Olivetolic acid

Base Information

• Chemical Name: Olivetolic acid
• CAS No.: 491-72-5
• Molecular Formula: C12H16O4
• Molecular Weight: 224.257
• UNII: 3Y8J575L93
• DSSTox Substance ID: DTXSID20197688
• Nikkaji Number: J11.760I
• Wikipedia: Olivetolic_acid
• Wikidata: Q3604545
• Metabolomics Workbench ID: 64877
• ChEMBL ID: CHEMBL3134414
• Mol file: 491-72-5.mol

Synonyms:olivetolate;olivetolic acid

Chemical Property of Olivetolic acid

Chemical Property:

• Vapor Pressure: 3.01E-07mmHg at 25°C
• Melting Point: 143 °C
• Boiling Point: 403.9°Cat760mmHg
• PKA: 3.41±0.34(Predicted)
• Flash Point: 212.2°C
• PSA: 77.76000
• Density: 1.237g/cm³
• LogP: 2.52870
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 224.10485899
• Heavy Atom Count: 16
• Complexity: 229

Purity/Quality:

98% ^*data from raw suppliers

OlivetolicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=C(C(=CC(=C1)O)O)C(=O)O
• Uses: Olivetolic Acid is a precursor in the synthesis of primin and tetrahydrocannabinol.

Technology Process of Olivetolic acid

There total 21 articles about Olivetolic 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: 97.0%

2,4-bis(benzyloxy)-6-pentylbenzoic acid (104307-50-8) → 2,4-dihydroxyl-6-pentylbenzoic acid (491-72-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 24h; under 750.075 Torr;

DOI:10.1039/c3md00238a

Reference yield: 78.0%

2,4-dihydroxyl-6-pentylbenzaldehyde (855875-40-0) → 2,4-dihydroxyl-6-pentylbenzoic acid (491-72-5)

Guidance literature:

With sodium chlorite; sodium dihydrogen phosphate monohydrate; In water; dimethyl sulfoxide; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jnatprod.8b00227

Reference yield: 71.0%

2,4-dihydroxy-3,5-dibromo-6-pentylbenzoic acid (86791-41-5) → 2,4-dihydroxyl-6-pentylbenzoic acid (491-72-5)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; Ambient temperature;

DOI:10.1248/cpb.31.407

upstream raw materials:

ethanol

olivetoric acid

semicarbazide acetate

anziaic acid

Downstream raw materials:

anziaic acid

benzyl 2,4-dihydroxy-6-pentylbenzoate

cannabidiolic acid

Δ⁹-tetrahydrocannabinolic acid

Refernces

• 1、 -. "CANNABINOID DERIVATIVES". Paragraph 0139. . Retrieved 2021/01/23.
• 2、 -. "CANNABICHROMENIC ACID SYNTHASE FROM CANNABIS SATIVA". Sheet 1/4. . Retrieved 2016/04/09.