950-99-2

Usage

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 
• 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 
• 119529-12-3 8a-methoxy-2,2,5,7,8-pentamethylchroman-6-one 
• 92014-26-1 8a-hydroperoxy-2,2,5,7,8-pentamethylchroman-6(8aH)-one 

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 academic research and scientific papers

BORYL ETHERS, CARBONATES, AND CYCLIC ACETALS AS OXIDATIVELY-TRIGGERED DRUG DELIVERY VEHICLES

A compound, or a pharmaceutically acceptable salt thereof, having a structure of Formula (I), wherein L is a cleavable linker group; X is a cargo moiety-containing group; and R1 and R2 are each independently hydrogen, alkyl, or substituted alkyl; or R1 and R2 together form a boronic ester ring or a substituted boronic ester group.

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.

Mesoporous and hexagonally ordered CuAl-SBA-15-catalyzed tandem C-C and C-O bond formation between phenols and allylic alcohols

A novel mesoporous catalyst, CuAl-SBA-15, with a hexagonally ordered porous structure prepared via a soft-templating approach in a highly acidic medium is used for tandem C-C and C-O bond formation between phenols and allylic alcohols to afford a variety of dihydrobenzopyrans in good yields. The catalyst is also found to be highly active for the synthesis of vitamin E and can be recycled several times without significant loss of its activity.

Hybrid-increased radical-scavenging activity of resveratrol derivatives by incorporating a chroman moiety of vitamin e

A winning combination: Resveratrol derivatives incorporating a chroman moiety of vitaminE were constructed, resulting in the remarkable enhancement in tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl radical (HNTTM)-scavenging activity as compared with the parent molecules (see scheme). Reaction kinetic analysis, oxidative product identification, and redox potential determination demonstrate that the reaction is governed by a sequential proton-loss electron-transfer (SPLET) mechanism.

InIII-catalysed tandem C-C and C-O bond formation between phenols and allylic acetates

Indium triflate catalysed tandem allylation-intramolecular hydroalkoxylation was efficiently carried out by using 1 mol-% of the catalyst under mild conditions to afford the dihydrobenzopyran ring system (chroman-type structure) in good yields. Kinetic, mechanistic and theoretical studies are also presented. Tandem allylation-intramolecular hydroalkoxylation carried out in the presence of an indium catalyst (1 mol-%) under mild conditions provides the dihydrobenzopyranring system in good yields. Kinetic, mechanistic and theoretical studies are presented.

Synthesis of chromans via [3 + 3] cyclocoupling of phenols with allylic alcohols using a Mo/o-chloranil catalyst system

(Chemical Equation Presented) The combination of a molybdenum complex (CpMoCl(CO)3 or [CpMo(CO)3]2) and o-chloranil was used as a catalyst in the [3 + 3] cyclocoupling of phenols and allylic alcohols under microwave heating conditions. Substituted chromans were selectively obtained in moderate to good isolated yields.

Antioxidant properties of natural and synthetic chromanol derivatives: Study by fast kinetics and electron spin resonance spectroscopy

(Chemical Equation Presented) Chromanol-type compounds act as antioxidants in biological systems by reduction of oxygen-centered radicals. Their efficiency is determined by the reaction rate constants for the primary antioxidative reaction as well as for disproportionation and recycling reactions of the antioxidant-derived radicals. We studied the reaction kinetics of three novel chromanols: cis- and trans-oxachromanol and the dimeric twin-chromanol, as well as ubichromanol and ubichromenol, in comparison to α-tocopherol and pentamethylchromanol. The antioxidant-derived radicals were identified by optical and electron spin resonance spectroscopy (ESR). The kinetics of the primary antioxidative reaction and the disproportionation of the chromanoxyl radicals were assessed by stopped-flow photometry in different organic solvents to simulate the different polarities associated with biomembranes. Furthermore, the reduction of the chromanoxyl radicals by ubiquinol and ascorbate was measured after laser-induced one-electron chromanol oxidation in ethanol and in a micellar system, respectively. The rate constants showed that twin-chromanol had better radical scavenging properties than α-tocopherol and a significantly slower disproportionation rate of its corresponding chromanoxyl radical. In addition, the radical derived from twin-chromanol is reduced by ubiquinol and ascorbate at a faster rate than the tocopheroxyl radical. Finally, twin-chromanol can deliver twice as many reducing equivalents, which makes this compound a promising new candidate as artificial antioxidant in biological systems.

Effects of magnesium ion on kinetic stability and spin distribution of phenoxyl radical derived from a vitamin E analogue: Mechanistic insight into antioxidative hydrogen-transfer reaction of vitamin E

The phenoxyl radical 1. of a vitamin E analogue, generated by the reaction of 2,2,5,7,8-pentamethylchroman-6-ol (1H) with 2,2-di(4-tert-octylphenyl)-1-picrylhydrazyl (DPPH.) or galvinoxyl (G.), was significantly stabilized by the presence of Mg2+. Addition of Mg2+ into a solution of 1. resulted in a red shift of the absorption band of 1. as well as a decrease in the g value of the EPR spectrum of 1., indicating a complex formation between 1. and Mg2+. The complexation between the phenoxyl radical and Mg2+ significantly retards the disproportionation reaction of 1. by electronic repulsion between the metal cation and a generated organic cation (1+), leading to stabilization of the organic radical species. No effect of Mg2+ on the rate of hydrogen atom transfer from 1H to DPPH. or to G. was observed, suggesting that the hydrogen-transfer reaction between 1H and DPPH. or G. proceeds via a one-step hydrogen atom transfer mechanism rather than electron-transfer followed by proton transfer.