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

Uses

2,2,5,7,8-Pentamethyl-6-chromanol is the suitable reagent used 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. It may be employed as α-tocopherol model compound and on oxidation by t-butyl hydroperoxide in chloroform, in the presence of alcohol, affords 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanol. It may be used as internal standard for the determination of α- and γ-tocopherol in the rabbit serum and liver by HPLC.

General Description

2,2,5,7,8-Pentamethyl-6-chromanol has been reported as an vitamin E model compound. It undergoes oxidation in presence of various alcohols, ranging from methanol to cholesterol, affords 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanols. Antioxidant moiety of vitamin E, 2,2,5,7,8-pentamethyl-6-chromanol (PMCol), is reported to have antiandrogen activity in prostate carcinoma cells.

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

• 67120-56-3 2.3.5-trimethyl-6-(3-hydroxy-3-methyl-butyl)-hydroquinone 
• 121239-44-9 6-methoxy-2,2,5,7,8-pentamethylchroman 
• 700-13-0 Trimethylhydroquinone 
• 556-82-1 3-methyl-2-buten-1-ol 
• 103808-42-0 2,5-dimethoxy-3,4,6-trimethylbenzaldehyde 
• 115-18-4 2-methyl-3-buten-2-ol 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 78-79-5 isoprene 
• 697-82-5 2,3,5-trimethylphenol 
• 55646-01-0 2,2,5,7,8-pentamethyl-chromane 
• 854647-18-0 (2,5-dimethoxy-3,4,6-trimethyl-phenyl)-acetic acid ethyl ester 
• 91906-19-3 2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethanol 
• 79579-90-1 2,2,5,7,8-pentamethyl-6-hydroxychroman radical 
• 870-63-3 prenyl bromide 

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 
• 6133-18-2 6-hydroxy-2,2,7,8-tetramethylchroman-5-carbaldehyde 
• 1404094-86-5 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl (5-((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-1-((2,2,5,7,8-pentamethylchroman-7-yl)oxy)pentyl)carbamate 
• 1416565-19-9 benzyl (5-((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-1-((2,2,5,7,8-pentamethylchroman-6-yl)oxy)pentyl)carbamate 
• 52471-79-1 2,2,5,7,8-Pentamethyl-6-oxo-2,3,4,6-tetrahydro-chromenylium 
• 79579-90-1 2,2,5,7,8-Pentamethyl-chroman-6-ol 
• 79579-90-1 2,2,5,7,8-pentamethyl-6-hydroxychroman radical 
• 28230-32-2 3-hydroxy-3,4-dihydrobenzotriazine-4-one 
• 5319-71-1 3-hydroxy-4-oxo-3,4-dihydroquinazoline 

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.