2,4-Dihydroxy-6-methylbenzoic acid

Base Information

• Chemical Name: 2,4-Dihydroxy-6-methylbenzoic acid
• CAS No.: 480-64-8
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 2918290000
• European Community (EC) Number: 610-404-4
• UNII: 11XLA0494B
• DSSTox Substance ID: DTXSID20197385
• Nikkaji Number: J6.167K
• Wikipedia: Orsellinic_acid
• Wikidata: Q414421
• Metabolomics Workbench ID: 27911
• ChEMBL ID: CHEMBL457583
• Mol file: 480-64-8.mol

Synonyms:orsellinic acid

Chemical Property of 2,4-Dihydroxy-6-methylbenzoic acid

Chemical Property:

• Vapor Pressure: 7.89E-07mmHg at 25°C
• Melting Point: 173-174°C
• Refractive Index: 1.645
• Boiling Point: 391.4 °C at 760 mmHg
• PKA: pK (25°) 3.90
• Flash Point: 204.7 °C
• PSA: 77.76000
• Density: 1.46 g/cm³
• LogP: 1.10440
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water, dimethyl sulfoxide or 100% ethanol.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

99%, ^*data from raw suppliers

Orsellinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1C(=O)O)O)O
• 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.

Technology Process of 2,4-Dihydroxy-6-methylbenzoic acid

There total 48 articles about 2,4-Dihydroxy-6-methylbenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2,4-dihydroxy-6-methylbenzaldehyde (487-69-4) → orsellinic acid (480-64-8)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; dimethyl sulfoxide;

DOI:10.1021/ol030109m

Reference yield: 95.0%

orcinol (504-15-4) + carbon dioxide (124-38-9,18923-20-1) → orsellinic acid (480-64-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 40 ℃; for 24h; under 15001.5 Torr; Autoclave;

DOI:10.1039/c9cc04550c

Reference yield: 87.0%

3-bromoorsellinic acid → orsellinic acid (480-64-8)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4020(01)81801-9

upstream raw materials:

1-methyl-4-nitrosobenzene

gyrophoric acid

lecanoric acid

ethyl orselinate

Downstream raw materials:

orcinol

2,4,6-tribromo-3,5-dihydroxytoluene

Dibromorsellinsaeure

ethyl orselinate

Refernces

• 1、 Hamasaki,Kimura,Hatsuda,Sugawara. "Isolation and structure of funicin, antimicrobial substance, produced by Aspergillus funiculosus". . p. 1357 - 1360. Retrieved 1980.
• 2、 Cueto-Díaz, Eduardo J.,Ebiloma, Godwin U.,Alfayez, Ibrahim A.,Ungogo, Marzuq A.,Lemgruber, Leandro,González-García, M. Carmen,Giron, Maria D.,Salto, Rafael,Fueyo-González, Francisco José,Shiba, Tomoo,González-Vera, Juan A.,Ruedas Rama, Maria José,Orte, Angel,de Koning, Harry P.,Dardonville, Christophe. "Synthesis, biological, and photophysical studies of molecular rotor-based fluorescent inhibitors of the trypanosome alternative oxidase". . . Retrieved 2021/05/03.
• 3、 Wu, Zehong,Liu, Dong,Huang, Jian,Proksch, Peter,Zhu, Kui,Lin, Wenhan. "Hansforesters A-M, polyesters from the sponge-associated fungus Hansfordia sinuosae with antibacterial activities". . p. 39756 - 39768. Retrieved 2018/12/13.