53188-07-1

Basic information

• Product Name: 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID
• Synonyms: 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-benzopyran-2-carboxylicaci;troloxc;6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID;(+/-)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMANE-2-CARBOXYLIC ACID;TROLOX;TROLOX(R);TROLOXTM C;TIMTEC-BB SBB005933
• CAS NO: 53188-07-1
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.29
• EINECS: 258-422-8
• Mol File: 53188-07-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 187-189 °C(lit.)
• Boiling Point: 313.42°C (rough estimate)
• Flash Point: 171 °C
• Appearance: White to faintly beige/Crystalline Powder
• Density: 1.0616 (rough estimate)
• Vapor Pressure: 6.8E-09mmHg at 25°C
• Refractive Index: 1.4970 (estimate)
• 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.
• PKA: 3.35±0.20(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
• BRN: 1384051
• CAS DataBase Reference: 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID(53188-07-1)
• EPA Substance Registry System: 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID(53188-07-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: DJ2273000
• Hazardous Substances Data: 53188-07-1(Hazardous Substances Data)

Usage

Description

6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID, also known as Trolox, is a water-soluble derivative of vitamin E. It exhibits antioxidant and radical scavenging activities, making it a valuable compound in various applications. Trolox is a white to faintly beige crystalline powder and is used as a standard for measuring the antioxidant capacity of complex mixtures.

Uses

Used in Antioxidant Applications:
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID is used as an antioxidant for its ability to prevent lipid peroxidation induced by CYP2E1 in Hep G2 cells and inhibit peroxynitrite-mediated oxidative stress and apoptosis in rat thymocytes.
Used in Neuroprotective Applications:
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID is used as a neuroprotective product due to its antioxidant capabilities, which are similar to those of vitamin E.
Used in Pharmaceutical Industry:
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID is used as a standard for measuring the antioxidant capacity of complex mixtures, aiding in the development and evaluation of new pharmaceutical products.
Used in Cosmetics Industry:
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID is used as an antioxidant in the cosmetics industry to protect skin from oxidative stress and promote overall skin health.
Used in Food Industry:
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID is used as an additive to enhance the shelf life of food products by preventing oxidation and maintaining freshness.
Used in Research and Development:
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID is used as a research tool for studying the effects of antioxidants on various biological systems and understanding their potential applications in healthcare and other industries.

References

1) Massey et al. (1990), Free radical damage in neonatal rat cardiac myocyte cultures: effects of alpha-tocopherol, Trolox and phytol; Free Radic. Biol. Med., 8 449 2) Chen et al. (1998), Cytotoxicity and apoptosis produced by cytochrome P450 2E1 in Hep G2 cells; Mol. Pharmacol., 53 638 3) Brookes et al. (1996), Trolox inhibits peroxynitrite-mediated oxidative stress and apoptosis in rat thymocytes; Arch. Biochem. Biophys., 333 482

InChI:InChI=1/C14H18O4/c1-7-8(2)12-10(9(3)11(7)15)5-6-14(4,18-12)13(16)17/h15H,5-6H2,1-4H3,(H,16,17)/p-1/t14-/m1/s1

Upstream product

• 70897-17-5 (S)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester 
• 120-80-9 benzene-1,2-diol 
• 105868-72-2 trolox c radical 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 137475-52-6 perfluorobutylperoxyl radical 
• 56305-04-5 trolox 
• 90-82-4 pseudoephedrine 
• 221324-51-2 (S)-6-(benzyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 
• 69400-39-1 (+) (S)-6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbaldhyde 
• 174681-06-2 (E)-5-(5-(benzyloxy)-2-hydroxy-3,4,6-trimethylphenyl)-3-methylpent-2-en-1-ol 
• 130627-49-5 (2S,5S)-2-(tert.-Butyl)5-<2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl>-1,3-dioxolan-4-on 
• 103808-37-3 (2S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutansaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>ester 
• 103808-39-5 (2S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutansaeure-<(1R,2S,3S,4S)-3-benzyl-1,7,7-trimethylbicyclo<2.2.1>hept-2-yl>ester 
• 130627-47-3 (2S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutansaeure-<(1S)-1-(benzylcarbamoyl)-ethyl>ester 

Downstream Products

• 53101-49-8 trolox radical cation 
• 122003-25-2 1-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)carbonyl]-4-(4-methoxyphenyl)piperazine 
• 86646-83-5 methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate 
• 658061-89-3 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [6-amino-1-(2-methoxy-phenyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide 
• 658061-88-2 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid (6-amino-3-methyl-2,4-dioxo-1-o-tolyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide 
• 658061-91-7 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [6-amino-3-methyl-1-(2-methylsulfanyl-phenyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide 
• 658061-90-6 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [6-amino-1-(2-ethoxy-phenyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide 
• 658061-96-2 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [6-amino-1-(2,3-dichloro-phenyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide 

Relevant articles and documents

SYNTHESIS OF TOCOTRIENOLS FROM O-CRESOL DERIVATIVES

The present invention provides an environmentally benign, facile process for preparation of Tocotrienols from commercially available derivatives of o-Cresol.

POLYMORPHIC AND AMORPHOUS FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDE

Disclosed herein are polymorphic and amorphous forms of anhydrate, hydrate, and solvates of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide and methods of using such compositions for treating or suppressing oxidative stress disorders, including mitochondrial disorders, impaired energy processing disorders, neurodegenerative diseases and diseases of aging. Further disclosed are methods of making such polymorphic and amorphous forms.

Cyclodextrin inclusion interferes with trolox oxygen radical scavenging capacity measurement

The interference of cyclodextrin solubilization with the measurement of oxygen radical scavenging capacity was investigated. Cyclodextrin (CD) that can solubilize water-insoluble compounds has been used in the oxygen radical scavenging capacity assay called oxygen radical absorbance capacity (ORAC) method. A vitamin E analog, trolox (2-hydroxy-2,5,7,8-tetramethylchroman-2- carboxylic acid) has been employed as a standard compound in ORAC methods and the results were often expressed in the trolox equivalent unit. We found that trolox ORAC values measured with electron spin resonance-based ORAC method, were markedly dependent on the CD concentration, i.e., it decreased by 50% when [CD]/[Trolox]=100 was present. 2D ROESY NMR study of trolox/CD inclusion complex revealed that trolox resided within the CD cavity. The reactive phenoxyl group in trolox is shielded from the attack by the oxygen radical, suggesting that this hindrance was causal for the decrease in ORAC values. by Oldenbourg Wissenschaftsverlag, Mu?nchen.