α-Tocopherol

α-Tocopherol
Names
	Preferred IUPAC name (2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Identifiers
CAS Number	59-02-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18145 ;
ChEMBL	ChEMBL47 ;
ChemSpider	14265 ;
DrugBank	DB00163 ;
ECHA InfoCard	100.000.375
EC Number	200-412-2;
E number	E307a (antioxidants, ...)
PubChem CID	14985;
UNII	N9PR3490H9 ;
CompTox Dashboard (EPA)	DTXSID0026339 ;
	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 Key: GVJHHUAWPYXKBD-IEOSBIPESA-N ; InChI=1/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 Key: GVJHHUAWPYXKBD-IEOSBIPEBS;
	SMILES Cc1c(O)c(C)c(CC[C@](CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)(C)O2)c2c1C;
Properties
Chemical formula	C29H50O2
Molar mass	430.71 g/mol
Appearance	yellow-brown viscous liquid
Density	0.950 g/cm3
Melting point	2.5 to 3.5 °C (36.5 to 38.3 °F; 275.6 to 276.6 K)
Boiling point	200 to 220 °C (392 to 428 °F; 473 to 493 K) at 0.1 mmHg
Solubility in water	insoluble
Solubility	soluble in alcohol, ether, acetone, oils
Pharmacology
ATC code	A11HA03 (WHO)
Hazards
NFPA 704 (fire diamond)	1 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

α-Tocopherol (alpha-tocopherol) is a type of vitamin E.

It is found most in the membrane's non-raft domains, associated with omega-3 and 6 fatty acids, to partially prevent oxidation. The most prevalent form, α-tocopherol, is involved in molecular, cellular, biochemical processes closely related to overall lipoprotein and lipid homeostasis. Compared to the others, α-tocopherol is preferentially absorbed and accumulated in humans.

Vitamin E exists in 8 different forms: 4 tocopherols and 4 tocotrienols. Each form has a chromane ring, and an alkyl side chain, which is hydrophobic. The chromane ring contains a hydroxyl group that can donate a hydrogen atom to free radicals. This reaction helps reduce oxidative damage. In this way, a vitamin E acts as an antioxidant. The hydrophobic side chain helps vitamin E enter biological membranes. In the membrane, the aromatic ring of the chromane (the chromanol ring) lies near the carbonyl groups of the fatty chains of phospholipids. This allows vitamin E to concentrate from the surrounding aqueous solution into biological membranes.

Because vitamin E is lipid-soluble, it is found in many tissues. The body absorbs and distributes vitamin E through several pathways. Malaria parasites may use α-tocopherol to protect themselves from the highly oxidative environment in erythrocytes. In cardiovascular disease, α-tocopherol acts as an antioxidant. It can help prevent oxidation of low-density lipoprotein (LDL). Lower levels of oxidation of LDL may reduce atherosclerosis and arterial plaque formation.