13-Docosenoic acid, 1,2,3-propanetriyl ester Glyceryl tri (cis-13-docosenoate) Glyceryl trierucate 1,2,3-Propanetriol tri (13-docosenoate) Propane-1,2,3-triyl tris[(Z)-docos-13-enoate]... 

Z)-Docos-13-enoic acid, monoester with glycerol. See Glyceryl erucate 13-Docosenoic acid, 9-octadecenyl ester. See Oleyl erucate 13-Docosenoic acid, octadecyl ester. See Stearyl erucate Docosyl docosanoate. See Behenyl behenate... 

Synonyms 13-Docosenoic acid, 9-octadecenyl ester Erucic acid, oleyl ester 9-Octadecenyl 13-docosenoate (Z)-Octadec-9-enyl (Z)-docos-13-enoate Definition Ester of oleyl alcohol and erucic acid Empirical ... 

---