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426091

Sigma-Aldrich

Methyl 2,5-dihydroxybenzoate

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
EC Number:
218-427-8
MDL number:
MFCD00016464
UNSPSC Code:
12352100
PubChem Substance ID:
24866683
NACRES:
NA.22

assay

99%

mp

86-88 °C (lit.)

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

Related Categories

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

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)

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