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Chemistry

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Also known as: Alpha-tocopherol, D-alpha-tocopherol, 59-02-9, (+)-alpha-tocopherol, 5,7,8-trimethyltocol, Aquasol e
Molecular Formula
C29H50O2
Molecular Weight
430.7  g/mol
InChI Key
GVJHHUAWPYXKBD-IEOSBIPESA-N
FDA UNII
N9PR3490H9

Vitamin E
A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.
1 2D Structure

Vitamin E

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
2.1.2 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/t21-,22-,29-/m1/s1
2.1.3 InChI Key
GVJHHUAWPYXKBD-IEOSBIPESA-N
2.1.4 Canonical SMILES
CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C
2.1.5 Isomeric SMILES
CC1=C(C2=C(CC[C@@](O2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C(=C1O)C)C
2.2 Other Identifiers
2.2.1 UNII
N9PR3490H9
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Alpha-tocopherol

2. D-alpha-tocopherol

3. 59-02-9

4. (+)-alpha-tocopherol

5. 5,7,8-trimethyltocol

6. Aquasol E

7. Tocopherol

8. 2074-53-5

9. (r,r,r)-alpha-tocopherol

10. Phytogermine

11. Eprolin

12. A-tocopherol

13. (2r,4'r,8'r)-alpha-tocopherol

14. Dl-a-tocopherol

15. Denamone

16. Viteolin

17. Esorb

18. Alpha-tocopherol, D-

19. Tocopherol Alpha

20. Alpha-vitamin E

21. Alpha Tocopherol

22. D-alpha Tocopherol

23. (2r)-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]chroman-6-ol

24. (r)-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)chroman-6-ol

25. Vitamin Ea

26. Mixed Tocopherols

27. 1406-18-4

28. Syntopherol

29. Tocopherol (r,s)

30. Chebi:18145

31. Vitamin-e

32. Evitaminum

33. Profecundin

34. Waynecomycin

35. Almefrol

36. Emipherol

37. Epsilan

38. Etamican

39. Tokopharm

40. Vascuals

41. Vitayonon

42. Etavit

43. Ilitia

44. Evion

45. (2r)-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydro-2h-chromen-6-ol

46. (2r)-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol

47. Bpbio1_000362

48. 18920-62-2

49. Vitaplex E

50. Eprolin S

51. Spavit E

52. Ido-e

53. Endo E

54. N9pr3490h9

55. Vita E

56. Lan-e

57. Med-e

58. Antisterility Vitamin

59. A-vitamin E

60. 2h-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-, (2r)-

61. Vi-e

62. E307

63. Dsstox_cid_6339

64. (+/-)-alpha-tocopherol

65. 2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol

66. Dsstox_rid_78103

67. Dsstox_gsid_26339

68. 2h-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-, (2r)-rel-

69. Viprimol

70. Alpha-tokoferol

71. D-a-tocopherol

72. Mfcd00072045

73. Rrr-alpha-tocopherol

74. Vitamin E Alpha

75. Viterra E

76. E Prolin

77. Cas-59-02-9

78. 2h-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)-, (2r)-

79. 2h-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, (2r-(2r*(4r*,8r*)))-

80. 2h-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2r-[2r*(4r*,8r*)]]-

81. Smr000471844

82. Viv

83. Alpha-tocopherol Acid

84. Tenox Gt 1

85. Rhenogran Ronotec 50

86. Covitol F 1000

87. 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2h-benzopyran-6-ol

88. E 307 (tocopherol)

89. (all-r)-alpha-tocopherol

90. Phytogermin

91. Palmvtee

92. Alpha-tocoferol

93. (+-)-med-e

94. E-oil 1000

95. Unii-n9pr3490h9

96. Vitamin Ealpha

97. Ccris 3588

98. Nsc-20812

99. A-d-tocopherol

100. .alpha.-tocopherol, D-

101. Hsdb 2556

102. Pheryl-e

103. Vita Plus E

104. D-..-tocopherol

105. Vitamin E D-alpha

106. Ncgc00016688-02

107. (+)--tocopherol

108. Prestwick_653

109. Einecs 200-412-2

110. Einecs 215-798-8

111. Einecs 218-197-9

112. .alpha.-vitamin E

113. (+)-a-tocopherol

114. Nsc 20812

115. Nsc 82623

116. Rrr-alpha-tocopheryl

117. Vitamin E [usp]

118. ()-alpha-tocopherol

119. Delta-alpha-tocopherol

120. Alpha-delta-tocopherol

121. Tocopherol, D-alpha-

122. Vitamin E (d-form)

123. Chembl47

124. (r,r,r)-a-tocopherol

125. Prestwick3_000404

126. E 307

127. (+)- Alpha -tocopherol

128. (+)-.alpha.-tocopherol

129. Bmse000600

130. R,r,r-.alpha.-tocopherol

131. Ec 200-412-2

132. Schembl3097

133. Unii-h4n855pnz1

134. Bidd:pxr0174

135. Bspbio_000328

136. Mls001066396

137. Mls001335981

138. Mls001335982

139. Bidd:er0562

140. Ins No.307a

141. T1539_sigma

142. H4n855pnz1

143. Ins-307a

144. (+)-alpha-tocopherol-

145. Alpha-tocopherol [hsdb]

146. Rrr-alpha-tocopherol Concentrate

147. Dtxsid0026339

148. (2r,4'r,8'r)-a-tocopherol

149. .alpha.-tocopherol [mi]

150. Hms2096a10

151. Hms2231g08

152. C29h50o2 (d-alpha-tocopherol)

153. D-alpha Tocopherol [mart.]

154. Hy-n0683

155. Zinc4095858

156. Tox21_110563

157. Tox21_113208

158. Tox21_202081

159. Bdbm50458513

160. E-307a

161. Lmpr02020001

162. Akos004910417

163. Cs-8161

164. Db00163

165. (2r)-2-((4r,8r)-4,8,12-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol

166. Ncgc00142625-01

167. Ncgc00142625-04

168. Ncgc00142625-05

169. Ncgc00142625-06

170. Ncgc00142625-07

171. Ncgc00142625-10

172. Ncgc00259630-01

173. (2r*(4r*,8r*))-(1)-3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2h-benzopyran-6-ol

174. As-13990

175. J24.260h

176. T2309

177. (+/-)-alpha-tocopherol (vitamin E) Solution

178. Rrr-alpha-tocopherol Concentrate [fcc]

179. C02477

180. D-alpha, D-beta, D-gamma & D-delta Tocopherols

181. Q158348

182. Q-201932

183. W-107596

184. W-109164

185. 07aa93f0-3339-4eec-b50b-adb70f657087

186. (+)-alpha-tocopherol, From Vegetable Oil, Type V, ~1000 Iu/g

187. (2r,4'r,8'r)-2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol

188. 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2h-1- -benzopyran-6-ol

189. (+)-alpha-tocopherol, Type Vi, From Vegetable Oil, Neat (liquid, >=0.88m Based On Potency, Density And Molecular Wt.), Bioreagent, Suitable For Insect Cell Culture, >=1000 Iu/g

190. (2r)-3,4-dihydro-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-2h-1-benzopyran-6-ol

191. (r)-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)-3,4-dihydro-2h-chromen-6-ol

192. 2h-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, 2r- 2r*(4r*,8r*) -

193. 2h-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, (2r*(4r*,8r*))-(+-)-

194. Alpha-tocopherol (constituent Of Lycopene And Tomato Extract Containing Lycopene) [dsc]

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 430.7 g/mol
Molecular Formula C29H50O2
XLogP310.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count12
Exact Mass430.381080833 g/mol
Monoisotopic Mass430.381080833 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count31
Formal Charge0
Complexity503
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

As a dietary supplement when vitamin E intake may be inadequate.

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 15


Vitamin E deficiency in premature infants may result in hemolytic anemia, thrombocytosis, and increased platelet aggregation.

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 16


/Vitamin E/ has also been used in cancer, skin conditions, sexual dysfunction, to reduce the incidence of non-fatal myocardial infarction, to lower the incidence of coronary artery disease, aging, fibrocystic breast disease (cystic mastitis), to treat dapsone-associated hemolysis, and arthritis. /not included in the US product label/

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 15


Vitamin E has been used in certain premature infants to reduce the toxic effects of oxygen therapy on the lung parenchyma... and the retina... /not included in the US product label/

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 15


For more Therapeutic Uses (Complete) data for VITAMIN E (19 total), please visit the HSDB record page.


4.2 Drug Warning

Vitamin E in high doses (greater than 4000 IU) may increase the hypoprothrombinemic effects of oral anticoagulants.

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 16


Vitamin E may impair the hematologic response to iron therapy in children with iron-defiiency anemia.

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 16


FDA Pregnancy Risk Category: A CONTROLLED STUDIES SHOW NO RISK. Adequate, well controlled studies in pregnant women have failed to demonstrate a risk to the fetus in any trimester of pregnancy.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1020


Vitamin E has not been shown to be teratogenic. There is no evidence that vitamin E requirements in pregnant women differ from women who are not pregnant.

American Society of Health-System Pharmacists 2015; Drug Information 2015. Bethesda, MD. 2015


Reports of toxicity to enterally administered vitamin E are rare in infants. However, increased risks of sepsis and necrotizing enterocolitis have been reported after both enteral and parenteral vitamin E, primarily when plasma (or serum) vitamin E levels exceed 3.5 mg/dL. Levels this high are seldom seen with enteral vitamin E when intake is 25 mg d-tocopherol equivalent/(kg/day) or less. Intakes below this threshold will be provided by infant formulas with vitamin E to energy ratios of up to 20 mg/100 kcal (30 IU/100 kcal) so long as energy intake does not exceed 125 kcal/(kg/day).

PMID:2693643 Bell EF; J Nutr 119 (12 Suppl): 1829-31 (1989)


4.3 Drug Indication

Vitamin E supplementation is indicated for treatment of vitamin E deficiency which can occur in cystic fibrosis, cholestasis and severe liver disease, abetalipoproteinemia or simply poor diet.


Tocopherol can be used as a dietary supplement for patients with a deficit of vitamin E; this is mainly prescribed in the alpha form. Vitamin E deficiency is rare, and it is primarily found in premature babies of very low birth weight, patients with fat malabsorption or patients with abetalipoproteinemia. Tocopherol, due to its antioxidant properties, is studied for its use in prevention or treatment in different complex diseases such as cancer, atherosclerosis, cardiovascular diseases, and age-related macular degeneration.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Vitamin E is a collective term used to describe 8 separate fat soluble antioxidants, most commonly alpha-tocopherol. Vitamin E acts to protect cells against the effects of free radicals, which are potentially damaging by-products of the body's metabolism. Vitamin E deficiency is seen in persons with abetalipoproteinemia, premature, very low birth weight infants (birth weights less than 1500 grams, or 3½ pounds), cystic fibrosis, and cholestasis and severe liver disease. Preliminary research suggests vitamin E may help prevent or delay coronary heart disease and protect against the damaging effects of free radicals, which may contribute to the development of chronic diseases such as cancer. It also protects other fat-soluble vitamins (A and B group vitamins) from destruction by oxygen. Low levels of vitamin E have been linked to increased incidence of breast and colon cancer.


The antioxidant effects of tocopherol can be translated into different changes at the pharmacodynamic level. In vitro studies have shown that this antioxidant activity can produce modification in protein kinase C (PKC) which will later be translated into an inhibition of cell death. Some other derivate effects are the anti-inflammatory properties of tocopherol which can be related to the modulation of cytokines or prostaglandins, prostanoids and thromboxanes.


5.2 MeSH Pharmacological Classification

Vitamins

Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body. (See all compounds classified as Vitamins.)


Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


5.3 Absorption, Distribution and Excretion

Absorption

10-33% of deuterium labelled vitamin E is absorbed in the small intestine. Absorption of Vitamin E is dependant upon absorption of the fat in which it is dissolved. For patients with poor fat absorption, a water soluble form of vitamin E may need to be substituted such as tocopheryl polyethylene glycol-1000 succinate. In other studies the oral bioavailability of alpha-tocopherol was 36%, gamma-tocotrienol was 9%. The time to maximum concentration was 9.7 hours for alpha-tocopherol and 2.4 hours for gamma-tocotrienol.


Route of Elimination

Alpha tocopherol is excreted in urine as well as bile in the feces mainly as a carboxyethyl-hydrochroman (CEHC) metabolite, but it can be excreted in it's natural form.


Volume of Distribution

0.41L/kg in premature neonates given a 20mg/kg intramuscular injection.


Clearance

6.5mL/hr/kg in premature neonates given a 20mg/kg intramuscular injection.


Absorption

The absorption of tocopherol in the digestive tract requires the presence of fat. The approximate tmax of the four different isomers of tocopherol is attained in the range of 3-6 hours. When compared with tocotrienols, tocopherols showed a reduced bioavailability. The bioavailability of tocopherols is highly dependent on the type of isomer that is administered where the alpha-tocopherol can present a bioavailability of 36%. This isomer specificity also determines the intestinal permeability in which the gamma-tocopherol presents a very low permeability. After oral administration, the Cmax, AUC and mean residence time of tocopherols showed to be dependent on the isomer and ranged from 590-2915 ng/ml, 3740-10169 ng/ml and 4.85-5.74 h, respectively.


Route of Elimination

The pharmacokinetic profile of tocopherol indicates a longer time of excretion for tocopherols when compared to tocotrienols. The different conjugated metabolites are excreted in the urine or feces depending on the length of their side-chain. Due to their polarity, intermediate-chain metabolites and short-chain metabolites are excreted via urine as glucoside conjugates. A mixture of all the metabolites and precursors can be found in feces. The long-chain metabolites correspond to >60% of the total metabolites in feces. It is estimated that the fecal excretion accounts for even 80% of the administered dose.


Volume of Distribution

The apparent volume of distribution of tocopherol is approximately 0.5 ml.


Clearance

The clearance rate of tocopherol is approximately 0.15 l/h.


alpha-Tocopherol is absorbed via the lymphatic pathway and transported in association with chylomicrons. In plasma, alpha-tocopherol is found in all lipoprotein fractions but mostly is associated with apo B containing lipoproteins. alpha-Tocopherol is associated with very low density lipoprotein when it is secreted from the liver. In the rat, about 90% of total body mass of alpha-tocopherol is recovered in the liver, skeletal muscle and adipose tissue. Most alpha-tocopherol is located in the mitochondrial fractions and in the endoplasmic reticulum, whereas little is found in cytosol and peroxisomes.

PMID:2181082 Bjorneboe A et al; J Nutr 120 (3): 233-42 (1990)


The level of retinal alpha-tocopherol of newborn rats could be altered by dietary manipulation of the mothers. The mothers were fed diets containing either 1 g alpha-tocopherol acetate/kg food or none, starting 21-25 days before the birth of their litters and lasting throughout the exposure period. This treatment resulted in three to fourfold differences in the retinal alpha-tocopherol levels of the pups. The combination of dietary and oxygen treatments also resulted in significant differences in retinal glutathione peroxidase activity, with the vitamin E deprived, oxygen exposed group having highest levels. Newborn rats both supplemented with and deprived of alpha-tocopherol had less vasoobliteration than did those nursed by mothers fed rat chow.

PMID:1582786 Penn JS et al; Invest Ophthalmol Vis Sci 33 (6): 1836-45 (1992)


Vitamin E is stored unmodified in tissues (principally the liver and adipose tissue) and excreted via the feces. Excess vitamin E is converted to a lactone, esterified to glucuronic acid, and subsequently excreted in the urine.

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 16


Vitamin E is 20% to 50% absorbed by intestinal epithelial cells in the small intestine. Bile and pancreatic juice are needed for tocopherol absorption. Absorption is increased when administered with medium-chain triglycerides. Distribution to tissues via the lymphatic system occurs as a lipoprotein complex. High concentrations of vitamin E are found in the adrenals, pituitary, testes, and trombocytes.

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 16


For more Absorption, Distribution and Excretion (Complete) data for VITAMIN E (11 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

Alpha and gamma tocopherol are undergo beta oxidation and a process mediated by cytochrome P450s such as CYP4F2, CYP3A4, and CYP3A5. These processes convert alpha and gamma tocopherol to alpha-CEHC (2,5,7,8-tetramethyl-2-(2-carboxyethyl)-6-hydroxychroman) and gamma-CEHC (2,7,8-trimethyl-2-(2-carboxyethyl)-6-hydroxychroman) respectively, however the full process is not known.


Excess tocopherol is converted into their corresponding carboxyethylhydroxychroman (CEHC), based on the isomer of tocopherol. More deeply, the metabolism of tocopherol begins with the hepatic metabolism which is led by a CYP4F2/CYP3A4-dependent -hydroxylation of the side chains which leads to the formation of 13'-carboxychromanol. The metabolic pathway is followed by five cycles of -oxidation. The -oxidation cycles function by shortening the side chains, the first cycle results in the formation of carboxydimethyldecylhydroxychromanol followed by carboxymethyloctylhydroxychromanol. These two metabolites are categorized as long-chain metabolites and they are not excreted in the urine. Some intermediate-chain metabolites that are products of two rounds of -oxidation are carboxymethylhexylhydroxychromanol and carboxymethylbutylhydroxychromanol. These intermediate-chain metabolites can be found in human feces and urine. The catabolic end-product of tocopherols, as stated before, is CEHC which can be largely found in urine and feces. Two new metabolites have been detected in human and mice feces. These new metabolites are 12'-hydroxychromanol and 11'-hydroxychromanol. Because of their chemistry, it is thought that these metabolites can be the evidence for a -1 and -2 hydroxylation which leads to an impaired oxidation of 12'-OH followed side-chain truncation.


Vitamin E is stored unmodified in tissues (principally the liver and adipose tissue) and excreted via the feces. Excess vitamin E is converted to a lactone, esterified to glucuronic acid, and subsequently excreted in the urine.

Drug Facts and Comparisons 2015. Clinical Drug Information, LLC St. Louis, MO 2015, p. 16


Alpha-tocopherol (Vitamin E), formed from homogentisic acid yields, in rabbits 4-hydroxy-4-methyl-6-(2,4,5-trimethyl-3,6-quinonyl)caproic acid ...

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. T-15


Vitamin E is likely the most important antioxidant in the human diet and alpha-tocopherol is the most active isomer. Alpha-tocopherol exhibits anti-oxidative capacity in vitro, and inhibits oxidation of ldl. Beside this, alpha-tocopherol shows anti-inflammatory activity and modulates expression of proteins involved in uptake, transport and degradation of tocopherols, as well as the uptake, storage and export of lipids such as cholesterol. Despite promising anti-atherogenic features in vitro, vitamin E failed to be atheroprotective in clinical trials in humans. Recent studies highlight the importance of long-chain metabolites of alpha-tocopherol, which are formed as catabolic intermediate products in the liver and occur in human plasma. These metabolites modulate inflammatory processes and macrophage foam cell formation via mechanisms different than that of their metabolic precursor alpha-tocopherol and at lower concentrations. Here we summarize the controversial role of vitamin E as a preventive agent against atherosclerosis and point the attention to recent findings that highlight a role of these long-chain metabolites of vitamin E as a proposed new class of regulatory metabolites. We speculate that the metabolites contribute to physiological as well as pathophysiological processes.

PMID:24624339 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3949092 Wallert M et al; Redox Biol. 2: 495-503 (2014)


5.5 Biological Half-Life

44 hours in premature neonates given a 20mg/kg intramuscular injection. 12 minutes in intravenous injection of intestinal lymph.


The elimination half-life of tocopherol is approximately 2.6 hours.


Little is known about alpha-tocopherol's bioavailability as a constituent of food or its dependence on a subject's age. To evaluate the alpha-tocopherol bioavailability from food, we used collard greens grown in deuterated water ((2)H collard greens) as a source of deuterium-labeled ((2)H) alpha-tocopherol consumed by younger and older adults in a post hoc analysis of a vitamin K study. Younger (mean +/- SD age: 32 +/- 7 y; n = 12 women and 9 men) and older (aged 67 +/- 8 y; n = 8 women and 12 men) adults consumed a test breakfast that included 120 g (2)H collard greens (1.2 +/- 0.1 mg (2)H-alpha-tocopherol). Plasma unlabeled alpha-tocopherol and (2)H-alpha-tocopherol were measured by using liquid chromatography-mass spectrometry from fasting (>12 hr) blood samples drawn before breakfast (0 hr) and at 24, 48, and 72 hr and from postprandial samples collected at 4, 5, 6, 7, 9, 12, and 16 hr. Times (12.6 +/- 2.5 h) of maximum plasma (2)H-alpha-tocopherol concentrations (0.82% +/- 0.59% total alpha-tocopherol), fractional disappearance rates (0.63 +/- 0.26 pools/d), half-lives (30 +/- 11 hr), and the minimum estimated (2)H-alpha-tocopherolabsorbed (24% +/- 16%) did not vary between age groups or sexes (n = 41). Unlabeled alpha-tocopherol concentrations were higher in older adults (26.4 +/- 8.6 umol/L) than in younger adults (19.3 +/- 4.2 umol/L; P = 0.0019) and correlated with serum lipids (r = 0.4938, P = 0.0012). In addition, (2)H-alpha-tocopherol half-lives were correlated with lipids (r = 0.4361, P = 0.0044). Paradoxically, alpha-tocopherol remained in circulation longer in participants with higher serum lipids, but the (2)H-alpha-tocopherol absorbed was not dependent on the plasma lipid status. Neither variable was dependent on age. These data suggest that plasma alpha-tocopherol concentrations are more dependent on mechanisms that control circulating lipids rather than those related to its absorption and initial incorporation into plasma.

PMID:25739929 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4381779 Traber MG et al; Am J Clin Nutr. 101 (4): 752-9 (2015)


5.6 Mechanism of Action

The mechanism of action for most of vitamin E's effects are still unknown. Vitamin E is an antioxidant, preventing free radical reactions with cell membranes. Though in some cases vitamin E has been shown to have pro-oxidant activity. One mechanism of vitamin E's antioxidant effect is in the termination of lipid peroxidation. Vitamin E reacts with unstable lipid radicals, producing stable lipids and a relatively stable vitamin E radical. The vitamin E radical is then reduced back to stable vitamin E by reaction with ascorbate or glutathione.


Tocopherol acts as a radical scavenger. It mainly acts as an antioxidant for lipid bilayers. Tocopherol's functions depend on the H-atom donating ability, location, and movement within the membrane, as well as the efficiency in the radical recycling by some cytosolic reductants such as ascorbate. Tocopherol actions are related to the trap of radicals, and it has been shown that even in the absence of substituents in the ortho-positions, tocopherol can trap more than two radicals. The type of radicals available for tocopherol are alkyl and peroxy.


Cancer development and progression are closely associated with inflammation. NF-kappaB (nuclear factor kappaB) provides a mechanistic link between inflammation and cancer, and is a major factor controlling the ability of malignant cells to resist tumor surveillance mechanisms. NF-kappaB might also regulate tumor angiogenesis and invasiveness and the signalling pathways that mediate its activation provide attractive targets for new chemopreventive and chemotherapeutic approaches. ROS (reactive oxygen species) initiate inflammation by up-regulation of pro-inflammatory cytokines and therefore antioxidants provide a major defence against inflammation. alpha-Tocopherol is a lipid-soluble antioxidant. In addition to decreasing lipid peroxidation, alpha-tocopherol may exert intracellular effects. Hence, the aim of this study was to test the effect of alpha-tocopherol supplementation in cancer prevention via suppression of NF-kappaB-mediated pro-inflammatory cytokines. alpha-Tocopherol treatment significantly down-regulates expression, synthesis as well as secretion of pro-inflammatory cytokine IL-6 (interleukin-6) in cancerous mice. It also suppresses NF-kappaB binding to IL-6 promoter in liver leading to decreased secretion of IL-6 in serum. The regulation of the signalling pathway by alpha-tocopherol is found apart from its antioxidant capacity to reduce lipid peroxidation. Thus, the present study provides evidence for the hypothesis that besides the powerful free radical scavenging effects, alpha-tocopherol has genomic effects in down-regulation of pro-inflammatory cytokine and cancer prevention via the NF-kappaB-dependent pathway.

PMID:21320073 Sharma R, Vinayak M; Biosci Rep. 31 (5): 421-8 (2011)


Mitocans are drugs selectively killing cancer cells by destabilizing mitochondria and many induce apoptosis via generation of reactive oxygen species (ROS). However, the molecular events by which ROS production leads to apoptosis has not been clearly defined. In this study with the mitocan alpha-tocopheryl succinate (alpha-TOS) the role of the Bcl-2 family proteins in the mechanism of malignant cell apoptosis has been determined. Exposure of several different cancer cell lines to alpha-TOS increased expression of the Noxa protein, but none of the other proteins of the Bcl-2 family, an event that was independent of the cellular p53 status. alpha-TOS caused a profound conformational change in the pro-apoptotic protein, Bak, involving oligomerization in all cell types, and this also applied to the Bax protein, but only in non-small cell lung cancer cells. Immunoprecipitation studies indicated that alpha-TOS activates the two BH1-3 proteins, Bak or Bax, to form high molecular weight complexes in the mitochondria. RNAi knockdown revealed that Noxa and Bak are required for alpha-TOS-induced apoptosis, and the role of Bak was confirmed using Bak- and/or Bax-deficient cells. We conclude that the major events induced by alpha-TOS in cancer cells downstream of ROS production leading to mitochondrial apoptosis involve the Noxa-Bak axis. It is proposed that this represents a common mechanism for mitochondrial destabilization activated by a variety of mitocans that induce accumulation of ROS in the early phases of apoptosis. /alpha-Tocopheryl succinate/

PMID:20217235 Prochazka L et al; Apoptosis. 15 (7): 782-94 (2010)


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03-Jan-2021
30-Oct-2024
KGS
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Average Price (USD/KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL...DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL;0.02MG/VIAL;0.001MG/VIAL;5MG/VIAL;0.01MG/VIAL;0.14MG/VIAL;17MG/VIAL;0.2MG/VIAL;1MG/VIAL;1.4MG/VIAL;EQ 1.2MG BASE/VIAL;0.7MG/VIAL;7MG/VIAL

USFDA APPLICATION NUMBER - 18920

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DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;...DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;0.06MG/VIAL;0.005MG/VIAL;15MG/VIAL;0.005MG/VIAL;0.6MG/VIAL;40MG/VIAL;6MG/VIAL;3.6MG/VIAL;6MG/VIAL;1MG/VIAL;10MG/VIAL;0.15MG/VIAL

USFDA APPLICATION NUMBER - 21625

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DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006...DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006MG/ML;0.05MCG/ML;1.5MG/ML;0.0005MG/ML;0.06MG/ML;4MG/ML;0.6MG/ML;0.36MG/ML;0.6MG/ML;0.1MG/ML;1MG/ML

USFDA APPLICATION NUMBER - 8809

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