53101-49-8

Basic information

• Product Name: (R)-(+)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID
• Synonyms: (R)-(+)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID;(R)-(+)-6-hydroxy-2,5,7,8-tetramethyl-chroman-2-C;(2R)-2,5,7,8-Tetramethyl-6-hydroxychroman-2-carboxylic acid;(R)-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid;(R)-Trolox;(R)-(+)-6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid 98%;(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid
• CAS NO: 53101-49-8
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.29
• Product Categories: Benzopyrans;Chiral Building Blocks;Heterocyclic Building Blocks
• Mol File: 53101-49-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 162 °C (dec.)(lit.)
• Boiling Point: 450.3°Cat760mmHg
• Flash Point: 171°C
• Appearance: /
• Density: 1.219g/cm³
• Vapor Pressure: 6.8E-09mmHg at 25°C
• Refractive Index: 1.567
• PKA: 3.35±0.20(Predicted)
• CAS DataBase Reference: (R)-(+)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID(53101-49-8)
• EPA Substance Registry System: (R)-(+)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID(53101-49-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 53101-49-8(Hazardous Substances Data)

Usage

Uses

(R)-Trolox is used in synthesis of vitamin E analogs.

General Description

(R)-(+)-6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, a vitamin E analog, is a mushroom tyrosinase inhibitor.

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)/t14-/m1/s1

Upstream product

• 137475-52-6 perfluorobutylperoxyl radical 
• 56305-04-5 trolox 
• 103808-46-4 (+)-(S)-2-Hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butansaeure 
• 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 
• 123294-74-6 (E)-4-(2,5-Dimethoxy-3,4,6-trimethyl-phenyl)-2-methyl-but-2-enoic acid 
• 123294-75-7 (E)-4-(2,5-Dimethoxy-3,4,6-trimethyl-phenyl)-2-methyl-but-2-enoyl chloride 
• 123294-76-8 (R)-1-[(E)-4-(2,5-Dimethoxy-3,4,6-trimethyl-phenyl)-2-methyl-but-2-enoyl]-pyrrolidine-2-carboxylic acid 
• 123294-77-9 (3R,8aR)-3-[1-Bromo-2-(2,5-dimethoxy-3,4,6-trimethyl-phenyl)-ethyl]-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 
• 77257-11-5 (R)-2-Hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-butyric acid 
• 103808-42-0 2,5-dimethoxy-3,4,6-trimethylbenzaldehyde 
• 130627-46-2 4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-oxobut-3-ensaeure 
• 103808-41-9 4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-oxobutansaeure 
• 130627-48-4 (S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxybutansaeure 

Downstream Products

• 221324-50-1 benzyl (S)-6-(benzyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate 
• 204980-81-4 (S)-6-amino-5-(6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamido)-3-methyl-1-phenyl-2,4-(1H,3H)-pyrimidinedione 
• 103808-46-4 (+)-(S)-2-Hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butansaeure 
• 918876-09-2 (S)-6-(benzyloxy)-2-(12-(benzyloxy)dodec-1-enyl)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene 
• 69400-39-1 (+) (S)-6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbaldhyde 
• 269725-87-3 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether 
• 269725-95-3 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-heptyl ether 
• 269725-96-4 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-octyl ether 
• 269725-97-5 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl(dimethyl)silyl]oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)nonyl ether 
• 221324-51-2 (S)-6-(benzyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 
• 221324-52-3 (S)-6-(benzyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid benzyl amide 
• 895518-38-4 vitamin E 
• 79397-72-1 (-)-(S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-carboxylic acid methyl ester 
• 1406-70-8 (2R,4'RS,8'RS)-α-tocopheryl acetate 

Relevant articles and documents

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.

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.

Perfluorobutylperoxyl Radical as an Oxidant in Various Solvents

Perfluorobutylperoxyl radicals were produced by pulse radiolysis of aerated solutions of perfluorobutyl iodide.The rate constants for reaction of this radical with several organic reductants, chlorpromazine, trolox, hydroquinone, and several other phenols, were determined in various solvents and were found to be in the range of 105 -109 M-1 s-1.By comparison with other haloalkylperoxyl radicals, C4F9OO. was found to be a much more powerful oxidant, whose reactions took place more rapidly and were less sensitive to solvent and substituent effects.The rate constants (k) for oxidation of a series of para-substituted phenols by C4F9OO. gave a good linear correlation between log k and the electrophilic substituent constant ?+, with a slope of ρ+ = -2.3, indicating formation of a positively charged transition state.Parallel experiments with CCl3OO. were limited to the most reactive phenols and gave a higher slope, ρ+ = -3.3.The rates of reaction of C4F9OO. with trolox and chlorpromazine were found to depend on solvent viscosity, but much less on solvent polarity and acid-base properties, probably because they were closer to the diffusion-controlled limit.The longer chain C10F21OO. was somewhat less reactive than C4F9OO. because of geometric factors.