3-Pentadecylcatechol

Base Information

• Chemical Name: 3-Pentadecylcatechol
• CAS No.: 492-89-7
• Molecular Formula: C21H36 O2
• Molecular Weight: 320.516
• NSC Number: 403211
• UNII: 51M8X101ML
• DSSTox Substance ID: DTXSID70197714
• Nikkaji Number: J6.062C
• Wikidata: Q27104847
• Metabolomics Workbench ID: 52623
• ChEMBL ID: CHEMBL8087
• Mol file: 492-89-7.mol

Synonyms:3-n-pentadecylcatechol;3-PDC;3-pentadecacatechol;3-pentadecylpyrocatechol;hydrourushiol

Chemical Property of 3-Pentadecylcatechol

Chemical Property:

• Vapor Pressure: 1.49E-08mmHg at 25°C
• Melting Point: 59.5°C
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 445.6°Cat760mmHg
• PKA: 9.89±0.10(Predicted)
• Flash Point: 191.7°C
• PSA: 40.46000
• Density: 0.96g/cm³
• LogP: 6.73150
• XLogP3: 9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 320.271530387
• Heavy Atom Count: 23
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

3-PENTADECYLCATECHOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC1=C(C(=CC=C1)O)O
• Description: Pentadecykatechol is the main allergen of the Anacardiaceae poison ivy (Toxicodendron radicans) and of poison oak (Toxicodendron diversiloba, Rhus diversiloba).
• Uses: 3-Pentadecylcatechol is an urushiol derivative that displays anti-Helicobacter pylori activity in vivo. Found in the sap of the lacquer tree (Rhus verniciflua Stokes).

Technology Process of 3-Pentadecylcatechol

There total 33 articles about 3-Pentadecylcatechol 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: 86.0%

1-(2,5-dimethoxy-tetrahydro-furan-2-yl)-heptadecan-1-one (102542-25-6) → 3-pentadecylcatechol (492-89-7)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 10h; Heating;

DOI:10.1055/s-1990-26889

Reference yield: 80.3%

1,2-dimethoxy-3-pentadecyl-benzene (7461-75-8) → 3-pentadecylcatechol (492-89-7)

Guidance literature:

With boron tribromide; In hexane; dichloromethane; at 0 - 20 ℃; for 14h;

DOI:10.1016/j.freeradbiomed.2014.03.041

Reference yield: 62.0%

[(10Z)-pentadec-10′-en-1-yl]catechol → 3-pentadecylcatechol (492-89-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 4h; under 1500.15 Torr;

DOI:10.1016/j.phytochem.2020.112359

upstream raw materials:

1,2-dimethoxy-3-pentadecyl-benzene

1,2-dihydroxy-3-(pentadec-8-enyl)benzene

1,2-dihydroxy-3-(pentadeca-8,11-dienyl)benzene

1,2-bis-benzyloxy-3-pentadec-1-en-ξ-yl-benzene

Downstream raw materials:

1,2-bis-benzyloxy-3-pentadecyl-benzene

1,2-dimethoxy-3-pentadecyl-benzene

(S)-2-tert-Butoxycarbonylamino-propionic acid 2-((S)-2-tert-butoxycarbonylamino-propionyloxy)-6-pentadecyl-phenyl ester

oxalic acid

Refernces

• 1、 Mascayano-Collado, Carolina,Mu?oz-Ramírez, Alejandra,Torrent-Farías, Claudia,Urzúa-Moll, Alejandro. "Study of two isoforms of lipoxygenase by kinetic assays, docking and molecular dynamics of a specialised metabolite isolated from the aerial portion of Lithrea caustica (Anacardiaceae) and its synthetic analogs". . . Retrieved 2020.
• 2、 Barriga, Andrés,Echeverría, Javier,Mascayano-Collado, Carolina,Mu?oz-Ramírez, Alejandra,Urzúa, Alejandro. "Inhibition of Soybean 15-Lipoxygenase and Human 5-Lipoxygenase by Extracts of Leaves, Stem Bark, Phenols and Catechols Isolated From Lithraea caustica (Anacardiaceae)". . . Retrieved 2020/12/18.
• 3、 Kim, Jin Young,Cho, Jeong-Yong,Ma, Young Kyu,Lee, Yu Geon,Moon, Jae-Hak. "Nonallergenic urushiol derivatives inhibit the oxidation of unilamellar vesicles and of rat plasma induced by various radical generators". . p. 379 - 389. Retrieved 2014/05/20.