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CAS 4345-03-3
Also known as: 4345-03-3, Alpha-tocopheryl succinate, D-alpha-tocopherol succinate, Tocopherol succinate, Alpha-tocopherol succinate, D-alpha-tocopheryl succinate
Molecular Formula
C33H54O5
Molecular Weight
530.8  g/mol
InChI Key
IELOKBJPULMYRW-NJQVLOCASA-N
FDA UNII
LU4B53JYVE

A natural tocopherol and one of the most potent antioxidant tocopherols. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. It has four methyl groups on the 6-chromanol nucleus. The natural d form of alpha-tocopherol is more active than its synthetic dl-alpha-tocopherol racemic mixture.
1 2D Structure

CAS 4345-03-3

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-oxo-4-[[(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl]oxy]butanoic acid
2.1.2 InChI
InChI=1S/C33H54O5/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-20-33(8)21-19-28-27(7)31(25(5)26(6)32(28)38-33)37-30(36)18-17-29(34)35/h22-24H,9-21H2,1-8H3,(H,34,35)/t23-,24-,33-/m1/s1
2.1.3 InChI Key
IELOKBJPULMYRW-NJQVLOCASA-N
2.1.4 Canonical SMILES
CC1=C(C(=C(C2=C1OC(CC2)(C)CCCC(C)CCCC(C)CCCC(C)C)C)OC(=O)CCC(=O)O)C
2.1.5 Isomeric SMILES
CC1=C(C(=C(C2=C1O[C@](CC2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)OC(=O)CCC(=O)O)C
2.2 Other Identifiers
2.2.1 UNII
LU4B53JYVE
2.3 Synonyms
2.3.1 MeSH Synonyms

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

2. Acetate, Tocopherol

3. Alpha Tocopherol

4. Alpha Tocopherol Acetate

5. Alpha Tocopherol Hemisuccinate

6. Alpha Tocopherol Succinate

7. Alpha Tocopheryl Calcium Succinate

8. Alpha-tocopherol

9. Alpha-tocopherol Acetate

10. Alpha-tocopherol Hemisuccinate

11. Alpha-tocopherol Succinate

12. Alpha-tocopheryl Calcium Succinate

13. D Alpha Tocopherol

14. D Alpha Tocopheryl Acetate

15. D-alpha Tocopherol

16. D-alpha-tocopheryl Acetate

17. R,r,r-alpha-tocopherol

18. Tocopherol Acetate

19. Tocopherol Succinate

20. Tocopherol, D-alpha

21. Tocopheryl Acetate

2.3.2 Depositor-Supplied Synonyms

1. 4345-03-3

2. Alpha-tocopheryl Succinate

3. D-alpha-tocopherol Succinate

4. Tocopherol Succinate

5. Alpha-tocopherol Succinate

6. D-alpha-tocopheryl Succinate

7. Vitamin E Hemisuccinate

8. Alpha-tocopherol Succinate, D-

9. D-alpha-tocopherol Acid Succinate

10. D-

11. A-tocopherol Succinate

12. Alpha Tocopheryl Acid Succinate

13. Alpha-tocopheryl Acid Succinate

14. (+)-alpha-tocopheryl Succinate

15. Alpha-vitamin E Succinate

16. Vitamine E Succinate

17. Lu4b53jyve

18. .alpha.-tocopherol Succinate

19. 4-oxo-4-[[(2r)-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl]oxy]butanoic Acid

20. Rrr-alpha-tocopheryl Hydrogen Succinate

21. Ncgc00167561-01

22. Dsstox_cid_6151

23. Nsc 173849

24. Dsstox_rid_78037

25. Dsstox_gsid_26151

26. 4-oxo-4-(((r)-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)chroman-6-yl)oxy)butanoic Acid

27. D-alpha Tocopheryl Acid Succinate

28. D-alpha-tocopheryl Acid Succinate

29. Butanedioic Acid, 1-((2r)-3,4-dihydro-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-yl) Ester

30. Butanedioic Acid, Mono((2r)-3,4-dihydro-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-yl) Ester

31. Cas-4345-03-3

32. Covitol 1210

33. D-.alpha.-tocopherol Succinate

34. D-.alpha.-tocopheryl Succinate

35. Alpha-tocopherol, Succinate

36. Alpha-tocopherol Hemisuccinate

37. Ccris 4734

38. Alpha-tocopheryl Succinate, D-

39. Nsc173849

40. Nsc-173849

41. Tocopherol Acid Succinate, Alpha-

42. 6-chromanol, 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, Hydrogen Succinate, (+)-

43. Alpha-tocopheryl Hydrogen Succinate

44. Vitamin-e Dragees

45. 4-oxo-4-((r)-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)chroman-6-yloxy)butanoic Acid

46. Butanedioic Acid, Mono(3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-yl) Ester, (2r-(2r*(4r*,8r*)))-

47. Butanedioic Acid, Mono[(2r)-3,4-dihydro-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-2h-1-benzopyran-6-yl] Ester

48. Succinic Acid, Mono(2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanyl) Ester, (+)-

49. Tocopheryl Succinate

50. Alpha-tocopherol Acid Succinate, D-

51. Dal-e

52. Einecs 224-403-8

53. Einecs 241-433-7

54. Cv 104

55. Mfcd00072055

56. Tocopheryl Acid Succinate,d-alpha

57. .alpha.-tocopherol Succinate, D-

58. Unii-lu4b53jyve

59. D-alpha-tocopherolsuccinate

60. D-alpha-tocopheryl-succinate

61. .alpha.-tocopheryl Succinate

62. White-e [veterinary] (tn)

63. Chembl81421

64. Schembl134422

65. D- Alpha -tocopheryl Succinate

66. Dtxsid2026151

67. Alpha-tocopherol, Succinate, D-

68. .alpha.-tocopheryl Succinate, D-

69. Chebi:135821

70. Tocopheryl Acid Succinate, D-alpha

71. Tocopheryl Succinate [inci]

72. Act03492

73. Zinc4214779

74. Tox21_112556

75. Tox21_200568

76. Bdbm50458511

77. D-alpha-tocopheryl Hydrogen Succinate

78. Akos015902063

79. Dal-vita Brand Of Vitamin E Succinate

80. Wiedemann Brand Of Vitamin E Succinate

81. (+)-.alpha.-tocopherol Acid Succinate

82. Ac-1132

83. Ccg-207945

84. Db14001

85. 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanyl Hydrogen Succinate, (+)-

86. Mono(2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanyl) Succinate, (+)-

87. Ncgc00167561-02

88. Ncgc00167561-03

89. Ncgc00258122-01

90. Tocopheryl Acid Succinate [vandf]

91. 3-{[(2r)-2-((4r,8r)-4,8,12-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-yl] Oxycarbonyl}propanoic Acid

92. 4-oxo-4-[(2r)-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]chroman-6-yl]oxy-butanoic Acid

93. As-75106

94. Butanedioic Acid,mono[(2r)-3,4-dihydro-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-2h-1-benzopyran-6-yl] Ester

95. J24.824j

96. Mono(3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-yl) Butanedioate, (2r-(2r*(4r*,8r*)))-

97. .alpha.-tocopherol Succinate [mi]

98. Dl-alpha-tocopherolhydrogensuccinate

99. Rrr-alpha-tocopheryl Acid Succinate

100. Tocopheryl Acid Succinate [who-dd]

101. Hy-131553

102. Cs-0136520

103. T2628

104. Vitamin E (alpha-tocopheryl Succinate)

105. C90299

106. D08612

107. D-alpha Tocoferil Acid Succinate [mart.]

108. D-alpha-tocopherol Succinate, Analytical Standard

109. Rrr-.alpha.-tocopheryl Hydrogen Succinate

110. C033716

111. Rrr-alpha-tocopheryl Acid Succinate [fcc]

112. Sr-01000883728

113. Tocopheryl Acid Succinate,d-alpha [vandf]

114. Sr-01000883728-1

115. Q27283185

116. D-alpha-tocopherol Succinate, Semisynthetic, 1210 Iu/g

117. D-alpha-tocopherol Succinate, Bioxtra, >=98.0% (hplc)

118. Rrr-.alpha.-tocopheryl Hydrogen Succinate [ep Impurity]

119. Alpha Tocopheryl Acid Succinate, United States Pharmacopeia (usp) Reference Standard

120. Rrr-alpha-tocopheryl Hydrogen Succinate, European Pharmacopoeia (ep) Reference Standard

121. (3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-yl) Hydrogen Succinate

122. 4-oxo-4-(((r)-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)chroman-6-yl)oxy)butanoicacid

123. 4-oxo-4-{[(2r)-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydro-2h-1-benzopyran-6-yl]oxy}butanoic Acid

124. 55134-51-5

125. Mono((2r)-3,4-dihydro-2,5,7,8-tetramethyl-2-((4r,8r)-4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-yl) Butanedioate

126. Tocopheryl Acid Succinate, A, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 530.8 g/mol
Molecular Formula C33H54O5
XLogP310.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count17
Exact Mass530.39712482 g/mol
Monoisotopic Mass530.39712482 g/mol
Topological Polar Surface Area72.8 Ų
Heavy Atom Count38
Formal Charge0
Complexity720
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 Drug Indication

The primary health-related use for which alpha-tocopherol succinate is formally indicated is as a dietary supplement for patients who demonstrate a genuine vitamin E deficiency. At the same time, vitamin E deficiency is generally quite rare but may occur in premature babies of very low birth weight (< 1500 grams), individuals with fat-malabsorption disorders (as fat is required for the digestive tract to absorb vitamin E), or individuals with abetalipoproteinemia - a rare, inherited disorder that causes poor absorption of dietary fat - who require extremely large doses of supplemental vitamin E daily (around 100 mg/kg or 5-10 g/day). In all such cases, alpha-tocopherol is largely the preferred form of vitamin E to be administered. Elsewhere, vitamin E's chemical profile as a fat-soluble antioxidant that is capable of neutralizing free radicals in the body continues to generate ongoing interest and study regarding how and whether or not the vitamin can help prevent or delay various chronic diseases associated with free radicals or other potential biological effects that vitamin E possesses like cardiovascular diseases, diabetes, ocular conditions, immune illnesses, cancer, and more. None of these ongoing studies have yet to elucidate any formally significant evidence, however. Similarly, more effective clinical trials are necessary to confirm what has only been accrued as preliminary data when it comes to studies proposing the demonstration of alpha-tocopherol succinate's capability to act as an anti-cancer therapy or as a regulator of inflammation.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Of the eight separate variants of vitamin E, alpha-tocopherol is the predominant form of vitamin E in human and animal tissues, and it has the highest bioavailability. This is because the liver preferentially resecretes only alpha-tocopherol by way of the hepatic alpha-tocopherol transfer protein (alpha-TTP); the liver metabolizes and excretes all the other vitamin E variants, which is why blood and cellular concentrations of other forms of vitamin E other than alpha-tocopherol are ultimately lower. Furthermore, the term alpha-tocopherol generally refers to a group of eight possible stereoisomers which is often called all-rac-tocopherol for being a racemic mixture of all eight stereoisomers. Of the eight stereoisomers, the RRR-alpha-tocopherol - or sometimes referred to as the d-alpha-tocopherol - stereoisomer is the naturally occurring form of alpha-tocopherol that is perhaps best recognized by the alpha-TTP and has been reported to demonstrate approximately twice the systemic availability of all-rac-tocopherol. As a result, often times (but certainly not always) the discussion of vitamin E - at least within the context of using the vitamin for health-related indications - is generally in reference to the use of RRR- or d-alpha-tocopherol. Subsequently, without further evidence to suggest otherwise, alpha-tocpherol succinate is generally believed to undergo a logical de-esterification in the gastrointestinal tract before being subsequently absorbed as free tocopherol.


5.2 MeSH Pharmacological Classification

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.)


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.)


5.3 Absorption, Distribution and Excretion

Absorption

_In addition to any following information, owing to alpha-Tocopherol succinate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data._ It is generally believed that alpha-tocopherol succinate is ultimately de-esterified or cleaved to provide alpha-tocopherol once administered to the human body. It is consequently expected that pharmacodynamics and pharmacokinetics similar to that of alpha-tocopherol to be followed. 50 to 80% absorbed from gastrointestinal tract.


Route of Elimination

_In addition to any following information, owing to alpha-Tocopherol succinate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data._ It is generally believed that alpha-tocopherol succinate is ultimately de-esterified or cleaved to provide alpha-tocopherol once administered to the human body. It is consequently expected that pharmacodynamics and pharmacokinetics similar to that of alpha-tocopherol to be followed.


Volume of Distribution

_In addition to any following information, owing to alpha-Tocopherol succinate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data._ It is generally believed that alpha-tocopherol succinate is ultimately de-esterified or cleaved to provide alpha-tocopherol once administered to the human body. It is consequently expected that pharmacodynamics and pharmacokinetics similar to that of alpha-tocopherol to be followed.


Clearance

_In addition to any following information, owing to alpha-Tocopherol succinate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data._ It is generally believed that alpha-tocopherol succinate is ultimately de-esterified or cleaved to provide alpha-tocopherol once administered to the human body. It is consequently expected that pharmacodynamics and pharmacokinetics similar to that of alpha-tocopherol to be followed.


5.4 Metabolism/Metabolites

_In addition to any following information, owing to alpha-Tocopherol succinate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data._ It is generally believed that alpha-tocopherol succinate is ultimately de-esterified or cleaved to provide alpha-tocopherol once administered to the human body. It is consequently expected that pharmacodynamics and pharmacokinetics similar to that of alpha-tocopherol to be followed. Hepatic.


5.5 Biological Half-Life

_In addition to any following information, owing to alpha-Tocopherol succinate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data._ It is generally believed that alpha-tocopherol succinate is ultimately de-esterified or cleaved to provide alpha-tocopherol once administered to the human body. It is consequently expected that pharmacodynamics and pharmacokinetics similar to that of alpha-tocopherol to be followed.


5.6 Mechanism of Action

Without further evidence to suggest otherwise, alpha-tocpherol succinate is generally believed to undergo a logical de-esterification in the gastrointestinal tract before being subsequently absorbed as free tocopherol. The free alpha-tocopherol is therefore available and capable of the following activities. Vitamin E's antioxidant capabilities are perhaps the primary biological action associated with alpha-tocopherol. In general, antioxidants protect cells from the damaging effects of free radicals, which are molecules that consist of an unshared electron. These unshared electrons are highly energetic and react rapidly with oxygen to form reactive oxygen species (ROS). In doing so, free radicals are capable of damaging cells, which may facilitate their contribution to the development of various diseases. Moreover, the human body naturally forms ROS when it converts food into energy and is also exposed to environmental free radicals contained in cigarette smoke, air pollution, or ultraviolet radiation from the sun. It is believed that perhaps vitamin E antioxidants might be able to protect body cells from the damaging effects of such frequent free radical and ROS exposure. Specifically, vitamin E is a chain-breaking antioxidant that prevents the propagation of free radical reactions. The vitamin E molecule is specifically a peroxyl radical scavenger and especially protects polyunsaturated fatty acids within endogenous cell membrane phospholipids and plasma lipoproteins. Peroxyl free radicals react with vitamin E a thousand times more rapidly than they do with the aforementioned polyunsaturated fatty acids. Furthermore, the phenolic hydroxyl group of tocopherol reacts with an organic peroxyl radical to form an organic hydroperoxide and tocopheroxyl radical. This tocopheroxyl radical can then undergo various possible reactions: it could (a) be reduced by other antioxidants to tocopherol, (b) react with another tocopheroxyl radical to form non-reactive products like tocopherol dimers, (c) undergo further oxidation to tocopheryl quinone, or (d) even act as a prooxidant and oxidize other lipids. In addition to the antioxidant actions of vitamin E, there have been a number of studies that report various other specific molecular functions associated with vitamin E. For example, alpha-tocopherol is capable of inhibiting protein kinase C activity, which is involved in cell proliferation and differentiation in smooth muscle cells, human platelets, and monocytes. In particular, protein kinase C inhibition by alpha-tocopherol is partially attributable to its attenuating effect on the generation of membrane-derived dialglycerol, a lipid that facilitates protein kinase C translocation, thereby increasing its activity. In addition, vitamin E enrichment of endothelial cells downregulates the expression of intercellular cell adhesion molecule (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1), thereby decreasing the adhesion of blood cell components to the endothelium. Vitamin E also upregulates the expression of cytosolic phospholipase A2 and cyclooxygenase-1. The increased expression of these two rate-limiting enzymes in the arachidonic acid cascade explains the observation that vitamin E, in a dose-dependent fashion, enhanced the release of prostacyclin, a potent vasodilator and inhibitor of platelet aggregation in humans. Furthermore, vitamin E can inhibit platelet adhesion, aggregation, and platelet release reactions. The vitamin can also evidently inhibit the plasma generation of thrombin, a potent endogenous hormone that binds to platelet receptors and induces aggregation of platelets. Moreover, vitamin E may also be able to decrease monocyte adhesion to the endothellium by downregulating expression of adhesion molecules and decreasing monocyte superoxide production. Given these proposed biological activities of vitamin E, the substance continues to generate ongoing interest and studies in whether or not vitamin E can assist in delaying or preventing various diseases with any one or more of its biologic actions. For instance, studies continue to see whether vitamin E's ability to inhibit low-density lipoprotein oxidation can aid in preventing the development of cardiovascular disease or atherogenesis. Similarly, it is also believed that if vitamin E can decrease the chance of cardiovascular disease then it can also decrease the chance of related diabetic disease and complications. In much the same way, it is also believed that perhaps the antioxidant abilities of vitamin E can neutralize free radicals that are constantly reacting and damaging cellular DNA. Furthermore, it is also believed that free radical damage does contribute to protein damage in the ocular lens - another free radical-mediated condition that may potentially be prevented by vitamin E use. Where it is also suggested that various central nervous system disorders like Parkinson's disease, Alzheimer's disease, Down's syndrome, and Tardive Dyskinesia possess some form of oxidative stress component, it is also proposed that perhaps vitamin E use could assist with its antioxidant action. There have also been studies that report the possibility of vitamin E supplementation can improve or reverse the natural decline in cellular immune function in healthy, elderly individuals. As of this time, however, there is either only insufficient data or even contradicting data (where certain doses of vitamin E supplementation could even potentially increase all-cause mortality) on which to suggest the use of vitamin E could formally benefit in any of these proposed indications. Furthermore, there are ongoing studies that demonstrate alpha-tocopherol succinate's unique possession of capabilities that allow it to induce differentiation, inhibit proliferation and apoptosis in cancer cells, enhance the growth-inhibitory effect of ionizing radiation, hyperthermia, and some chemotherapeutic agents and biological response modifiers on tumor cells, all the while protecting normal cells against any adverse effects. Despite being able to demonstrate such effects on animal and human cells in culture, the value of these effects has not drawn significant attention from researchers and clinicians and nor has the specific mechanisms of action been elucidated. Additionally, other studies have also shown that alpha-tocopherol succinate seemingly possesses an ability exclusive from other tocopherol esters to inhibit and minimize prostaglandin E2 production in human lung epithelial cells. Considering increased prostaglandin E2 production has been observed frequently in lung cancer patients, there may be another avenue in which alpha-tocopherol succinate may be able to treat lung cancer. Nevertheless, the possibility of such activity requires further elucidation.


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