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

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

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

• 137475-52-6 perfluorobutylperoxyl radical 
• 56305-04-5 trolox 
• 86646-83-5 methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate 
• 77286-98-7 (R)-4-(2,5-Dihydroxy-3,4,6-trimethyl-phenyl)-2-hydroxy-2-methyl-butyric acid 
• 123294-78-0 (3S,8aR)-3-[2-(2,5-Dimethoxy-3,4,6-trimethyl-phenyl)-ethyl]-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 
• 53713-29-4 2-cyano-6-hydroxy-2,5,7,8-tetramethylchroman 
• 53713-02-3 (+/-)-4-(2,5-dihydroxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutanoic acid 
• 53101-72-7 rac-3,4-dihydro-6-acetyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ol 
• 53101-70-5 (+/-)-2-cyano-4-(2,5-diacetoxy-3,4,6-trimethylphenyl)butan-2-ol 
• 7732-18-5 water 
• 89363-90-6 2-Carboxy-2,5,7,8-tetramethyl-chroman-6-ol anion 
• 120-80-9 benzene-1,2-diol 
• 105868-72-2 trolox c radical 
• 697-82-5 2,3,5-trimethylphenol 

Downstream Products

• 53101-49-8 trolox radical cation 
• 57028-37-2 2-Hydroxy-2-methyl-4-(2,5,6-trimethyl-2,4-dioxo-2,5-cyclohexadienyl)butanoic acid 
• 86646-83-5 methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate 
• 53101-49-8 (S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid 
• 1448960-10-8 (±)-{6-[2-(4-formylphenoxymethyl)-2,5,7,8-tetramethylchroman-6-yl]hexyl}carbamic acid tert-butyl ester 
• 214124-57-9 3,4-dihydro-2,5,7,8-tetramethyl-2-{4-[(4-nitrophenyl)-1-piperazinyl]-carbonyl}-2H-1-benzopyran-6-ol 

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.

A green multicomponent synthesis of tocopherol analogues with antiproliferative activities

A one-pot efficient, practical and eco-friendly synthesis of tocopherol analogues has been developed using water or solvent free conditions via Passerini and Ugi multicomponent reactions. These reactions can be optimized using microwave irradiation or ultrasound as the energy source. Accordingly, a small library of 30 compounds was prepared for biological tests. The evaluation of the antiproliferative activity in the human solid tumor cell lines A549 (lung), HBL-100 (breast), HeLa (cervix), SW1573 (lung), T-47D (breast), and WiDr (colon) provided lead compounds with GI50 values between 1 and 5 μM. A structure–activity relationship is also discussed. One of the studied compounds comes up as a future candidate for the development of potent tocopherol-mimetic therapeutic agents for cancer.

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.

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

The enantioselective synthesis of α- and γ-tocopherol (the most biologically active members of vitamin E family) and analogues has been accomplished employing a new enantioselective gold catalyzed intramolecular allylic alkylation reaction followed by an olefin cross-metathesis as key steps. The methodology proved to be applicable to different olefins highlighting its potential for the synthesis of diverse libraries. The enantioselective synthesis of α- and γ-tocopherol (the most biologically active members of vitamin E family) and analogues has been accomplished employing an enantioselective gold-catalyzed intramolecular allylic alkylation reaction followed by an olefin cross-metathesis as key steps (see scheme).

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.

PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE ORGANIC CARBOXYLIC ACID

The present invention is a simple method, in which a specific amount of alkali is added to an enantiomeric mixture of an optically active organic carboxylic acid where enantiomers are present in a non-equimolar ratio, or in which the enantiomeric mixture of an optically active organic carboxylic acid is neutralized with an alkali, and then a specific amount of acid is added thereto, thereby separating an organic carboxylic acid salt in the mother liquor and a crystallized organic carboxylic acid from each other. The method makes it possible to obtain an optically active organic carboxylic acid with improved enantiomeric excess. The present invention provides a simple production method for obtaining an optically active organic carboxylic acid with improved enantiomeric excess from an enantiomeric mixture of an optically active organic carboxylic acid where enantiomers are present in a non-equimolar ratio.

METHOD OF PRODUCING S-(-)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMANE-2-CARBOXYLIC ACID AND PRODUCT OBTAINED BY THE METHOD

The present invention provides an industrially available method for efficiently producing high-purit y S-(-)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid excellent in solid-liquid separability from an S-(-)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid ester, and also provides products obtained by the method. Under a temperature condition of 50-80°C in an aqueous solvent, (A) an S-(-)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid ester represented by the general formula (1) is hydrolyzed under a basic condition for 1-3 hours; then (B) the insoluble matters contained in the reaction solution resulting from the hydrolysis are removed; and (C) an acid is added to the resulting solution to effect crystallization; provided that R in the general formula (1) represents an alkyl or aryl group.

PROCESS FOR PRODUCING CHROMAN COMPOUND

The invention provides a process for producing a chroman compound represented by formula (1) (wherein each of substituents R1 to R6 and X represents a hydrogen atom, a halogen atom, a hydroxyl group, a methoxy group, an ethoxy group, a carboxyl group, a C1 to C12 alkyl group which may have a substituent, a C6 to C12 aryl group which may have a substituent, a C7 to C12 aralkyl group which may have a substituent, or an ester residue; R1 to R4 may be linked to one another; and at least one of the substituents X and R6 is an ester residue), characterized in that the process includes allowing a phenol, an olefin, and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol. According to the present invention, a high-purity chroman compound can be produced in the absence of catalyst and under mild conditions. In addition, the invention provides an industrial means for producing the compound, without using a large amount of an acid or a base serving as a reaction promoter or a catalyst, which would otherwise cause side reactions, apparatus corrosion, etc. [F1]

Chroman derivatives for the reduction of inflammation symptoms

The present invention provides a composition comprising chroman derivatives, for use in the reduction of inflammatory markers associated with inflammation, particularly for the reduction of C-reactive protein (CRP) and for use in the treatment and/or amelioration of symptoms of inflammation.

Phenol radical cations and phenoxyl radicals in electron transfer from the natural phenols sesamol, curcumin and trolox to the parent radical cations of 1-chlorobutane

The free electron transfer from sesamol, curcumin and trolox to solvent (1-chlorobutane) radical cations was studied. The solutes (ArOH) react with BuCl.+ at diffusion-controlled rates (～1010dm 3mol-1s-1/s