1-O-Hexyl-2,3,5-trimethylhydroquinone

Base Information

• Chemical Name: 1-O-Hexyl-2,3,5-trimethylhydroquinone
• CAS No.: 148081-72-5
• Molecular Formula: C15H24 O2
• Molecular Weight: 236.354
• UNII: 70BK60I8RP
• DSSTox Substance ID: DTXSID1020697
• Nikkaji Number: J624.096H
• Wikidata: Q27265853
• Metabolomics Workbench ID: 153202
• ChEMBL ID: CHEMBL3182532
• Mol file: 148081-72-5.mol

Synonyms:1-O-hexyl-2,3,5-trimethylhydroquinone;HTHQ-2,3,5;HX-1171

Chemical Property of 1-O-Hexyl-2,3,5-trimethylhydroquinone

Chemical Property:

• Vapor Pressure: 1.29E-05mmHg at 25°C
• Melting Point: 72.5-73℃
• Boiling Point: 357.8°Cat760mmHg
• PKA: 11.22±0.30(Predicted)
• Flash Point: 154.4°C
• PSA: 29.46000
• Density: 0.971g/cm³
• LogP: 3.60910
• Storage Temp.: Refrigerator
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 236.177630004
• Heavy Atom Count: 17
• Complexity: 205

Purity/Quality:

98%Min ^*data from raw suppliers

1-O-Hexyl-2,3,5-trimethylhydroquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCOC1=C(C(=C(C(=C1)C)O)C)C
• Recent ClinicalTrials: A Phase I Clinical Study of the Safety, Tolerability and Pharmacokinetics of HX-1171 in Healthy Male Subjects.
• Uses: A novel phenolic antioxidant that showed strong antimutagenic activity against eight carcinogenic heterocyclic amines (HCA), produced during cooking processes. Its antimutagenic activity appeared to inhibit both metabolic activation of HCA and action on activated N-Hydroxy species.

Technology Process of 1-O-Hexyl-2,3,5-trimethylhydroquinone

There total 2 articles about 1-O-Hexyl-2,3,5-trimethylhydroquinone 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: 64.0%

Trimethylhydroquinone (700-13-0) + hexan-1-ol (111-27-3) → 2,3,5-trimethylhydroquinone-1-hexyl ether (148081-72-5)

Guidance literature:

With phosphomolybdic acid; for 6h; Heating;

DOI:10.1248/cpb.42.570 DOI:10.1248/cpb.42.576

Reference yield:

Trimethylhydroquinone (700-13-0) + 1-Iodohexane (638-45-9) → 2,3,5-trimethylhydroquinone-1-hexyl ether (148081-72-5)

Guidance literature:

With potassium hydroxide; ethanol; at 80 ℃; Durchleiten von Wasserstoff;

Reference yield: 42.0%

2,3,5-trimethylhydroquinone-1-hexyl ether (148081-72-5) + β-D-glucose pentaacetate (604-69-3) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-hexyloxy-2,3,6-trimethyl-phenoxy)-tetrahydro-pyran-3-yl ester (148081-73-6)

Guidance literature:

With boron trifluoride diethyl etherate; In benzene; for 8h; Ambient temperature;

DOI:10.1248/cpb.42.570

upstream raw materials:

Trimethylhydroquinone

1-Iodohexane

hexan-1-ol

Downstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-hexyloxy-2,3,6-trimethyl-phenoxy)-tetrahydro-pyran-3-yl ester

Refernces

• 1、 Nihro,Furukawa,Sogawa,Wang,Miyataka,Matsumoto,Miki,Satoh. "Synthesis and anti lipid-peroxidation activity of hydroquinone monoalkyl ethers". . p. 576 - 579. Retrieved 2007/10/02.