Basic information
- CAS
480-64-8- Standard SMILES
Cc1cc(O)cc(O)c1C(=O)O- InChIKey
AMKYESDOVDKZKV-UHFFFAOYSA-N- Molecular formula
- C8H8O4
- Average molar mass
- 168.15 g/mol
- Monoisotopic mass
- 168.04225873
Overview
O-orsellinic acid is a dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group. It has a role as a metabolite, a marine metabolite and a fungal metabolite. It is a dihydroxybenzoic acid and a member of resorcinols. It is a conjugate acid of an o-orsellinate.
Names & identifiers
- Preferred name
- Orsellinic Acid
- IUPAC
- 2,4-dihydroxy-6-methylbenzoic acid
- English name
- 2,4-DIHYDROXY-6-METHYLBENZOIC ACID
- Molecular formula
- C8H8O4
- Molecular weight
- 168.15
Names & synonyms
Orsellinic acid2,4-Dihydroxy-6-methylbenzoic acid480-64-8o-Orsellinic acidOrsellic acid4,6-Dihydroxy-o-toluic acidOrsellinateCHEBI:3280711XLA0494BDTXSID201973852,4-Dihydroxy-6-methylbenzoateRefChem:565301
Show more names
133346o-orsellinicaciORSELLINIC ACID MONOHYDRATE6-Methyl-2,4-dihydroxybenzoic acid2-Methyl-4,6-dihydroxybenzoic acid
DTXCID30119876Orcinolcarboxylic acid2,4-dihydroxy-6-methyl-benzoic acidMFCD00210536Benzoic acid, 2,4-dihydroxy-6-methyl-2,4-Dihydroxy-6-methylbenzenecarboxylic acid6-Methyl-.beta.-resorcylic acid4,6-Dihydroxy-2-methylbenzoic acid
Database identifiers
- CAS
480-64-8- PubChem CID
- 68072
- DTXSID
DTXSID20197385- ChEMBL
CHEMBL457583- ChEBI
CHEBI:32807- UNII
- 11XLA0494B
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 180
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Monocyclic aromatic polyketides [PK1301]
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section129.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 173 · 173-174°C
- Boiling point
- 257.07 °C · 257.07°C (rough estimate)
- Density
- 1.3037 · 1.3037 (rough estimate)
- refractive index
- 1.509 · 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
DescriptionOrsellinic 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.
UsesOrsellinic acid is a benzoic acid compound shown to block PAF-mediated neuronal apoptosis.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers97 total
Related reactions
1 records
Compound notes
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