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59-02-9 molecular structure
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(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 and InChIs

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

Cite this record

CBID:49 http://www.chembase.cn/molecule-49.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
vitamin E
VitaE
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
alpha-Tocopherol
Tocopherol
Vitamin E
2,5,7,8-Tetramethyl-2-(4′,8′,12′-trimethyltridecyl)-6-chromanol
5,7,8-Trimethyltocol
D-α-Tocopherol
Vitamin E
(+)-α-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
a-Vitamin E
α-Tocopherol
CAS Number
59-02-9
EC Number
200-412-2
MDL Number
MFCD00072045
Beilstein Number
4712525
PubChem SID
24899979
46506524
160963512
24900154
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.802178  H Acceptors
H Donor LogD (pH = 5.5) 10.507715 
LogD (pH = 7.4) 10.507546  Log P 10.507717 
Molar Refractivity 135.3741 cm3 Polarizability 52.98319 Å3
Polar Surface Area 29.46 Å2 Rotatable Bonds 12 
Lipinski's Rule of Five false 
Log P 8.84  LOG S -7.79 
Solubility (Water) 7.04e-06 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Ethanol expand Show data source
Insoluble in water, but water-dispersible. expand Show data source
Methanol expand Show data source
Apperance
clear yellow liquid expand Show data source
clear yellow neat (liquid, ≥0.88M based on potency, density and molecular wt.) expand Show data source
clear yellow to red expand Show data source
Oil expand Show data source
Pale Yellow Thick Oil expand Show data source
yellow-brown viscous liquid expand Show data source
Melting Point
2.5–3.5 °C expand Show data source
Boiling Point
200-220 °C/0.1 mmHg(lit.) expand Show data source
200–220 °C at 0.1 mmHg expand Show data source
Flash Point
110 °C expand Show data source
230 °F expand Show data source
Density
0.95 g/mL at 25 °C(lit.) expand Show data source
0.950 g/cm3 expand Show data source
Refractive Index
n20/D 1.505(lit.) expand Show data source
Hydrophobicity(logP)
10 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
DJ2900000 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
1 expand Show data source
NFPA704
NFPA 704 diagram
1
1
0
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US) expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
95+% expand Show data source
Potency
≥600 mg d-α-tocopherol per g expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
suitable for insect cell culture expand Show data source
Biological Source
from vegetable oil expand Show data source
Type
Type V expand Show data source
Type VI expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00163 external link
Item Information
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 external link
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 external link
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 external link
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

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