950-99-2

Basic information

• Product Name: 2,2,5,7,8-PENTAMETHYL-6-CHROMANOL
• Synonyms: 2,2,5,7,8-pentamethyl-1-hydroxychroman;3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-Benzopyran-6-ol;2,2,5,7,8-PENTAMETHYL-6-CHROMANOL;2,2,5,7,8-PENTAMETHYL-6-HYDROXYCHROMAN;2,2,5,7,8-Pentamethyl-6-chromanolTMC-5;6-Hydroxy-2,2,5,7,8-pentamethylchroman;Chromane C-1;Chromanol C1
• CAS NO: 950-99-2
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.31
• Product Categories: Benzopyrans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 950-99-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 89-91 °C(lit.)
• Boiling Point: 344.3°C at 760 mmHg
• Flash Point: 146.1°C
• Appearance: /
• Density: 1.034g/cm³
• Vapor Pressure: 3.34E-05mmHg at 25°C
• Refractive Index: 1.529
• PKA: 11.41±0.40(Predicted)
• CAS DataBase Reference: 2,2,5,7,8-PENTAMETHYL-6-CHROMANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,5,7,8-PENTAMETHYL-6-CHROMANOL(950-99-2)
• EPA Substance Registry System: 2,2,5,7,8-PENTAMETHYL-6-CHROMANOL(950-99-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 950-99-2(Hazardous Substances Data)

Usage

Description

2,2,5,7,8-Pentamethyl-6-chromanol, also known as a vitamin E model compound, is a synthetic compound that exhibits antioxidant properties similar to those of vitamin E. It undergoes oxidation in the presence of various alcohols, ranging from methanol to cholesterol, and has been reported to have antiandrogen activity in prostate carcinoma cells.

Uses

Used in Analytical Chemistry:
2,2,5,7,8-Pentamethyl-6-chromanol is used as a suitable reagent for the quantitative analysis of α-tocopherol by plasma-based gas chromatography/tandem mass spectrometry (GC/MS/MS) using a tabletop quadrupole ion trap mass spectrometer.
Used in Pharmaceutical Research:
2,2,5,7,8-Pentamethyl-6-chromanol may be employed as an α-tocopherol model compound for studying the oxidation process by t-butyl hydroperoxide in chloroform, in the presence of alcohol, which affords 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanol.
Used in Chromatography:
2,2,5,7,8-Pentamethyl-6-chromanol may be used as an internal standard for the determination of αand γ-tocopherol in rabbit serum and liver by high-performance liquid chromatography (HPLC).
Used in Cancer Research:
The antioxidant moiety of vitamin E, 2,2,5,7,8-pentamethyl-6-chromanol (PMCol), has been reported to exhibit antiandrogen activity in prostate carcinoma cells, making it a potential candidate for further research in cancer treatment.

InChI:InChI=1/C14H20O2/c1-8-9(2)13-11(10(3)12(8)15)6-7-14(4,5)16-13/h15H,6-7H2,1-5H3

Upstream product

• 700-13-0 Trimethylhydroquinone 
• 870-63-3 prenyl bromide 
• 873416-77-4 6-bromo-2,2,5,7,8-pentamethyl-chroman 
• 62257-91-4 2,2,5,7,8-pentamethyl-6-chromanyl-(15N)amine 
• 19017-66-4 3,4-dihydro-2,2,5,7,8-pentamethyl-6-hydroxy-2H-1-benzopyran-4-one 
• 40740-31-6 6-hydroxy-5,7,8-trimethylchroman-2-one 
• 30876-55-2 1,1-dimethyl-3-(3,5,6-trimethylbenzoquinon-2-yl)propanol 
• 67120-56-3 2.3.5-trimethyl-6-(3-hydroxy-3-methyl-butyl)-hydroquinone 
• 873968-33-3 1-(2-chloro-ethyl)-2,5-dimethoxy-3,4,6-trimethyl-benzene 
• 197297-77-1 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)butan-2-one 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 78-79-5 isoprene 
• 115-18-4 2-methyl-3-buten-2-ol 
• 72863-21-9 (dimethyl-1,1 propene-2 yl) sulfonyl-1 methyl-4 benzene 

Downstream Products

• 30876-55-2 1,1-dimethyl-3-(3,5,6-trimethylbenzoquinon-2-yl)propanol 
• 64122-19-6 2,2,5,7,8-pentamethylchroman-6-yl ethyl carbonate 
• 57721-81-0 3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol acetate 
• 14053-24-8 5-benzoyloxymethyl-2,2,7,8-tetramethyl-chroman-6-ol 
• 14053-19-1 2,2,7,8-tetramethylchroman-5,6-dione 
• 56306-89-9 6-hydroxy-2,2,5,7,8-pentamethyl-2H-chromene 
• 119529-13-4 4-methoxy-2,2,5,7,8-pentamethylchroman-6-ol 
• 119529-12-3 8a-methoxy-2,2,5,7,8-pentamethylchroman-6-one 
• 6133-18-2 6-hydroxy-2,2,7,8-tetramethylchroman-5-carbaldehyde 
• 14053-20-4 5-ethyloxymethyl-2,2,7,8-tetramethyl-chroman-6-ol 
• 15868-54-9 dimeres 6-Hydroxy-2,2,5,7,8-pentamethyl-chroman 
• 134358-31-9 2,3-dihydro-3,5,5,6,9,10,11a(R)-heptamethyl-7a(S)-(3-hydroxy-3-methylbutyl)1H-pyrano<2,3-a>xanthene-8(7aH),11(11aH)-dione 
• 18801-88-2 2,2,7,8,2',2',7',8'-octamethyl-5,5'-ethane-1,2-diyl-bis-chroman-6-ol 
• 147649-84-1 4a,5-Epoxy-4a,5-dihydro-8a-hydroperoxy-2,2,5,7,8-pentamethylchroman-6(8aH)-one 

Relevant articles and documents

Synthesis of 2,2-dialkyl chromanes by intramolecular Ullmann C–O coupling reactions toward the total synthesis of D-α-tocopherol

The complete synthesis of D-α-tocopherol was achieved using our developed-Ullmann C–O coupling reaction as a key reaction. The synthesis of the core structure of D-α-tocopherol, which is a chiral chromane, has never been reported using intramolecular Ullmann C–O coupling reactions owing to the low reactivity of electron-rich iodoarenes with tertiary alcohols. Because the developed intramolecular C–O coupling reactions prefer electron-rich iodoarenes with tertiary alcohols, we successfully synthesized the chiral chromane core and achieved the total synthesis of D-α-tocopherol.

Alcohol, Aldehyde, and Ketone Liberation and Intracellular Cargo Release through Peroxide-Mediated α-Boryl Ether Fragmentation

α-Boryl ethers, carbonates, and acetals, readily prepared from the corresponding alcohols that are accessed through ketone diboration, react rapidly with hydrogen peroxide to release alcohols, aldehydes, and ketones through the collapse of hemiacetal intermediates. Experiments with α-boryl acetals containing a latent fluorophore clearly demonstrate that cargo can be released inside cells in the presence of exogenous or endogenous hydrogen peroxide. These experiments show that this protocol can be used for drug activation in an oxidative environment without generating toxic byproducts.

Versatile approach to α-alkoxy carbamate synthesis and stimulus-responsive alcohol release

A series of α-alkoxy carbamates that cleave under mild conditions to release alcohols has been synthesized through a multicomponent process. The relationship between structural features in these compounds and the rate of alcohol release in the presence of basic hydrogen peroxide has been studied. The preparation of carbamates that cleave under other conditions has been demonstrated.