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D-gamma-Tocopherol
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Name

D-gamma-Tocopherol

 EINECS 200-201-5
CAS No. 54-28-4 Density 0.933g/cm3
PSA 29.46000 LogP 8.53180
Solubility N/A Melting Point N/A
Formula C28H48 O2 Boiling Point 200 ºC (0.1 mmHg)
Molecular Weight 416.688 Flash Point 206°C
Transport Information N/A Appearance clear light brown viscous liquid
Safety 93072 Risk Codes 11-23/24/25-39/23/24/25
Molecular Structure Molecular Structure of 54-28-4 (D-gamma-Tocopherol) Hazard Symbols 93072
Synonyms

2H-1-Benzopyran-6-ol,3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-,[2R-[2R*(4R*,8R*)]]-; 6-Chromanol,2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-, (+)- (8CI); (+)-g-Tocopherol; (2R,4'R,8'R)-g-Tocopherol; (R,R,R)-g-Tocopherol; D-g-Tocopherol; all-(R)-g-Tocopherol; d-g-Tocopherol; g-Tocopherol

Article Data 8

D-gamma-Tocopherol Synthetic route

187677-37-8

(2R,4'R,8'R)-γ-tocopherol-5-carboxylic acid

54-28-4

gamma-tocopherol

Conditions
ConditionsYield
at 170℃; for 3h;91%
96480-20-5

phytylplastoquinol

54-28-4

gamma-tocopherol

Conditions
ConditionsYield
With 2,6-di-O-methyl-β-cyclodextrin; ascorbic acid In water at 35℃; for 15h; tocopherol-cyclase enzyme;90%
With tocopherol cyclase from spheroplasts of Anabaena variabilis In acetone

(3R,7R,11R)-(E)-3,7,11,15-tetramethyl-1-(2,5-dimethoxy-3,4-dimethylphenyl)hexadecan-3-ol

54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Stage #1: (3R,7R,11R)-(E)-3,7,11,15-tetramethyl-1-(2,5-dimethoxy-3,4-dimethylphenyl)hexadecan-3-ol With ammonium cerium (IV) nitrate In water; acetonitrile at 0℃; for 2h;
Stage #2: With sodium dithionite In water; acetone at 20℃; for 0.5h;
Stage #3: With toluene-4-sulfonic acid In toluene at 65℃; for 0.5h;		72%

8a-hydroperoxy γ-tocopherone

A

8a-hydroxy γ-tocopherone

B

54-28-4

gamma-tocopherol

C

8a-ethoxy γ-tocopherone

Conditions
ConditionsYield
With ethanol; ascorbic acid at 37℃; Product distribution;
34816-26-7

2-methyl-6-phythyl-1,4-benzoquinone

A

96480-20-5

phytylplastoquinol

B

54-28-4

gamma-tocopherol

C

59-02-9

Tocopherol

Conditions
ConditionsYield
With SAM; chloroplast suspension In ethanol; sulfuric acid at 20℃; for 0.5h; Mechanism; Irradiation;
75513-85-8

6-phytyltoluquinol

A

96480-20-5

phytylplastoquinol

B

54-28-4

gamma-tocopherol

C

59-02-9

Tocopherol

Conditions
ConditionsYield
With SAM; chloroplast suspension In ethanol; sulfuric acid at 20℃; for 0.5h; Mechanism; Irradiation;
119-13-1

delta tocopherol

A

54-28-4

gamma-tocopherol

B

59-02-9

Tocopherol

Conditions
ConditionsYield
With SAM; chloroplast suspension In ethanol; sulfuric acid at 20℃; for 0.5h; Mechanism; Irradiation;

2,3-Dimethyl-5-((E)-3,7,11,15-tetramethyl-hexadec-2-enyl)-benzene-1,4-diol

A

(R)-2,7,8-Trimethyl-2-((4R,8S)-4,8,12-trimethyl-tridecyl)-chroman-6-ol

B

(R)-2,7,8-Trimethyl-2-((4S,8R)-4,8,12-trimethyl-tridecyl)-chroman-6-ol

C

γ-tocopherol

D

54-28-4

gamma-tocopherol

Conditions
ConditionsYield
With tocopherol cyclase from spheroplasts of Anabaena variabilis In acetone Title compound not separated from byproducts;A 16 % Chromat.
B 13 % Chromat.
C 23 % Chromat.
D 48 % Chromat.

d-γ-tocopheroxyl radical

54-28-4

gamma-tocopherol

Conditions
ConditionsYield
With sodium L-ascorbate In ethanol; water at 25℃; Kinetics;
2140-91-2

5-bromomethyl-3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-chromen-6-ol

54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: AcOH; H2SO4 / CH2Cl2 / 20 °C
2: N-methylmorpholine N-oxide / acetonitrile / 5 h / 20 °C
3: NH2SO3H; NaClO2 / dioxane; H2O / 0.83 h / 20 °C
4: KOH / methanol / 2 h / 50 °C
5: 91 percent / 3 h / 170 °C
View Scheme

D-gamma-Tocopherol Chemical Properties

Molecular structure of D-gamma-Tocopherol (CAS NO.54-28-4) is:

Product Name: D-gamma-Tocopherol
CAS Registry Number: 54-28-4
IUPAC Name: (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
Molecular Weight: 416.67952 [g/mol]  
Molecular Formula: C28H48O2  
XLogP3-AA: 10.3  
H-Bond Donor: 1  
H-Bond Acceptor: 2
EINECS: 200-201-5
Alpha: 30 °(C=2.0 IN ISOOCTANE 25 °C)
Refractive index: n20/D 1.505
Storage temp.: 2-8 °C
Index of Refraction: 1.495 
Molar Refractivity: 130.24 cm3 
Molar Volume: 446.5 cm3
Surface Tension: 34.9 dyne/cm 
Density: 0.933 g/cm3 
Flash Point: 206 °C 
Enthalpy of Vaporization: 82.04 kJ/mol 
Boiling Point: 518.1 °C at 760 mmHg 
Vapour Pressure: 2.35E-11 mmHg at 25 °C 
Canonical SMILES: CC1=C(C=C2CCC(OC2=C1C)(C)CCCC(C)CCCC(C)CCCC(C)C)O
Isomeric SMILES: CC1=C(C=C2CC[C@@](OC2=C1C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)O
InChI: InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1 
InChIKey: QUEDXNHFTDJVIY-DQCZWYHMSA-N

D-gamma-Tocopherol Safety Profile

Safty information about D-gamma-Tocopherol (CAS NO.54-28-4) is:
Safety Statements: 24/25 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
F: 8-10-23

D-gamma-Tocopherol Specification

 D-gamma-Tocopherol , its cas register number is 54-28-4. It also can be called gamma-Tocopherol ; gamma-Tocopherol, d- ; (2R(2R*(4R*,8R*)))-3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol ; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)- .It is a  clear light brown viscous liquid.

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