Trolox

Base Information

• Chemical Name: Trolox
• CAS No.: 53188-07-1
• Deprecated CAS: 56305-04-5
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Hs Code.: 29339900
• European Community (EC) Number: 258-422-8
• UNII: S18UL9710X
• DSSTox Substance ID: DTXSID60866306
• Nikkaji Number: J236.392E
• Wikipedia: Trolox
• Wikidata: Q245489
• Pharos Ligand ID: 28Q6DRX4YKZ9
• Metabolomics Workbench ID: 48338
• ChEMBL ID: CHEMBL153
• Mol file: 53188-07-1.mol

Synonyms:(+--)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid;(+--)-trolox;(R,S)-6-hydroxy-2,5,7,8-tetramethyl-2-chromanecarboxylic acid;2h-1-benzopyran-2-carboxylic acid, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-;2h-1-benzopyran-2-carboxylic acid, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-, (+--)-;3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-benzopyran-2- carboxylic acid;6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2h-chromene-2-carboxylic acid;6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid;KH176;Trolox;Trolox C

Chemical Property of Trolox

Chemical Property:

• Appearance/Colour: white to fainly beige crystalline powder
• Vapor Pressure: 6.8E-09mmHg at 25°C
• Melting Point: 187-189 °C(lit.)
• Refractive Index: 1.4970 (estimate)
• Boiling Point: 450.3 °C at 760mmHg
• PKA: 3.35±0.20(Predicted)
• Flash Point: 171 °C
• PSA: 66.76000
• Density: 1.219 g/cm³
• LogP: 2.48570
• Storage Temp.: 0-6°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml). Also soluble in Water at alkalinepH.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 250.12050905
• Heavy Atom Count: 18
• Complexity: 343

Purity/Quality:

Analysis control,GC≥98% ^*data from raw suppliers

Trolox ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(CCC(O2)(C)C(=O)O)C(=C1O)C)C
• Description: Trolox (53188-07-1) is a water soluble derivative of vitamin E. Displays antioxidant and radical scavenging activities.1 Prevents lipid peroxidation induced by CYP2E1 in Hep G2 cells.2 Trolox inhibits peroxynitrite-mediated oxidative stress and apoptosis in rat thymocytes.3
• Uses: Trolox is a Vitamin E analog that also maintains the antioxidant capabilities which Vitamin E shows. An antioxidant derived from water-soluble vitamin E Trolox is a Vitamin E analog that also maintains the antioxidant capabilities which Vitamin E shows. Neuroprotective product.

Technology Process of Trolox

There total 47 articles about Trolox 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: 99.3%

methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate (86646-83-5) → trolox (56305-04-5,53188-07-1)

Guidance literature:

methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate; With sodium hydroxide; water; In methanol; at 80 ℃; for 2h;

With potassium hydrogensulfate; In methanol; water; at 80 ℃; for 2h;

Reference yield: 97.0%

(S)-6-(benzyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid (221324-51-2) → (S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (53101-49-8,53174-06-4,53188-07-1,56305-04-5)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; for 8h;

DOI:10.1002/chem.201403768

Reference yield: 94.9%

(S)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester (70897-17-5) → (S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (53101-49-8,53174-06-4,53188-07-1,56305-04-5)

Guidance literature:

(S)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester; With water; sodium hydroxide; In methanol; at 80 ℃; for 1h; Inert atmosphere;

With potassium hydrogensulfate; water; In methanol; at 60 ℃; pH=5; Product distribution / selectivity;

upstream raw materials:

perfluorobutylperoxyl radical

trolox

4-(N,N-dimethylamino)phenol

trolox c radical

Downstream raw materials:

trolox radical cation

(+/-)-3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxilic acid

4-(N,N-dimethylamino)phenol

trolox c radical

Refernces

• 1、 Ingold, Mariana,Dapueto, Rosina,Victoria, Sabina,Galliusi, Germán,Batthyàny, Carlos,Bollati-Fogolín, Mariela,Tejedor, David,García-Tellado, Fernando,Padrón, José M.,Porcal, Williams,López, Gloria V.. "A green multicomponent synthesis of tocopherol analogues with antiproliferative activities". . p. 1888 - 1902. Retrieved 2017/11/15.
• 2、 Uria, Uxue,Vila, Carlos,Lin, Ming-Yuan,Rueping, Magnus. "Gold-catalyzed asymmetric allylic substitution of free alcohols: An enantioselective approach to chiral chromans with quaternary stereocenters for the synthesis of Vitamin E and analogues". supporting information. p. 13913 - 13917. Retrieved 2016/02/18.