2,4-DIHYDROXY-6-METHYLBENZOIC ACID Chemical Properties

Melting point:

173-174°C

Boiling point:

257.07°C (rough estimate)

Density 

1.3037 (rough estimate)

refractive index 

1.5090 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

pka

pK (25°) 3.90

color 

White to Pale Gray

Water Solubility 

Soluble in water, dimethyl sulfoxide or 100% ethanol.

Stability:

Hygroscopic

CAS DataBase Reference

480-64-8

2,4-DIHYDROXY-6-METHYLBENZOIC ACID Usage And Synthesis

Description

Orsellinic acid is a fungal metabolite and benzoic acid derivative with antioxidant and neuroprotective activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals with an IC₅₀ value of 5 mM. Orsellinic acid (1 μg/ml) prevents PARP cleavage induced by platelet-activating factor (PAF) in PC12-AC cells and PAF-induced cytotoxicity in PAF receptor null (Pafr^-/-) mouse cerebellar granule cells.

Uses

Orsellinic acid is a benzoic acid compound shown to block PAF-mediated neuronal apoptosis.

Definition

ChEBI: A dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group.

Biosynthesis

One of the simplest polyketide derivatives, orsellinic acid is widely distributed in fungi. It is biosynthesised from an acetate starter unit and three malonyl units, as shown in Figure. Intramolecular condensation of the polyketide chain gives orsellinic acid without further modification.

The biosynthesis of orsellinic acid.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 3566, 1965 DOI: 10.1021/jo01021a507

References

[1] VIVEK H KHAMBHATI. First Report of the Production of Mycotoxins and Other Secondary Metabolites by Macrophomina phaseolina (Tassi) Goid. Isolates from Soybeans (Glycine max L.) Symptomatic with Charcoal Rot Disease.[J]. Journal of fungi (Basel, Switzerland), 2020. DOI: 10.3390/jof6040332
[2] T. I. B. LOPES. Radical-scavenging activity of orsellinates.[J]. Chemical & pharmaceutical bulletin, 2008, 7 1: 1551-1554. DOI: 10.1248/cpb.56.1551
[3] SCOTT D. RYAN. Platelet activating factor-induced neuronal apoptosis is initiated independently of its G-protein coupled PAF receptor and is inhibited by the benzoate orsellinic acid[J]. Journal of Neurochemistry, 2007, 103 1: 88-97. DOI: 10.1111/j.1471-4159.2007.04740.x

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