171270-07-8Relevant academic research and scientific papers
Radical scavenging activity and performance of novel phenolic antioxidants in oils during storage and frying
Catel, Yohann,Aladedunye, Felix,Przybylski, Roman
, p. 55 - 66 (2012/03/27)
Novel phenolic antioxidants: 2a (6′-hydroxy-2′,5′, 7′,8′-tetramethylchroman-2′-yl)methyl 3-methoxy-4- hydroxycinnamate, 2b (6′-hydroxy-2′,5′,7′,8′- tetramethylchroman-2′-yl)methyl 3,5-dimethoxy-4-hydroxycinnamate, 2c (6′-hydroxy-2′,5′,7′,8′-tetramethylchr
New possibilities in a synthesis of (2R,4'R,8'R)-α-tocopherol (natural vitamin E)
Spivak, Anna Yu,Shafikov, Ruslan V.,Odinokov, Victor N.
scheme or table, p. 67 - 75 (2011/06/21)
New methods for the synthesis of homochiral C14 and C 15-terpenoids desired as building blocks for phytilic side chain of natural α-tocopherol have been developed. A natural phytone resulted from the proposed effective method of chlo
Synthesis, radical scavenging activity, protection during storage, and frying by novel antioxidants
Catel, Yohann,Aladedunye, Felix,Przybylski, Roman
, p. 11081 - 11089 (2011/06/21)
Novel antioxidants, derivatives of trolox, and selected phenolic acids have been prepared in good yields and fully characterized by 1H NMR, 13C NMR, and MS. Their antioxidant activities have been assessed by DPPH and ORAC assays, and during frying and accelerated storage tests. Novel phenolic compounds exhibited higher radical scavenging activities than both trolox and R-tocopherol. Trolox hydroxybenzoate showed a significantly higher protection than R-tocopherol under storage conditions. All new antioxidants performed better than R-tocopherol under frying conditions. Moreover, their outstanding thermal stability makes them more valuable than R-tocopherol for frying applications.
Enantioselective transesterification of (±)-6-benzyloxy-2,5,7,8- tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol catalyzed by the Amano PS lipase in the ionic liquid [bmim]PF6
Shafikov,Spivak, A. Yu.,Odinokov
, p. 2129 - 2132 (2011/07/30)
(S)-(-)-6-Benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2- ylmethanol, a synthon for the design of natural α-tocopherol, was obtained by kinetically selective acetylation of the corresponding racemic alcohol in the presence of the Amano PS lipase from Burkholderia cepacia in the ionic liquid 1-butyl-3-methylimidazolinium hexafluorophosphate ([bmim]PF6).
Synthesis of triterpene acids conjugates with α-tocopherol synthetic analogs
Spivak,Mufazzalova,Shakurova,Odinokov
scheme or table, p. 1355 - 1363 (2011/01/04)
Heterodimers were synthesized of pharmacologically important α-tocopherol synthetic analogs with triterpene acids(betulonic, betulinic), potential polyfunctionsl drugs possessing antioxidant activity. The combination of the fragments of biologically active substances was performed through linkers (residues of succinic acid, hydrazine, glycine, tetramethylenediamine) binding the side chain of the antioxidant molecule with atoms C3 or C28 of the terpenoid.
Development of small-molecule cyclin D1-ablative agents
Huang, Jui-Wen,Shiau, Chung-Wai,Yang, Jian,Wang, Da-Sheng,Chiu, Hao-Chieh,Chen, Ching-Yu,Chen, Ching-Shih
, p. 4684 - 4689 (2007/10/03)
Previously, we demonstrated that the peroxisome proliferator-activated receptor γ (PPARγ) agonist troglitazone mediated the repression of cyclin D1 in MCF-7 breast cancer cells by facilitating proteasome-facilitated proteolysis. This PPARγ-independent mec
Improved synthesis of tocopherol fatty alcohols and analogs: microglial activation modulators
Muller, Thierry,Coowar, Djalil,Hanbali, Mazen,Heuschling, Paul,Luu, Bang
, p. 12025 - 12040 (2007/10/03)
The synthesis of tocopherol fatty alcohols (TFAs), potent microglial activation modulators, was achieved via C-alkylation of trimethylhydroquinone. Several analogs, in particular water-soluble prodrugs, have been synthesized using a Wittig reaction and th
Enantioselective synthesis of (2R,4'R,8'R)-α-tocopherol (Vitamin E) based on enzymatic function
Nozawa, Masako,Takahashi, Keiko,Kato, Keisuke,Akita, Hiroyuki
, p. 272 - 277 (2007/10/03)
Syntheses of (S)-chroman-2-carboxaldehyde congener 1 and (S)-chiral isoprene unit 3 were achieved based on the enzymatic acetylation of (±)- chroman-2-methanol 6 and (±)-(2,3)-anti-2-methyl-3-(p-methoxyphenyl)-1,3- propane diol 12, respectively. Synthesis of the side-chain part corresponding to (3R,7R)-3,7,11-trimethyldodecan-1-ol 27 was achieved by the coupling reaction of (S)-3 and (R)-3,7-dimethyloctyl iodide 4. The Wittig reaction of (3R,7R)-phosphonium salt 2 derived from (3R,7R)-27 and (S)-1 gave the olefin 28 which was subjected to catalytic hydrogenation to afford (2R,4'R,8'R)-α- tocopherol.
Synthesis of α-tocopherol analogues
Suarna, Cacang,Dean, Roger T.,Southwell-Keely, Peter T.
, p. 1129 - 1135 (2007/10/03)
A range of α-tocopherol analogues of varying side-chain length and structure has been prepared by the Wittig reaction of alkyltriphenylphosphonium bromides with either 6-benzyloxy-2,5,7,8-tetramethylchroman-2-carbaldehyde (8) or 6-acetoxy-2,5,7,8,-tetramethylchroman-2-carbaldehyde (14). These analogues include 2-hexyl-2,5,7,8-tetramethylchroman-6-ol (11), 2-heptyl-2,5,7,8-tetramethylchroman-6-ol (12) and 2,5,7,8-tetramethyl-2-(pent-l-enyl)chroman-6-ol (15). Methoxycarbonylmethyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate (2) was formed by reaction of the triethylammonium salt of trolox (1) with methyl bromoacetate. Reaction of methoxycarbonylmethyltriphenylphosphonium bromide (16) with (8) did not produce the expected methyl 3-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)prop-2-enoate (17), but rather 4-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)but-3-en-2-one (22). A proposed mechanism for this unusual reaction is discussed.
Chroman derivatives and their preparation
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, (2008/06/13)
Chroman derivatives of the general formula I STR1 where A--B is --CH2 --CH2 --(Ia), --CH=CH--(Ib), --CHOH--CH2 --(Ic) or --CO--CH2 --(Id), R1 is --CH2 --O--R' or STR2 where R' is C1/s
