10,15-Dihydroxyhexadecanoic acid

Hydroxyalkanoic monohydroxy) 2-Hydroxyhexadecanoic acid 15-Hydroxyhexadecanoic acid 2-Hydroxyoctadecanoic acid 2-Hydroxyeicosanoic acid 2-Hydroxytriacontanoic acid 2-Hydroxytetracontanoic acid (Hydroxyalkanoic dihydroxy) 10,15-Dihydroxyhexadecanoic acid Phospholipids... 

The most common major components of cutin are derivatives of saturated C16 (palmitic) acid and unsaturated C18 acids (Fig. 4). The major component of the C16 family of acids is 9- or 10,16-dihydroxyhexadecanoic acid (and some mid-chain positional isomers), with less 16-hydroxyhexadecanoic acid and much smaller amounts of hexadecanoic acid. In some cases other derivatives are significant constituents. For example, in citrus cutin 16-hydroxy-10-oxo-C16 acid, and in young Vicia faba leaves 16-oxo-9 or 10-hydroxy C16 acid are significant... 

Table 2.8 Polymeric form of dihydroxyhexadecanoic acid and related Cis acids in four plant cutins...

Diglycosyldiphytanylglycerol diether, 158 Dihydroperoxides, 455 Dihydrosphingosine, 281,439 Dihydroxystearic acids, 57 Dihydrosterculic acid, 53 Dihydroxy acetone phosphate, 504 Dihydroxyhexadecanoic acid, 44 Diimine, 452 Dilatation, 253,254,374 Dilaurin, 366,367... 

Dihydroxyhexadecanoic acid Me ester, in D-10176 Nerifol, in D-30182 Ustilic acid A Me ester, in D-30183... 

Kolattukudy (1984) states that cutin is a network of interesterified hydroxyl fatty acids embedded in a layer of waxy material. Loss of a constituent of the cuticle (i.e., 16-dihydroxyhexadecanoic acid) may best provide an indication of the degree of retting (Morrison and Akin 2001). Wax evaluations of high and low quality flax fiber have indicated that an inverse relationship exists between the amount of palmitic acid, sinapylaldehyde, and sinapyl alcohol and fiber quality (Morrison and Archibald 1998). Some fiber characterization studies have been performed, which have created preliminary testing procedures for analyzing natural fibers... 

Constit. of the capsular antigen of Klebsiella K12, K18, K41 type specific antigen of Streptococcus pneumoniae type 2, type 6A O-antigen of Serratia marces-cens extracellular polysaccharide from Mycobacterium album B-88 in operculinic acid (see 3,12-Dihydroxyhexadecanoic acid) formed from the resin of Ipomoea operculata. 

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... 

Turpetholic acid C = 4,12-dihydroxyhexadecanoic acid = 4,12-dihydroxypalmitic acid Sugars (monosaccharides). ... 

One of the most commonly found mid-chain hydroxylated components is dihydroxyhexadecanoic acid, which has hydroxyl moieties at C-10, C-9, C-8 or C-7, and on C-16 (232, 243, 244). A crude cell-free preparation from excised epidermis of V. faba catalyzed C-10 hydroxylation of 16-hydroxyhexadecanoic acid (473). This hydroxylation reaction was also catalyzed by the endoplasmic reticulum fraction from the embryonic shoots of K faba. This preparation required O2 and NADPH to catalyze mid-chain hydroxylation and the activity was inhibited by the typical mixed-function oxidase inhibitors and also by CO (427). The inhibition by CO was photoreversible, as expected of a cytochrome P450 hydroxylase. 

The major components of the C16 cutins are 9- or 10,16-dihydroxyhexadecanoic acid, and 16-hydroxyhexadecanoic acid. 16-Hydroxy-10-oxo-C16 acid and 16-oxo-9 or 10-hydroxy C16 acid are monomers in only some cases. The major components of the C18 family of monomers are 18-hydroxy-9,10-epoxyoctadecanoic acid and 9,10,18-trihydroxyoctadecanoic acid, together with their monounsaturated homologs. Omega hydroxyacids and their derivatives are the main components of cutin, which are interhnked via ester bonds, forming a polyester polymer of indeterminate size [211]. 

The building units of cutin are called cutin acids, which include mono-, di- and trihydroxycarboxylic fatty acids and also higher dicarboxylic, dihy-droxydicarboxylic and also other acids. The characteristic monomers are 18-hydroxyoctadeca-9,12-dienoic, 10,16-dihydroxyhexadecanoic and threo-9,10,18-trihydroxyoctadecanoic acids. 

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