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426091

Methyl 2,5-dihydroxybenzoate

Name: Methyl 2,5-dihydroxybenzoate
Brand: ALDRICH

99%

Synonym(s):

Methyl gentisate

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About This Item

Linear Formula:

(HO)₂C₆H₃CO₂CH₃

CAS Number:

2150-46-1

Molecular Weight:

168.15

NACRES:

NA.22

PubChem Substance ID:

24866683

UNSPSC Code:

12352100

EC Number:

218-427-8

MDL number:

MFCD00016464

Assay:

99%

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Properties

Quality Level

200

assay

99%

mp

86-88 °C (lit.)

functional group

ester

SMILES string

COC(=O)c1cc(O)ccc1O

InChI

1S/C8H8O4/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4,9-10H,1H3

InChI key

XGDPKUKRQHHZTH-UHFFFAOYSA-N

Description

General description

Methyl 2,5-dihydroxybenzoate (methyl gentisate) is an alkyl ester of gentisic acid. It is reported to show less cytotoxic and mutagenic activity than hydroquinone with a potential to inhibit melanogenesis. It has been synthesized from 2,5-dihydroxybenzoic acid. The crystal structure of the molecule was found to be planar.

Application

Methyl 2,5-dihydroxybenzoate (methyl gentisate) may be used as a starting material in the synthesis of euonyminol.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors.

E V Curto et al.

Biochemical pharmacology, 57(6), 663-672 (1999-02-26)

To discover safe and effective topical skin-lightening agents, we have evaluated alkyl esters of the natural product gentisic acid (GA), which is related to our lead compound methyl gentisate (MG), and four putative tyrosinase inhibitors, utilizing mammalian melanocyte cell cultures

Total Synthesis of (.+-.)-Euonyminol, the Sesquiterpenoid Nucleus of Cathedulin K-19, via an Epoxide Cascade Cyclization.

White JD, et al.

Journal of the American Chemical Society, 117(38), 9780-9781 (1995)

Methyl 2, 5-dihydroxybenzoate.

Brown CL, et al.

Acta Crystallographica Section E, Structure Reports Online, 59(5), 630-631 (2003)

Global Trade Item Number

SKU	GTIN
426091-25G	04061831820270