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L1751 Sigma

Ethyl linoleate

≥99%

Synonym: Linoleic acid ethyl ester

  • CAS Number 544-35-4

  • Linear Formula CH3(CH2)3(CH2CH=CH)2(CH2)7COOC2H5

  • Molecular Weight 308.50

  •  Beilstein Registry Number 1727827

  •  EC Number 208-868-4

  •  MDL number MFCD00009535

  •  PubChem Substance ID 24896290

  • Popular Documents:  FTNMR (PDF)  

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Properties

Related Categories Aloe Vera, Biochemicals and Reagents, Cell Biology, Esters, Ethyl Ester,
assay   ≥99%
refractive index   n20/D 1.455(lit.)
bp   224 °C/17 mmHg(lit.)
density   0.876 g/mL at 25 °C(lit.)
storage temp.   −20°C

Description

Packaging

1, 5, 25 g in glass bottle

Biochem/physiol Actions

Ethyl linoleate may be used as a reference material in assays that quantify fatty acid ethyl esters (FAEEs) for detection of alcohol abuse. Linoleic acid ethyl ester (Ethyl linoleate) may be used and studied as an acetylcholinesterase (AChE) inhibitor.

Ethyl linoleate solated from Oxalis triangularis inhibits forskolin-induced melanogenesis and tyrosinase activity in mouse B16 melanoma cells . This anti-melanogenic effect is mediated by inhibiting cAMP production.

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Safety & Documentation

Safety Information

WGK Germany 
1
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C

Protocols & Articles

Peer-Reviewed Papers

References

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An improved method for rapidly quantifying fatty acid ethyl esters in meconium suitable for prenatal alcohol screening. Hutson JR, Rao C, Fulga N, Aleksa K, Koren G. Alcohol 45, 193-199, (2011)

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Quantitation of fatty acid ethyl esters in human meconium by an improved liquid chromatography/tandem mass spectrometry. Kwak HS, Kang YS, Han KO, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 878, 1871-1874, (2010)

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Quantification of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in meconium from newborns for detection of alcohol abuse in a maternal health evaluation study. Bakdash A, Burger P, Goecke TW, et al. Anal. Bioanal. Chem 396, 2469-2477, (2010)

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Bio-guided isolation of cholinesterase inhibitors from the bulbs of Crinum x powellii. Kissling J, Ioset JR, Marston A, Hostettmann K. Phytother Res. 19, 984-987, (2005)

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Determination of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in hair: a promising way for retrospective detection of alcohol abuse during pregnancy? Pragst F, Yegles M. Ther. Drug Monit. 30, 255-263, (2008)

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Fatty acid ethyl esters: a novel biologic marker for heavy in utero ethanol exposure: a case report. Klein J, Karaskov T, and Korent G Ther. Drug Monit. 21(6), 644-6, (1999)

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1'-Acetoxychavicol acetate, a superoxide anion generation inhibitor, potently inhibits tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in ICR mouse skin. Murakami A, Ohura S, Nakamura Y, et al. Oncology 53(5), 386-91, (1996)

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[Screening and identifying of hepatoprotective compounds in paeoniae radix rubra]. Lu L, Zhang M, Wang Y, et al. Zhongguo Zhong Yao Za Zhi 37(5), 597-600, (2012)

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A bioactive complex to protect proteins from UV-induced oxidation in human epidermis. Schweikert K, Gafner F, and Dell'Acqua G Int. J. Cosmet. Sci. 32(1), 29-34, (2010)

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[Study on chemical constituents and anti-bacterial activity of volatile oil from seed of Aquilaria sinensis]. Liu J, Mei WL, Cui HB, et al. Zhong Yao Cai 31(3), 340-2, (2008)

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Antioxidant mechanism studies on ferulic acid: identification of oxidative coupling products from methyl ferulate and linoleate. Masuda T, Yamada K, Maekawa T, et al. J. Agric. Food Chem. 54(16), 6069-74, (2006)

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Fatty acid ethyl esters in meconium are associated with poorer neurodevelopmental outcomes to two years of age. Peterson J, Kirchner HL, Xue W, et al. J. Pediatr. 152(6), 788-92, (2008)

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4-Hydroxy-2-nonenal and ethyl linoleate form N(2),3-ethenoguanine under peroxidizing conditions. Ham AJ, Ranasinghe A, Koc H, et al. Chem. Res. Toxicol. 13(12), 1243-50, (2000)

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Ethyl linoleate in meconium: a biomarker for prenatal ethanol exposure. Bearer CF, Lee S, Salvator AE, et al. Alcohol. Clin. Exp. Res. 23(3), 487-93, (1999)

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Acid-promoted reactions of ethyl linoleate with nitrite ions: formation and structural characterization of isomeric nitroalkene, nitrohydroxy, and novel 3-nitro-1,5-hexadiene and 1,5-dinitro-1, 3-pentadiene products. Napolitano A, Camera E, Picardo M, et al. J. Org. Chem. 65(16), 4853-60, (2000)

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Simultaneous determination of acrolein, malonaldehyde and 4-hydroxy-2-nonenal produced from lipids oxidized with Fenton's reagent. Miyake T and Shibamoto T Food Chem. Toxicol. 34(10), 1009-11, (1996)

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Double-blind, randomized, placebo-controlled study of a lotion containing triethyl citrate and ethyl linoleate in the treatment of acne vulgaris. Charakida A, Charakida M, and Chu AC Br. J. Dermatol. 157(3), 569-74, (2007)

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Inhibitory effect of 2"-O-glycosyl isovitexin and alpha-tocopherol on genotoxic glyoxal formation in a lipid peroxidation system. Nishiyama T, Hagiwara Y, Hagiwara H, et al. Food Chem. Toxicol. 32(11), 1047-51, (1994)

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Novel oral formulation of paclitaxel inhibits neointimal hyperplasia in a rat carotid artery injury model. Kim DW, Kwon JS, Kim YG, et al. Circulation 109(12), 1558-63, (2004)

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Oxidized ethyl linoleate induces mucosal hypertrophy of the large intestine and affects cecal fermentation of dietary fiber in rats. Hara H, Miyashita K, Ito S, et al. J. Nutr. 126(4), 800-6, (1996)

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Turnover of ethyl-linoleate in rat plasma and its distribution in various organs. Hungund BL, Zheng Z, and Barkai AI Alcohol. Clin. Exp. Res. 19(2), 374-7, (1995)

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A comparison of the specific activities of linoleate and arachidonate in liver, heart and kidney phospholipids after feeding rats ethyl linoleate-9,10,12,13-d4. Luthria DL and Sprecher H Biochim. Biophys. Acta 1213(1), 1-4, (1994)

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Development of a novel self-microemulsifying drug delivery system for reducing HIV protease inhibitor-induced intestinal epithelial barrier dysfunction. Lei B, Zha W, Wang Y, et al. Mol. Pharm. 7(3), 844-53, (2010)

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Kinetic study of the prooxidant effect of alpha-tocopherol. Hydrogen abstraction from lipids by alpha-tocopheroxyl radical. Ouchi A, Ishikura M, Konishi K, et al. Lipids 44(10), 935-43, (2009)

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Interaction of C(60) fullerene with lipids. Cataldo F Chem. Phys. Lipids 163(6), 524-9, (2010)

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Differences in the fatty acid composition of fatty acid ethyl esters in organs and their secretions. Laposata M, Kabakibi A, Walden MP, et al. Alcohol. Clin. Exp. Res. 24(10), 1488-91, (2000)

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In vitro anti- and pro-oxidative effects of natural polyphenols. Stadler RH, Markovic J, and Turesky RJ Biol. Trace Elem. Res. 47(1-3), 299-305, (1995)

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The questionable role of a microsomal delta8 acyl-coA-dependent desaturase in the biosynthesis of polyunsaturated fatty acids. Chen Q, Yin FQ, and Sprecher H Lipids 35(8), 871-9, (2000)

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Ethyl arachidonate is the predominant fatty acid ethyl ester in the brains of alcohol-intoxicated subjects at autopsy. Refaai MA, Nguyen PN, Cluette-Brown JE, et al. Lipids 38(3), 269-73, (2003)

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Linoleic and linolenic acids and acne vulgaris. Logan AC Br. J. Dermatol. 158(1), 201-2, (2008)

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Merck 14,3820

Beil. 2,IV,1757

Aldrich MSDS 1, 1138:C / Corp MSDS 1 (1), 2128:D / FT-IR 2 (1), 1038:A / FT-IR 1 (1), 643:C / FT-NMR 1 (1), 989:C / IR-Spectra (3), 380:B / IR-Spectra (2), 336:E / NMR-Reference 2 (1), 542:A / RegBook 1 (1), 723:O / Sigma FT-IR 1 (1), 1414:D / Structure Index 1, 110:A:9 / Vapor Phase 3, 687:A

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