950-99-2,MFCD00210347
Catalog No.:AA006PQK

950-99-2 | 2,2,5,7,8-Pentamethyl-6-chromanol

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1g
97%
in stock  
$75.00   $53.00
- +
5g
97%
in stock  
$152.00   $107.00
- +
25g
97%
in stock  
$726.00 $508.00
  • Technical Information
  • Properties
  • Literature
  • Application
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA006PQK
Chemical Name:
2,2,5,7,8-Pentamethyl-6-chromanol
CAS Number:
950-99-2
Molecular Formula:
C14H20O2
Molecular Weight:
220.3074
MDL Number:
MFCD00210347
SMILES:
Cc1c2OC(C)(C)CCc2c(c(c1C)O)C
NSC Number:
226236
Properties
Properties
 
BP:
344.3±42.0 °C(Predicted)  
Form:
Solid  
MP:
89-91 °C(lit.)  

Computed Properties
 
Complexity:
262  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
3.6  

Literature

Title: Chlorine atom substitution influences radical scavenging activity of 6-chromanol.

Journal: Bioorganic & medicinal chemistry 20120701

Title: How lipid unsaturation, peroxyl radical partitioning, and chromanol lipophilic tail affect the antioxidant activity of α-tocopherol: direct visualization via high-throughput fluorescence studies conducted with fluorogenic α-tocopherol analogues.

Journal: Journal of the American Chemical Society 20120620

Title: Is the chromanol head group of vitamin E nature's final truth on chain-breaking antioxidants?

Journal: FEBS letters 20120323

Title: Potassium 2,2,5,7,8-pentamethylchroman-6-oxide: a rationally designed base for Pd-catalysed amination.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120116

Title: Toxicogenomics and metabolomics of pentamethylchromanol (PMCol)-induced hepatotoxicity.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20111201

Title: 6-Hy-droxy-2,5,7,8-tetra-methyl-3,4-dihydro-2H-1-benzopyran-2-carbonitrile, from synchrotron data.

Journal: Acta crystallographica. Section E, Structure reports online 20110801

Title: Toxic metabolite formation from Troglitazone (TGZ): new insights from a DFT study.

Journal: Chemical research in toxicology 20110718

Title: On the way to understand antioxidants: chromanol and dimethoxyphenols gas-phase acidities.

Journal: Journal of mass spectrometry : JMS 20110701

Title: 2,2,5,7,8-Penta-methyl-chroman-6-yl 2,3,4,6-tetra-O-acetyl-α-d-glucopyran-oside from synchrotron data.

Journal: Acta crystallographica. Section E, Structure reports online 20110301

Title: Hypothyroidism of gene-targeted mice lacking Kcnq1.

Journal: Pflugers Archiv : European journal of physiology 20110101

Title: Chromanol derivatives--a novel class of CETP inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: Blocking effect of NIP-142 on the KCNQ1/KCNE1 channel current expressed in HEK293 cells.

Journal: Biological & pharmaceutical bulletin 20110101

Title: Lipid antioxidants: free radical scavenging versus regulation of enzymatic lipid peroxidation.

Journal: Journal of clinical biochemistry and nutrition 20110101

Title: Chromanols from Sargassum siliquastrum and their antioxidant activity in HT 1080 cells.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: Analysis of lipid content and quality in Arabidopsis plastids.

Journal: Methods in molecular biology (Clifton, N.J.) 20110101

Title: Cytoprotective effects of vitamin E homologues against glutamate-induced cell death in immature primary cortical neuron cultures: Tocopherols and tocotrienols exert similar effects by antioxidant function.

Journal: Free radical biology & medicine 20101130

Title: Inhibition of vascular smooth muscle cell proliferation by the vitamin E derivative pentamethylhydroxychromane in an in vitro and in vivo study: pivotal role of hydroxyl radical-mediated PLCgamma1 and JAK2 phosphorylation.

Journal: Free radical biology & medicine 20100901

Title: Inhibitory effect of PMC, a potent hydrophilic α-tocopherol derivative, on vascular smooth muscle cell proliferation: the pivotal role of PKC-α translocation.

Journal: Pharmaceutical biology 20100801

Title: Assessment of oral toxicity and safety of pentamethylchromanol (PMCol), a potential chemopreventative agent, in rats and dogs.

Journal: Toxicology 20100629

Title: Synthesis and characterization of BODIPY-alpha-tocopherol: a fluorescent form of vitamin E.

Journal: The Journal of organic chemistry 20100507

Title: Asymmetric synthesis of alpha-tocopherol.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20100125

Title: In-vitro and in-vivo metabolic studies of the candidate chemopreventative pentamethylchromanol using liquid chromatography/tandem mass spectrometry.

Journal: The Journal of pharmacy and pharmacology 20091001

Title: Organocatalytic asymmetric Friedel-Crafts alkylation/cyclization cascade reaction of 1-naphthols and alpha,beta-unsaturated aldehydes: an enantioselective synthesis of chromanes and dihydrobenzopyranes.

Journal: The Journal of organic chemistry 20090904

Title: Impact of glucose concentration on cardiac ventricular repolarization under I Kr/I Ks blocking agents.

Journal: Journal of molecular and cellular cardiology 20090801

Title: Glycosidic moiety changes the spectroscopic properties of dl-alpha-tocopherol in DMSO/water solution and in organic solvents.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20090715

Title: Diversity-oriented synthesis of furo[3,2-f]chromanes with antimycobacterial activity.

Journal: European journal of medicinal chemistry 20090601

Title: In vitro assessment of P450 induction potential of novel chemopreventive agents SR13668, 9-cis-UAB30, and pentamethychromanol in primary cultures of human hepatocytes.

Journal: Chemico-biological interactions 20090515

Title: Phenol-based lipophilic fluorescent antioxidant indicators: a rational approach.

Journal: The Journal of organic chemistry 20090515

Title: Cholesterol-mediated activation of P-glycoprotein: distinct effects on basal and drug-induced ATPase activities.

Journal: Journal of pharmaceutical sciences 20090501

Title: Chain-breaking antioxidant activity of reduced forms of mitochondria-targeted quinones, a novel type of geroprotectors.

Journal: Aging 20090501

Title: Comparison of the inhibitory effects of vitamin E analogues on melanogenesis in mouse B16 melanoma cells.

Journal: Cytotechnology 20090401

Title: Effects of nitric oxide donor antioxidants containing the phenol vitamin E substructure and a furoxan moiety on ischemia/reperfusion injury.

Journal: Arzneimittel-Forschung 20090101

Title: [Highly effective test-system for determination of the total antioxidant activity of human blood serum].

Journal: Biomeditsinskaia khimiia 20090101

Title: The specificity of neuroprotection by antioxidants.

Journal: Journal of biomedical science 20090101

Title: Diastereoselective synthesis of alpha-tocopherol: a new concept for the formation of chromanols.

Journal: Organic letters 20081120

Title: Tocochromanols, plastoquinol, and other biological prenyllipids as singlet oxygen quenchers-determination of singlet oxygen quenching rate constants and oxidation products.

Journal: Free radical biology & medicine 20080915

Title: Selective block of IKs plays a significant role in MAP triangulation induced by IKr block in isolated rabbit heart.

Journal: Journal of pharmacological and toxicological methods 20080101

Title: A theoretical investigation on the geometry and vibrational spectra of 10,10,2,6,5-pentamethyl-1-hydroxychroman: a model of alpha-tocopherol.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20071231

Title: The effect of the lipophilic cation lucigenin on mitochondria depends on the site of its reduction.

Journal: Biochemical pharmacology 20070815

Title: Calculation of the relative acidities and oxidation potentials of para-substituted phenols. A model for alpha-tocopherol in solution.

Journal: Organic & biomolecular chemistry 20070607

Title: Chromanol 293B binding in KCNQ1 (Kv7.1) channels involves electrostatic interactions with a potassium ion in the selectivity filter.

Journal: Molecular pharmacology 20070601

Title: Generation of superoxide and singlet oxygen from alpha-tocopherolquinone and analogues.

Journal: Free radical research 20070601

Title: Identification and quantitation of novel vitamin E metabolites, sulfated long-chain carboxychromanols, in human A549 cells and in rats.

Journal: Journal of lipid research 20070501

Title: Modulation of ERG channels by XE991.

Journal: Basic & clinical pharmacology & toxicology 20070501

Title: Advantages and limitation of BODIPY as a probe for the evaluation of lipid peroxidation and its inhibition by antioxidants in plasma.

Journal: Bioorganic & medicinal chemistry letters 20070401

Title: Neuroprotective effects of PMC, a potent alpha-tocopherol derivative, in brain ischemia-reperfusion: reduced neutrophil activation and anti-oxidant actions.

Journal: Biochemical pharmacology 20070301

Title: Kinetic and thermochemical study of the antioxidant activity of sulfur-containing analogues of vitamin E.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: Role of kinases and G-proteins in the hyposmotic stimulation of cardiac IKs.

Journal: Biochimica et biophysica acta 20061001

Title: A pharmacological action of vitamin E unrelated to its antioxidant capacity.

Journal: Methods and findings in experimental and clinical pharmacology 20061001

Title: Rb+ efflux through functional activation of cardiac KCNQ1/minK channels by the benzodiazepine R-L3 (L-364,373).

Journal: Assay and drug development technologies 20060801

Title: Incorporated sarcolemmal fish oil fatty acids shorten pig ventricular action potentials.

Journal: Cardiovascular research 20060601

Title: NO-donor phenols: a new class of products endowed with antioxidant and vasodilator properties.

Journal: Journal of medicinal chemistry 20060518

Title: Formation of singlet oxygen from solutions of vitamin E.

Journal: Free radical research 20060301

Title: A biomimetic chromanol cyclization leading to alpha-tocopherol.

Journal: Angewandte Chemie (International ed. in English) 20060206

Title: Transformation of alpha-tocopherol (vitamin E) and related chromanol model compounds into their phenoxonium ions by chemical oxidation with the nitrosonium cation.

Journal: The Journal of organic chemistry 20051209

Title: The protection of bioenergetic functions in mitochondria by new synthetic chromanols.

Journal: Biochemical pharmacology 20051101

Title: Prooxidant and antioxidant activity of vitamin E analogues and troglitazone.

Journal: Chemical research in toxicology 20051001

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

Journal: The Journal of organic chemistry 20050429

Title: Electron-transfer mechanism in radical-scavenging reactions by a vitamin E model in a protic medium.

Journal: Organic & biomolecular chemistry 20050221

Title: Role of nitric oxide in Ca2+ sensitivity of the slowly activating delayed rectifier K+ current in cardiac myocytes.

Journal: Circulation research 20050107

Title: Both beta-adrenergic receptor stimulation and cardiac tissue type have important roles in elucidating the functional effects of I(Ks) channel blockers in vitro.

Journal: Journal of pharmacological and toxicological methods 20050101

Title: Development of a new class of potential antiatherosclerosis agents: NO-donor antioxidants.

Journal: Bioorganic & medicinal chemistry letters 20041220

Title: 13C CP/MAS NMR studies of vitamin E model compounds.

Journal: Magnetic resonance in chemistry : MRC 20041001

Title: Kinetic studies on stilbazulenyl-bis-nitrone (STAZN), a nonphenolic chain-breaking antioxidant in solution, micelles, and lipid membranes.

Journal: The Journal of organic chemistry 20040430

Title: Inhibitory mechanisms of YC-1 and PMC in the induction of iNOS expression by lipoteichoic acid in RAW 264.7 macrophages.

Journal: Biochemical pharmacology 20040401

Title: Alpha-tocopherol influences the lipid membrane affinity of desipramine in a pH-dependent manner.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20040201

Title: Soft ionization mass spectrometry of chromanols produces radical cation molecular ions.

Journal: European journal of mass spectrometry (Chichester, England) 20040101

Title: Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium.

Journal: Organic & biomolecular chemistry 20031121

Title: Blockers of the slowly delayed rectifier potassium IKs channel: potential antiarrhythmic agents.

Journal: Current medicinal chemistry. Cardiovascular and hematological agents 20031001

Title: Androgen antagonist activity by the antioxidant moiety of vitamin E, 2,2,5,7,8-pentamethyl-6-chromanol in human prostate carcinoma cells.

Journal: Molecular cancer therapeutics 20030801

Title: Antioxidant effects of phytosterol and its components.

Journal: Journal of nutritional science and vitaminology 20030801

Title: Transmural heterogeneity of the action potential configuration in the feline left ventricle.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20030501

Title: Diesel exhaust particle-induced cell death of cultured normal human bronchial epithelial cells.

Journal: Biological & pharmaceutical bulletin 20030401

Title: Direct evidence for recycling of myeloperoxidase-catalyzed phenoxyl radicals of a vitamin E homologue, 2,2,5,7,8-pentamethyl-6-hydroxy chromane, by ascorbate/dihydrolipoate in living HL-60 cells.

Journal: Biochimica et biophysica acta 20030317

Title: Antioxidant action of 2,2,4,6-tetra-substituted 2,3-dihydro-5-hydroxybenzofuran against lipid peroxidation: effects of substituents and side chain.

Journal: Free radical research 20021101

Title: Naphthalene diols: a new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals.

Journal: The Journal of organic chemistry 20020726

Title: Antithrombotic effect of PMC, a potent alpha-tocopherol analogue on platelet plug formation in vivo.

Journal: British journal of haematology 20020601

Title: Reduction of 8a-hydroxy-2,2,5,7,8-pentamethyl-6-chromanone.

Journal: Redox report : communications in free radical research 20020101

Title: Cellular basis for complex T waves and arrhythmic activity following combined I(Kr) and I(Ks) block.

Journal: Journal of cardiovascular electrophysiology 20011201

Title: Pharmacokinetics and metabolism of a cysteinyl leukotriene-1 receptor antagonist from the heterocyclic chromanol series in rats: in vitro-in vivo correlation, gender-related differences, isoform identification, and comparison with metabolism in human hepatic tissue.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20011101

Title: Ionic basis for membrane potential changes induced by hypoosmotic stress in guinea-pig ventricular myocytes.

Journal: Cardiovascular research 20010701

Title: Diesel exhaust particle-induced cell death of human leukemic promyelocytic cells HL-60 and their variant cells HL-NR6.

Journal: Biological & pharmaceutical bulletin 20010401

Title: Co-oxidation of 2,2,5,7,8-pentamethyl-6-chromanol and diphenyl disulfide with 3-chloroperoxybenzoic acid.

Journal: Redox report : communications in free radical research 20010101

Title: Antioxidant activity of 5-alkoxymethyl-6-chromanols.

Journal: Redox report : communications in free radical research 20010101

Title: Kyriakopoulos CE, et al. A multicenter phase 1/2a dose-escalation study of the antioxidant moiety of vitamin E 2,2,5,7,8-pentamethyl-6-chromanol (APC-100) in men with advanced prostate cancer. Invest New Drugs. 2016 Apr;34(2):225-30.

Application
2,2,5,7,8-Pentamethyl-6-chromanol serves as a reagent for the quantitative analysis of α-tocopherol by GC/MS/MS. It can function as a model compound for α-tocopherol and undergo oxidation to yield 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanol. Additionally, it acts as an internal standard in HPLC for determining α- and γ-tocopherol levels in rabbit serum and liver.
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Tags:950-99-2 Molecular Formula|950-99-2 MDL|950-99-2 SMILES|950-99-2 2,2,5,7,8-Pentamethyl-6-chromanol
Catalog No.: AA006PQK
950-99-2,MFCD00210347
950-99-2 | 2,2,5,7,8-Pentamethyl-6-chromanol
Pack Size: 1g
Purity: 97%
in stock
$75.00 $53.00
Pack Size: 5g
Purity: 97%
in stock
$152.00 $107.00
Pack Size: 25g
Purity: 97%
in stock
$726.00 $508.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA006PQK
Chemical Name: 2,2,5,7,8-Pentamethyl-6-chromanol
CAS Number: 950-99-2
Molecular Formula: C14H20O2
Molecular Weight: 220.3074
MDL Number: MFCD00210347
SMILES: Cc1c2OC(C)(C)CCc2c(c(c1C)O)C
NSC Number: 226236
Properties
BP: 344.3±42.0 °C(Predicted)  
Form: Solid  
MP: 89-91 °C(lit.)  
Complexity: 262  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 16  
Hydrogen Bond Acceptor Count: 2  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 3.6  
Literature fold

Title: Chlorine atom substitution influences radical scavenging activity of 6-chromanol.

Journal: Bioorganic & medicinal chemistry20120701

Title: How lipid unsaturation, peroxyl radical partitioning, and chromanol lipophilic tail affect the antioxidant activity of α-tocopherol: direct visualization via high-throughput fluorescence studies conducted with fluorogenic α-tocopherol analogues.

Journal: Journal of the American Chemical Society20120620

Title: Is the chromanol head group of vitamin E nature's final truth on chain-breaking antioxidants?

Journal: FEBS letters20120323

Title: Potassium 2,2,5,7,8-pentamethylchroman-6-oxide: a rationally designed base for Pd-catalysed amination.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20120116

Title: Toxicogenomics and metabolomics of pentamethylchromanol (PMCol)-induced hepatotoxicity.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20111201

Title: 6-Hy-droxy-2,5,7,8-tetra-methyl-3,4-dihydro-2H-1-benzopyran-2-carbonitrile, from synchrotron data.

Journal: Acta crystallographica. Section E, Structure reports online20110801

Title: Toxic metabolite formation from Troglitazone (TGZ): new insights from a DFT study.

Journal: Chemical research in toxicology20110718

Title: On the way to understand antioxidants: chromanol and dimethoxyphenols gas-phase acidities.

Journal: Journal of mass spectrometry : JMS20110701

Title: 2,2,5,7,8-Penta-methyl-chroman-6-yl 2,3,4,6-tetra-O-acetyl-α-d-glucopyran-oside from synchrotron data.

Journal: Acta crystallographica. Section E, Structure reports online20110301

Title: Hypothyroidism of gene-targeted mice lacking Kcnq1.

Journal: Pflugers Archiv : European journal of physiology20110101

Title: Chromanol derivatives--a novel class of CETP inhibitors.

Journal: Bioorganic & medicinal chemistry letters20110101

Title: Blocking effect of NIP-142 on the KCNQ1/KCNE1 channel current expressed in HEK293 cells.

Journal: Biological & pharmaceutical bulletin20110101

Title: Lipid antioxidants: free radical scavenging versus regulation of enzymatic lipid peroxidation.

Journal: Journal of clinical biochemistry and nutrition20110101

Title: Chromanols from Sargassum siliquastrum and their antioxidant activity in HT 1080 cells.

Journal: Chemical & pharmaceutical bulletin20110101

Title: Analysis of lipid content and quality in Arabidopsis plastids.

Journal: Methods in molecular biology (Clifton, N.J.)20110101

Title: Cytoprotective effects of vitamin E homologues against glutamate-induced cell death in immature primary cortical neuron cultures: Tocopherols and tocotrienols exert similar effects by antioxidant function.

Journal: Free radical biology & medicine20101130

Title: Inhibition of vascular smooth muscle cell proliferation by the vitamin E derivative pentamethylhydroxychromane in an in vitro and in vivo study: pivotal role of hydroxyl radical-mediated PLCgamma1 and JAK2 phosphorylation.

Journal: Free radical biology & medicine20100901

Title: Inhibitory effect of PMC, a potent hydrophilic α-tocopherol derivative, on vascular smooth muscle cell proliferation: the pivotal role of PKC-α translocation.

Journal: Pharmaceutical biology20100801

Title: Assessment of oral toxicity and safety of pentamethylchromanol (PMCol), a potential chemopreventative agent, in rats and dogs.

Journal: Toxicology20100629

Title: Synthesis and characterization of BODIPY-alpha-tocopherol: a fluorescent form of vitamin E.

Journal: The Journal of organic chemistry20100507

Title: Asymmetric synthesis of alpha-tocopherol.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20100125

Title: In-vitro and in-vivo metabolic studies of the candidate chemopreventative pentamethylchromanol using liquid chromatography/tandem mass spectrometry.

Journal: The Journal of pharmacy and pharmacology20091001

Title: Organocatalytic asymmetric Friedel-Crafts alkylation/cyclization cascade reaction of 1-naphthols and alpha,beta-unsaturated aldehydes: an enantioselective synthesis of chromanes and dihydrobenzopyranes.

Journal: The Journal of organic chemistry20090904

Title: Impact of glucose concentration on cardiac ventricular repolarization under I Kr/I Ks blocking agents.

Journal: Journal of molecular and cellular cardiology20090801

Title: Glycosidic moiety changes the spectroscopic properties of dl-alpha-tocopherol in DMSO/water solution and in organic solvents.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy20090715

Title: Diversity-oriented synthesis of furo[3,2-f]chromanes with antimycobacterial activity.

Journal: European journal of medicinal chemistry20090601

Title: In vitro assessment of P450 induction potential of novel chemopreventive agents SR13668, 9-cis-UAB30, and pentamethychromanol in primary cultures of human hepatocytes.

Journal: Chemico-biological interactions20090515

Title: Phenol-based lipophilic fluorescent antioxidant indicators: a rational approach.

Journal: The Journal of organic chemistry20090515

Title: Cholesterol-mediated activation of P-glycoprotein: distinct effects on basal and drug-induced ATPase activities.

Journal: Journal of pharmaceutical sciences20090501

Title: Chain-breaking antioxidant activity of reduced forms of mitochondria-targeted quinones, a novel type of geroprotectors.

Journal: Aging20090501

Title: Comparison of the inhibitory effects of vitamin E analogues on melanogenesis in mouse B16 melanoma cells.

Journal: Cytotechnology20090401

Title: Effects of nitric oxide donor antioxidants containing the phenol vitamin E substructure and a furoxan moiety on ischemia/reperfusion injury.

Journal: Arzneimittel-Forschung20090101

Title: [Highly effective test-system for determination of the total antioxidant activity of human blood serum].

Journal: Biomeditsinskaia khimiia20090101

Title: The specificity of neuroprotection by antioxidants.

Journal: Journal of biomedical science20090101

Title: Diastereoselective synthesis of alpha-tocopherol: a new concept for the formation of chromanols.

Journal: Organic letters20081120

Title: Tocochromanols, plastoquinol, and other biological prenyllipids as singlet oxygen quenchers-determination of singlet oxygen quenching rate constants and oxidation products.

Journal: Free radical biology & medicine20080915

Title: Selective block of IKs plays a significant role in MAP triangulation induced by IKr block in isolated rabbit heart.

Journal: Journal of pharmacological and toxicological methods20080101

Title: A theoretical investigation on the geometry and vibrational spectra of 10,10,2,6,5-pentamethyl-1-hydroxychroman: a model of alpha-tocopherol.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy20071231

Title: The effect of the lipophilic cation lucigenin on mitochondria depends on the site of its reduction.

Journal: Biochemical pharmacology20070815

Title: Calculation of the relative acidities and oxidation potentials of para-substituted phenols. A model for alpha-tocopherol in solution.

Journal: Organic & biomolecular chemistry20070607

Title: Chromanol 293B binding in KCNQ1 (Kv7.1) channels involves electrostatic interactions with a potassium ion in the selectivity filter.

Journal: Molecular pharmacology20070601

Title: Generation of superoxide and singlet oxygen from alpha-tocopherolquinone and analogues.

Journal: Free radical research20070601

Title: Identification and quantitation of novel vitamin E metabolites, sulfated long-chain carboxychromanols, in human A549 cells and in rats.

Journal: Journal of lipid research20070501

Title: Modulation of ERG channels by XE991.

Journal: Basic & clinical pharmacology & toxicology20070501

Title: Advantages and limitation of BODIPY as a probe for the evaluation of lipid peroxidation and its inhibition by antioxidants in plasma.

Journal: Bioorganic & medicinal chemistry letters20070401

Title: Neuroprotective effects of PMC, a potent alpha-tocopherol derivative, in brain ischemia-reperfusion: reduced neutrophil activation and anti-oxidant actions.

Journal: Biochemical pharmacology20070301

Title: Kinetic and thermochemical study of the antioxidant activity of sulfur-containing analogues of vitamin E.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20070101

Title: Role of kinases and G-proteins in the hyposmotic stimulation of cardiac IKs.

Journal: Biochimica et biophysica acta20061001

Title: A pharmacological action of vitamin E unrelated to its antioxidant capacity.

Journal: Methods and findings in experimental and clinical pharmacology20061001

Title: Rb+ efflux through functional activation of cardiac KCNQ1/minK channels by the benzodiazepine R-L3 (L-364,373).

Journal: Assay and drug development technologies20060801

Title: Incorporated sarcolemmal fish oil fatty acids shorten pig ventricular action potentials.

Journal: Cardiovascular research20060601

Title: NO-donor phenols: a new class of products endowed with antioxidant and vasodilator properties.

Journal: Journal of medicinal chemistry20060518

Title: Formation of singlet oxygen from solutions of vitamin E.

Journal: Free radical research20060301

Title: A biomimetic chromanol cyclization leading to alpha-tocopherol.

Journal: Angewandte Chemie (International ed. in English)20060206

Title: Transformation of alpha-tocopherol (vitamin E) and related chromanol model compounds into their phenoxonium ions by chemical oxidation with the nitrosonium cation.

Journal: The Journal of organic chemistry20051209

Title: The protection of bioenergetic functions in mitochondria by new synthetic chromanols.

Journal: Biochemical pharmacology20051101

Title: Prooxidant and antioxidant activity of vitamin E analogues and troglitazone.

Journal: Chemical research in toxicology20051001

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

Journal: The Journal of organic chemistry20050429

Title: Electron-transfer mechanism in radical-scavenging reactions by a vitamin E model in a protic medium.

Journal: Organic & biomolecular chemistry20050221

Title: Role of nitric oxide in Ca2+ sensitivity of the slowly activating delayed rectifier K+ current in cardiac myocytes.

Journal: Circulation research20050107

Title: Both beta-adrenergic receptor stimulation and cardiac tissue type have important roles in elucidating the functional effects of I(Ks) channel blockers in vitro.

Journal: Journal of pharmacological and toxicological methods20050101

Title: Development of a new class of potential antiatherosclerosis agents: NO-donor antioxidants.

Journal: Bioorganic & medicinal chemistry letters20041220

Title: 13C CP/MAS NMR studies of vitamin E model compounds.

Journal: Magnetic resonance in chemistry : MRC20041001

Title: Kinetic studies on stilbazulenyl-bis-nitrone (STAZN), a nonphenolic chain-breaking antioxidant in solution, micelles, and lipid membranes.

Journal: The Journal of organic chemistry20040430

Title: Inhibitory mechanisms of YC-1 and PMC in the induction of iNOS expression by lipoteichoic acid in RAW 264.7 macrophages.

Journal: Biochemical pharmacology20040401

Title: Alpha-tocopherol influences the lipid membrane affinity of desipramine in a pH-dependent manner.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences20040201

Title: Soft ionization mass spectrometry of chromanols produces radical cation molecular ions.

Journal: European journal of mass spectrometry (Chichester, England)20040101

Title: Kinetic study of the electron-transfer oxidation of the phenolate anion of a vitamin E model by molecular oxygen generating superoxide anion in an aprotic medium.

Journal: Organic & biomolecular chemistry20031121

Title: Blockers of the slowly delayed rectifier potassium IKs channel: potential antiarrhythmic agents.

Journal: Current medicinal chemistry. Cardiovascular and hematological agents20031001

Title: Androgen antagonist activity by the antioxidant moiety of vitamin E, 2,2,5,7,8-pentamethyl-6-chromanol in human prostate carcinoma cells.

Journal: Molecular cancer therapeutics20030801

Title: Antioxidant effects of phytosterol and its components.

Journal: Journal of nutritional science and vitaminology20030801

Title: Transmural heterogeneity of the action potential configuration in the feline left ventricle.

Journal: Circulation journal : official journal of the Japanese Circulation Society20030501

Title: Diesel exhaust particle-induced cell death of cultured normal human bronchial epithelial cells.

Journal: Biological & pharmaceutical bulletin20030401

Title: Direct evidence for recycling of myeloperoxidase-catalyzed phenoxyl radicals of a vitamin E homologue, 2,2,5,7,8-pentamethyl-6-hydroxy chromane, by ascorbate/dihydrolipoate in living HL-60 cells.

Journal: Biochimica et biophysica acta20030317

Title: Antioxidant action of 2,2,4,6-tetra-substituted 2,3-dihydro-5-hydroxybenzofuran against lipid peroxidation: effects of substituents and side chain.

Journal: Free radical research20021101

Title: Naphthalene diols: a new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals.

Journal: The Journal of organic chemistry20020726

Title: Antithrombotic effect of PMC, a potent alpha-tocopherol analogue on platelet plug formation in vivo.

Journal: British journal of haematology20020601

Title: Reduction of 8a-hydroxy-2,2,5,7,8-pentamethyl-6-chromanone.

Journal: Redox report : communications in free radical research20020101

Title: Cellular basis for complex T waves and arrhythmic activity following combined I(Kr) and I(Ks) block.

Journal: Journal of cardiovascular electrophysiology20011201

Title: Pharmacokinetics and metabolism of a cysteinyl leukotriene-1 receptor antagonist from the heterocyclic chromanol series in rats: in vitro-in vivo correlation, gender-related differences, isoform identification, and comparison with metabolism in human hepatic tissue.

Journal: Drug metabolism and disposition: the biological fate of chemicals20011101

Title: Ionic basis for membrane potential changes induced by hypoosmotic stress in guinea-pig ventricular myocytes.

Journal: Cardiovascular research20010701

Title: Diesel exhaust particle-induced cell death of human leukemic promyelocytic cells HL-60 and their variant cells HL-NR6.

Journal: Biological & pharmaceutical bulletin20010401

Title: Co-oxidation of 2,2,5,7,8-pentamethyl-6-chromanol and diphenyl disulfide with 3-chloroperoxybenzoic acid.

Journal: Redox report : communications in free radical research20010101

Title: Antioxidant activity of 5-alkoxymethyl-6-chromanols.

Journal: Redox report : communications in free radical research20010101

Title: Kyriakopoulos CE, et al. A multicenter phase 1/2a dose-escalation study of the antioxidant moiety of vitamin E 2,2,5,7,8-pentamethyl-6-chromanol (APC-100) in men with advanced prostate cancer. Invest New Drugs. 2016 Apr;34(2):225-30.

Application fold
2,2,5,7,8-Pentamethyl-6-chromanol serves as a reagent for the quantitative analysis of α-tocopherol by GC/MS/MS. It can function as a model compound for α-tocopherol and undergo oxidation to yield 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanol. Additionally, it acts as an internal standard in HPLC for determining α- and γ-tocopherol levels in rabbit serum and liver.
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