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.{{cite journal | last1 = Kolattukudy | first1 = P. E. | last2 = Walton | first2 = T. J. | year = 1972 | title = Structure and biosynthesis of the hydroxy fatty acids of cutin in Vicia faba leaves | journal = Biochemistry | volume = 11 | issue = 10| pages = 1897–1907 | doi=10.1021/bi00760a026| pmid = 5025632}}{{cite journal | last1 = Soliday | first1 = C. L. | last2 = Kolattukudy | first2 = P. E. | year = 1977 | title = Biosynthesis of Cutin ω-hydroxylation of fatty acids by a microsomal preparation from germinating Vicia faba | journal = Plant Physiology | volume = 59 | issue = 6| pages = 1116–1121 | doi=10.1104/pp.59.6.1116| pmc = 542517 | pmid=16660004}} 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. {{ISBN|0-12-199920-3}} 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.{{cite journal | vauthors = Hoopes SL, Garcia V, Edin ML, Schwartzman ML, Zeldin DC | title = Vascular actions of 20-HETE | journal = Prostaglandins & Other Lipid Mediators | volume = 120 | pages = 9–16 | date = Jul 2015 | pmid = 25813407 | doi = 10.1016/j.prostaglandins.2015.03.002 | pmc=4575602}} 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.{{cite journal | doi = 10.1016/j.abb.2009.01.012 | volume=484 | title=20-Hydroxylation is the CYP-dependent and retinoid-inducible leukotriene B4 inactivation pathway in human and mouse skin cells | journal=Archives of Biochemistry and Biophysics | pages=80–86 | pmid=19467632 | pmc=2687325 | last1 = Du | first1 = L | last2 = Yin | first2 = H | last3 = Morrow | first3 = JD | last4 = Strobel | first4 = HW | last5 = Keeney | first5 = DS | year=2009| issue=1 }}J Immunol. 1986 Nov 15;137(10):3277-83{{cite journal | doi = 10.1016/j.bbalip.2014.10.008 | pmid=25449650 | volume=1851 | title=Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. | date=Apr 2015 | journal=Biochim Biophys Acta | pages=340–355 | last1 = Powell | first1 = WS | last2 = Rokach | first2 = J| issue=4 | pmc=5710736 }}
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.
| class="wikitable"
!C# !trivial name !systematic name !melting point °C !formula !SMILES !CASNo !PubChem CID !ChemSpiderID !UNII !ChEBI !occurrence |
| 2
|2-Hydroxyethanoic acid |75 |C2H4O3 |OCC(=O)O |79-14-1 |757 |737 |0WT12SX38S |17497 |plants |
| 3
|139-140 |C3H6O3 |OCCC(=O)O |503-66-2 |68152 |61460 | | | |
| 4
|gamma-Hydroxybutyric acid |? |C4H8O3 |OCCCC(=O)O |591-81-1 |10413 |9984 |30IW36W5B2 |30830 |human neurotransmitter |
| 5
|5-hydroxyvaleric acid | |C5H10O3 |OCCCCC(=O)O |13392-69-3 |25945 |24171 |H5EVV4LP59 |45564 |
| 6
|6-Hydroxycaproic acid |6-Hydroxyhexanoic 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
|omega-hydroxycaprylic acid |8-hydroxyoctanoic acid | |C8H16O3 |OCCCCCCCC(=O)O |764-89-6 |69820 |63018 | |79162 | |
| 9
|9-hydroxypelargonic acid |9-hydroxynonanoic acid | |C9H18O3 |OCCCCCCCCC(=O)O |3788-56-5 |138052 |121694 |HV672SU12G |79121 | |
| 10
|10-hydroxycapric acid |10-hydroxydecanoic 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
|sabinic acid{{Cite journal |last1=Lycan |first1=W. H. |last2=Adams |first2=Roger |title=Omega-Hydroxy Aliphatic Acids. Synthesis of Sabinic Acid |date=February 1929 |url=https://pubs.acs.org/doi/abs/10.1021/ja01377a042 |journal=Journal of the American Chemical Society |language=en |volume=51 |issue=2 |pages=625–629 |doi=10.1021/ja01377a042 |issn=0002-7863|url-access=subscription }} |12-hydroxydodecanoic acid | |C12H24O3 |OCCCCCCCCCCCC(=O)O |505-95-3 |79034 |71366 |SUH3LR2K9D |39567 | |
| 13
|13-hydroxytridecanoic acid | | |C13H26O3 |OCCCCCCCCCCCCC(=O)O |7735-38-8 |139065 |122656 | |79166 | |
| 14
|ω-hydroxymyristic acid |14-hydroxytetradecanoic 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 |
| 16
|16-hydroxyhexadecanoic acid | |C16H32O3 |OCCCCCCCCCCCCCCCC(=O)O |506-13-8 |10466 |10034 | |55328 |
| 17
|17-hydroxyheptadecanoic acid | | |C17H34O3 |OCCCCCCCCCCCCCCCCC(=O)O |13099-34-8 |4308451 |3513977 | |79177 |
| 18
|ω-hydroxystearic acid |18-hydroxyoctadecanoic 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
|ω-hydroxyarachidic acid |20-hydroxyicosanoic 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-hydroxybehenic acid |22-Hydroxydocosanoic 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
|ω-hydroxycerotic acid |26-hydroxyhexacosanoic 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
|omega-hydroxynonacosanoic acid |29-hydroxynonacosanoic acid | |C29H58O3 |OCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O | |14325178 |34449103 | |84865 | |
| 30
|30-hydroxytriacontanoic acid | | |C30H60O3 |OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O |52900-18-2 |5312787 |4472212 | |76220 | |