Methyl 2,4-dihydroxy-6-pentylbenzoate

Base Information

• Chemical Name: Methyl 2,4-dihydroxy-6-pentylbenzoate
• CAS No.: 58016-28-7
• Molecular Formula: C13H18O4
• Molecular Weight: 238.284
• Hs Code.: 2918290090
• European Community (EC) Number: 810-693-9
• DSSTox Substance ID: DTXSID00552918
• Wikidata: Q82433330
• Mol file: 58016-28-7.mol

Synonyms:methyl 2,4-dihydroxy-6-pentylbenzoate;58016-28-7;methyl olivetolate;2,4-dihydroxy-6-pentyl-benzoic acid methyl ester;SCHEMBL2762730;AMY6568;DTXSID00552918;RQGAOBDPFOADCM-UHFFFAOYSA-N;MFCD06737776;methyl2,4-dihydroxy-6-pentylbenzoate;AKOS030528230;Methyl 6-n-pentyl-2,4-dihydroxybenzoate;AS-56960;CS-0152318;C16022;A930141;A1-00503

Chemical Property of Methyl 2,4-dihydroxy-6-pentylbenzoate

Chemical Property:

• Melting Point: 105-106 °C(Solv: benzene (71-43-2))
• Boiling Point: 409.3±30.0 °C(Predicted)
• PKA: 8.30±0.23(Predicted)
• PSA: 66.76000
• Density: 1.153±0.06 g/cm3(Predicted)
• LogP: 2.61710
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Dichloromethane; Ethyl Acetate
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 238.12050905
• Heavy Atom Count: 17
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

Methylolivetolate 97% ^*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)OC
• Uses: Methyl Olivetolate is an intermediate in synthesizing Δ9-Tetrahydrocannabinolic Acid (Acid A & B) (T293235). It is one of the substances screened for in meconium drug testings for medicinal opiods among addicted mothers. Δ9-Tetrahydrocannabinolic Acid has been shown to protect dopaminergic neurons against 1-methyl-4-Ph pyridinium (MPP+) induced cell death.

Technology Process of Methyl 2,4-dihydroxy-6-pentylbenzoate

There total 14 articles about Methyl 2,4-dihydroxy-6-pentylbenzoate 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: 55.0%

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1) + (2-Pentyl-[1,3]dioxolan-2-yl)-acetyl chloride (83578-33-0) → methyl 2,6-dihydroxy-6-pentylbenzoate (58016-28-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)87498-5

Reference yield: 52.0%

1-(1-imidazolyl)-1-hexanone (60988-34-3) + 1,3,5-tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene (102342-54-1) → methyl 2,6-dihydroxy-6-pentylbenzoate (58016-28-7)

Guidance literature:

With titanium(IV) isopropylate; titanium tetrachloride; In dichloromethane; 1.) -78 deg C, 5 h, 2.) RT, overnight;

DOI:10.1021/jo00363a004

Reference yield: 36.0%

N,N-dimethylhexanamide (5830-30-8) + 3,5-dioxohexanoic acid methyl ester (29736-80-9) → methyl 2,6-dihydroxy-6-pentylbenzoate (58016-28-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -20 ℃; for 5h;

upstream raw materials:

diazomethane

2,4-dihydroxyl-6-pentylbenzoic acid

methanol

anziaic acid

Downstream raw materials:

(E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid methyl ester

tetrahydrocannabinolic acid

cannabidiolic acid

(+)-CBD methyl ester