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MedKoo Cat#: 563528 | Name: Linoleyl ethanolamide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Linoleylethanolamide is an endocannabinoid agent. It acts by binding to TRPV1, increasing ERK phosphorylation and AP-1 dependent transcription in CB-receptor in an independent manner.

Chemical Structure

Linoleyl ethanolamide
CAS#68171-52-8

Theoretical Analysis

MedKoo Cat#: 563528

Name: Linoleyl ethanolamide

CAS#: 68171-52-8

Chemical Formula: C20H37NO2

Exact Mass: 323.2824

Molecular Weight: 323.52

Elemental Analysis: C, 74.25; H, 11.53; N, 4.33; O, 9.89

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
200mg USD 450.00 2 Weeks
500mg USD 750.00 2 Weeks
1g USD 1,250.00 2 Weeks
2g USD 1,950.00 2 Weeks
5g USD 3,850.00 2 Weeks
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No Data
Synonym
Linoleyl ethanolamide; Linoleamide MEA; LEA;
IUPAC/Chemical Name
(9Z,12Z)-N-(2-Hydroxyethyl)octadeca-9,12-dienamide
InChi Key
KQXDGUVSAAQARU-HZJYTTRNSA-N
InChi Code
InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-
SMILES Code
CCCCC/C=C\C/C=C\CCCCCCCC(NCCO)=O
Appearance
To be determined
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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Linoleylethanolamide is an endocannabinoid agent.
In vitro activity:
In mouse RAW264.7 macrophages, LE (linoleoyl ethanolamide) suppressed the lipopolysaccharide (LPS)-induced expression of pro-inflammatory cytokines, such as tumor necrosis factor-α (TNF-α), interleukin (IL)-1β, and IL-6. In addition, LE inhibited LPS-induced increases in the levels of cyclooxygenase enzyme-2 and prostaglandin E(2), which are indicators of inflammation. Reference: Eur J Pharmacol. 2013 Jan 15;699(1-3):6-13. https://pubmed.ncbi.nlm.nih.gov/23201070/
In vivo activity:
The neuroprotective properties of two NAEs (N-acylethanolamines) were measured in rats subjected to MCAO followed by 24 h reperfusion. Pretreatment with NAE 18:2 (linoleylethanolamide) prior to ischemia/reperfusion (I/R) injury resulted in both significantly reduced cortical infarct volume and improved functional outcome as determined using the neurological deficit score. Reference: Neurosci Lett. 2011 Apr 4;492(3):134-8. https://pubmed.ncbi.nlm.nih.gov/21296126/
Solvent mg/mL mM comments
Solubility
DMF 25.0 77.27
DMSO 25.0 77.27
Ethanol 50.0 154.55
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 323.52 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
Formulation protocol:
1. Ishida T, Nishiumi S, Tanahashi T, Yamasaki A, Yamazaki A, Akashi T, Miki I, Kondo Y, Inoue J, Kawauchi S, Azuma T, Yoshida M, Mizuno S. Linoleoyl ethanolamide reduces lipopolysaccharide-induced inflammation in macrophages and ameliorates 2,4-dinitrofluorobenzene-induced contact dermatitis in mice. Eur J Pharmacol. 2013 Jan 15;699(1-3):6-13. doi: 10.1016/j.ejphar.2012.11.030. Epub 2012 Nov 28. PMID: 23201070. 2. Garg P, Duncan RS, Kaja S, Zabaneh A, Chapman KD, Koulen P. Lauroylethanolamide and linoleoylethanolamide improve functional outcome in a rodent model for stroke. Neurosci Lett. 2011 Apr 4;492(3):134-8. doi: 10.1016/j.neulet.2011.01.073. Epub 2011 Feb 4. PMID: 21296126; PMCID: PMC3057422. 3. Diep TA, Madsen AN, Holst B, Kristiansen MM, Wellner N, Hansen SH, Hansen HS. Dietary fat decreases intestinal levels of the anorectic lipids through a fat sensor. FASEB J. 2011 Feb;25(2):765-74. doi: 10.1096/fj.10-166595. Epub 2010 Oct 19. PMID: 20959516.
In vitro protocol:
1. Ishida T, Nishiumi S, Tanahashi T, Yamasaki A, Yamazaki A, Akashi T, Miki I, Kondo Y, Inoue J, Kawauchi S, Azuma T, Yoshida M, Mizuno S. Linoleoyl ethanolamide reduces lipopolysaccharide-induced inflammation in macrophages and ameliorates 2,4-dinitrofluorobenzene-induced contact dermatitis in mice. Eur J Pharmacol. 2013 Jan 15;699(1-3):6-13. doi: 10.1016/j.ejphar.2012.11.030. Epub 2012 Nov 28. PMID: 23201070.
In vivo protocol:
1. Garg P, Duncan RS, Kaja S, Zabaneh A, Chapman KD, Koulen P. Lauroylethanolamide and linoleoylethanolamide improve functional outcome in a rodent model for stroke. Neurosci Lett. 2011 Apr 4;492(3):134-8. doi: 10.1016/j.neulet.2011.01.073. Epub 2011 Feb 4. PMID: 21296126; PMCID: PMC3057422. 2. Diep TA, Madsen AN, Holst B, Kristiansen MM, Wellner N, Hansen SH, Hansen HS. Dietary fat decreases intestinal levels of the anorectic lipids through a fat sensor. FASEB J. 2011 Feb;25(2):765-74. doi: 10.1096/fj.10-166595. Epub 2010 Oct 19. PMID: 20959516.
1: Agrawal K, Bosviel R, Piccolo BD, Newman JW. Oral ibuprofen differentially affects plasma and sweat lipid mediator profiles in healthy adult males. Prostaglandins Other Lipid Mediat. 2018 Jul;137:1-8. doi: 10.1016/j.prostaglandins.2018.05.009. Epub 2018 May 17. PubMed PMID: 29778785; PubMed Central PMCID: PMC6057826. 2: Mennella I, Di Monaco R, Balazy A, Ferracane R, Miele NA, Cavella S, Vitaglione P. Salivary endocannabinoids and N-acylethanolamines upon mastication of a semisolid food: implications in fat taste, appetite and food liking. Food Funct. 2018 Jan 24;9(1):476-484. doi: 10.1039/c7fo01772c. PubMed PMID: 29235594. 3: Antón M, Rodríguez-González A, Rodríguez-Rojo IC, Pastor A, Correas Á, Serrano A, Ballesta A, Alén F, Gómez de Heras R, de la Torre R, Rodríguez de Fonseca F, Orio L. Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women. Addict Biol. 2017 Nov 27. doi: 10.1111/adb.12580. [Epub ahead of print] PubMed PMID: 29178411. 4: Olatinsu AO, Sihag J, Jones PJH. Relationship Between Circulating Fatty Acids and Fatty Acid Ethanolamide Levels After a Single 2-h Dietary Fat Feeding in Male Sprague-Dawley Rats : Elevated levels of oleoylethanolamide, palmitoylethanolamide, linoleoylethanolamide, arachidonoylethanolamide and docosahexanoylethanolamide after a single 2 h dietary fat feeding in male Sprague Dawley rats. Lipids. 2017 Nov;52(11):901-906. doi: 10.1007/s11745-017-4293-7. Epub 2017 Oct 14. PubMed PMID: 29032410. 5: Wortley MA, Adcock JJ, Dubuis ED, Maher SA, Bonvini SJ, Delescluse I, Kinloch R, McMurray G, Perros-Huguet C, Papakosta M, Birrell MA, Belvisi MG. Targeting fatty acid amide hydrolase as a therapeutic strategy for antitussive therapy. Eur Respir J. 2017 Sep 20;50(3). pii: 1700782. doi: 10.1183/13993003.00782-2017. Print 2017 Sep. PubMed PMID: 28931663. 6: Alarcón-Yaquetto DE, Caballero L, Gonzales GF. Association Between Plasma N-Acylethanolamides and High Hemoglobin Concentration in Southern Peruvian Highlanders. High Alt Med Biol. 2017 Dec;18(4):322-329. doi: 10.1089/ham.2016.0148. Epub 2017 Jun 30. PubMed PMID: 28665150. 7: Pezzilli R, Ciuffreda P, Ottria R, Ravelli A, Melzi d'Eril G, Barassi A. Serum endocannabinoids in assessing pain in patients with chronic pancreatitis and in those with pancreatic ductal adenocarcinoma. Scand J Gastroenterol. 2017 Oct;52(10):1133-1139. doi: 10.1080/00365521.2017.1342139. Epub 2017 Jun 20. PubMed PMID: 28631495. 8: Gouveia-Figueira S, Goldin K, Hashemian SA, Lindberg A, Persson M, Nording ML, Laurell K, Fowler CJ. Plasma levels of the endocannabinoid anandamide, related N-acylethanolamines and linoleic acid-derived oxylipins in patients with migraine. Prostaglandins Leukot Essent Fatty Acids. 2017 May;120:15-24. doi: 10.1016/j.plefa.2017.04.005. Epub 2017 Apr 21. PubMed PMID: 28515018. 9: Kong X, Ferracane R, De Luca L, Vitaglione P. Salivary concentration of N-acylethanolamines upon food mastication and after meal consumption: Influence of food dietary fiber. Food Res Int. 2016 Nov;89(Pt 1):186-193. doi: 10.1016/j.foodres.2016.07.026. Epub 2016 Aug 2. PubMed PMID: 28460904. 10: Ottria R, Cappelletti L, Ravelli A, Mariotti M, Gigli F, Romagnoli S, Ciuffreda P, Banfi G, Drago L. Plasma endocannabinoid behaviour in total knee and hip arthroplasty. J Biol Regul Homeost Agents. 2016 Oct-Dec;30(4):1147-1152. PubMed PMID: 28078867. 11: Friedman AN, Kim J, Kaiser S, Pedersen TL, Newman JW, Watkins BA. Association between plasma endocannabinoids and appetite in hemodialysis patients: A pilot study. Nutr Res. 2016 Jul;36(7):658-62. doi: 10.1016/j.nutres.2016.03.009. Epub 2016 Apr 1. PubMed PMID: 27333956; PubMed Central PMCID: PMC4919598. 12: Pu S, Eck P, Jenkins DJ, Connelly PW, Lamarche B, Kris-Etherton PM, West SG, Liu X, Jones PJ. Interactions between dietary oil treatments and genetic variants modulate fatty acid ethanolamides in plasma and body weight composition. Br J Nutr. 2016 Mar 28;115(6):1012-23. doi: 10.1017/S0007114515005425. Epub 2016 Jan 25. PubMed PMID: 26806592. 13: Lindgren L, Gouveia-Figueira S, Nording ML, Fowler CJ. Endocannabinoids and related lipids in blood plasma following touch massage: a randomised, crossover study. BMC Res Notes. 2015 Sep 29;8:504. doi: 10.1186/s13104-015-1450-z. PubMed PMID: 26420002; PubMed Central PMCID: PMC4589181. 14: Mennella I, Ferracane R, Zucco F, Fogliano V, Vitaglione P. Food Liking Enhances the Plasma Response of 2-Arachidonoylglycerol and of Pancreatic Polypeptide upon Modified Sham Feeding in Humans. J Nutr. 2015 Sep;145(9):2169-75. doi: 10.3945/jn.114.207704. Epub 2015 Jul 15. PubMed PMID: 26180248. 15: Igarashi M, DiPatrizio NV, Narayanaswami V, Piomelli D. Feeding-induced oleoylethanolamide mobilization is disrupted in the gut of diet-induced obese rodents. Biochim Biophys Acta. 2015 Sep;1851(9):1218-26. doi: 10.1016/j.bbalip.2015.05.006. Epub 2015 May 27. PubMed PMID: 26024927; PubMed Central PMCID: PMC4516666. 16: Woolcott OO, Richey JM, Kabir M, Chow RH, Iyer MS, Kirkman EL, Stefanovski D, Lottati M, Kim SP, Harrison LN, Ionut V, Zheng D, Hsu IR, Catalano KJ, Chiu JD, Bradshaw H, Wu Q, Kolka CM, Bergman RN. High-fat diet-induced insulin resistance does not increase plasma anandamide levels or potentiate anandamide insulinotropic effect in isolated canine islets. PLoS One. 2015 Apr 9;10(4):e0123558. doi: 10.1371/journal.pone.0123558. eCollection 2015. Erratum in: PLoS One. 2015;10(6):e0131033. Kolka, Cathryn M [added]. PubMed PMID: 25855974; PubMed Central PMCID: PMC4391925. 17: Keereetaweep J, Blancaflor EB, Hornung E, Feussner I, Chapman KD. Lipoxygenase-derived 9-hydro(pero)xides of linoleoylethanolamide interact with ABA signaling to arrest root development during Arabidopsis seedling establishment. Plant J. 2015 Apr;82(2):315-27. doi: 10.1111/tpj.12821. PubMed PMID: 25752187. 18: Mennella I, Savarese M, Ferracane R, Sacchi R, Vitaglione P. Oleic acid content of a meal promotes oleoylethanolamide response and reduces subsequent energy intake in humans. Food Funct. 2015 Jan;6(1):204-10. doi: 10.1039/c4fo00697f. Epub 2014 Oct 27. PubMed PMID: 25347552. 19: Diep TA, Madsen AN, Krogh-Hansen S, Al-Shahwani M, Al-Sabagh L, Holst B, Hansen HS. Dietary non-esterified oleic Acid decreases the jejunal levels of anorectic N-acylethanolamines. PLoS One. 2014 Jun 24;9(6):e100365. doi: 10.1371/journal.pone.0100365. eCollection 2014. PubMed PMID: 24959837; PubMed Central PMCID: PMC4068999. 20: Ottria R, Ravelli A, Gigli F, Ciuffreda P. Simultaneous ultra-high performance liquid chromathograpy-electrospray ionization-quadrupole-time of flight mass spectrometry quantification of endogenous anandamide and related N-acylethanolamides in bio-matrices. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 May 1;958:83-9. doi: 10.1016/j.jchromb.2014.03.019. Epub 2014 Mar 24. PubMed PMID: 24705535.