methyl orsellinate Chemical Properties

Melting point:

141-142℃

Boiling point:

339℃

Density 

1.296

Flash point:

138℃

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

8.27±0.23(Predicted)

color 

White to Off-White

InChI

InChI=1S/C9H10O4/c1-5-3-6(10)4-7(11)8(5)9(12)13-2/h3-4,10-11H,1-2H3

InChIKey

NCCWCZLEACWJIN-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=C(C)C=C(O)C=C1O

LogP

2.380 (est)

EPA Substance Registry System

Benzoic acid, 2,4-dihydroxy-6-methyl-, methyl ester (3187-58-4)

Safety Information

HS Code 

2918290090

methyl orsellinate Usage And Synthesis

Uses

Methyl 2,4-Dihydroxy-6-methylbenzoate (methyl orsellinate) is a useful synthetic intermediate in the synthesis of Grifolic Acid (G786500); a selective partial GPR120 agonist. Grifolic Acid induces ERK and [Ca2+]i responses in cells expressing GPR120, but has no effects on those expressing GPR40.

Definition

ChEBI: Orsellinic acid methyl ester is a hydroxybenzoic acid. It has a role as a metabolite.

Biochem/physiol Actions

Methyl orsellinate, an antifungal compound, is produced during submerged culture from Sparassis crispa. Methyl orsellinate have appeared to have higher antifungal activity than sparassol. Methyl orsellinate is a phytotoxic compound; it can cause significant inhibition of radicle growth of Amaranthus hypochondriacus and Echinochloa crus-galli, interact with bovine-brain calmodulin and inhibit the activation of the calmodulin-dependent enzyme cAMP phosphodiesterase. It could inhibit PTP1B activity with 50% inhibitory concentration values of 277 +/- 8.6 microM; the selective inhibition of PTP1B has been widely recognized as a potential drug target for the treatment of type 2 diabetes and obesity; methyl orsellinate may treat the type 2 diabetes and obesity.

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