(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

• ChemBase ID: 49
• Molecular Formular: C29H50O2
• Molecular Mass: 430.7061
• Monoisotopic Mass: 430.38108084
• SMILES: O1[C@](CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)(CCc2c1c(c(c(O)c2C)C)C)C
• Canonical SMILES: C[C@@H](CCC[C@]1(C)CCc2c(O1)c(C)c(c(c2C)O)C)CCC[C@@H](CCCC(C)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/t21-,22-,29-/m1/s1
• InChIKey: GVJHHUAWPYXKBD-IEOSBIPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
• IUPAC Traditional name: VitaE; vitamin E
• Brand Name: Amino-Opti-E; Aquasol E; Daltose; E-200 I.U. Softgels; E-Complex-600; E-Ferol; E-Vitamin succinate; Gordo-Vite E; Vitamin Plus E Softgells; Vitec
• Synonyms: 2,5,7,8-Tetramethyl-2-(4′,8′,12′-trimethyltridecyl)-6-chromanol; 5,7,8-Trimethyltocol; D-α-Tocopherol; Vitamin E; (+)-α-Tocopherol; Alpha-Tocopherol; (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol; (+)-α-Tocopherol; (all-R)-α-Tocopherol; Acros; Almefrol; Biopass E 20; Optovit; Tocovital; α-Vitamin E; α-Tocopherol; alpha-Tocopherol; Tocopherol; Vitamin E; a-Vitamin E; α-Tocopherol

Database IDs

• CAS Number: 59-02-9
• EC Number: 200-412-2
• MDL Number: MFCD00072045
• Beilstein Number: 4712525
• PubChem SID: 46506524; 160963512; 24900154; 24899979
• PubChem CID: 14985
• CHEBI ID: 18145
• ATC CODE: A11HA03
• CHEMBL: 47
• Chemspider ID: 14265
• DrugBank ID: DB00163
• Unique Ingredient Identifier: N9PR3490H9
• Wikipedia Title: Alpha-Tocopherol

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.802178
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 10.507715
• LogD (pH = 7.4): 10.507546
• Log P: 10.507717
• Molar Refractivity: 135.3741 cm^3
• Polarizability: 52.98319 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 8.84
• LOG S: -7.79
• Solubility (Water): 7.04e-06 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Insoluble in water, but water-dispersible.; Methanol
• Apperance: clear yellow liquid; clear yellow neat (liquid, ≥0.88M based on potency, density and molecular wt.); clear yellow to red; Oil; Pale Yellow Thick Oil; yellow-brown viscous liquid
• Melting Point: 2.5–3.5 °C
• Boiling Point: 200-220 °C/0.1 mmHg(lit.); 200–220 °C at 0.1 mmHg
• Flash Point: 110 °C; 230 °F
• Density: 0.95 g/mL at 25 °C(lit.); 0.950 g/cm3
• Refractive Index: n20/D 1.505(lit.)
• Hydrophobicity(logP): 10

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: DJ2900000
• German water hazard class: 1
• NFPA704:
  

  1

  1

  0
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: 95+%
• Potency: ≥600 mg d-α-tocopherol per g
• Suitability: suitable for insect cell culture
• Biological Source: from vegetable oil
• Type: Type V; Type VI

DETAILS

DrugBank - DB00163

• Drug Groups: approved; nutraceutical
• Description: 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. [PubChem]
• Indication: Vitamin E, known for its antioxidant activities, is protective against cardiovascular disease and some forms of cancer and has also demonstrated immune-enhancing effects. It may be of limited benefit in some with asthma and rheumatoid arthritis. It may be helpful in some neurological diseases including Alzheimer's, some eye disorders including cataracts, and diabetes and premenstrual syndrome. It may also help protect skin from ultraviolet irradiation although claims that it reverses skin aging, enhances male fertility and exercise performance are poorly supported. It may help relieve some muscle cramps.
• Pharmacology: Vitamin E has antioxidant activity. It may also have anti-atherogenic, antithrombotic, anticoagulant, neuroprotective, antiviral, immunomodulatory, cell membrane-stabilizing and antiproliferative actions. Vitamin E is a collective term used to describe eight separate forms, the best-known form being alpha-tocopherol. Vitamin E is a fat-soluble vitamin and is an important antioxidant. It acts to protect cells against the effects of free radicals, which are potentially damaging by-products of the body's metabolism. Vitamin E is often used in skin creams and lotions because it is believed to play a role in encouraging skin healing and reducing scarring after injuries such as burns. There are three specific situations when a vitamin E deficiency is likely to occur. It is seen in persons who cannot absorb dietary fat, has been found in premature, very low birth weight infants (birth weights less than 1500 grams, or 3½ pounds), and is seen in individuals with rare disorders of fat metabolism. A vitamin E deficiency is usually characterized by neurological problems due to poor nerve conduction. Symptoms may include infertility, neuromuscular impairment, menstrual problems, miscarriage and uterine degradation. Preliminary research has led to a widely held belief that vitamin E may help prevent or delay coronary heart disease. Antioxidants such as vitamin E help 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: 50 to 80% absorbed from gastrointestinal tract.
• Protein Binding: Bound to beta-lipoproteins in blood.
• References: Iuliano L, Micheletta F, Maranghi M, Frati G, Diczfalusy U, Violi F: Bioavailability of vitamin E as function of food intake in healthy subjects: effects on plasma peroxide-scavenging activity and cholesterol-oxidation products. Arterioscler Thromb Vasc Biol. 2001 Oct;21(10):E34-7. [Pubmed] ; Miller ER 3rd, Pastor-Barriuso R, Dalal D, Riemersma RA, Appel LJ, Guallar E: Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality. Ann Intern Med. 2005 Jan 4;142(1):37-46. Epub 2004 Nov 10. [Pubmed] ; Horwitt MK, Elliott WH, Kanjananggulpan P, Fitch CD: Serum concentrations of alpha-tocopherol after ingestion of various vitamin E preparations. Am J Clin Nutr. 1984 Aug;40(2):240-5. [Pubmed] ; Rumbold AR, Crowther CA, Haslam RR, Dekker GA, Robinson JS: Vitamins C and E and the risks of preeclampsia and perinatal complications. N Engl J Med. 2006 Apr 27;354(17):1796-806. [Pubmed] ; Poston L, Briley AL, Seed PT, Kelly FJ, Shennan AH: Vitamin C and vitamin E in pregnant women at risk for pre-eclampsia (VIP trial): randomised placebo-controlled trial. Lancet. 2006 Apr 8;367(9517):1145-54. [Pubmed] ; Linus Pauling Institute / [Link]
• External Links: Wikipedia; PDRhealth; Drugs.com

Sigma Aldrich - T4389

Other Notes
Mixed isomers
Quality
Approx. 400 mg of D-α-tocopherol per gram.The non-α-content varies from 5-50 mg per gram, the remainder is soybean oil.

Sigma Aldrich - T1539

Application
Use in insect cell culture applications as an antioxidant.
Other Notes
Mixed isomers
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T1539.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - T3634

Caution
Subject to air oxidation.
Other Notes
Mixed isomers
包装
Packaged under argon in a sealed ampule.
Quality
Approx. 670 mg D-α-tocopherol per gram. The non-α content is typically between 5-35 mg/g
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. Various isofroms and analogues of tocopherol have opposing and differentiated regulatory activities in vivo.
Physical properties
This product is miscible with chloroform or ethanol. It is practically insoluble in water but it is miscible with ether, acetone, and vegetable oils. It is unstable to alkaline conditions.

Toronto Research Chemicals - T526125

α-Tocopherol is the most bioactive of the naturally occurring forms of Vitamin E. Richest sources are green vegetables, grains, and oils, particularly palm, safflower and sunflower oils.

REFERENCES

• Linus Pauling Institute Link/
• Iuliano L, Micheletta F, Maranghi M, Frati G, Diczfalusy U, Violi F: Bioavailability of vitamin E as function of food intake in healthy subjects: effects on plasma peroxide-scavenging activity and cholesterol-oxidation products. Arterioscler Thromb Vasc Biol. 2001 Oct;21(10):E34-7. Pubmed
• Miller ER 3rd, Pastor-Barriuso R, Dalal D, Riemersma RA, Appel LJ, Guallar E: Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality. Ann Intern Med. 2005 Jan 4;142(1):37-46. Epub 2004 Nov 10. Pubmed
• Horwitt MK, Elliott WH, Kanjananggulpan P, Fitch CD: Serum concentrations of alpha-tocopherol after ingestion of various vitamin E preparations. Am J Clin Nutr. 1984 Aug;40(2):240-5. Pubmed
• Rumbold AR, Crowther CA, Haslam RR, Dekker GA, Robinson JS: Vitamins C and E and the risks of preeclampsia and perinatal complications. N Engl J Med. 2006 Apr 27;354(17):1796-806. Pubmed
• Poston L, Briley AL, Seed PT, Kelly FJ, Shennan AH: Vitamin C and vitamin E in pregnant women at risk for pre-eclampsia (VIP trial): randomised placebo-controlled trial. Lancet. 2006 Apr 8;367(9517):1145-54. Pubmed
• Bianchi, G., et al.: Eur. J. Lipid Sci. Technology, 105, 229 (2003)
• Sakouhi, F., et al.: Food Chem., 108, 833 (2003)