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Methyl salicylate

$52

  • Brand : BIOFRON

  • Catalogue Number : BD-D1340

  • Specification : 98%(HPLC)

  • CAS number : 119-36-8

  • Formula : C8H8O3

  • Molecular Weight : 152.15

  • PUBCHEM ID : 4133

  • Volume : 0.1ML

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Catalogue Number

BD-D1340

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8℃

Molecular Weight

152.15

Appearance

Colorless liquid

Botanical Source

Ilex chinensis Sims

Structure Type

Simple Phenolic Compounds

Category

Standards;Natural Pytochemical;API

SMILES

COC(=O)C1=CC=CC=C1O

Synonyms

2-HYDROXY-BENZOIC ACID METHYL ESTER/2-Hydroxybenzoic acid methyl ester/Benzoic acid, 2-hydroxy-, methyl ester/salicylic-acid methyl ester/Wintergreen oil (generic)/2-Hydroxybenzoic acid methyl ester,Methyl 2-hydroxybenzoate,Oil of wintergreen/METHYL SALICYLATE NF FCC/2-Hydroxybenzoic acid methyl ester,Methyl 2-hydroxybenzoate,Methylis salicylas/2-METHYL-5-(PROPAN-2-YL)PHENOL/methyl 2-hydroxybenzoate/Oil of wintergreen/methyl-2-hydroxybenzoate/methyl o-hydroxybenzoate/2-hydroxymethylbenzoate/QR BVO1/2-CARBOMETHOXYPHENOL/METHYL SALICYLATE NF/salicylic acid methyl ester/METHYL SALICYLATE: NF/Methyl salicylate/Wintergreen oil/METHYL SAL ICY LATE/METHYL 2-HYDROXYBENZOATE/SALICYLIC ACID METHYL ESTER/methylsalicylate/METHYL SALICYLATE 1 L/SALICYLIC ACID METHYLESTER/GAULTHERIN/BIRCH OIL

IUPAC Name

methyl 2-hydroxybenzoate

Applications

Methyl Salicylate (Wintergreen oil) is a topical analgesic and anti-inflammatory agent. Also used as a pesticide, a denaturant, a fragrance ingredient, and a flavoring agent in food and tobacco products[1]. A systemic acquired resistance (SAR) signal in tobacco[2]. A topical nonsteroidal anti-inflammatory drug (NSAID). Methyl salicylate lactoside is a COX inhibitor[4].

Density

1.2±0.1 g/cm3

Solubility

Methanol

Flash Point

86.8±12.6 °C

Boiling Point

222.0±0.0 °C at 760 mmHg

Melting Point

-8 °C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918290000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:119-36-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30669582

Abstract

The phytohormone salicylic acid (SA) is a secondary metabolite that regulates plant growth, development and responses to stress. However, the role of SA in the biosynthesis of flavonoids (a large class of secondary metabolites) in tea (Camellia sinensis L.) remains largely unknown. Here, we show that exogenous methyl salicylate (MeSA, the methyl ester of SA) increased flavonoid concentration in tea leaves in a dose-dependent manner. While a moderate concentration of MeSA (1 mM) resulted in the highest increase in flavonoid concentration, a high concentration of MeSA (5 mM) decreased flavonoid concentration in tea leaves. A time-course of flavonoid concentration following 1 mM MeSA application showed that flavonoid concentration peaked at 2 days after treatment and then gradually declined, reaching a concentration lower than that of control after 6 days. Consistent with the time course of flavonoid concentration, MeSA enhanced the activity of phenylalanine ammonia-lyase (PAL, a key enzyme for the biosynthesis of flavonoids) as early as 12 h after the treatment, which peaked after 1 day and then gradually declined upto 6 days. qRT-PCR analysis of the genes involved in flavonoid biosynthesis revealed that exogenous MeSA upregulated the expression of genes such as CsPAL, CsC4H, Cs4CL, CsCHS, CsCHI, CsF3H, CsDFR, CsANS and CsUFGT in tea leaves. These results suggest a role for MeSA in modulating the flavonoid biosynthesis in green tea leaves, which might have potential implications in manipulating the tea quality and stress tolerance in tea plants.

KEYWORDS

flavonoids; phenylalanine ammonia-lyase (PAL); phenylpropanoid pathway; salicylic acid; tea quality.

Title

Methyl Salicylate Enhances Flavonoid Biosynthesis in Tea Leaves by Stimulating the Phenylpropanoid Pathway

Author

Xin Li 1 , Li-Ping Zhang 2 , Lan Zhang 3 , Peng Yan 4 , Golam Jalal Ahammed 5 , Wen-Yan Han 6

Publish date

2019 Jan 21

PMID

30980406

Abstract

Background: In some cultivars, yellowing resulting from chlorophyll breakdown has a direct and negative effect on food supply and health. The ‘Zaosu’ pear (Pyrus bretschneideri Rehd.), a commercial Asian pear cultivar in China, rapidly turns yellow when stored at room temperature after harvest. To develop techniques that delay or suppress chlorophyll degradation, the effects of methyl salicylate (MeSA) on yellowing in ‘Zaosu’ pear fruit during storage were evaluated.
Results: Compared with the untreated fruit, the application of 0.05 mmol L-1 MeSA delayed the decline of the total chlorophyll, chlorophyll a and chlorophyll b content, and maintained more intact chloroplasts with fewer and smaller plastoglobuli. Methyl salicylate suppressed enzyme activities, including chlorophyllase, chlorophyll-degrading peroxidase, Mg dechelatase, and pheophytinase, and the expression levels of NYC, NOL, CLH, SGR, PPH, PAO and RCCR in treated fruit.
Conclusion: Methyl salicylate could delay chlorophyll breakdown in the fruit. The results also suggested that the conversion from chlorophyll a to pheophorbide a could proceed via two pathways, and that alternative pathways for the breakdown of chlorophyll a exist in ‘Zaosu’ pears. © 2019 Society of Chemical Industry.

KEYWORDS

MeSA; chlorophyll breakdown gene; chlorophyll degradation enzyme; chloroplast ultrastructure; pear; yellowing.

Title

Methyl Salicylate Delays Peel Yellowing of 'Zaosu' Pear (Pyrus Bretschneideri) During Storage by Regulating Chlorophyll Metabolism and Maintaining Chloroplast Ultrastructure

Author

Huaiyu Zhang 1 , Rui Wang 1 , Tian Wang 1 , Chunxia Fang 1 , Junjie Wang 1

Publish date

2019 Aug 15

PMID

31500198

Abstract

Glycosides are ubiquitous plant secondary metabolites consisting of a non-sugar component called an aglycone, attached to one or more sugars. One of the most interesting aglycones in grapes and wine is methyl salicylate (MeSA), an organic ester naturally produced by many plants, particularly wintergreens. To date, nine different MeSA glycosides from plants have been reported, mainly spread over the genera Gaultheria, Camellia, Polygala, Filipendula, and Passiflora. From a sensorial point of view, MeSA has a balsamic-sweet odor, known as Wintergreen. MeSA was found in Vitis riparia grapes, in Vitis vinifera sp. and in the Frontenac interspecific hybrid. We found that the MeSA glycosides content in Verdicchio wines and in some genetically related varieties (Trebbiano di Soave and Trebbiano di Lugana) was very high. In order to understand which glycosides were present in wine, the methanolic extract of Verdicchio wine was injected into a UPLC-Q-TOF-HDMS and compared to the extracts of different plants rich in such glycosides. Using pure standards, we confirmed the existence of two glycosides in wine: MeSA 2-O--d-glucoside and MeSA 2-O--d-xylopyranosyl (1-6) -d-glucopyranoside (gaultherin). For the first time, we also tentatively identified other diglycosides in wine: MeSA 2-O--l-arabinopyranosyl (1-6)--d-glucopyranoside (violutoside) and MeSA 2-O--d-apiofuranosyl (1-6)--d-glucopyranoside (canthoside A), MeSA 2-O--d-glucopyranosyl (1-6)-O--d-glucopyranoside (gentiobioside) and MeSA 2-O--l-rhamnopyranosyl (1-6)--d-glucopyranoside (rutinoside). Some of these glycosides have been isolated from Gaultheria procumbens leaves by preparative liquid chromatography and structurally annotated by 1H- and 13C-NMR analysis. Two of the peaks isolated from Gaultheria procumbens leaves, namely MeSA sambubioside and MeSA sophoroside, were herein observed for the first time. Six MeSA glycosides were quantified in 64 Italian white wines, highlighting the peculiar content and pattern in Verdicchio wines and related cultivars. The total concentration in bound and free MeSA in Verdicchio wines varied in the range of 456-9796 g/L and 5.5-143 g/L, respectively, while in the other wines the bound and free MeSA was below 363 g/L and 12 g/L, respectively. As this compound’s olfactory threshold is between 50 and 100 g/L, our data support the hypothesis that methyl salicylate can contribute to the balsamic scent, especially in old Verdicchio wines.

KEYWORDS

Verdicchio wine; gaultherin; glycosides; methyl salicylate; methyl salicylate canthoside A; methyl salicylate gentiobioside; methyl salicylate glucoside; methyl salicylate rutinoside; methyl salicylate sambubioside; violutoside.

Title

Methyl Salicylate Glycosides in Some Italian Varietal Wines

Author

Silvia Carlin 1 2 , Domenico Masuero 3 , Graziano Guella 4 , Urska Vrhovsek 5 , Fulvio Mattivi 6 7

Publish date

2019 Sep 6