480-64-8

Basic information

• Product Name: 2,4-DIHYDROXY-6-METHYLBENZOIC ACID
• Synonyms: 2,4-DIHYDROXY-6-METHYLBENZOIC ACID;ORSELLINIC ACID;ORSELLINIC ACID MONOHYDRATE;o-orsellinic acid;2,4-Dihydroxy-6-methylbenzoic acid hydrate, 97%;2-Methyl-4,6-dihydroxybenzoic acid;6-Methyl-2,4-dihydroxybenzoic acid;Orsellic acid
• CAS NO: 480-64-8
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Inhibitors
• Mol File: 480-64-8.mol
• Article Data: 25

Chemical Properties

• Melting Point: 173-174°C
• Boiling Point: 257.07°C (rough estimate)
• Flash Point: 204.7 °C
• Appearance: /
• Density: 1.3037 (rough estimate)
• Vapor Pressure: 7.89E-07mmHg at 25°C
• Refractive Index: 1.5090 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: pK (25°) 3.90
• Water Solubility: Soluble in water, dimethyl sulfoxide or 100% ethanol.
• Stability: Hygroscopic
• CAS DataBase Reference: 2,4-DIHYDROXY-6-METHYLBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIHYDROXY-6-METHYLBENZOIC ACID(480-64-8)
• EPA Substance Registry System: 2,4-DIHYDROXY-6-METHYLBENZOIC ACID(480-64-8)

Safety Data

• Hazardous Substances Data: 480-64-8(Hazardous Substances Data)

Usage

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

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

Upstream product

• 106-99-0 buta-1,3-diene 
• 67-56-1 methanol 
• 110064-65-8 isoelecanoric acid 
• 866997-22-0 2,4-bis-ethoxycarbonyloxy-6-methyl-benzoic acid 
• 860752-66-5 2,4-bis-methoxycarbonyloxy-6-methyl-benzoic acid 
• 480-56-8 lecanoric acid 
• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 67-63-0 isopropyl alcohol 
• 78-92-2 iso-butanol 
• 75-65-0 tert-butyl alcohol 
• 71-36-3 butan-1-ol 
• 7028-40-2 3,5,7-Trioxo-octansaeure 
• 4860-88-2 4-hydroxy-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione 

Downstream Products

• 520-43-4 2-hydroxy-4-methoxy-6-methyl-benzoic acid methyl ester 
• 3187-58-4 methyl orsellinate 
• 504-15-4 orcinol 
• 3163-24-4 2,4,6-tribromo-3,5-dihydroxytoluene 
• 92455-24-8 Dibromorsellinsaeure 
• 859069-22-0 2,4-diacetoxy-6-methyl-benzoic acid 
• 30448-89-6 3-chloro-4,6-dihydroxy-2-methylbenzoic acid 
• 124-38-9 carbon dioxide 
• 214483-47-3 benzyl 4-benzyloxy-2-hydroxy-6-methylbenzoate 
• 6110-37-8 methyl 2,4-dimethoxy-6-methylbenzoate 
• 68048-04-4 benzyl-2,4-bis(benzyloxy)-6-methylbenzoate 
• 156998-32-2 4-[1-(4-Hydroxy-phenyl)-ethyl]-5-methyl-benzene-1,3-diol 
• 860752-66-5 2,4-bis-methoxycarbonyloxy-6-methyl-benzoic acid 
• 859948-97-3 2-hydroxy-4-methoxycarbonyloxy-6-methyl-benzoic acid 

Relevant articles and documents

An orsellinic acid glucoside from Syzygium aromatica

The buds of Syzygium aromatica yielded two triterpenoid acids, oleanolic acid and crategolic acid, and a new phenolic glucoside, orsellinic-2-O-β-D- glucopyranoside, from its methanolic extract. The structure was elucidated by spectroscopic methods and acid hydrolysis.

CRUSTINIC ACID, A TRIDEPSIDE FROM UMBILICARIA CRUSTULOSA

The structure of crustinic acid extracted from Umbilicaria crustulosa has been elucidated as 4,6-dihydroxy-3-carboxy-2-methylphenyl lecanorate by spectroscopic and chemical means.Key Word Index - Umbilicaria crustulosa; Umbilicariaceae; crustinic acid; tridepside; lichen substance.

Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base

The combined use of an organic base for resorcinols realized a Kolbe-Schmitt type reaction under ambient conditions. When resorcinols (3-hydroxyphenol derivatives) were treated with DBU under a carbon dioxide atmosphere, nucleophilic addition to carbon dioxide proceeded to afford the corresponding salicylic acid derivatives in high yields.

New orsellinic acid esters from fungus chaetomium globosporum

Seven new orsellinic acid esters, 1-7, and four known compounds were isolated from the solid, fermented rice culture of Chaetomium globosporum (cib-132). Their structures were elucidated by 1D- and 2D-NMR spectra, and the relative configuration of compoun