DELTA-TOCOPHEROL

Delta-Tocopherol = (2R)-2,8-Dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol

CAS Number : 119-13-1 
EC  Number : 204-299-0
ECHA InfoCard    : 100.003.909 
PubChem CID    : 92094
ChemSpider    : 83144 
Chemical formula : C27H46O2
Molar mass     : 402.65 g/mol

δ-Tocopherol (delta-tocopherol) is a tocopherol and one of the chemical compounds that is considered vitamin E. As a food additive, it has E number E309.
Delta-Tocopherol is the orally bioavailable delta form of the naturally-occurring fat-soluble vitamin E, mostly found in soybean and corn oils, with potential antioxidant activity. 
Although the exact mechanism of action of this tocopherol has yet to be fully identified, delta-tocopherol appears to have the ability to scavenge free radicals, thereby protecting cells against oxidative damage.

Delta-tocopherol is a tocopherol in which the chroman-6-ol core is substituted by a methyl group at position 8. 
Delta-tocopherol is found particularly in maize (corn) oil and soya bean (soybean) oils. 
Delta-tocopherol has a role as a plant metabolite and a food antioxidant. 
Delta-tocopherol is a vitamin E and a tocopherol.

Delta-Tocopherol is a natural product found in Hypericum perfoliatum, Hypericum tomentosum, and other organisms with data available.
Delta-Tocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. 
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. 
Natural vitamin E exists in eight different forms or isomers, four tocopherols and four tocotrienols. 
All isomers have a chromanol ring, with a hydroxyl group which can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain which allows for penetration into biological membranes. 

There is an alpha, beta, gamma and delta form of both the tocopherols and tocotrienols, determined by the number of methyl groups on the chromanol ring. 
Each form has its own biological activity, the measure of potency or functional use in the body.
Delta-Tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. 
The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to Delta-Tocopherol.
Delta-Tocopherol increases naturally to about 150% of normal in the maternal circulation during human pregnancies.

Delta-Tocopherol is one of the forms of vitamin E and in animal tissues has been found to have much less retention than alpha-tocopherol.
Due to its having only one methyl group meta to the phenolic hydroxyl group and no ortho-methyl groups, delta-tocopherol has much less antioxidant activity in vivo than alpha-tocopherol which has two ortho-methyl groups and a meta-methyl group. 
Delta-Tocopherol is involved in immune function, cell signaling, regulation of gene expression, and other metabolic processes. 
Vitamin E also inhibits lipid oxidation by donating its phenolic hydrogen to lipid free radicals.

Antioxidant activity in vivo is normally alpha>beta>gamma>delta but the antioxidant potency may depend on various chemical and physical situations.
The ortho-methyl substitution of the chroman head plays a vital role in the antioxidant activity of tocopherols while the phytyl tail is very important for proper positioning in the biomembranes. 
The antioxidant properties of Delta-Tocopherol may delay memory loss in Down’s syndrome patients due to their protection from harmful oxidation caused by excess activity of Superoxide dismutase. 
Delta-Tocopherol is only naturally produced in plants, algae, and some cyanobacteria and is therefore an important dietary nutrient for humans and animals.

Delta-Tocopherol is one of the forms of vitamin E (four tocopherols (α, β, δ, and γ) and four tocotrienols (α, β, δ, and γ)), which is known for its antioxidant activity. 
At 0.1-10 µM, Delta-Tocopherol significantly suppresses H2O2-induced cell death of rat striatal neurons and provides protection against S-nitrocysteine-induced cell death and SIN-1 cytotoxicity in a concentration dependent manner. 
At concentrations of 10 µM, Delta-Tocopherol displays more inhibitory action on adhesiveness of HAECs to U937 monocytic cells, via inhibition of VCAM-1 expression, than α-tocopherol and other tocotrienols at the same concentration.

Application of Delta-Tocopherol
Delta-Tocopherol  may be used as an internal standard in the determination of α-tocopherol in human serum or plasma samples using high performance chromatography (HPLC). 
Delta-Tocopherol may also be used pharmaceutical reference standard for the quantification of the analyte in pharmaceutical formulations using spectrophotometric technique.
These Secondary Standards are qualified as Certified Reference Materials. 
These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Delta-Tocopherol, also known as 8-methyltocol or δ-tocopherol, belongs to the class of organic compounds known as tocopherols. 
These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. 
The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. 
Thus, delta-tocopherol is considered to be a quinone lipid molecule. 
Delta-Tocopherol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Vitamin E or Delta-Tocopherol has been used for >50 years in experimental and clinical dermatology.
Delta-tocopherol , hereafter delta-TC) is a precursor of vitamin E, well known for its antioxidation potential and associated with a better stability and gradual delivery of free tocopherol in the skin.
In a clinical study, an association of RAL and delta-TC significantly decreased the number of UV-generated free radicals, resulting in a superior restoration of laminin, elastic fiber and collagen network and increased the collagen synthesis more than RAL alone.

Delta-Tocopherol has strong vitamin E activity, while Beta, Gamma, and Alpha-Toc have strong antioxidant activity in foodstuffs. 
Therefore, Toc preparations which have a high Alpha-Toc content are suitable for health foods and vitamin E enrichment.
Tocopherols are another group of chemicals that make up the vitamin E family. 
Both tocotrienols and tocopherols comes in four forms: alpha, beta, delta, and gamma.

Delta-Tocopherol may be used as an analytical reference standard for the determination of the analyte in food and beverage products and crops by high-performance liquid chromatography technique.
Delta-Tocopherol, a homolog of vitamin E, is a phytochemical with potent antioxidant activity. 
Delta-Tocopherol has been investigated for its potential medical, biological, and physio-chemical applications.

Delta-Tocopherol is a fat-soluble vitamin composed of compounds called tocopherols and tocotrienols. 
This supplement contains the full spectrum of Delta-Tocopherol as it occurs in nature, i.e. all four tocopherols and all four tocotrienols (alpha, beta, delta, gamma). 
Most vitamin E supplements only contain Delta-Tocopherol. 
Vitamin E contributes to the protection of cells from oxidative stress, this means it is an antioxidant.

Delta-Tocopherol, concentrate is a form of Vitamin E obtained by the vacuum steam distillation of edible vegetable oil products, comprising a concentrated form of d-alpha-tocopherol. 
Delta-Tocopherol may contain an edible vegetable oil added to adjust the required amount of total tocopherols, and the content of Delta-Tocopherol may be adjusted by suitable physical and chemical means.

First-aid measures of Delta-Tocopherol

Eye Contact :
Rinse immediately with plenty of water, also under the eyelids, for at least 15 minutes. 
Get medical attention.

Skin Contact :
Wash off immediately with plenty of water for at least 15 minutes. 
Get medical attention immediately if symptoms occur.

Inhalation :
Remove to fresh air. 
Get medical attention immediately if symptoms occur.

Ingestion :
Clean mouth with water and drink afterwards plenty of water. 
Get medical attention if symptoms occur.

Substance identity

EC / List no.: 204-299-0
CAS no.: 119-13-1
Mol. formula: C27H46O2

Hazard classification & labelling of Delta-Tocopherol
According to the majority of notifications provided by companies to ECHA in CLP notifications no hazards have been classified.

About Delta-Tocopherol
Delta-Tocopherol is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 to < 10 tonnes per annum.
Delta-Tocopherol is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.

Consumer Uses of Delta-Tocopherol
Delta-Tocopherol is used in the following products: cosmetics and personal care products.
Other release to the environment of Delta-Tocopherol is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).

Article service life of Delta-Tocopherol
ECHA has no public registered data on the routes by which Delta-Tocopherol is most likely to be released to the environment. 
ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers of Delta-Tocopherol
Delta-Tocopherol is used in the following products: cosmetics and personal care products.
Delta-Tocopherol is used for the manufacture of: .
Other release to the environment of Delta-Tocopherol is likely to occur from: indoor use as processing aid.

Formulation or re-packing of Delta-Tocopherol
Delta-Tocopherol is used in the following products: cosmetics and personal care products.
Release to the environment of Delta-Tocopherol can occur from industrial use: formulation of mixtures.

Uses at industrial sites of Delta-Tocopherol
Delta-Tocopherol is used in the following products: cosmetics and personal care products.
Delta-Tocopherol is used for the manufacture of: .
Release to the environment of Delta-Tocopherol can occur from industrial use: in the production of articles and as an intermediate step in further manufacturing of another substance (use of intermediates).

Manufacture of Delta-Tocopherol
ECHA has no public registered data on the routes by which Delta-Tocopherol is most likely to be released to the environment.

Synonyms:
delta-Tocopherol
(+)-delta-Tocopherol
D-delta-TOCOPHEROL
8-Methyltocol
119-13-1
UNII-JU84X1II0N
JU84X1II0N
CHEBI:47772
(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol
NCGC00160622-01
(2R)-3,4-dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol
DSSTox_CID_26263
DSSTox_RID_81490
DSSTox_GSID_46263
.delta.-Tocopherol
delta-Vitamin E
delta-D-Tocopherol
(2R(2R*(4R*,8R*)))-3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
[2R[2R*(4R*,8R*)]]-3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
251562-63-7
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-
CAS-119-13-1
Rel-(2R)-3,4-Dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol
(R,R,R)-delta-Tocopherol
Vitamine E
(2R,4'R,8'R)-delta-Tocopherol
EINECS 204-299-0
.delta.-Vitamin E
()-delta-Tocopherol
bmse000547
(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
6-Chromanol, 2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-
SCHEMBL886921
CHEMBL1451395
DTXSID1046263
(+)-delta-Tocopherol, >=90%
AMY25540
ZINC4215541
Tox21_111941
delta-Tocopherol, analytical standard
LMPR02020066
s6348
Tox21_111941_1
NCGC00160622-02
NCGC00160622-03
NCGC00160622-04
E309
HY-113026
CS-0059380
E80733
Q155751
J-004070
D94B2EA5-AEC1-47F2-94D1-A1F978E6C436
UNII-N53I4V2IA6 component GZIFEOYASATJEH-VHFRWLAGSA-N
UNII-R0ZB2556P8 component GZIFEOYASATJEH-VHFRWLAGSA-N
UNII-ZL0RFA4E5N component GZIFEOYASATJEH-VHFRWLAGSA-N
(R)-2,8-Dimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol
[2R[2R*(4R*,8R*)]]-3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
[2R[2R*(4R*,8R*)]]-3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-6-chromanol
(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-
2R 2R (4R, 8R)-3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
[2R[2R*(4R*,8R*)]]-3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
[2R[2R*(4R*,8R*)]]-3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
d-delta Tocopherol
delta-Tocopherol
119-13-1