Omega hydroxy acid


Omega hydroxy acids are a class of naturally occurring straight-chain aliphatic organic acids n carbon atoms long with a carboxyl group at position 1, 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. Only the epidermal cells of plants synthesize cutin.
Omega hydroxy fatty acids also occur in animals. Cytochrome P450 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, a bioactive product involved in various physiological and pathological processes; 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.

List

The definition for "omega" includes number of carbons greater or equal to three. Lower numbers are included here to match the formula pattern CnH2nO3.
C#trivial namesystematic namemelting point
°C		formulaSMILESCASNoPubChem CIDChemSpiderIDUNIIChEBIoccurrence
2Glycolic acid2-Hydroxyethanoic acid75C2H4O3OCCO79-14-17577370WT12SX38S17497plants
3Hydroacrylic acid3-Hydroxypropionic acid139-140C3H6O3OCCCO503-66-26815261460
4gamma-Hydroxybutyric acid4-Hydroxybutanoic acid?C4H8O3OCCCCO591-81-110413998430IW36W5B230830human neurotransmitter
55-hydroxyvaleric acid5-Hydroxypentanoic acidC5H10O3OCCCCCO13392-69-32594524171H5EVV4LP5945564from engineered Corynebacterium glutamicum
66-Hydroxycaproic acid6-Hydroxyhexanoic acidC6H12O3OCCCCCCO1191-25-914490138353Y3OX37NM817869
77-Hydroxyheptanoic acidC7H14O3OCCCCCCCO3710-42-713801612166079112
8omega-hydroxycaprylic acid8-hydroxyoctanoic acidC8H16O3OCCCCCCCCO764-89-6698206301879162
99-hydroxypelargonic acid9-hydroxynonanoic acidC9H18O3OCCCCCCCCCO3788-56-5138052121694HV672SU12G79121
1010-hydroxycapric acid10-hydroxydecanoic acidC10H20O3OCCCCCCCCCCO1679-53-47430066903NP03XO416B17409
1111-hydroxyundecanoic acid C11H22O3OCCCCCCCCCCCO3669-80-57723769664SD6J9LX2XK79126
12sabinic acid12-hydroxydodecanoic acidC12H24O3OCCCCCCCCCCCCO505-95-37903471366SUH3LR2K9D39567
1313-hydroxytridecanoic acidC13H26O3OCCCCCCCCCCCCCO7735-38-813906512265679166
14ω-hydroxymyristic acid14-hydroxytetradecanoic acidC14H28O3OCCCCCCCCCCCCCCO17278-74-9084276234136977168engineered Candida tropicalis
1515-hydroxypentadecanoic acidC15H30O3OCCCCCCCCCCCCCCCO4617-33-87836070730FU65P3692T79169Angelica archangelica
16juniperic acid16-hydroxyhexadecanoic acidC16H32O3OCCCCCCCCCCCCCCCCO506-13-8104661003455328plant cuticle
1717-hydroxyheptadecanoic acidC17H34O3OCCCCCCCCCCCCCCCCCO13099-34-84308451351397779177Pinus radiata
18ω-hydroxystearic acid18-hydroxyoctadecanoic acidC18H36O3OCCCCCCCCCCCCCCCCCCO3155-42-852829154446042CCR5P6ICT279182plant cutin
1919-hydroxynonadecanoic acidC19H38O3OCCCCCCCCCCCCCCCCCCCO5282917444604479179
20ω-hydroxyarachidic acid20-hydroxyicosanoic acidC20H40O3OCCCCCCCCCCCCCCCCCCCCO62643-46-35282919444604679190stem and seed cutin
2121-hydroxyhenicosanoic acidC21H42O3OCCCCCCCCCCCCCCCCCCCCCO5282920444604779195
2222-hydroxybehenic acid22-Hydroxydocosanoic acidC22H44O3OCCCCCCCCCCCCCCCCCCCCCCO506-45-65282922444604976322
2323-hydroxytricosanoic acidC23H46O3OCCCCCCCCCCCCCCCCCCCCCCCO61658-18-2117604429935141cutin
2424-hydroxytetracosanoic acidC24H48O3OCCCCCCCCCCCCCCCCCCCCCCCCO75912-18-453127804472205
2525-hydroxypentacosanoic acidC25H50O3OCCCCCCCCCCCCCCCCCCCCCCCCCO82612-07-51432517657507583
26ω-hydroxycerotic acid26-hydroxyhexacosanoic acidC26H52O3OCCCCCCCCCCCCCCCCCCCCCCCCCCO506-47-85312785447221076325
2727-hydroxyheptacosanoic acidC27H54O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCO143251771373962484861
2828-hydroxyoctacosanoic acidC28H56O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCCO52900-17-15312786447221184863
29omega-hydroxynonacosanoic acid29-hydroxynonacosanoic acidC29H58O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO143251783444910384865
3030-hydroxytriacontanoic acidC30H60O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO52900-18-25312787447221276220