Omega hydroxy acid

Source: Wikipedia, the free encyclopedia.

Omega hydroxy acids (ω-hydroxy acids) are a class of naturally occurring straight-chain

esterification of omega hydroxy acids and derivatives of them that are substituted in mid-chain, such as 10,16-dihydroxy palmitic acid.[3][4] Only the epidermal cells of plants synthesize cutin.[5]

Omega hydroxy fatty acids also occur in animals.

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.[8][9][10]

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# systematic name trivial name melting point

°C

formula SMILES CASNo PubChem CID ChemSpiderID UNII ChEBI occurrence reference
1 Carbonic acid CH2O3 OC(=O)O 463-79-6 767 747 142M471B3J 28976
2 2-Hydroxyethanoic acid Glycolic acid 75 C2H4O3 OCC(=O)O 79-14-1 757 737 0WT12SX38S 17497 plants
3 3-Hydroxypropionic acid β-Lactic acid 139-140 C3H6O3 OCCC(=O)O 503-66-2 68152 61460 most living organisms
4 4-Hydroxybutanoic acid gamma-Hydroxybutyric acid ? C4H8O3 OCCCC(=O)O 591-81-1 10413 9984 30IW36W5B2 30830 human neurotransmitter
5 5-Hydroxypentanoic acid 5-hydroxyvaleric acid C5H10O3 OCCCCC(=O)O 13392-69-3 25945 24171 H5EVV4LP59 45564
6 6-Hydroxyhexanoic acid 6-Hydroxycaproic acid C6H12O3 OCCCCCC(=O)O 1191-25-9 14490 13835 3Y3OX37NM8 17869
7 7-Hydroxyheptanoic acid C7H14O3 OCCCCCCC(=O)O 3710-42-7 138016 121660 79112
8 8-Hydroxyoctanoic acid omega-hydroxycaprylic acid C8H16O3 OCCCCCCCC(=O)O 764-89-6 69820 63018 79162
9 9-Hydroxynonanoic acid 9-hydroxypelargonic acid C9H18O3 OCCCCCCCCC(=O)O 3788-56-5 138052 121694 HV672SU12G 79121
10 10-Hydroxydecanoic acid 10-hydroxy capric acid C10H20O3 OCCCCCCCCCC(=O)O 1679-53-4 74300 66903 NP03XO416B 17409
11 11-Hydroxyundecanoic acid 11-HUDA C11H22O3 OCCCCCCCCCCC(=O)O 3669-80-5 77237 69664 SD6J9LX2XK 79126
12 12-Hydroxydodecanoic acid Sabinic acid C12H24O3 OCCCCCCCCCCCC(=O)O 505-95-3 79034 71366 SUH3LR2K9D 39567 [11]
13 13-Hydroxytridecanoic acid C13H26O3 OCCCCCCCCCCCCC(=O)O 7735-38-8 139065 122656 79166
14 14-Hydroxytetradecanoic acid ω-hydroxy myristic acid C14H28O3 OCCCCCCCCCCCCCC(=O)O 17278-74-9 084276 2341369 77168
15 15-Hydroxypentadecanoic acid C15H30O3 OCCCCCCCCCCCCCCC(=O)O 4617-33-8 78360 70730 FU65P3692T 79169 Angelica archangelica
16 16-hydroxyhexadecanoic acid Juniperic acid C16H32O3 OCCCCCCCCCCCCCCCC(=O)O 506-13-8 10466 10034 55328 plant cuticle [12]
17 17-Hydroxyheptadecanoic acid C17H34O3 OCCCCCCCCCCCCCCCCC(=O)O 13099-34-8 4308451 3513977 79177 Pinus radiata
18 18-Hydroxyoctadecanoic acid ω-hydroxystearic acid C18H36O3 OCCCCCCCCCCCCCCCCCC(=O)O 3155-42-8 5282915 4446042 CCR5P6ICT2 79182 plant cutin
19 19-Hydroxynonadecanoic acid C19H38O3 OCCCCCCCCCCCCCCCCCCC(=O)O 5282917 4446044 79179
20 20-Hydroxyicosanoic acid ω-hydroxyarachidic acid C20H40O3 OCCCCCCCCCCCCCCCCCCCC(=O)O 62643-46-3 5282919 4446046 79190 stem and seed cutin
21 21-Hydroxyhenicosanoic acid C21H42O3 OCCCCCCCCCCCCCCCCCCCCC(=O)O 5282920 4446047 79195
22 22-Hydroxydocosanoic acid 22-hydroxybehenic acid C22H44O3 OCCCCCCCCCCCCCCCCCCCCCC(=O)O 506-45-6 5282922 4446049 76322
23 23-Hydroxytricosanoic acid C23H46O3 OCCCCCCCCCCCCCCCCCCCCCCC(=O)O 61658-18-2 11760442 9935141 cutin
24 24-Hydroxytetracosanoic acid C24H48O3 OCCCCCCCCCCCCCCCCCCCCCCCC(=O)O 75912-18-4 5312780 4472205
25 25-Hydroxypentacosanoic acid C25H50O3 OCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O 82612-07-5 14325176 57507583
26 26-Hydroxyhexacosanoic acid ω-hydroxycerotic acid C26H52O3 OCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O 506-47-8 5312785 4472210 76325
27 27-Hydroxyheptacosanoic acid C27H54O3 OCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O 14325177 13739624 84861
28 28-Hydroxyoctacosanoic acid C28H56O3 OCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O 52900-17-1 5312786 4472211 84863
29 29-hydroxynonacosanoic acid omega-Hydroxynonacosanoic acid C29H58O3 OCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O 14325178 34449103 84865
30 30-Hydroxytriacontanoic acid C30H60O3 OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O 52900-18-2 5312787 4472212 76220

See also

  • Alpha hydroxy acid
  • Beta hydroxy acid

References

  1. PMID 5025632
    .
  2. PMID 16660004
    .
  3. ^ 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), 16–21
  4. ISBN 0-12-199920-3
  5. ^ 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
  6. PMID 25813407
    .
  7. ^ Annu Rev Pharmacol Toxicol. 2005;45:413-38
  8. PMID 19467632
    .
  9. ^ J Immunol. 1986 Nov 15;137(10):3277-83
  10. PMID 25449650
    .
  11. ISSN 0002-7863
    .
  12. S2CID 4108900
    .
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