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2,4-DIHYDROXY-6-METHYLBENZOIC ACID

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2,4-DIHYDROXY-6-METHYLBENZOIC ACID Basic information

Product Name:
2,4-DIHYDROXY-6-METHYLBENZOIC ACID
Synonyms:
  • 2,4-DIHYDROXY-6-METHYLBENZOIC ACID
  • ORSELLINIC ACID
  • ORSELLINIC ACID MONOHYDRATE
  • 2,4-Dihydroxy-6-methylbenzoic acid hydrate, 97%
  • 2-Methyl-4,6-dihydroxybenzoic acid
  • 6-Methyl-2,4-dihydroxybenzoic acid
  • Orsellic acid
  • o-orsellinic acid
CAS:
480-64-8
MF:
C8H8O4
MW:
168.15
Product Categories:
  • Inhibitors
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
Mol File:
480-64-8.mol
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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
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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

2,4-DIHYDROXY-6-METHYLBENZOIC ACID Preparation Products And Raw materials

Preparation Products

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