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M6752 Sigma-Aldrich

Methyl salicylate

ReagentPlus®, ≥99% (GC)

Synonym: 2-Hydroxybenzoic acid methyl ester, Methyl 2-hydroxybenzoate, Oil of wintergreen, Wintergreen oil

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Properties

Related Categories Aromatic Compounds, Cell Biology, Nutrition Research, Phytochemicals by Chemical Classification
grade   ReagentPlus®
vapor density   5.26 (vs air)
vapor pressure   1 mmHg ( 54 °C)
assay   ≥99% (GC)
autoignition temp.   847 °F
refractive index   n20/D 1.536(lit.)
bp   222 °C(lit.)
mp   −8-−7 °C(lit.)
density   1.174 g/mL at 25 °C(lit.)

Description

Packaging

1 L in glass bottle

1 gal in glass bottle

250, 500 mL in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
WGK Germany 
1
RTECS 
VO4725000
Flash Point(F) 
204.8 °F
Flash Point(C) 
96 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Determination of Water Content in Methyl salicylate Using Karl Fischer Titration

Phenols behave differently. Most of them can be titrated in the usual manner, some are oxidized by iodine. o-Cresol shows a slight tendency towards oxidation, divalent phenols are easily oxidized. Py...
Keywords: Oxidations, Titrations

Peer-Reviewed Papers

References

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Differential effects of plant ontogeny and damage type on phloem and foliage monoterpenes in jack pine (Pinus banksiana). Erbilgin N and Colgan LJ Tree Physiol. 32(8), 946-57, (2012)

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What happens if people start drinking mouthwash as surrogate alcohol? A quantitative risk assessment. Lachenmeier DW, Monakhova YB, Markova M, et al. Food Chem. Toxicol. 51, 173-8, (2013)

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Complex odor from plants under attack: herbivore's enemies react to the whole, not its parts. van Wijk M, de Bruijn PJ, and Sabelis MW PLoS ONE 6(7), e21742, (2011)

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Differences in volatile profiles of turnip plants subjected to single and dual herbivory above- and belowground. Pierre PS, Jansen JJ, Hordijk CA, et al. J. Chem. Ecol. 37(4), 368-77, (2011)

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Scalable ionic gelation synthesis of chitosan nanoparticles for drug delivery in static mixers. Dong Y, Ng WK, Shen S, et al. Carbohydr. Polym. 94(2), 940-5, (2013)

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Isosorbide-based aspirin prodrugs: integration of nitric oxide releasing groups. Michael Jones et al J. Med. Chem. 52, 6588-98, (2009)

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In-vitro comparison of instrumentation time and cleaning capacity between endodontic handpiece and manual preparation techniques in primary molar teeth. Seraj B, Ramezani G, Ghadimi S, et al. Minerva Stomatol. 62(1-2), 17-22, (2013)

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UV-C-irradiated Arabidopsis and tobacco emit volatiles that trigger genomic instability in neighboring plants. Yao Y, Danna CH, Zemp FJ, et al. Plant Cell 23(10), 3842-52, (2011)

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Solid phase extraction method for the separation and determination of chromium(III) in the presence of chromium(VI) using silica gel modified by N,N'-bis-(α-methylsalicylidene)-2,2-dimethyl-1,3-propanediimine. Bartyzel A and Cukrowska EM Anal. Chim. Acta 707(1-2), 204-9, (2011)

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Subgingival ultrasonic instrumentation of residual pockets irrigated with essential oils: a randomized controlled trial. Feng HS, Bernardo CC, Sonoda LL, et al. J. Clin. Periodontol. 38(7), 637-43, (2011)

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Optimization and validation of liquid chromatography and headspace-gas chromatography based methods for the quantitative determination of capsaicinoids, salicylic acid, glycol monosalicylate, methyl salicylate, ethyl salicylate, camphor and l-menthol in a topical formulation. Pauwels J, D'Autry W, Van den Bossche L, et al. J. Pharm. Biomed. Anal. 60, 51-8, (2012)

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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Facility monitoring of chemical warfare agent simulants in air using an automated, field-deployable, miniature mass spectrometer. Smith JN, Noll RJ, and Cooks RG Rapid Commun. Mass Spectrom. 25(10), 1437-44, (2011)

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Function and immunocytochemical localization of two novel odorant-binding proteins in olfactory sensilla of the scarab beetle Holotrichia oblita Faldermann (Coleoptera: Scarabaeidae). Deng S, Yin J, Zhong T, et al. Chem. Senses 37(2), 141-50, (2012)

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Methyl salicylate-induced arginine catabolism is associated with up-regulation of polyamine and nitric oxide levels and improves chilling tolerance in cherry tomato fruit. Zhang X, Shen L, Li F, et al. J. Agric. Food Chem. 59(17), 9351-7, (2011)

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Potential dangers from topical preparations containing methyl salicylate. Chan TY Hum. Exp. Toxicol. 15(9), 747-50, (1996)

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Topical anti-inflammatory and analgesic activity of kirenol isolated from Siegesbeckia orientalis. Wang JP, Zhou YM, Ye YJ, et al. J. Ethnopharmacol. 137(3), 1089-94, (2011)

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Aphid antixenosis in cotton is activated by the natural plant defence elicitor cis-jasmone. Hegde M, Oliveira JN, da Costa JG, et al. Phytochemistry 78, 81-8, (2012)

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Sequence comparisons of odorant receptors among tortricid moths reveal different rates of molecular evolution among family members. Carraher C, Authier A, Steinwender B, et al. PLoS ONE 7(6), e38391, (2012)

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Design, synthesis and antileishmanial in vitro activity of new series of chalcones-like compounds: a molecular hybridization approach. Ticiano P Barbosa et al Bioorg. Med. Chem. 19, 4250-6, (2011)

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Experience with local lymph node assay performance standards using standard radioactivity and nonradioactive cell count measurements. Basketter D, Kolle SN, Schrage A, et al. J. Appl. Toxicol. 32(8), 590-6, (2012)

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Fragrance material review on methyl salicylate. Lapczynski A, Jones L, McGinty D, et al. Food Chem. Toxicol. 45 Suppl 1, S428-52, (2007)

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Exploring hydrogen bond in the excited state leading toward intramolecular proton transfer: detailed analysis of the structure and charge density topology along the reaction path using QTAIM. Mitra S, Chandra AK, Gashnga PM, et al. J. Mol. Model. 18(9), 4225-37, (2012)

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Sequence and expression of the zebrafish alpha-actinin gene family reveals conservation and diversification among vertebrates. Holterhoff CK Dev. Dyn. 238(11), 2936-47, (2009)

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Time-dependent density functional theory (TD-DFT) study on the excited-state intramolecular proton transfer (ESIPT) in 2-hydroxybenzoyl compounds: significance of the intramolecular hydrogen bonding. Lan X, Yang D, Sui X, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 102, 281-5, (2013)

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Evaluation of airborne methyl salicylate for improved conservation biological control of two-spotted spider mite and hop aphid in Oregon hop yards. Woods JL, James DG, Lee JC, et al. Exp. Appl. Acarol. 55(4), 401-16, (2011)

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Testing for phytochemical synergism: arthropod community responses to induced plant volatile blends across crops. Braasch J, Wimp GM, and Kaplan I J. Chem. Ecol. 38(10), 1264-75, (2012)

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Volatile dose and exposure time impact perception in neighboring plants. Girón-Calva PS, Molina-Torres J, and Heil M J. Chem. Ecol. 38(2), 226-8, (2012)

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Evaluation of drug release profile from patches based on styrene-isoprene-styrene block copolymer: the effect of block structure and plasticizer. Wang C, Han W, Tang X, et al. AAPS PharmSciTech 13(2), 556-67, (2012)

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Are one or two dangerous? Methyl salicylate exposure in toddlers. Davis JE J. Emerg. Med. 32(1), 63-9, (2007)

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Structure-activity relationship of salicylic acid derivatives on inhibition of TNF-? dependent NF?B activity: Implication on anti-inflammatory effect of N-(5-chlorosalicyloyl)phenethylamine against experimental colitis. Jihye Kim et al Eur. J. Med. Chem. 48, 36-44, (2012)

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Methyl salicylate: a reactive chemical warfare agent surrogate to detect reaction with hypochlorite. Salter WB, Owens JR, and Wander JD ACS Appl. Mater. Interfaces 3(11), 4262-7, (2011)

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Treatment of post-electroconvulsive therapy headache with topical methyl salicylate. Logan CJ and Stewart JT J. ECT 28(2), e17-8, (2012)

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In vitro evaluation of chitosan coated- and uncoated-calcium alginate beads containing methyl salicylate-lactose physical mixture. Tamilvanan S and Karmegam S Pharm. Dev. Technol. 17(4), 494-501, (2012)

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Merck 14,6120

Beil. 10,IV,143

Aldrich MSDS 1, 1305:C / Arctander, 2241 / Corp MSDS 1 (2), 2436:B / FT-IR 1 (2), 295:C / FT-IR 2 (2), 2842:B / FT-NMR 1 (2), 1251:A / Fenaroli / IR-Spectra (2), 901:B / IR-Spectra (3), 1029:C / NMR-Reference 2 (2), 283:C / RegBook 1 (2), 1905:D / RegBook 41 (2), 1905:D / Sax 6, 1927 / Sigma FT-IR 1 (2), 750:B / Structure Index 1, 305:B:3 / Vapor Phase 3, 1363:B

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