α-Tocopherol

α-Tocopherol

File:Tocopherol, alpha-.svg
File:Vitamin-E-from-xtal-3D-bs-17.png
File:Sample of alpha-tocopherol.jpg
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 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18145 checkY
ChEMBL	ChEMBL47 checkY
ChemSpider	14265 checkY
DrugBank	DB00163 checkY
ECHA InfoCard
EC Number	200-412-2
E number
PubChem CID	14985
UNII	N9PR3490H9 checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
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 checkY Key: GVJHHUAWPYXKBD-IEOSBIPESA-N checkY 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). checkY verify (what is checkY☒N ?) Infobox references

α-Tocopherol (alpha-tocopherol) is a type of vitamin E. Its E number is "E307". Vitamin E exists in eight different forms, four tocopherols and four tocotrienols. All feature a chromane ring, with a hydroxyl group that can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain, along with an aromatic ring is situated near the carbonyls in the fatty acyl chains of the phospholipid bilayer, allows for penetration into biological membranes. 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 is found in a variety of tissues, being lipid-soluble, and taken up by the body in a wide variety of ways. Ongoing research is believed to be "critical for manipulation of vitamin E homeostasis in a variety of oxidative stress-related disease conditions in humans." One of these disease conditions is the α-tocopherol role in the use by malaria parasites to protect themselves from the highly oxidative environment in erythrocytes. A second of these disease conditions is the α-tocopherol antioxidant properties' role cardiovascular heart disease. In preventing LDL (low-density lipoprotein) oxidation, it is able to decrease chances of atherosclerosis and arterial build-up.

Synthesis

To synthesize the ⍺-diastereomer selectively, tocol acetate is transformed to the naturally occurring, kinetically favored α-tocopherol after being catalyzed by the lipase enzyme. This reaction occurs under biological conditions, commonly in the digestive system.

Stereoisomers

α-Tocopherol has three stereocenters, so it is a chiral molecule. The eight stereoisomers of α-tocopherol differ in the configuration of these stereocenters. RRR-α-tocopherol is the natural one. The older name of RRR-α-tocopherol is d-α-tocopherol, but this d/l naming should no longer be used, because whether l-α-tocopherol should mean SSS enantiomer or the SRR diastereomer is not clear, from historical reasons. The SRR may be named 2-epi-α-tocopherol, the diastereomeric mixture of RRR-α-tocopherol and 2-epi-α-tocopherol may be called 2-ambo-α-tocopherol (formerly named dl-α-tocopherol). The mixture of all eight diastereomers is called all-rac-α-tocopherol. The α-Tocopherol is the most active diastereomer biologically, while being maintained at a high level in plasma and tissues of many different animal species.

One IU of tocopherol is defined as 2⁄3 milligram of RRR-α-tocopherol (formerly named d-α-tocopherol). 1 IU is also defined as 0.9 mg of an equal mix of the eight stereoisomers, which is a racemic mixture, all-rac-α-tocopheryl acetate. This mix of stereoisomers is often called dl-α-tocopheryl acetate. Starting with May 2016, the IU unit is made obsolete, such that 1 mg of "Vitamin E" is 1 mg of d-alpha-tocopherol or 2 mg of dl-alpha-tocopherol.