| Identification | Back Directory | [Name]
2,4-DIHYDROXY-6-METHYLBENZOIC ACID | [CAS]
480-64-8 | [Synonyms]
133346
Orsellic acid
o-orsellinicaci
ORSELLINIC ACID
o-orsellinic acid
ORSELLINIC ACID MONOHYDRATE
2-Methyl-4,6-dihydroxybenzoic acid
6-Methyl-2,4-dihydroxybenzoic acid
2,4-DIHYDROXY-6-METHYLBENZOIC ACID
Benzoic acid, 2,4-dihydroxy-6-Methyl-
2,4-Dihydroxy-6-methylbenzoic acid hydrate, 97% | [Molecular Formula]
C8H8O4 | [MDL Number]
MFCD00210536 | [MOL File]
480-64-8.mol | [Molecular Weight]
168.15 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 | [storage]
Store at -20°C | [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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Alfa Aesar
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Energy Chemical
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www.energy-chemical.com |
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