Name | DL-alpha-Tocopherol |
Synonyms | A-TOCOPHEROL IRGANOX E 201 DL-α-Tocopherol ALPHA-TOCOPHEROLUM DL-alpha-Tocopherol ALPHA-DL-TOCOPHEROL 5,7,8-TRIMETHYLTOCOL ALL-RAC-ALPHA-TOCOPHEROL (2S)-2,5,7,8-tetramethyl-2-[(4S,8S)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol (2R)-2,5,7,8-tetramethyl-2-[(4R,8S)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol |
CAS | 10191-41-0 |
EINECS | 233-466-0 |
InChI | InChI=1/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/t21-,22+,29+/m0/s1 |
InChIKey | GVJHHUAWPYXKBD-IEOSBIPESA-N |
Molecular Formula | C29H50O2 |
Molar Mass | 430.71 |
Density | 0.950g/mLat 20°C(lit.) |
Melting Point | 2-4°C |
Boling Point | 200-220°C 0,1mm |
Specific Rotation(α) | [α]D20 - 0.02 - +0.02゜ (neat) |
Flash Point | 240°C |
Water Solubility | Miscible with chloroform, vegetable oils, ether, acetone and alcohol. Immiscible with water. |
Solubility | Soluble in ethanol, chloroform, acetone and vegetable oil, insoluble in water |
Vapor Presure | 4.59E-10mmHg at 25°C |
Appearance | Transparent liquid |
Color | Colourless to Dark Yellow to Thick |
Merck | 14,9495 |
BRN | 94012 |
pKa | 11.40±0.40(Predicted) |
Storage Condition | 2-8°C |
Sensitive | Light Sensitive |
Refractive Index | n20/D 1.506 |
MDL | MFCD00006848 |
Use | Antioxidants protect cells from oxidative stress or damage. |
Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. |
UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
WGK Germany | 1 |
RTECS | GA8746000 |
FLUKA BRAND F CODES | 8-10-23 |
TSCA | Yes |
HS Code | 29362800 |
Reference Show more | 1. Huang Yuzhe Gui Shuangying Chu Xiaoqin. Optimization of formulation and process of sorafenib PLGA-TPGS polymer nanoparticles by Box-Behnken response surface methodology [J]. Journal of Anhui University of Traditional Chinese Medicine 2019 38(01):80-86. 2. Elegant Chen Xinmei, Zhao Yuan, Wan Xinhuan, Ding Zhiyuan, Xu Aiping. Optimization of Extraction Process and Antioxidation of Total Flavonoids from Kunlun Snow Chrysanthemum by Box-Behnken Response Surface Methodology [J]. 2019 on Research and Practice of Modern Traditional Chinese Medicine 33(05):54-61. 3. Yang Jingjing Zero Little Sister Zhang Xuhui et al. Determination of Anti-aging Components in Serum of Oviductus Oviductus Oviductus Oviductus and Its Drug-Containing Rats by HPLC [J]. Journal of Guangdong Pharmaceutical University 2018 034(004): p.417 -421. 4. Su Kun, Shi Songli, Zheng Donghua, et al. HPLC determination of α-vitamin E in Mongolian almond seeds [J]. Chinese Journal of Experimental Presentation 2013 19(12):70-72. 5. Tang Linlin, Sang Ying, Chen Sirui, et al. Comparison of the quality and in vitro antioxidant activity of red raspberry seed oil with different extraction methods [J]. Modern Food Science and Technology 2020 v.36; no.247 (03):86-94. 6. Nuramina Abduhalik Zulifia Wusman Mai Wulanijiang Izibra et al. Study on the Metabolomics of Nuclear Magnetic Resonance Hydrogen Spectrum of Chinese Medicine Compound Granules on Urine of D-Galactose-induced Aging Model Mice [J]. Journal of Food Safety and Quality Testing 2019 v.10(09):149-157. 7. He Hua, Li Xiankuan, Ding Pu, et al.. Antioxidant Activity of Schisandra Chinensis Red Pigment [J]. Chinese Journal of Experimental Prescription 2012 18(18):140-143. 8. Li Xiaoting, Bai Yubin, Li Bing, et al.. Study on Compatibility of Excipients of Pentachlorosamide Albendazole Compound Suspension [J]. Animal Husbandry and Veterinary v.51;No.407(06):57-62. 9. Xiong Wen, Wu Ting, Cao Weiwei, et al. Effects of in vitro Digestion on Polyphenol Content and Antioxidant Activity of Artemisia selengensis Leaves [J]. 2020 of Modern Food Science and Technology v.36;No.245(01):84-89 293. 10. Li Juanjuan, Fan Jinshuan, Wei Yichu, et al. Analysis of Oil Nutrients of Several Acer Plants [J]. Chinese Journal of Cereals and Oils 2018 v.33(05):63-67. 11. Si Tianlei Ma Jingxuan Ma Chuanguo. Study on the Effect of Molecular Distillation on the Quality of Seabuckthorn Fruit Oil [J]. China Oil 2018 43(05):18-22. 12. Zhou Guangzhi Lu Min An Huaming. Analysis of Main Active Substances and Antioxidant Activity in Leaves of Rosa roxburghii Pear and Its Related Germplasm [J]. Journal of Nuclear Agriculture 2019 v.33(08):214-221. 13. qi zhou Ceng Ying Zhu Zunling. Response Surface Methodology Optimization of Extraction Process and Antioxidant Activity of Lotus Polyphenols in Perfume [J]. 2018 of Modern Food Science and Technology 34(11):13 206-213. 14. Li Mengfan Tao Ningping Yu Jun Liu Chengchu Pan Jing Shen Juquan. Preparation of Microencapsulated Tilapia Oil by Spray Drying [J]. Journal of Shanghai Ocean University 2015 24(04):617-624. 15. Wang Qiuyang, Zhao Xinrui, Wang Chao, et al. Antioxidant Activity of Membrane-coated Flavonoids from Pinus koraiensis Pine Kernel Purified by Macroporous Resin [J]. Food Science and Technology, 2019, v.44;No.335(09):230-234. 16. Kang Zhongchun, Chen Yuanlan, Zou Yuliang. Vitamin A in Preeclampsia Pregnant Women, analysis of E Level and Its Influencing Factors [J]. Clinical Medical Research and Practice, 2018(30). 17. Tai Jia, Zou Junbo, Shi Yajun, et al. Study on Thermal Stability of Turmeric Volatile Oil and Its Antioxidant Screening [J]. Chinese Pharmaceutical Journal, 2019(15). 18. Tai Jia, Zou Junbo, Shi Yajun, et al.. Study on Thermal Stability of Fennel Volatile Oil and Its Antioxidant Screening [J]. Chinese Journal of Traditional Chinese Medicine, 2019, v.34(11):389-393. 19. Wang Yuqin, Shuangquan. Optimization of Enzymatic Extraction Process and Quality Analysis of Jatropha curcas Oil and Water [J]. Food and Machinery, 2018, 34(11):162-166. 20. Guo Gangjun, Hu Xiaojing, Xu Rong, etc. Effects of drying methods on nutrition, functional components and amino acid composition of Moringa oleifera leaves [J]. Food Science, 2018, 39(011):39-45. 21. Zhang Qiqi, Cheng Junxia, Wang Qi, et al. Study on sensory physical and chemical properties, polyphenol composition and antioxidant activity of matcha tea soup [J]. Food and Machinery, 2019, 035(009):181-186. 22. Wang Fangmei, zhangxin, Gu Panpan, et al. Study on Oxidation Stability and Shelf Life Forecast of Xinjiang Melon Seed Oil [J]. Food and Fermentation Industry, 2019, 45(05):168-173. 23. Zhang Yufeng, Wang Hui, Shen Xiaojun, etc. Effects of Fermentation Killing Methods on Micronutrients and Volatile Aroma Substances in Oil Palm Fruits [J]. Chinese Journal of Cereals and Oils, 2018, 033(004):43-48. 24. Hu Qianying, Ding Yanxia, Tian Jixin, et al. Study on Anti-skin Photoaging Mechanism of Aractin [J]. Journal of Henan University: Medical Edition, 2016, 035(004):244-248. 25. Liu Shengnan, Yu Minmin, Pan Jingjing, et al. Changes in total phenol and antioxidant activity of rosemary extract during simulated gastrointestinal digestion [J]. Food Industry Technology, 2019, v.40;No.433(17):300-304. 26. Yan Chenjing, Zhou Qian, Dong Xiaohan, Han Xue, Cai Dongwei, Bai Bingyao, Zhao Wen. Analysis and Evaluation of Nutritional Components of Main Coarse Cereals in Hebei Province [J]. Food Industry Science and Technology, 2017,38(10):351-355. 27. Wang Zongcheng, Wang Shan, Chen Dan, et al. Study on the Effect of Storage Time of Camellia oleifera Seed on Aqueous Enzymatic Oil Extraction [J]. China Oil and Fat, 2018, 43(11):8-11. 28. Li Lina, Tian Ying. Application of Starch Octenyl Aluminum Succinate in Skin Care Products [J]. Daily Chemical Science, 2012, 035(012):19-22. 29. Wen Pengcheng, Cui Na, Liang Qi, et al. Study on Vitamin Changes in Yak Colostrum and Its Transition Milk [J]. Food Industry Science and Technology, 2014, 35(16):121-121. 30. Lu Shuangshuang, Ren Tingting, li Shuguo. Study on Simultaneous Extraction of Phytosterols and VE from Deodorization Distillate of Corn Germ Oil [J]. Food Science and Technology, 2014, 039(006):182-187. 31. Liu Bentong, Qin Yuchuan, Zhang Duhai, et al. Analysis of Nutritional Components in Edible Parts of Provincial Oil [J]. Zhejiang Forestry Science and Technology, 2018, 038(005):27-32. 32. Gao Li, peng Xiaoming, Huo Shixia, et al. The expression of neurotrophic factor 3 in subacute aging mice brain tissue enhanced by cimicifugin [J]. Journal of Cell and Molecular Immunology, 2014, 30(10):1022-1025. 33. Peng Xiaoming, Gao Li, Huo Shixia, etc. effects of cimicifugin on gene expression of cortical caspase-3 in mice with Alzheimer's disease [J]. Chinese pharmacological bulletin, 2014, 000(012):1763-1768. 34. Zhang Jinping, Zhang Xiyu, Yin Zhenxiong, et al. UV spectrophotometry to detect the effect of VE on antioxidant activity of peony seed oil [J]. Spectroscopy Laboratory, 2013, 030(005):2357-2360. 35. Chen Mengran, Gao Haoze, Zhou Peipei, Liu Jun, Li Yongjun. Effects of vitamin E and glutamine on capacitation of rabbit semen and expression of capacitation-related genes [J]. Jiangsu Agricultural Sciences, 2016,44(08):306-308. 36. Anaguli Mahemuti, Rebiguli Islam, Manerdan Niyazi. Effect of Uyghur Medicine Gaoziban Extract on D-galactose-induced Aging Mouse Model [J]. China Pharmaceutical, 2019. 37. Hu Yanqiu, Yu Lian, Hu Junhua, et al. Preparation of lung-targeted pirfenidone liposomes and study on drug release properties in vitro [J]. Heilongjiang Medical Sciences, 2012, 35(3):28-30. 38. Liu Zhen, Wang Shiqing, Xiao Junxia, et al. Effects of Peanut Components on Degradation of Aflatoxin B1 by Low Temperature Radio Frequency Plasma [J]. Food Science, 2016, 37(21):219-223. 39. Liu Yangyang, Zhao Xiuhua, Zu Yuangang, et al. Solubility and Antioxidant Properties of Su Seed Oil in Supercritical CO_2 Fluid [J]. Food Industry Science and Technology, 2016, 37(13). 40. Zhang Jiankui, Gao Rui, Kang Tingguo, et al. Comparison of protein, vitamin C, vitamin E, volatile oil components and superoxide dismutase activity between fresh and dried American ginseng [J]. Chinese Journal of Experimental Prescritique, 2013, 19(008):102-106. 41. Wang Meng, Zhao Peixia, Zhang Peng, et al. Study on Antioxidant Effect of Capsaicin Monomer, Dihydrocapsaicin Monomer and Dihydrocapsaicin Monomer [J]. Chemistry and Bioengineering, 2019, 036(002):8-11. 42. Xu Fei, Yang Xijuan, Dang Bin, et al. Optimization of Acid Extraction of Highland Barley Bran Combined with Phenol [J]. Journal of Agricultural Engineering, 2016, 32(017):301-308. 43. Xie Chenhong, Liu Junqiu, kaiguoyin. Study on Chemical Constituents and Antioxidant Activity of n-butanol Fractions in Ginkgo Biloba Leaves [J]. Journal of Zhejiang University of Traditional Chinese Medicine, Volume 43, Issue 10, 2019, 1114-1118,1137 pages, ISTIC CA, 2019. 44. Dang Bin. Analysis of Phenols and Antioxidant Activities in Quinoa Resources in Qinghai [J]. Food Industry Science and Technology, 2019, 040(017):30-37. 45. Tai Jia, Zou Junbo, shi Yajun, et al. Study on Thermal Stability of Galangal Volatile Oil and Its Antioxidant Screening [J]. Chinese Seasoning, 2019(9). 46. Peng Xiaoming, Huo Shixia, Gao Li, et al. Protective Effect of Galangin on Oxidative Damage of A375 Cells Induced by H_2O_2 [J]. Northwest Journal of Pharmacy, 2015(1):51-54. 47. Huo Shixia, Peng Xiaoming, gao Li, Huang Yi, Gan Ping, Yan Ming. Effect of galangin on Nrf2 and γ-GCS gene expression after hydrogen peroxide-induced oxidative damage in A375 cells [J]. Chinese Journal of Traditional Chinese Medicine Information, 2015,22(11):69-72. 48. Wang Qian, He Ping, Lin Ruge, et al. Structure, Composition Analysis and Functional Activity of Duck Egg Albumin [J]. Food Industry Science and Technology, 2020, v.41;No.448(08):73-79. 49. Ming Lisa, Tang Xiaoying, Liu Jianqiao, et. Study on Refining and Antioxidant Activity of Total Ketones in Swertia rosetia [J]. Food Industry, 2019, 40(02):66-70. 50. Wang Liang, Gu Panpan, Wang Fangmei, et al. Study on Oxidative Stability of Black Fruit Lycium barbarum Seed Oil [J]. China Oil, 44(10). 51. Xia Tianjuan, Bi Liangwu, Zhao Zhendong, etc. Study on Antioxidant Activity and Antimicrobial Activity of Salvia Acid [J]. Research and Development of Natural Products, 2015, 027(001):35-40. 52. Tai Jia, Zou Junbo, Shi Yajun, et al. Stability Investigation and Antioxidant Screening of Fennel Volatile Oil in Accelerated Oxidation Environment [J]. Chinese Journal of Experimental Prescribes, 2019(18). 53. Wang Yu, zou Junbo, Shi Yajun, Zhang Xiaofei, Tai Jia, Liang Yulin, Guo Dongyan. Investigation on Accelerated Oxidation Stability of Turmeric Volatile Oil and Screening of Antioxidant [J]. Chinese herbal medicine, 2019,42(11):2627-2630. 54. Liu Meng, Gao Haiyan, Fang Xiangjun, Wu Weijie, Chen Hangjun, Liu Ruiling. Optimization of Ultrasonic-Microwave Synergy Extraction of Myricetin with Different Maturity and Comparison of Antioxidant Activity [J]. Food Science, 2021,42(03):112-120. 55. Chen Qingqing, Li Ke, Tang Xiaoqing, Geng Li, Wang Lei, Peng Yaping. Analysis of Phenolic Components and Antioxidant Activities in Fruit, Stem and Leaves of Raspberry from East China [J]. Food Science, 2020,41(24):209-215. 56. Rao Chuanyan, Nie Menglin, Mo Minggui, Huang Yanting, Pan Haibo, Qin Luqi, Li Quanyang. Analysis of 7 Dietary Fiber Components and Antioxidant Activities in Guangxi Bama Longevity Population [J]. Journal of Food Safety and Quality Inspection, 2020,11(19):6990-6999. 57. Luo Xuexia, Chen Zihang, Wang Simin, Yang Yanhong. Effect and mechanism of vitamin E on H-22 transplanted tumor in mice [J]. Biotechnology, 2020,30(04):368-374 410. 58. Zhang Xu, Tang Zhanyang, Huang Kai, Wang Liqun, Su Zhijian, Liu Ting, Wang Jingjie, Ma Yanqun. Effects of Vitamin E on Growth and Gonad Development of Nile Tilapia [J]. Aquatic Science, 2020,39(06):887-893. 59. Zhang Yanfei. Study on Degradation Mechanism and Antioxidant Capacity of Anthocyanin in Purple Eggplant during Thermal Processing [D]. Nanchang University, 2020. 60. Liu Huimin, Nie Qin, Huang Zhao, Yang Mengzhu, Wu Mengdi, Cao Xiaoqin. Establishment and pretreatment of fat-soluble vitamins in breast milk by HPLC [J]. Food Industry, 2020,41(12):313-317. |
LogP | 12.2 at 25℃ |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Introduction | DL-α-tocopherol, the chemical name is (±)-2,5,7,8-tetramethyl -2-(4 ', 8', 12 '-trimethyltridecyl)-6-color full alcohol, also known as vitamin E alcohol, is a class of compounds that mainly exhibit vitamin E activity. Because its vitamin activity was first identified in 1936 experiments on fecundity factors in rats, it was named "tocopherol". It is found in edible oil, fruits, vegetables and grains. It is a fat-soluble vitamin and an important antioxidant. The similar substances of DL-α-tocopherol are: d-α-tocopherol; d-α-tocopherol ester; dl-α-tocopherol ester; hydrogen succinate d-α-tocopherol ester; hydrogen succinate dl-α-tocopherol ester; β-tocopherol; γ-tocopherol; δ-tocopherol; tocopherol oil; all have the physiological activity of vitamin E, of which DL-α-tocopherol has the largest activity and the strongest antioxidant capacity. |
source | natural vitamin e mainly exists in fruits and vegetables, nuts, lean meat, milk, eggs and pressed vegetable oil. 1. Fruits and vegetables: kiwi fruit, spinach, cabbage, vegetable stuffed flower, kale, lettuce, sweet potato, yam. 2. Nuts: almonds, hazelnuts and walnuts. 3. Squeezed vegetable oils: sunflower seeds, sesame seeds, corn, olives, peanuts, camellia, etc. in addition, safflower, soybean, cottonseed, wheat germ and cod liver oil all have a certain content of vitamin e, and wheat germ is the most abundant. |
Discovery history | In 1922, American scientist Ivan discovered that the fertility of male white mice decreased, and female white mice were prone to abortion and lack of a fat-soluble substance. In 1938, the Swiss chemist Kara synthesized this substance and named it tocopherol, or vitamin E. Tocopherol can promote the secretion of sex hormones, increase the vitality and number of men's sperm; increase the concentration of female estrogen, improve fertility, and prevent abortion. It can also prevent and treat menopausal syndrome. |
physiological function | vitamin e is a fat-soluble vitamin, also known as tocopherol or gestational phenol. it is a phenolic compound and is one of the most important antioxidants. it has the functions of anti-oxidation, promoting protein renewal and synthesis, regulating platelet adhesion and aggregation. the daily reference dosage of vitamin supplement for adults is vitamin a 1.5mg; Vitamin e is 30mg. there are many kinds of natural vitamin e. the structural difference is only in the side chains R1, R2 and R3, and exists in edible oil, fruits, vegetables and grain. it was successfully synthesized in 1988, can maintain the normal function of reproductive organs, has a good effect on the metabolism of the body, can make the ovaries weigh, promote its function, promote the maturation of follicles, and enlarge the corpus luteum, and can inhibit the oxidation of progesterone in the whole, thereby increasing the effect of progesterone. In addition, vitamin E has an adjuvant therapeutic effect on menorrhagia, vulvar pruritus, nocturnal calf spasm, and hemorrhoids. In recent years, vitamin E has been widely used in anti-aging. It is believed that it can eliminate the deposition of lipofuscin in cells, improve the normal function of cells, and slow down the aging process of tissue cells. |
main efficacy | 1. vitamin e is a highly effective antioxidant, which can protect cell membranes from free radical damage and protect blood vessels, heart, breasts, eyes, skin, glands and other organs. So as to prevent a variety of chronic diseases. Such as breast cancer, cardiovascular disease, rectal cancer, etc. 2. Promote protein renewal and synthesis, which can promote wound healing. 3. Promote the proliferation of capillaries and small blood vessels, improve the surrounding blood circulation, increase the supply of oxygen in the tissue, and create good nutritional conditions for ulcer healing. 4. It is related to reproductive function and sperm production, preventing abortion, infertility and maintaining ovaries. 5. Protect erythrocyte membrane and prevent hemolytic anemia. 6. whitening and freckle removal, hairdressing and hair care, sunscreen and skin care. 7. Improve immune function and delay aging. 8. Inhibit the growth of Helicobacter pylori and reduce the recurrence rate after ulcer healing. |
use | antioxidant to protect cells from oxidative stress or damage. (±)-α-tocopherol has been used to prepare mycobacterial emulsions, and has also been used to study immunomodulatory effects in influenza virus infection |
Production method | Using 1,2, 4-trimethylbenzene as raw material, it is obtained by iodination, nitration, reduction, and oxidation to obtain 2,3, 5-trimethylbenzoquinone, then reduction, and condensation with chloroplast. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |