Omega hydroxy acid

Omega hydroxy acids (ω-hydroxy acids) are a class of naturally occurring straight-chain aliphatic organic acids n carbon atoms long with a carboxyl group at position 1 (the starting point for the family of carboxylic acids), and a hydroxyl at terminal position n where n > 3. They are a subclass of hydroxycarboxylic acids. The C16 and C18 omega hydroxy acids 16-hydroxy palmitic acid and 18-hydroxy stearic acid are key monomers of cutin in the plant cuticle. The polymer cutin is formed by interesterification of omega hydroxy acids and derivatives of them that are substituted in mid-chain, such as 10,16-dihydroxy palmitic acid.T.J. Walton TJ and P.E. Kolattukudy (1972) Enzymatic conversion of 16-hydroxypalmitic acid into 10,16-dihydroxypalmitic acid in Vicia faba epidermal extracts. Biochem Biophys Res Communications 46, (1), 16–21P. J. Holloway (1982) The chemical constitution of plant cutins. p45-85 in In "The Plant Cuticle". ed. by DF Cutler, KL Alvin and CE Price. Academic Press, London. Only the epidermal cells of plants synthesize cutin.Kolattukudy, PE (1996) Biosynthetic pathways of cutin and waxes, and their sensitivity to environmental stresses. In: Plant Cuticles. Ed. by G. Kerstiens, BIOS Scientific publishers, Oxford, pp 83-108

Omega hydroxy fatty acids also occur in animals. Cytochrome P450 (CYP450) microsome ω-hydroxylases such as CYP4A11, CYP4A22, CYP4F2, and CYP4F3 in humans, Cyp4a10 and Cyp4a12 in mice, and Cyp4a1, Cyp4a2, Cyp4a3, and Cyp4a8 in rats metabolize arachidonic acid and many arachidonic acid metabolites to their corresponding omega hydroxyl products. This metabolism of arachidonic acid produces 20-hydroxyarachidonic acid (i.e. 20-hydroxyeicosatetraeonic acid or 20-HETE), a bioactive product involved in various physiological and pathological processes;Annu Rev Pharmacol Toxicol. 2005;45:413-38 and this metabolism of certain bioactive arachidonic acid metabolites such as leukotriene B4 and 5-hydroxyicosatetraenoic acid produces 20-hydroxylated products which are 100- to 1,000-fold weaker than, and therefore represents the inactivation of, their respective precursors.J Immunol. 1986 Nov 15;137(10):3277-83

List The definition for "omega" includes number of carbons (C#) greater or equal to three. Lower numbers are included here to match the formula pattern CnH2nO3.

C#trivial namesystematic namemelting point

°CformulaSMILESCASNoPubChem CIDChemSpiderIDUNIIChEBIoccurrence2Glycolic acid2-Hydroxyethanoic acid75C2H4O3OCC(=O)O79-14-17577370WT12SX38S17497plants3Hydroacrylic acid3-Hydroxypropionic acid139-140C3H6O3OCCC(=O)O503-66-268152614604gamma-Hydroxybutyric acid4-Hydroxybutanoic acid?C4H8O3OCCCC(=O)O591-81-110413998430IW36W5B230830human neurotransmitter55-hydroxyvaleric acid5-Hydroxypentanoic acidC5H10O3OCCCCC(=O)O13392-69-32594524171H5EVV4LP5945564from engineered Corynebacterium glutamicum66-Hydroxycaproic acid6-Hydroxyhexanoic acidC6H12O3OCCCCCC(=O)O1191-25-914490138353Y3OX37NM81786977-Hydroxyheptanoic acidC7H14O3OCCCCCCC(=O)O3710-42-7138016121660791128omega-hydroxycaprylic acid8-hydroxyoctanoic acidC8H16O3OCCCCCCCC(=O)O764-89-669820630187916299-hydroxypelargonic acid9-hydroxynonanoic acidC9H18O3OCCCCCCCCC(=O)O3788-56-5138052121694HV672SU12G791211010-hydroxycapric acid10-hydroxydecanoic acidC10H20O3OCCCCCCCCCC(=O)O1679-53-47430066903NP03XO416B174091111-hydroxyundecanoic acid (11-HUDA)C11H22O3OCCCCCCCCCCC(=O)O3669-80-57723769664SD6J9LX2XK7912612sabinic acid12-hydroxydodecanoic acidC12H24O3OCCCCCCCCCCCC(=O)O505-95-37903471366SUH3LR2K9D395671313-hydroxytridecanoic acidC13H26O3OCCCCCCCCCCCCC(=O)O7735-38-81390651226567916614ω-hydroxymyristic acid14-hydroxytetradecanoic acidC14H28O3OCCCCCCCCCCCCCC(=O)O17278-74-9084276234136977168engineered Candida tropicalis1515-hydroxypentadecanoic acidC15H30O3OCCCCCCCCCCCCCCC(=O)O4617-33-87836070730FU65P3692T79169Angelica archangelica16juniperic acid16-hydroxyhexadecanoic acidC16H32O3OCCCCCCCCCCCCCCCC(=O)O506-13-8104661003455328plant cuticle1717-hydroxyheptadecanoic acidC17H34O3OCCCCCCCCCCCCCCCCC(=O)O13099-34-84308451351397779177Pinus radiata18ω-hydroxystearic acid18-hydroxyoctadecanoic acidC18H36O3OCCCCCCCCCCCCCCCCCC(=O)O3155-42-852829154446042CCR5P6ICT279182plant cutin1919-hydroxynonadecanoic acidC19H38O3OCCCCCCCCCCCCCCCCCCC(=O)O528291744460447917920ω-hydroxyarachidic acid20-hydroxyicosanoic acidC20H40O3OCCCCCCCCCCCCCCCCCCCC(=O)O62643-46-35282919444604679190stem and seed cutin2121-hydroxyhenicosanoic acidC21H42O3OCCCCCCCCCCCCCCCCCCCCC(=O)O52829204446047791952222-hydroxybehenic acid22-Hydroxydocosanoic acidC22H44O3OCCCCCCCCCCCCCCCCCCCCCC(=O)O506-45-652829224446049763222323-hydroxytricosanoic acidC23H46O3OCCCCCCCCCCCCCCCCCCCCCCC(=O)O61658-18-2117604429935141cutin2424-hydroxytetracosanoic acidC24H48O3OCCCCCCCCCCCCCCCCCCCCCCCC(=O)O75912-18-4531278044722052525-hydroxypentacosanoic acidC25H50O3OCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O82612-07-5143251765750758326ω-hydroxycerotic acid26-hydroxyhexacosanoic acidC26H52O3OCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O506-47-853127854472210763252727-hydroxyheptacosanoic acidC27H54O3OCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O1432517713739624848612828-hydroxyoctacosanoic acidC28H56O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O52900-17-1531278644722118486329omega-hydroxynonacosanoic acid29-hydroxynonacosanoic acidC29H58O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O1432517834449103848653030-hydroxytriacontanoic acidC30H60O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O52900-18-25312787447221276220

See also Alpha hydroxy acid Beta hydroxy acid

References

ar:حمض هيدروكسي