α-tocopherol

α-tocopherol
Compound Structure:
Synonyms: VITAMIN E; alpha-Tocopherol ;D-alpha-Tocopherol ;59-02-9; 5,7,8-Trimethyltocol
Compound ID: NMPC-1638
PubChem ID:

14985
Molecular Formula: C29H50O2
Canonical SMILES: CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C
InChIKey: GVJHHUAWPYXKBD-IEOSBIPESA-N
About the compound:

(R,R,R)-alpha-tocopherol is an alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils. It has a role as an antioxidant, a nutraceutical, an antiatherogenic agent, an EC 2.7.11.13 (protein kinase C) inhibitor, an anticoagulant, an immunomodulator, an antiviral agent, a micronutrient, an algal metabolite and a plant metabolite. It is an enantiomer of a (S,S,S)-alpha-tocopherol. In 1922, vitamin E was demonstrated to be an essential nutrient. Vitamin E is a term used to describe 8 different fat soluble tocopherols and tocotrienols, alpha-tocopherol being the most biologically active. Vitamin E acts as an antioxidant, protecting cell membranes from oxidative damage. The antioxidant effects are currently being researched for use in the treatment of diseases causing bone loss, cardiovascular diseases, diabetes mellitus and associated comorbidities, eye diseases, inflammatory diseases (including skin conditions), lipid disorders, neurological diseases, and radiation damage. Though this research is so far inconclusive, vitamin E remains a popular supplement and is generally considered safe by the FDA.
Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

430.7 g/mol

XLogP3-AA

10.7

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

12

Exact Mass

430.381080833 g/mol

Monoisotopic Mass

430.381080833 g/mol

Topological Polar Surface Area

29.5Ų

Heavy Atom Count

31

Formal Charge

0

Complexity

503

Isotope Atom Count

0

Defined Atom Stereocenter Count

3

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Slightly yellow to amber, nearly odourless, clear, viscous oil which oxidises and darkens on exposure to air or light

Boiling Point

662 °F at 760 mmHg decomposes (NTP, 1992)

Melting Point

3°C

Density

0.95 at 77 °F (NTP, 1992) - Less dense than water; will float

Solubility 

Insoluble in water, freely soluble in ethanol, miscible in ether

Vapor Pressure

0.00000001 [mmHg]

Source:PubChem
Source Species: Phyllanthus amarus
Sapium ellipticum
Ficus thonningii
Download SDF