Hexadecanoate

Dodecanoic acid Tetradecanoic acid Hexadecanoic acid Octadecanoic acid Icosanoic acid... 

Waxes are water repelling solids that are part of the protective coatings of a number of living things including the leaves of plants the fur of animals and the feathers of birds They are usually mixtures of esters m which both the alkyl and acyl group are unbranched and contain a dozen or more carbon atoms Beeswax for example contains the ester triacontyl hexadecanoate as one component of a complex mixture of hydrocar bons alcohols and esters... 

Spermaceti is a wax obtained from the sperm whale It contains among other materials an ester known as cetyl palmitate which is used as an emollient in a number of soaps and cosmetics The systematic name for cetyl palmi tate IS hexadecyl hexadecanoate Write a structural formula for this substance... 

Z,Z,Z,)-9,12,15-octadecatrienoic acid). Fish oils contain esters of eicosanoic and docosanoic acids with four to six double bonds separated by single methylene groups, eg, (i7//-Z)-4,7,10,13,16,19-docosahexaenoic acid [6217-54-5] in menhaden oil (4). The fatty acid with conjugated double bonds in tung oil is a-eleostearic acid [506-23-0] ((F,Z,F)-9,ll,13-octadecatrienoic acid) the predominant fatty acid in oiticica oil is licanic acid [17699-20-6] (4-oxo-(F,Z,F)-9,ll,13-octadecatrienoic acid). In all oils, other fatty acids including palmitic acid [57-10-3] (hexadecanoic acid), stearic acid [57-11-4] (octadecanoic acid), and oleic acid [112-80-1] ((Z)-9-octadecenoic acid) also are present. 

Hexadecanoic acid (palmitic acid) [57-10-3] M 256.4, m 62-63°, b 215°/15mm, pK 6.46 (50% aq EtOH), 5.0 (H2O). Purified by slow (overnight) recrystn from hexane. Some samples were also crystd from acetone, EtOH or EtOAc. Crystals were stood in air to lose solvent, or were pumped dry of solvent on a vaeuum line. [Iwahashi et al. J Chem Soc, Faraday Trans 1 81 973 1985, pK White J Am Chem Soc 72 1858 1950]. 

R-Octylammonium hexadecanoate [88020-97-7] M 385.7, m 52-53 . Purified by several recrystns from R-hexane or ethyl acetate. The solid was then washed with cold anhydrous diethyl ether, and dried in vacuo over P2O5. 

Palmitic acid anhydride (hexadecanoic anhydride) [623-65-4] M 494.9, m 63-64 , 64 , d 0.838, n 1.436. It is moisture sensitive and hydrolyses in water. Purified by refluxing with acetic anhydride for Ihr, evaporating and freeing the residue of acetic acid and anhydride by drying the residue at high vac and crystallising from pet ether at low temperature. 

Acylation of mesoionic pyrido[l,2-u]pyrimidin-4-ones 150 with aroyl chlorides in the presence of NEts yielded 2-aroyloxy-4//-pyrido[l,2-u]pyrimidin-4-ones 178 (96JHC663). None of the esters 178 could be rearranged to the 2-hydroxy-3-aroyl derivatives 179. The hydroxy group of 9-hydroxy-2-methyl-3- 2-[4-(6-fluoro-l,2-benzisoxazol-3-yl)-l-piperidinyl] ethyl -6,7,8,9-tetrahydro-4//-pyrido[l, 2-u]pyrimidin-4-one was acylated with hexadecanoic acid in CH2CI2 in the presence of dicyclohexylcarbodi-imide and 4-pyrrolidinopyridine at room temperature for 3 days in 80% yield (97MIP7). 

Waxes are mixtures of esters of long-chain carboxylic acids with long-chain alcohols. The carboxylic acid usually has an even number of carbons from 16 through 36( while the alcohol has an even number of carbons from 24 through 36. One of the major components of beeswax( for instance, is triacontyl hexadecanoate, the ester of the C30 alcohol triacontanol and the C16 acid hexa-... 

CH3 CH2>14COiCH2)29CH3 Triacontyl hexadecanoate (from beeswax)... 

Beeswax (triacontanyl palmitate) octadecyl octadecanoate (stearyl stearate) dodecyl hexadecanoate (lauryl palmitate) cetyl palmitate lanolin carnauba wax glycol distearate jojoba oil... 

Watmough, N.J.. Turnbull, D.M., Sherratt. H.S.A. Bartlett. K. (1989). Measurement of the acyl-CoA intermediates of p-oxidation by hplc with on-line radiochemical and photodiode-array detection. Application to the study of [U- C]hexadecanoate by intact rat liver mitochondria. Biochem. J. 262,261-269. 

C23H4204Si 79902-31-1) see Simvastatin (2R,35,5lf)-3-[(l,l-dimethylethyl)dimethylsilyloxy]-2-hexyl-5-(phenylmethoxy)hexadecanoic acid... 

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