Description
16-
hydroxy Hexadecanoic acid is a metabolite of the saturated fatty acid palmitic acid (16:0) that has been hydroxylated on its terminal (ω) carbon. It is produced by ω-
hydroxylation of palmitic acid by cytochrome P450 in both plants and animals. In plants, it is commonly a component of cutin.
Chemical Properties
white crystalline solid
Uses
16-Hydroxyhexadecanoic acid was used in the synthesis of dihydroxypalmitic acids. It was also used to induce the expression of two GRP genes of
Arabidopsis thaliana, AtGRP5 and AtGRP23.
Application
16-Hydroxyhexadecanoic acid can be used to:
(1) Oxidative reactions: Cell lysates and intact cells of Escherichia coli JM101 recombinant, which synthesises the cyp102 gene for cytochrome P450BM-3 monooxygenase, biotransform 16-hydroxyhexa-decanoic acid into 1, 16-hexadecanedioic acid. a small amount of intermediate product accumulation accompanies the oxidation of 16-hydroxyhexadecanoic acid. hydroxyhexadecanoic acid oxidation is accompanied by the accumulation of a small amount of intermediate products. The by-products also include 13.16-dihydroxyhexadecanoic acid and 12,16-dihydroxyhexadecanoic acid
[1].
(2) 16-hydroxyhexadecanoic acid ethyl ester was synthesised from 16-hexadecanolactone by an intramolecular ester exchange reaction with PEG-lipase
[2].
(3) Lactonisation reaction: It has been demonstrated that Mucor javanicus L46 and Mucor miehei catalyse the lactonisation reaction of 15-hydroxypentadecanoic and 16- hydroxyhexadecanoic acids to appropriate macrocyclic mono- and oligolactones
[3].
Definition
ChEBI: 16-hydroxyhexadecanoic acid is an omega-hydroxy-long-chain fatty acid that is hexadecanoic acid (also known as palmitic acid) which is substituted at position 16 by a hydroxy group. It is a key monomer of cutin in the plant cuticle. It has a role as a plant metabolite. It is an omega-hydroxy-long-chain fatty acid and a hydroxypalmitic acid. It is a conjugate acid of a 16-hydroxyhexadecanoate.
References
[1] S. SCHNEIDER. Production Of Alkanedioic Acids By Cytochrome P450Bm-3 Monooxygenase: Oxidation Of 16-Hydroxyhexadecanoic Acid To Hexadecane-1, 16-Dioic Acid[J]. Biocatalysis and Biotransformation, 1999. DOI:10.3109/10242429909040113.
[2] YOH KODERA . Lactone synthesis from 16-hydroxyhexadecanoic acid ethyl ester in organic solvents catalyzed with polyethylene glycol-modified lipase[J]. Journal of biotechnology, 1993. DOI:10.1016/0168-1656(93)90162-G.
[3] U. ANTCZAK . Enzymatic lactonization of 15-hydroxypentadecanoic and 16-hydroxyhexadecanoic acids to macrocyclic lactones[J]. Enzyme and Microbial Technology, 1991. DOI:10.1016/0141-0229(91)90095-R.
