3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol (BioDeep_00000036088)

   

human metabolite Volatile Flavor Compounds


代谢物信息卡片


3,4-dihydro-6-Hydroxy-2,2,5,7,8-pentamethyl-2H-1-benzopyran

化学式: C14H20O2 (220.14632200000003)
中文名称: 2,2,5,7,8-五甲基-6-苯并甲醇, 2,2,5,7,8-五甲基-6-色满醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=C(C2=C(CCC(O2)(C)C)C(=C1O)C)C
InChI: InChI=1S/C14H20O2/c1-8-9(2)13-11(10(3)12(8)15)6-7-14(4,5)16-13/h15H,6-7H2,1-5H3

描述信息

3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol is found in fats and oils. 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol is an antioxidant for edible oils and fats.
Antioxidant for edible oils and fats. 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol is found in fats and oils.
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C146993 - Androgen Receptor Inhibitor
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen
D020011 - Protective Agents > D000975 - Antioxidants

同义名列表

10 个代谢物同义名

3,4-dihydro-6-Hydroxy-2,2,5,7,8-pentamethyl-2H-1-benzopyran; 2H-1-Benzopyran-6-ol,3,4-dihydro-2,2,5,7,8-pentamethyl-; 2,2,5,7,8-pentamethyl-3,4-dihydro-2H-1-benzopyran-6-ol; 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol; 2,2,5,7,8-pentamethyl-3,4-dihydro-1-benzopyran-6-ol; 2,2,5,7,8-Pentamethyl-benz[b]dihydropyran-6-ol; 2,2,5,7,8-Pentamethyl-6-chromanol; PMHCR; PMHC; 2,2,5,7,8-Pentamethyl-6-chromanol



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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Plant Reactome(0)

INOH(0)

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1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

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文献列表

  • Qianqian Wang, Ye Zhong, Nihong Li, Le Du, Rui Ye, Yicheng Xie, Fan Hu. Combination of dimethylmethoxy chromanol and turmeric root extract synergically attenuates ultraviolet-induced oxidative damage by increasing endogenous antioxidants in HaCaT cells. Skin research and technology : official journal of International Society for Bioengineering and the Skin (ISBS) [and] International Society for Digital Imaging of Skin (ISDIS) [and] International Society for Skin Imaging (ISSI). 2023 Dec; 29(12):e13539. doi: 10.1111/srt.13539. [PMID: 38115632]
  • P C Vogelaar, D Nakladal, D H Swart, Ľ Tkáčiková, S Tkáčiková, A C van der Graaf, R H Henning, G Krenning. Towards prevention of ischemia-reperfusion kidney injury: Pre-clinical evaluation of 6-chromanol derivatives and the lead compound SUL-138✰. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2022 Jan; 168(?):106033. doi: 10.1016/j.ejps.2021.106033. [PMID: 34610451]
  • Beatrycze Nowicka, Agnieszka Trela-Makowej, Dariusz Latowski, Kazimierz Strzalka, Renata Szymańska. Antioxidant and Signaling Role of Plastid-Derived Isoprenoid Quinones and Chromanols. International journal of molecular sciences. 2021 Mar; 22(6):. doi: 10.3390/ijms22062950. [PMID: 33799456]
  • Kilia Y Liu, Qing Jiang. Tocopherols and Tocotrienols Are Bioavailable in Rats and Primarily Excreted in Feces as the Intact Forms and 13'-Carboxychromanol Metabolites. The Journal of nutrition. 2020 02; 150(2):222-230. doi: 10.1093/jn/nxz217. [PMID: 31495894]
  • Aleksandra Szulczewska-Remi, Małgorzata Nogala-Kałucka, Krzysztof W Nowak. Study on the influence of palm oil on blood and liver biochemical parameters, beta-carotene and tocochromanols content as well as antioxidant activity in rats. Journal of food biochemistry. 2019 02; 43(2):e12707. doi: 10.1111/jfbc.12707. [PMID: 31353667]
  • Carla Souza, Patrícia M B G Maia Campos. Development and photoprotective effect of a sunscreen containing the antioxidants Spirulina and dimethylmethoxy chromanol on sun-induced skin damage. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2017 Jun; 104(?):52-64. doi: 10.1016/j.ejps.2017.03.026. [PMID: 28341613]
  • Yumi Jang, Na-Young Park, Agnetha Linn Rostgaard-Hansen, Jianjie Huang, Qing Jiang. Vitamin E metabolite 13'-carboxychromanols inhibit pro-inflammatory enzymes, induce apoptosis and autophagy in human cancer cells by modulating sphingolipids and suppress colon tumor development in mice. Free radical biology & medicine. 2016 06; 95(?):190-9. doi: 10.1016/j.freeradbiomed.2016.03.018. [PMID: 27016075]
  • Michał Gabruk, Iwona Habina, Jerzy Kruk, Jolanta Dłużewska, Renata Szymańska. Natural variation in tocochromanols content in Arabidopsis thaliana accessions - the effect of temperature and light intensity. Physiologia plantarum. 2016 Jun; 157(2):147-60. doi: 10.1111/ppl.12408. [PMID: 27174597]
  • Christos E Kyriakopoulos, Elisabeth I Heath, Jens C Eickhoff, Jill Kolesar, Mulusew Yayehyirad, Thomas Moll, George Wilding, Glenn Liu. 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. Investigational new drugs. 2016 Apr; 34(2):225-30. doi: 10.1007/s10637-016-0334-y. [PMID: 26924129]
  • Long Zou, Casimir C Akoh. Antioxidant activities of annatto and palm tocotrienol-rich fractions in fish oil and structured lipid-based infant formula emulsion. Food chemistry. 2015 Feb; 168(?):504-11. doi: 10.1016/j.foodchem.2014.07.098. [PMID: 25172741]
  • Maria Wallert, Sandy Mosig, Knut Rennert, Harald Funke, Michael Ristow, Roberto Maria Pellegrino, Gabriele Cruciani, Francesco Galli, Stefan Lorkowski, Marc Birringer. Long-chain metabolites of α-tocopherol occur in human serum and inhibit macrophage foam cell formation in vitro. Free radical biology & medicine. 2014 Mar; 68(?):43-51. doi: 10.1016/j.freeradbiomed.2013.11.009. [PMID: 24296243]
  • Katerina Krumova, Sayuri Friedland, Gonzalo Cosa. 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 of the American Chemical Society. 2012 Jun; 134(24):10102-13. doi: 10.1021/ja301680m. [PMID: 22568598]
  • Maike J Ohlow, Matthias Granold, Mathias Schreckenberger, Bernd Moosmann. Is the chromanol head group of vitamin E nature's final truth on chain-breaking antioxidants?. FEBS letters. 2012 Mar; 586(6):711-6. doi: 10.1016/j.febslet.2012.01.022. [PMID: 22281199]
  • Toufan Parman, Deborah I Bunin, Hanna H Ng, Jonathan E McDunn, Jacob E Wulff, Abraham Wang, Robert Swezey, Laura Rasay, David G Fairchild, Izet M Kapetanovic, Carol E Green. Toxicogenomics and metabolomics of pentamethylchromanol (PMCol)-induced hepatotoxicity. Toxicological sciences : an official journal of the Society of Toxicology. 2011 Dec; 124(2):487-501. doi: 10.1093/toxsci/kfr238. [PMID: 21920950]
  • Alejandro K Samhan-Arias, Yulia Y Tyurina, Valerian E Kagan. Lipid antioxidants: free radical scavenging versus regulation of enzymatic lipid peroxidation. Journal of clinical biochemistry and nutrition. 2011 Jan; 48(1):91-5. doi: 10.3164/jcbn.11-009fr. [PMID: 21297919]
  • Anna Maria Zbierzak, Peter Dörmann, Georg Hölzl. Analysis of lipid content and quality in Arabidopsis plastids. Methods in molecular biology (Clifton, N.J.). 2011; 775(?):411-26. doi: 10.1007/978-1-61779-237-3_22. [PMID: 21863456]
  • Henning Fröhlich, Krishna M Boini, Guiscard Seebohm, Nathalie Strutz-Seebohm, Oana N Ureche, Michael Föller, Melanie Eichenmüller, Ekaterina Shumilina, Ganesh Pathare, Anurag Kumar Singh, Ursula Seidler, Karl E Pfeifer, Florian Lang. Hypothyroidism of gene-targeted mice lacking Kcnq1. Pflugers Archiv : European journal of physiology. 2011 Jan; 461(1):45-52. doi: 10.1007/s00424-010-0890-5. [PMID: 20978783]
  • Jung Im Lee, Youngwan Seo. Chromanols from Sargassum siliquastrum and their antioxidant activity in HT 1080 cells. Chemical & pharmaceutical bulletin. 2011; 59(6):757-61. doi: 10.1248/cpb.59.757. [PMID: 21628914]
  • Yoshiro Saito, Keiko Nishio, Yoko Ogawa Akazawa, Kazunori Yamanaka, Akiko Miyama, Yasukazu Yoshida, Noriko Noguchi, Etsuo Niki. 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. Free radical biology & medicine. 2010 Nov; 49(10):1542-9. doi: 10.1016/j.freeradbiomed.2010.08.016. [PMID: 20736061]
  • Matthew Lindeblad, Izet M Kapetanovic, Kasim K Kabirov, Carol J Detrisac, Nancy Dinger, Irina Mankovskaya, Alexander Zakharov, Alexander V Lyubimov. Assessment of oral toxicity and safety of pentamethylchromanol (PMCol), a potential chemopreventative agent, in rats and dogs. Toxicology. 2010 Jun; 273(1-3):19-28. doi: 10.1016/j.tox.2010.04.011. [PMID: 20430063]
  • Gregory S Gorman, Lori Coward, Corenna Kerstner-Wood, Lea Freeman, Charles D Hebert, Izet M Kapetanovic. In-vitro and in-vivo metabolic studies of the candidate chemopreventative pentamethylchromanol using liquid chromatography/tandem mass spectrometry. The Journal of pharmacy and pharmacology. 2009 Oct; 61(10):1309-18. doi: 10.1211/jpp/61.10.0006. [PMID: 19814862]
  • Katerina Krumova, Paul Oleynik, Pierre Karam, Gonzalo Cosa. Phenol-based lipophilic fluorescent antioxidant indicators: a rational approach. The Journal of organic chemistry. 2009 May; 74(10):3641-51. doi: 10.1021/jo900335z. [PMID: 19364120]
  • Vitaly A Roginsky, Vadim N Tashlitsky, Vladimir P Skulachev. Chain-breaking antioxidant activity of reduced forms of mitochondria-targeted quinones, a novel type of geroprotectors. Aging. 2009 May; 1(5):481-9. doi: 10.18632/aging.100049. [PMID: 20195487]
  • Sara Belli, Priska M Elsener, Heidi Wunderli-Allenspach, Stefanie D Krämer. Cholesterol-mediated activation of P-glycoprotein: distinct effects on basal and drug-induced ATPase activities. Journal of pharmaceutical sciences. 2009 May; 98(5):1905-18. doi: 10.1002/jps.21558. [PMID: 18937360]
  • Iu A Grigorenko, D I Metelitsa, N V Piven', L N Lukhverchik, O I Shadyro. [Highly effective test-system for determination of the total antioxidant activity of human blood serum]. Biomeditsinskaia khimiia. 2009 May; 55(3):350-60. doi: NULL. [PMID: 19663008]
  • Jolanta Gruszka, Anna Pawlak, Jerzy Kruk. Tocochromanols, plastoquinol, and other biological prenyllipids as singlet oxygen quenchers-determination of singlet oxygen quenching rate constants and oxidation products. Free radical biology & medicine. 2008 Sep; 45(6):920-8. doi: 10.1016/j.freeradbiomed.2008.06.025. [PMID: 18634868]
  • Qing Jiang, Helene Freiser, Karl V Wood, Xinmin Yin. Identification and quantitation of novel vitamin E metabolites, sulfated long-chain carboxychromanols, in human A549 cells and in rats. Journal of lipid research. 2007 May; 48(5):1221-30. doi: 10.1194/jlr.d700001-jlr200. [PMID: 17299205]
  • Nanako Itoh, Jiaofei Cao, Zhi-Hua Chen, Yasukazu Yoshida, Etsuo Niki. Advantages and limitation of BODIPY as a probe for the evaluation of lipid peroxidation and its inhibition by antioxidants in plasma. Bioorganic & medicinal chemistry letters. 2007 Apr; 17(7):2059-63. doi: 10.1016/j.bmcl.2007.01.080. [PMID: 17300936]
  • Donatella Boschi, Gian Cesare Tron, Loretta Lazzarato, Konstantin Chegaev, Clara Cena, Antonella Di Stilo, Marta Giorgis, Massimo Bertinaria, Roberta Fruttero, Alberto Gasco. NO-donor phenols: a new class of products endowed with antioxidant and vasodilator properties. Journal of medicinal chemistry. 2006 May; 49(10):2886-97. doi: 10.1021/jm0510530. [PMID: 16686532]
  • Katrin Staniek, Thomas Rosenau, Wolfgang Gregor, Hans Nohl, Lars Gille. The protection of bioenergetic functions in mitochondria by new synthetic chromanols. Biochemical pharmacology. 2005 Nov; 70(9):1361-70. doi: 10.1016/j.bcp.2005.07.030. [PMID: 16150421]
  • Shahrzad Tafazoli, James S Wright, Peter J O'Brien. Prooxidant and antioxidant activity of vitamin E analogues and troglitazone. Chemical research in toxicology. 2005 Oct; 18(10):1567-74. doi: 10.1021/tx0500575. [PMID: 16533021]
  • Clara Cena, Donatella Boschi, Gian Cesare Tron, Kostantin Chegaev, Loretta Lazzarato, Antonella Di Stilo, Manuela Aragno, Roberta Fruttero, Alberto Gasco. Development of a new class of potential antiatherosclerosis agents: NO-donor antioxidants. Bioorganic & medicinal chemistry letters. 2004 Dec; 14(24):5971-4. doi: 10.1016/j.bmcl.2004.10.006. [PMID: 15546710]
  • Subhash C Mojumdar, David A Becker, Gino A DiLabio, James J Ley, L Ross C Barclay, K U Ingold. Kinetic studies on stilbazulenyl-bis-nitrone (STAZN), a nonphenolic chain-breaking antioxidant in solution, micelles, and lipid membranes. The Journal of organic chemistry. 2004 Apr; 69(9):2929-36. doi: 10.1021/jo030390i. [PMID: 15104428]
  • Marco Marenchino, Andrea L Alpstäg-Wöhrle, Barbara Christen, Heidi Wunderli-Allenspach, Stefanie D Krämer. Alpha-tocopherol influences the lipid membrane affinity of desipramine in a pH-dependent manner. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2004 Feb; 21(2-3):313-21. doi: 10.1016/j.ejps.2003.10.022. [PMID: 14757504]
  • Yasukazu Yoshida, Etsuo Niki. Antioxidant effects of phytosterol and its components. Journal of nutritional science and vitaminology. 2003 Aug; 49(4):277-80. doi: 10.3177/jnsv.49.277. [PMID: 14598915]
  • Yasukazu Yoshida, Noriko Noguchi, Akira Watanabe, Yoshihide Iwaki, Makoto Yanagisawa, Tatsuhiko Kodama, Osamu Cynshi, Etsuo Niki. Antioxidant action of 2,2,4,6-tetra-substituted 2,3-dihydro-5-hydroxybenzofuran against lipid peroxidation: effects of substituents and side chain. Free radical research. 2002 Nov; 36(11):1171-8. doi: 10.1080/1071576021000016436. [PMID: 12592669]
  • A V Kuperman, A S Kalgutkar, A Marfat, R J Chambers, T E Liston. 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. Drug metabolism and disposition: the biological fate of chemicals. 2001 Nov; 29(11):1403-9. doi: NULL. [PMID: 11602515]
  • L Velasco, F D Goffman, A J Pujadas-Salvà. Fatty acids and tocochromanols in seeds of Orobanche. Phytochemistry. 2000 Jun; 54(3):295-300. doi: 10.1016/s0031-9422(00)00085-6. [PMID: 10870184]
  • L R Barclay, M R Vinqvist. Do spin traps also act as classical chain-breaking antioxidants? A quantitative kinetic study of phenyl tert-butylnitrone (PBN) in solution and in liposomes. Free radical biology & medicine. 2000 Apr; 28(7):1079-90. doi: 10.1016/s0891-5849(00)00197-0. [PMID: 10832069]
  • A M Zatón, J P Villamor. Study of heterocycle rings binding to human serum albumin. Chemico-biological interactions. 2000 Jan; 124(1):1-11. doi: 10.1016/s0009-2797(99)00130-1. [PMID: 10658898]
  • C K Van Pelt, P Haggarty, J T Brenna. Quantitative subfemtomole analysis of alpha-tocopherol and deuterated isotopomers in plasma using tabletop GC/MS/MS. Analytical chemistry. 1998 Oct; 70(20):4369-75. doi: 10.1021/ac980295n. [PMID: 9796421]
  • J P Fabisiak, Y Y Tyurina, V A Tyurin, J S Lazo, V E Kagan. Random versus selective membrane phospholipid oxidation in apoptosis: role of phosphatidylserine. Biochemistry. 1998 Sep; 37(39):13781-90. doi: 10.1021/bi9808262. [PMID: 9753467]
  • K Yazu, Y Yamamoto, E Niki, K Miki, K Ukegawa. Mechanism of lower oxidizability of eicosapentaenoate than linoleate in aqueous micelles. II. Effect of antioxidants. Lipids. 1998 Jun; 33(6):597-600. doi: 10.1007/s11745-998-0245-3. [PMID: 9655375]
  • J M Ferrer, M J Leiton, A M Zatón. The binding of benzopyranes to human serum albumin. A structure-affinity study. Journal of protein chemistry. 1998 Feb; 17(2):115-9. doi: 10.1023/a:1022575315391. [PMID: 9535273]
  • T Koga, J Terao. Antioxidant behaviors of vitamin E analogues in unilamellar vesicles. Bioscience, biotechnology, and biochemistry. 1996 Jun; 60(6):1043-5. doi: 10.1271/bbb.60.1043. [PMID: 8695907]
  • D E Decker, S M Vroegop, S E Buxser. Inhibition of oxidative insult in cultured cells by a novel 6-chromanol-containing antioxidant. Biochemical pharmacology. 1995 Sep; 50(7):1063-70. doi: 10.1016/0006-2952(95)00241-q. [PMID: 7575662]
  • I Kohar, M Baca, C Suarna, R Stocker, P T Southwell-Keely. Is alpha-tocopherol a reservoir for alpha-tocopheryl hydroquinone?. Free radical biology & medicine. 1995 Aug; 19(2):197-207. doi: 10.1016/0891-5849(95)00010-u. [PMID: 7649491]
  • A M Zatón, J M Ferrer, J C Ruiz de Gordoa, M A Marquínez. Binding of coumarins to site I of human serum albumin. Effect of the fatty acids. Chemico-biological interactions. 1995 Jul; 97(2):169-74. doi: 10.1016/0009-2797(95)03613-q. [PMID: 7606814]
  • T Kaneko, K Kaji, M Matsuo. Protection of linoleic acid hydroperoxide-induced cytotoxicity by phenolic antioxidants. Free radical biology & medicine. 1994 Mar; 16(3):405-9. doi: 10.1016/0891-5849(94)90043-4. [PMID: 8063204]
  • D C Liebler, S Matsumoto, Y Iitaka, M Matsuo. Reactions of vitamin E and its model compound 2,2,5,7,8-pentamethylchroman-6-ol with ozone. Chemical research in toxicology. 1993 Jan; 6(1):69-74. doi: 10.1021/tx00031a011. [PMID: 8448353]
  • J J Maguire, V E Kagan, L Packer. Electron transport between cytochrome c and alpha tocopherol. Biochemical and biophysical research communications. 1992 Oct; 188(1):190-7. doi: 10.1016/0006-291x(92)92368-8. [PMID: 1329744]
  • V E Kagan, E A Serbinova, A Safadi, J D Catudioc, L Packer. NADPH-dependent inhibition of lipid peroxidation in rat liver microsomes. Biochemical and biophysical research communications. 1992 Jul; 186(1):74-80. doi: 10.1016/s0006-291x(05)80777-6. [PMID: 1632795]
  • V E Kagan, E A Serbinova, T Forte, G Scita, L Packer. Recycling of vitamin E in human low density lipoproteins. Journal of lipid research. 1992 Mar; 33(3):385-97. doi: 10.1016/s0022-2275(20)41529-9. [PMID: 1314881]
  • N V Gorbunov, V E Kagan, S M Alekseev, A N Erin. [Role of isoprenoid chain of lateral mobility of alpha-tocopherol in lipid bilayer]. Biulleten' eksperimental'noi biologii i meditsiny. 1991 Jul; 112(7):39-41. doi: ". [PMID: 1793848]
  • S A Novgorodov, T I Gudz, Y E Kushnareva, V A Roginsky, Y B Kudrjashov. Mechanism accounting for the induction of nonspecific permeability of the inner mitochondrial membrane by hydroperoxides. Biochimica et biophysica acta. 1991 Jun; 1058(2):242-8. doi: 10.1016/s0005-2728(05)80243-9. [PMID: 2049374]
  • T Kaneko, S Nakano, M Matsuo. Protective effect of vitamin E on linoleic acid hydroperoxide-induced injury to human endothelial cells. Lipids. 1991 May; 26(5):345-8. doi: 10.1007/bf02537196. [PMID: 1895879]
  • Y Aizawa, T Kanai, K Hasegawa, T Yamaguchi, Y Iizuka, T Iwaoka, T Yoshioka. Studies on hindered phenols and analogues. 2. 1,3-Benzoxathioles having SRS-A inhibiting activity. Journal of medicinal chemistry. 1990 May; 33(5):1491-6. doi: 10.1021/jm00167a032. [PMID: 2329571]
  • C Suarna, P T Southwell-Keely. Effect of alcohols on the oxidation of the vitamin E model compound, 2,2,5,7,8-pentamethyl-6-chromanol. Lipids. 1989 Jan; 24(1):56-60. doi: 10.1007/bf02535265. [PMID: 2747431]
  • A N Erin, N G Davitashvili, V E Kagan, E I Zakharova, I K Sarycheva. [The role of isoprenoid chain of alpha-tocopherol in the protection of synaptosomes against lipid peroxidation and phospholipase A2-induced damage]. Biokhimiia (Moscow, Russia). 1988 Apr; 53(4):591-7. doi: . [PMID: 3395640]
  • R F Kerimov, A N Goloshchapov, E B Burlakova, A I Dzhafarov. [Effect of the functional groups of tocopherol molecules on lipid viscosity of mitochondria]. Biulleten' eksperimental'noi biologii i meditsiny. 1987 May; 103(5):540-3. doi: ". [PMID: 3593919]
  • E A Serbinova, R A Bakalova, Ts S Stoĭchev, V E Kagan. [Effectiveness of lipid peroxidation inhibition in biomembranes by antioxidants with and without hydrocarbon chains]. Biulleten' eksperimental'noi biologii i meditsiny. 1986 Oct; 102(10):419-21. doi: ". [PMID: 3768505]
  • E Niki, A Kawakami, M Saito, Y Yamamoto, J Tsuchiya, Y Kamiya. Effect of phytyl side chain of vitamin E on its antioxidant activity. The Journal of biological chemistry. 1985 Feb; 260(4):2191-6. doi: 10.1016/s0021-9258(18)89536-9. [PMID: 3972787]
  • K Fukuzawa, H Chida, A Suzuki. Fluorescence depolarization studies of phase transition and fluidity in lecithin liposomes containing alpha-tocopherol. Journal of nutritional science and vitaminology. 1980; 26(5):427-34. doi: 10.3177/jnsv.26.427. [PMID: 6894310]
  • J S Dinning, A S Majaj, S A Azzam, W J Darby, C H Shunk, K Folkers. RESPONSE OF MACROCYTIC ANEMIA IN CHILDREN TO THE COENZYME Q4-CHROMANOL. The American journal of clinical nutrition. 1963 09; 13(?):169-72. doi: 10.1093/ajcn/13.3.169. [PMID: 14061588]