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.^[1]^[2] 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.^[3]^[4] Only the epidermal cells of plants synthesize cutin.^[5]

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.^[6] 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;^[7] 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.^[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 C_nH_2nO₃.

C#	trivial name	systematic name	melting point °C	formula	SMILES	CASNo	PubChem CID	ChemSpiderID	UNII	ChEBI	occurrence
2	Glycolic acid	2-Hydroxyethanoic acid	75	C₂H₄O₃	OCC(=O)O	79-14-1	757	737	0WT12SX38S	17497	plants
3	Hydroacrylic acid^[11]	3-Hydroxypropionic acid	139-140	C₃H₆O₃	OCCC(=O)O	503-66-2	68152	61460
4	gamma-Hydroxybutyric acid	4-Hydroxybutanoic acid	?	C₄H₈O₃	OCCCC(=O)O	591-81-1	10413	9984	30IW36W5B2	30830	human neurotransmitter
5	5-hydroxyvaleric acid	5-Hydroxypentanoic acid		C₅H₁₀O₃	OCCCCC(=O)O	13392-69-3	25945	24171	H5EVV4LP59	45564	from engineered Corynebacterium glutamicum^[12]
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^[13]	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	engineered Candida tropicalis^[14]
15		15-hydroxypentadecanoic acid		C₁₅H₃₀O₃	OCCCCCCCCCCCCCCC(=O)O	4617-33-8	78360	70730	FU65P3692T	79169	Angelica archangelica
16	juniperic acid	16-hydroxyhexadecanoic acid		C₁₆H₃₂O₃	OCCCCCCCCCCCCCCCC(=O)O	506-13-8	10466	10034		55328	plant cuticle^[15]
17	17-hydroxyheptadecanoic acid			C₁₇H₃₄O₃	OCCCCCCCCCCCCCCCCC(=O)O	13099-34-8	4308451	3513977		79177	Pinus radiata
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

References

^ Kolattukudy, P. E.; Walton, T. J. (1972). "Structure and biosynthesis of the hydroxy fatty acids of cutin in Vicia faba leaves". Biochemistry. 11 (10): 1897–1907. doi:10.1021/bi00760a026. PMID 5025632.
^ Soliday, C. L.; Kolattukudy, P. E. (1977). "Biosynthesis of Cutin ω-hydroxylation of fatty acids by a microsomal preparation from germinating Vicia faba". Plant Physiology. 59 (6): 1116–1121. doi:10.1104/pp.59.6.1116. PMC 542517. PMID 16660004.
^ 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
^ P. 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
^ 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
^ Hoopes SL, Garcia V, Edin ML, Schwartzman ML, Zeldin DC (Jul 2015). "Vascular actions of 20-HETE". Prostaglandins & Other Lipid Mediators. 120: 9–16. doi:10.1016/j.prostaglandins.2015.03.002. PMC 4575602. PMID 25813407.
^ Annu Rev Pharmacol Toxicol. 2005;45:413-38
^ Du, L; Yin, H; Morrow, JD; Strobel, HW; Keeney, DS (2009). "20-Hydroxylation is the CYP-dependent and retinoid-inducible leukotriene B4 inactivation pathway in human and mouse skin cells". Archives of Biochemistry and Biophysics. 484 (1): 80–86. doi:10.1016/j.abb.2009.01.012. PMC 2687325. PMID 19467632.
^ J Immunol. 1986 Nov 15;137(10):3277-83
^ Powell, WS; Rokach, J (Apr 2015). "Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid". Biochim Biophys Acta. 1851 (4): 340–355. doi:10.1016/j.bbalip.2014.10.008. PMC 5710736. PMID 25449650.
^ Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_507. ISBN 978-3-527-30385-4.
^ Sohn, Yu Jung; Kang, Minsoo; Baritugo, Kei-Anne; Son, Jina; Kang, Kyoung Hee; Ryu, Mi-Hee; Lee, Siseon; Sohn, Mingi; Jung, Ye Jean; Park, Kyungmoon; Park, Si Jae; Joo, Jeong Chan; Kim, Hee Taek (2021). "Fermentative High-Level Production of 5-Hydroxyvaleric Acid by Metabolically Engineered Corynebacterium glutamicum". ACS Sustainable Chemistry & Engineering. 9 (6): 2523–2533. doi:10.1021/acssuschemeng.0c08118.
^ Lycan, W. H.; Adams, Roger (February 1929). "Omega-Hydroxy Aliphatic Acids. Synthesis of Sabinic Acid". Journal of the American Chemical Society. 51 (2): 625–629. doi:10.1021/ja01377a042. ISSN 0002-7863.
^ Liu, Chen; Liu, Fei; Cai, Jiali; Xie, Wenchun; Long, Timothy E.; Turner, S. Richard; Lyons, Alan; Gross, Richard A. (2011). "Polymers from Fatty Acids: Poly(ω-hydroxyl tetradecanoic acid) Synthesis and Physico-Mechanical Studies". Biomacromolecules. 12 (9): 3291–3298. doi:10.1021/bm2007554. PMID 21793591.
^ Spring, F. S. (March 1945). "Naturally Occurring Polyesters". Nature. 155 (3931): 272. Bibcode:1945Natur.155..272S. doi:10.1038/155272b0. ISSN 0028-0836. S2CID 4108900.

[kolattukudy1972a-1] Kolattukudy, P. E.; Walton, T. J. (1972). "Structure and biosynthesis of the hydroxy fatty acids of cutin in Vicia faba leaves". Biochemistry. 11 (10): 1897–1907. doi:10.1021/bi00760a026. PMID 5025632.

[Soliday1977-2] Soliday, C. L.; Kolattukudy, P. E. (1977). "Biosynthesis of Cutin ω-hydroxylation of fatty acids by a microsomal preparation from germinating Vicia faba". Plant Physiology. 59 (6): 1116–1121. doi:10.1104/pp.59.6.1116. PMC 542517. PMID 16660004.

[Walton1972-3] 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

[Holloway1982-4] P. 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

[Kolattukudy1996-5] 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

[Hoopes_2015-6] Hoopes SL, Garcia V, Edin ML, Schwartzman ML, Zeldin DC (Jul 2015). "Vascular actions of 20-HETE". Prostaglandins & Other Lipid Mediators. 120: 9–16. doi:10.1016/j.prostaglandins.2015.03.002. PMC 4575602. PMID 25813407.

[7] Annu Rev Pharmacol Toxicol. 2005;45:413-38

[8] Du, L; Yin, H; Morrow, JD; Strobel, HW; Keeney, DS (2009). "20-Hydroxylation is the CYP-dependent and retinoid-inducible leukotriene B4 inactivation pathway in human and mouse skin cells". Archives of Biochemistry and Biophysics. 484 (1): 80–86. doi:10.1016/j.abb.2009.01.012. PMC 2687325. PMID 19467632.

[9] J Immunol. 1986 Nov 15;137(10):3277-83

[10] Powell, WS; Rokach, J (Apr 2015). "Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid". Biochim Biophys Acta. 1851 (4): 340–355. doi:10.1016/j.bbalip.2014.10.008. PMC 5710736. PMID 25449650.

[11] Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_507. ISBN 978-3-527-30385-4.

[12] Sohn, Yu Jung; Kang, Minsoo; Baritugo, Kei-Anne; Son, Jina; Kang, Kyoung Hee; Ryu, Mi-Hee; Lee, Siseon; Sohn, Mingi; Jung, Ye Jean; Park, Kyungmoon; Park, Si Jae; Joo, Jeong Chan; Kim, Hee Taek (2021). "Fermentative High-Level Production of 5-Hydroxyvaleric Acid by Metabolically Engineered Corynebacterium glutamicum". ACS Sustainable Chemistry & Engineering. 9 (6): 2523–2533. doi:10.1021/acssuschemeng.0c08118.

[13] Lycan, W. H.; Adams, Roger (February 1929). "Omega-Hydroxy Aliphatic Acids. Synthesis of Sabinic Acid". Journal of the American Chemical Society. 51 (2): 625–629. doi:10.1021/ja01377a042. ISSN 0002-7863.

[14] Liu, Chen; Liu, Fei; Cai, Jiali; Xie, Wenchun; Long, Timothy E.; Turner, S. Richard; Lyons, Alan; Gross, Richard A. (2011). "Polymers from Fatty Acids: Poly(ω-hydroxyl tetradecanoic acid) Synthesis and Physico-Mechanical Studies". Biomacromolecules. 12 (9): 3291–3298. doi:10.1021/bm2007554. PMID 21793591.

[15] Spring, F. S. (March 1945). "Naturally Occurring Polyesters". Nature. 155 (3931): 272. Bibcode:1945Natur.155..272S. doi:10.1038/155272b0. ISSN 0028-0836. S2CID 4108900.

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See also

References