Tocopherol (BioDeep_00000397418)

Main id: BioDeep_00000000778

 

PANOMIX_OTCML-2023


代谢物信息卡片


2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, radical ion(1+), (2R-(2R*(4R*,8R*)))-

化学式: C29H50O2 (430.38106)
中文名称: DL-α-生育酚, D-α-生育酚, 维生素 E, 维生素e
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)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C
InChI: InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3

描述信息

2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol is a tocopherol.
Tocopherol exists in four different forms designated as α, β, δ, and γ. They present strong antioxidant activities, and it is determined as the major form of vitamin E. Tocopherol, as a group, is composed of soluble phenolic compounds that consist of a chromanol ring and a 16-carbon phytyl chain. The classification of the tocopherol molecules is designated depending on the number and position of the methyl substituent in the chromanol ring. The different types of tocopherol can be presented trimethylated, dimethylated or methylated in the positions 5-, 7- and 8-. When the carbons at position 5- and 7- are not methylated, they can function as electrophilic centers that can trap reactive oxygen and nitrogen species. Tocopherols can be found in the diet as part of vegetable oil such as corn, soybean, sesame, and cottonseed. It is currently under the list of substances generally recognized as safe (GRAS) in the FDA for the use of human consumption.
DL-alpha-Tocopherol is a natural product found in Sida acuta, Tainia latifolia, and other organisms with data available.
dl-alpha-Tocopherol is a synthetic form of vitamin E, a fat-soluble vitamin with potent antioxidant properties. Considered essential for the stabilization of biological membranes (especially those with high amounts of polyunsaturated fatty acids), d-alpha-Tocopherol is a potent peroxyl radical scavenger and inhibits noncompetitively cyclooxygenase activity in many tissues, resulting in a decrease in prostaglandin production. Vitamin E also inhibits angiogenesis and tumor dormancy through suppressing vascular endothelial growth factor (VEGF) gene transcription. (NCI04)
DL-alpha-Tocopherol is a synthetic vitamin E, with antioxidation effect. DL-alpha-Tocopherol protects human skin fibroblasts against the cytotoxic effect of UVB[1].
DL-alpha-Tocopherol is a synthetic vitamin E, with antioxidation effect. DL-alpha-Tocopherol protects human skin fibroblasts against the cytotoxic effect of UVB[1].
rel-α-Vitamin E (rel-D-α-Tocopherol) is a vitamin with antioxidant properties and also a mixture[1].
α-Vitamin E ((+)-α-Tocopherol), a naturally occurring vitamin E form, is a potent antioxidant[1][2].
α-Vitamin E ((+)-α-Tocopherol), a naturally occurring vitamin E form, is a potent antioxidant[1][2].

同义名列表

111 个代谢物同义名

2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, radical ion(1+), (2R-(2R*(4R*,8R*)))-; 2H-1-Benzopyran-6-ol,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R*(4R*,8R*)]-(.+-.)-; 2H-1-Benzopyran-6-ol,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-; 3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol; Alpha Tocopherol, Pharmaceutical Secondary Standard; Certified Reference Material; 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol; 3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol; 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-ol; 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol; Alpha Tocopherol, United States Pharmacopeia (USP) Reference Standard; alpha-Tocopherol, European Pharmacopoeia (EP) Reference Standard; alpha-Tocopherol, British Pharmacopoeia (BP) Reference Standard; 6-Chromanol, 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-; 2,5,7,8-Tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol #; 2,5,7,8-Tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol; DL-alpha-Tocopherol (Vitamin E) 10 microg/mL in Acetonitrile; 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol; all-rac-alpha-TOCOPHERYL ACETATE IMPURITY C [EP IMPURITY]; (+/-)-alpha-Tocopherol, tested according to Ph.Eur.; (+/-)-alpha-Tocopherol, SAJ special grade, >=96.0\\%; (2R)-alpha-Tocopherol (Mixture of Diastereomers); (+/-)-alpha-Tocopherol, synthetic, >=96\\% (HPLC); 5-17-04-00168 (Beilstein Handbook Reference); (+/-)-alpha-Tocopherol, analytical standard; alpha-Tocopherol-[D6] (Vitamin E-[D6]); all-rac-alpha-Tocopherol (Vitamin E); 7A4513C3-131C-41D4-B6A0-7ED994AC2947; DL-alpha-Tocopherol (Vitamin E); C29H50O2 (DL-alpha-tocopherol); ALL-RAC-ALPHA-TOCOPHEROL [FCC]; (2S, 4R, 8R)-alpha-Tocopherol; (2S, 4S, 8S)-alpha-Tocopherol; (2S, 4S, 8R)-alpha-Tocopherol; (2R, 4S, 8R)-alpha-Tocopherol; (2R, 4S, 8S)-alpha-Tocopherol; (2S, 4R, 8S)-alpha-Tocopherol; DL-ALPHA TOCOPHEROL [WHO-DD]; .ALPHA.-TOCOPHEROL, DL- [II]; TOCOPHEROL,DL-ALPHA [VANDF]; DL-ALPHA TOCOPHEROL [MART.]; (.+/-.)-.alpha.-Tocopherol; (2R,8R)-.alpha.-Tocopherol; alpha-Tocopherol, >=95.5\\%; DL-.ALPHA.-TOCOPHEROL [MI]; (all-R)-.alpha.-Tocopherol; all-rac-alpha-Tocopherol; DL-5,7,8-trimethyltocol; .Alpha.-tocopherol, DL-; DL-all-rac-A-Tocopherol; RAC-.ALPHA.-TOCOPHEROL; 5,6 Trans-Calcipotriol; (+/-)-alpha-Tocopherol; alpha-Tocopherol, DL-; (+-)-alpha-Tocopherol; DL- alpha -Tocopherol; dl-.alpha.-Tocopherol; Antisterility vitamin; RRR-alpha-tocopherol; Tocopheroxyl radical; TOCOPHEROL, DL-ALPHA; d-.alpha.-Tocopherol; Tocopheroxy radical; DL-alpha tocopherol; DL-alpha-Tocopherol; Vitamin E DL-alpha; .alpha. Tocopherol; .alpha.-Tocopherol; 5,8-Trimethyltocol; .alpha.-Tokoferol; alpha-tochopherol; Tocopherol (JP17); dl-|A-tocopherol; Spectrum3_001338; Spectrum5_000381; Spectrum2_000722; Spectrum4_001771; alpha Tocopherol; DL-α-Tocopherol; UNII-7QWA1RIO01; DL-Tocopherol; DivK1c_000533; KBio3_002315; KBio2_004243; KBio2_001675; KBio2_006811; Waynecomycin; KBio1_000533; (.+-.)-Med-E; IDI1_000533; Vitaplex E; Evitaminum; 7QWA1RIO01; TOCOPHEROL; Emipherol; Vitayonon; VITAMIN E; Spavit E; J24.789H; Etamican; Almefrol; Ephanyl; Endo E; Vita E; Ilitia; ido-E; rel-D-α-Tocopherol; rel-α-Vitamin E; (+)-α-Tocopherol; D-α-Tocopherol; α-Vitamin E



数据库引用编号

20 个数据库交叉引用编号

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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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21 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。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Juan Carlos Guevara-Arauza, José de Jesús Ornelas Paz, Sergio Rosales Mendoza, Ruth Elena Soria Guerra, Luz María Teresita Paz Maldonado, Diana Jaqueline Pimentel González. Biofunctional activity of tortillas and bars enhanced with nopal. Preliminary assessment of functional effect after intake on the oxidative status in healthy volunteers. Chemistry Central journal. 2011 Mar; 5(1):10. doi: 10.1186/1752-153x-5-10. [PMID: 21371324]
  • Sylvain Losdat, Heinz Richner, Jonathan D Blount, Fabrice Helfenstein. Immune activation reduces sperm quality in the great tit. PloS one. 2011; 6(7):e22221. doi: 10.1371/journal.pone.0022221. [PMID: 21765955]
  • 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]
  • Sergejs Berdnikovs, Hiam Abdala-Valencia, Christine McCary, Michelle Somand, Rokeisha Cole, Alex Garcia, Paul Bryce, Joan M Cook-Mills. Isoforms of vitamin E have opposing immunoregulatory functions during inflammation by regulating leukocyte recruitment. Journal of immunology (Baltimore, Md. : 1950). 2009 Apr; 182(7):4395-405. doi: 10.4049/jimmunol.0803659. [PMID: 19299740]
  • Tyler Barker, Scott W Leonard, Roy H Trawick, Thomas B Martins, Carl R Kjeldsberg, Harry R Hill, Maret G Traber. Modulation of inflammation by vitamin E and C supplementation prior to anterior cruciate ligament surgery. Free radical biology & medicine. 2009 Mar; 46(5):599-606. doi: 10.1016/j.freeradbiomed.2008.11.006. [PMID: 19111610]
  • Jessica Wiser, Neil E Alexis, Qing Jiang, Weidong Wu, Carole Robinette, Robert Roubey, David B Peden. In vivo gamma-tocopherol supplementation decreases systemic oxidative stress and cytokine responses of human monocytes in normal and asthmatic subjects. Free radical biology & medicine. 2008 Jul; 45(1):40-9. doi: 10.1016/j.freeradbiomed.2008.03.002. [PMID: 18405673]
  • Jamie K Higgins, Birgit Puschner, Philip H Kass, Nicola Pusterla. Assessment of vitamin E concentrations in serum and cerebrospinal fluid of horses following oral administration of vitamin E. American journal of veterinary research. 2008 Jun; 69(6):785-90. doi: 10.2460/ajvr.69.6.785. [PMID: 18518659]
  • András Nemes, László Czibula, Csaba Szántay, Anikó Gere, Béla Kiss, Judit Laszy, István Gyertyán, Zsolt Szombathelyi, Csaba Szántay. Synthesis and evaluation of 2'-hydroxyethyl trans-apovincaminate derivatives as antioxidant and cognitive enhancer agents. Journal of medicinal chemistry. 2008 Feb; 51(3):479-86. doi: 10.1021/jm070618k. [PMID: 18183943]
  • M Maneesh, Sanjiba Dutta, Amit Chakrabarti, D M Vasudevan. Experimental therapeutic intervention with alpha tocopherol in ethanol induced testicular injuries in rats. Indian journal of clinical biochemistry : IJCB. 2007 Mar; 22(1):138-42. doi: 10.1007/bf02912898. [PMID: 23105669]
  • S Gorelik, R Kohen, M Ligumsky, J Kanner. Saliva plays a dual role in oxidation process in stomach medium. Archives of biochemistry and biophysics. 2007 Feb; 458(2):236-43. doi: 10.1016/j.abb.2006.12.006. [PMID: 17250799]
  • Karin Groenbaek, Henrik Friis, Max Hansen, Helmer Ring-Larsen, Henrik B Krarup. The effect of antioxidant supplementation on hepatitis C viral load, transaminases and oxidative status: a randomized trial among chronic hepatitis C virus-infected patients. European journal of gastroenterology & hepatology. 2006 Sep; 18(9):985-9. doi: 10.1097/01.meg.0000231746.76136.4a. [PMID: 16894312]
  • S Yoshikawa, T Morinobu, K Hamamura, F Hirahara, T Iwamoto, H Tamai. The effect of gamma-tocopherol administration on alpha-tocopherol levels and metabolism in humans. European journal of clinical nutrition. 2005 Aug; 59(8):900-5. doi: 10.1038/sj.ejcn.1602154. [PMID: 15928686]
  • G Nascimento Gomes, F T Barbosa, R F Radaeli, M F Cavanal, M Mello Aires, F Zaladek Gil. Effect of D-alpha-tocopherol on tubular nephron acidification by rats with induced diabetes mellitus. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2005 Jul; 38(7):1043-51. doi: 10.1590/s0100-879x2005000700007. [PMID: 16007275]
  • Rika Fukunaga-Takenaka, Yasuhito Shirai, Keiko Yagi, Naoko Adachi, Norio Sakai, Ernesto Merino, Isabel Merida, Naoaki Saito. Importance of chroman ring and tyrosine phosphorylation in the subtype-specific translocation and activation of diacylglycerol kinase alpha by D-alpha-tocopherol. Genes to cells : devoted to molecular & cellular mechanisms. 2005 Apr; 10(4):311-9. doi: 10.1111/j.1365-2443.2005.00842.x. [PMID: 15773894]
  • Iveta Becvarova, Korinn E Saker, William S Swecker, Gregory C Troy. Peroxidative protection of parenteral admixture by D-alpha-tocopherol. Veterinary therapeutics : research in applied veterinary medicine. 2005; 6(4):280-90. doi: ". [PMID: 16550490]
  • Begoña Manuel-Y-Keenoy, Marleen Vinckx, Jan Vertommen, Luc Van Gaal, Ivo De Leeuw. Impact of Vitamin E supplementation on lipoprotein peroxidation and composition in Type 1 diabetic patients treated with Atorvastatin. Atherosclerosis. 2004 Aug; 175(2):369-76. doi: 10.1016/j.atherosclerosis.2004.04.005. [PMID: 15262194]
  • Christopher J Bennett, Stuart T Caldwell, Donald B McPhail, Philip C Morrice, Garry G Duthie, Richard C Hartley. Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation. Bioorganic & medicinal chemistry. 2004 May; 12(9):2079-98. doi: 10.1016/j.bmc.2004.02.031. [PMID: 15080911]
  • Yasuko Ota, Takayo Sasagawa, Kazuhiko Suzuki, Kayoko Tomioka, Ayako Nagai, Gouichi Niiyama, Miwa Kawanaka, Gotaro Yamada, Misako Okita. Vitamin E supplementation increases polyunsaturated fatty acids of RBC membrane in HCV-infected patients. Nutrition (Burbank, Los Angeles County, Calif.). 2004 Apr; 20(4):358-63. doi: 10.1016/j.nut.2003.12.007. [PMID: 15043851]
  • Jerry H Exon, Elizabeth H South, Todd G Taruscio, G Dennis Clifton, Marc W Fariss. Chemopreventive effect of dietary d-alpha-tocopheryl succinate supplementation on precancer colon aberrant crypt formation and vitamin E analogue levels in young and old rats. Nutrition and cancer. 2004; 49(1):72-80. doi: 10.1207/s15327914nc4901_10. [PMID: 15456638]
  • Matthias Schneider, Andreas M Niess, Fabian Rozario, Cornelia Angres, Karja Tschositsch, Ines Golly, Nicole Battenfeld, Michael Schäffer, Hinnak Northoff, Hands-H Dickhuth, Elvira Fehrenbach, Wolfgang E Trommer, Hans K Biesalski. Vitamin E supplementation does not increase the vitamin C radical concentration at rest and after exhaustive exercise in healthy male subjects. European journal of nutrition. 2003 Aug; 42(4):195-200. doi: 10.1007/s00394-003-0414-6. [PMID: 12923650]
  • Sabina Mahmood, Gotaro Yamada, Gouichi Niiyama, Miwa Kawanaka, Kazumi Togawa, Miho Sho, Toshio Ito, Takayo Sasagawa, Misako Okita, Hajime Nakamura, Junji Yodoi. Effect of vitamin E on serum aminotransferase and thioredoxin levels in patients with viral hepatitis C. Free radical research. 2003 Jul; 37(7):781-5. doi: 10.1080/1071576031000102141. [PMID: 12911275]
  • Toru Abiko, Atsuko Abiko, Allen C Clermont, Brett Shoelson, Naoichi Horio, Junichi Takahashi, Anthony P Adamis, George L King, Sven-Erik Bursell. Characterization of retinal leukostasis and hemodynamics in insulin resistance and diabetes: role of oxidants and protein kinase-C activation. Diabetes. 2003 Mar; 52(3):829-37. doi: 10.2337/diabetes.52.3.829. [PMID: 12606527]
  • Patricia C Allen, Raymond H Fetterer. Effects of dietary vitamin E on chickens infected with eimeria maxima: observations over time of primary infection. Avian diseases. 2002 Oct; 46(4):839-46. doi: 10.1637/0005-2086(2002)046[0839:eodveo]2.0.co;2. [PMID: 12495044]
  • Takao Morinobu, Ryoichi Ban, Sosuke Yoshikawa, Takuji Murata, Hiroshi Tamai. The safety of high-dose vitamin E supplementation in healthy Japanese male adults. Journal of nutritional science and vitaminology. 2002 Feb; 48(1):6-9. doi: 10.3177/jnsv.48.6. [PMID: 12026191]
  • M Wasaki, J Sugimoto, K Shirota. Glucose alters the susceptibility of mesangial cells to contrast media. Investigative radiology. 2001 Jul; 36(7):355-62. doi: 10.1097/00004424-200107000-00001. [PMID: 11496090]
  • T Yasuda, A Inaba, M Ohmori, T Endo, S Kubo, K Ohsawa. Urinary metabolites of gallic acid in rats and their radical-scavenging effects on 1,1-diphenyl-2-picrylhydrazyl radical. Journal of natural products. 2000 Oct; 63(10):1444-6. doi: 10.1021/np0000421. [PMID: 11076575]
  • J M Grisar, G Marciniak, F N Bolkenius, J Verne-Mismer, E R Wagner. Cardioselective ammonium, phosphonium, and sulfonium analogues of alpha-tocopherol and ascorbic acid that inhibit in vitro and ex vivo lipid peroxidation and scavenge superoxide radicals. Journal of medicinal chemistry. 1995 Jul; 38(15):2880-6. doi: 10.1021/jm00015a010. [PMID: 7636848]
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