WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H463886
CAS#: 13487-46-2
Description: Arachidonyl alcohol is a polyunsaturated fatty alcohol produced by the reduction of arachidonic acid. It has been used as a substrate in the synthesis of various ether lipids.
Hodoodo Cat#: H463886
Name: Arachidonyl Alcohol
CAS#: 13487-46-2
Chemical Formula: C20H34O
Exact Mass: 290.26
Molecular Weight: 290.491
Elemental Analysis: C, 82.69; H, 11.80; O, 5.51
Synonym: Arachidonyl Alcohol; (all-Z)-5,8,11,14-Eicosatetraen-1-ol;
IUPAC/Chemical Name: (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-ol
InChi Key: NYBCZSBDKXGAGM-DOFZRALJSA-N
InChi Code: InChI=1S/C20H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21/h6-7,9-10,12-13,15-16,21H,2-5,8,11,14,17-20H2,1H3/b7-6-,10-9-,13-12-,16-15-
SMILES Code: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCO
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: >2 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
More Info:
| Biological target: | |
| In vitro activity: | |
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The following data is based on the product molecular weight 290.49 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.
| 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Paloczi J, Matyas C, Cinar R, Varga ZV, Hasko G, Schindler TH, Kunos G, Pacher P. Alcohol Binge-Induced Cardiovascular Dysfunction Involves Endocannabinoid-CB1-R Signaling. JACC Basic Transl Sci. 2019 Sep 23;4(5):625-637. doi: 10.1016/j.jacbts.2019.05.007. PMID: 31768478; PMCID: PMC6872859.
2: Ng EW, Aung MM, Abood ME, Martin BR, Razdan RK. Unique analogues of anandamide: arachidonyl ethers and carbamates and norarachidonyl carbamates and ureas. J Med Chem. 1999 Jun 3;42(11):1975-81. doi: 10.1021/jm980711w. PMID: 10354405.
3: Parkkari T, Savinainen JR, Rauhala AL, Tolonen TL, Nevalainen T, Laitinen JT, Gynther J, Järvinen T. Synthesis and CB1 receptor activities of novel arachidonyl alcohol derivatives. Bioorg Med Chem Lett. 2004 Jun 21;14(12):3231-4. doi: 10.1016/j.bmcl.2004.03.093. PMID: 15149681.
4: Pandey R, Ghorpade A. Cytosolic phospholipase A2 regulates alcohol-mediated astrocyte inflammatory responses in HIV-associated neurocognitive disorders. Cell Death Discov. 2015 Nov 30;1:15045. doi: 10.1038/cddiscovery.2015.45. PMID: 27551474; PMCID: PMC4979440.
5: Lu VB, Puhl HL 3rd, Ikeda SR. N-Arachidonyl glycine does not activate G protein-coupled receptor 18 signaling via canonical pathways. Mol Pharmacol. 2013 Jan;83(1):267-82. doi: 10.1124/mol.112.081182. Epub 2012 Oct 25. PMID: 23104136; PMCID: PMC3533477.
6: Urquhart P, Nicolaou A, Woodward DF. Endocannabinoids and their oxygenation by cyclo-oxygenases, lipoxygenases and other oxygenases. Biochim Biophys Acta. 2015 Apr;1851(4):366-76. doi: 10.1016/j.bbalip.2014.12.015. Epub 2014 Dec 24. PMID: 25543004.
7: Boring DL, Berglund BA, Howlett AC. Cerebrodiene, arachidonyl-ethanolamide, and hybrid structures: potential for interaction with brain cannabinoid receptors. Prostaglandins Leukot Essent Fatty Acids. 1996 Sep;55(3):207-10. doi: 10.1016/s0952-3278(96)90100-3. PMID: 8931121.
8: Zheng L, Wu X, Dong X, Ding X, Song C. Effects of Chronic Alcohol Exposure on the Modulation of Ischemia-Induced Glutamate Release via Cannabinoid Receptors in the Dorsal Hippocampus. Alcohol Clin Exp Res. 2015 Oct;39(10):1908-16. doi: 10.1111/acer.12845. Epub 2015 Sep 7. PMID: 26343919.
9: Colard O, Breton M, Bereziat G. Arachidonyl transfer from diacyl phosphatidylcholine to ether phospholipids in rat platelets. Biochem J. 1984 Sep 15;222(3):657-62. doi: 10.1042/bj2220657. PMID: 6435602; PMCID: PMC1144227.
10: Coronado-Álvarez A, Romero-Cordero K, Macías-Triana L, Tatum-Kuri A, Vera- Barrón A, Budde H, Machado S, Yamamoto T, Imperatori C, Murillo-Rodríguez E. The synthetic CB1 cannabinoid receptor selective agonists: Putative medical uses and their legalization. Prog Neuropsychopharmacol Biol Psychiatry. 2021 Aug 30;110:110301. doi: 10.1016/j.pnpbp.2021.110301. Epub 2021 Mar 17. PMID: 33741446.
11: Citraro R, Russo E, Leo A, Russo R, Avagliano C, Navarra M, Calignano A, De Sarro G. Pharmacokinetic-pharmacodynamic influence of N-palmitoylethanolamine, arachidonyl-2'-chloroethylamide and WIN 55,212-2 on the anticonvulsant activity of antiepileptic drugs against audiogenic seizures in DBA/2 mice. Eur J Pharmacol. 2016 Nov 15;791:523-534. doi: 10.1016/j.ejphar.2016.09.029. Epub 2016 Sep 20. PMID: 27663280.
12: Kemble AM, Hornsperger B, Ruf I, Richter H, Benz J, Kuhn B, Heer D, Wittwer M, Engelhardt B, Grether U, Collin L. A potent and selective inhibitor for the modulation of MAGL activity in the neurovasculature. PLoS One. 2022 Sep 9;17(9):e0268590. doi: 10.1371/journal.pone.0268590. PMID: 36084029; PMCID: PMC9462760.
13: Fride E. Endocannabinoids in the central nervous system--an overview. Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):221-33. doi: 10.1054/plef.2001.0360. PMID: 12052038.
14: Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z, Howlett A. Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol. 1997 Feb 7;53(3):255-60. doi: 10.1016/s0006-2952(96)00830-1. PMID: 9065728.
15: Jung YS, Kim YH, Radhakrishnan K, Kim J, Kim DK, Lee JH, Oh H, Lee IK, Kim W, Cho SJ, Choi CS, Dooley S, Egan JM, Lee CH, Choi HS. An inverse agonist of estrogen-related receptor γ regulates 2-arachidonoylglycerol synthesis by modulating diacylglycerol lipase expression in alcohol-intoxicated mice. Arch Toxicol. 2020 Feb;94(2):427-438. doi: 10.1007/s00204-019-02648-7. Epub 2020 Jan 7. PMID: 31912162; PMCID: PMC10131092.
16: Holub BJ. Metabolism and function of myo-inositol and inositol phospholipids. Annu Rev Nutr. 1986;6:563-97. doi: 10.1146/annurev.nu.06.070186.003023. PMID: 2425833.
17: Gonsiorek W, Lunn C, Fan X, Narula S, Lundell D, Hipkin RW. Endocannabinoid 2-arachidonyl glycerol is a full agonist through human type 2 cannabinoid receptor: antagonism by anandamide. Mol Pharmacol. 2000 May;57(5):1045-50. PMID: 10779390.
18: Raman P, Kaplan BL, Kaminski NE. 15-Deoxy-Δ¹²,¹⁴-prostaglandin J₂-glycerol, a putative metabolite of 2-arachidonyl glycerol and a peroxisome proliferator- activated receptor γ ligand, modulates nuclear factor of activated T cells. J Pharmacol Exp Ther. 2012 Sep;342(3):816-26. doi: 10.1124/jpet.112.193003. Epub 2012 Jun 13. PMID: 22700433; PMCID: PMC3422518.
19: Turcotte JG, Yu CS, Lee HL, Pavanaram SK, Sen S, Smeby RR. Synthesis of lysophosphatidylethanolamine analogs that inhibit renin activity. J Med Chem. 1975 Dec;18(12):1184-90. doi: 10.1021/jm00246a003. PMID: 1195274.
20: Jørgensen KM, Felberg HS, Berge RK, Laegreid A, Johansen B. Platelet activating factor stimulates arachidonic acid release in differentiated keratinocytes via arachidonyl non-selective phospholipase A2. Arch Dermatol Res. 2010 Apr;302(3):221-7. doi: 10.1007/s00403-009-1017-8. Epub 2009 Dec 30. PMID: 20041255; PMCID: PMC2829133.
