2-OHOA
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MedKoo CAT#: 412699

CAS#: 1229114-68-4

Description: 2-OHOA is an inducer of cell cycle arrest and apoptosis in several cancer cell lines, including glioma, leukemia, breast and colon cancer lines.


Chemical Structure

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2-OHOA
CAS# 1229114-68-4

Theoretical Analysis

MedKoo Cat#: 412699
Name: 2-OHOA
CAS#: 1229114-68-4
Chemical Formula: C18H33NaO3
Exact Mass: 320.2327
Molecular Weight: 320.45
Elemental Analysis: C, 67.47; H, 10.38; Na, 7.17; O, 14.98

Price and Availability

Size Price Availability Quantity
1.0g USD 344.0 2 Weeks
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Synonym: 2-OHOA; 2-hydroxyoleic acid (sodium salt)

IUPAC/Chemical Name: sodium (Z)-2-hydroxyoctadec-9-enoate

InChi Key: OOKRISSOAVEQFK-KVVVOXFISA-M

InChi Code: InChI=1S/C18H34O3.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21;/h9-10,17,19H,2-8,11-16H2,1H3,(H,20,21);/q;+1/p-1/b10-9-;

SMILES Code: O=C(C(O)CCCCCC/C=C\CCCCCCCC)O[Na]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 320.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Redondo Useros N, Gheorghe A, Perez de Heredia F, Díaz LE, Baccan GC, De la Fuente M, Marcos A. 2-OHOA supplementation reduced adiposity and improved cardiometabolic risk to a greater extent than n-3 PUFA in obese mice. Obes Res Clin Pract. 2019 Nov-Dec;13(6):579-585. doi: 10.1016/j.orcp.2019.10.009. Epub 2019 Nov 29. PMID: 31787558.

2: Avila-Martin G, Galan-Arriero I, Ferrer-Donato A, Busquets X, Gomez-Soriano J, Escribá PV, Taylor J. Oral 2-hydroxyoleic acid inhibits reflex hypersensitivity and open-field-induced anxiety after spared nerve injury. Eur J Pain. 2015 Jan;19(1):111-22. doi: 10.1002/ejp.528. Epub 2014 May 13. PMID: 24824524.

3: Borchert GH, Giggey M, Kolar F, Wong TM, Backx PH, Escriba PV. 2-hydroxyoleic acid affects cardiomyocyte [Ca2+]i transient and contractility in a region- dependent manner. Am J Physiol Heart Circ Physiol. 2008 Apr;294(4):H1948-55. doi: 10.1152/ajpheart.01209.2007. Epub 2008 Feb 22. PMID: 18296566.

4: Alemany R, Terés S, Baamonde C, Benet M, Vögler O, Escribá PV. 2-hydroxyoleic acid: a new hypotensive molecule. Hypertension. 2004 Feb;43(2):249-54. doi: 10.1161/01.HYP.0000107778.85528.b5. Epub 2003 Dec 8. PMID: 14662651.

5: Gheorghe A, Pérez de Heredia F, Hunsche C, Redondo N, Díaz LE, Hernández O, Marcos A, De la Fuente M. Oxidative stress and immunosenescence in spleen of obese mice can be reversed by 2-hydroxyoleic acid. Exp Physiol. 2017 May 1;102(5):533-544. doi: 10.1113/EP086157. PMID: 28205317.

6: Galán-Arriero I, Serrano-Muñoz D, Gómez-Soriano J, Goicoechea C, Taylor J, Velasco A, Ávila-Martín G. The role of Omega-3 and Omega-9 fatty acids for the treatment of neuropathic pain after neurotrauma. Biochim Biophys Acta Biomembr. 2017 Sep;1859(9 Pt B):1629-1635. doi: 10.1016/j.bbamem.2017.05.003. Epub 2017 May 8. PMID: 28495596.

7: Alemany R, Vögler O, Terés S, Egea C, Baamonde C, Barceló F, Delgado C, Jakobs KH, Escribá PV. Antihypertensive action of 2-hydroxyoleic acid in SHRs via modulation of the protein kinase A pathway and Rho kinase. J Lipid Res. 2006 Aug;47(8):1762-70. doi: 10.1194/jlr.M500520-JLR200. Epub 2006 May 10. PMID: 16687663.

8: Hunsche C, Martínez de Toda I, Hernandez O, Jiménez B, Díaz LE, Marcos A, De la Fuente M. The supplementations with 2-hydroxyoleic acid and n-3 polyunsaturated fatty acids revert oxidative stress in various organs of diet- induced obese mice. Free Radic Res. 2020 Jun;54(6):455-466. doi: 10.1080/10715762.2020.1800004. Epub 2020 Aug 4. PMID: 32752974.

9: Vögler O, López-Bellan A, Alemany R, Tofé S, González M, Quevedo J, Pereg V, Barceló F, Escriba PV. Structure-effect relation of C18 long-chain fatty acids in the reduction of body weight in rats. Int J Obes (Lond). 2008 Mar;32(3):464-73. doi: 10.1038/sj.ijo.0803768. Epub 2007 Dec 4. PMID: 18059405.

10: Hunsche C, Hernandez O, Gheorghe A, Díaz LE, Marcos A, De la Fuente M. Immune dysfunction and increased oxidative stress state in diet-induced obese mice are reverted by nutritional supplementation with monounsaturated and n-3 polyunsaturated fatty acids. Eur J Nutr. 2018 Apr;57(3):1123-1135. doi: 10.1007/s00394-017-1395-1. Epub 2017 Feb 23. PMID: 28229279.