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

• ChemBase ID: 155437
• Molecular Formular: C33H54O5
• Molecular Mass: 530.77886
• Monoisotopic Mass: 530.39712483
• SMILES: Cc1c(c(c(c2c1O[C@](CC2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)OC(=O)CCC(=O)O)C
• Canonical SMILES: C[C@@H](CCC[C@]1(C)CCc2c(O1)c(C)c(c(c2C)OC(=O)CCC(=O)O)C)CCC[C@@H](CCCC(C)C)C
• 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
• InChIKey: IELOKBJPULMYRW-NJQVLOCASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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
• IUPAC Traditional name: 4-oxo-4-{[(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-1-benzopyran-6-yl]oxy}butanoic acid
• Synonyms: CV 104; Covitol 1210; NSC 173849; d-α-Tocopherol Acid Succinate; 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; (+)-2,5,7,8-Tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol Hydrogen Succinate; d-α-Tocopheryl Acid Succinate; (+)-α-Tocopheryl Succinate; Succinic Acid (+)-mono[2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanyl] ester; α-Vitamin E Succinate; Vitamin E d-α-Tocosuccinate; α-Tocopheryl Succinate; Vitamin E succinate; D-α-Tocopherol succinate; 维生素 E 琥珀酸酯; D-α-生育酚琥珀酸酯

Database IDs

• CAS Number: 4345-03-3
• EC Number: 224-403-8
• MDL Number: MFCD00072055
• Beilstein Number: 4038233
• PubChem SID: 24871418; 24900107; 24890110; 162249575
• PubChem CID: 20353

CALCULATED PROPERTIES

• Acid pKa: 3.9952197
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 8.729335
• LogD (pH = 7.4): 7.0816007
• Log P: 10.243406
• Molar Refractivity: 155.4189 cm^3
• Polarizability: 60.94539 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: analytical standard
• Packaging: ampule of 100 mg
• Biological Source: semisynthetic
• Feature: standard type fat soluble vitamin
• Product Line: BioXtra
• Pharmacopeia Traceability: traceable to PhEur T1610000; traceable to USP 1667803
• Empirical Formula (Hill Notation): C33H54O5

DETAILS

Sigma Aldrich - T3126

Biochem/physiol Actions
Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by homo sapiens. α-Tocopherol succinate is used along the α-Tocopherol acetate, α-Tocopherol nicotinate and other esterified forms as a vitamin E supplement with similar but differential activities.

Sigma Aldrich - 95255

Biochem/physiol Actions
Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by homo sapiens. α-Tocopherol succinate is used along the α-Tocopherol acetate, α-Tocopherol nicotinate and other esterified forms as a vitamin E supplement with similar but differential activities.

Toronto Research Chemicals - T539950

A potent novel antineoplastic agent with high selectivity and cooperativity with tumor necrosis factor-related apoptosis-inducing ligand (Apo2 ligand). It inhibits proliferation of mesothelioma cells by selective down-regulation of fibroblast growth facto

REFERENCES

• Weber, T. et al.: Clin. Can Res., 8, 863 (2002)
• Staphelberg, M. et al.: Biochem. Biophys. Res. Comm., 318, 636 (2002)
• Ramathapuram, L.V. et al.: Cancer Immunol. Immununother., 55, 166 (2002)