Product Name

  • Name

    D-gamma-Tocopherol

  • EINECS 200-201-5
  • CAS No. 54-28-4
  • Article Data8
  • CAS DataBase
  • Density 0.933g/cm3
  • Solubility
  • Melting Point
  • Formula C28H48 O2
  • Boiling Point 200 ºC (0.1 mmHg)
  • Molecular Weight 416.688
  • Flash Point 206°C
  • Transport Information
  • 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
  • PSA 29.46000
  • LogP 8.53180

Synthetic route

(2R,4'R,8'R)-γ-tocopherol-5-carboxylic acid
187677-37-8

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

gamma-tocopherol
54-28-4

gamma-tocopherol

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

phytylplastoquinol

gamma-tocopherol
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

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

gamma-tocopherol
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

8a-hydroperoxy γ-tocopherone

A

8a-hydroxy γ-tocopherone

8a-hydroxy γ-tocopherone

B

gamma-tocopherol
54-28-4

gamma-tocopherol

C

8a-ethoxy γ-tocopherone

8a-ethoxy γ-tocopherone

Conditions
ConditionsYield
With ethanol; ascorbic acid at 37℃; Product distribution;
...Expand
2-methyl-6-phythyl-1,4-benzoquinone
34816-26-7

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

A

phytylplastoquinol
96480-20-5

phytylplastoquinol

B

gamma-tocopherol
54-28-4

gamma-tocopherol

C

Tocopherol
59-02-9

Tocopherol

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

6-phytyltoluquinol

A

phytylplastoquinol
96480-20-5

phytylplastoquinol

B

gamma-tocopherol
54-28-4

gamma-tocopherol

C

Tocopherol
59-02-9

Tocopherol

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

delta tocopherol

A

gamma-tocopherol
54-28-4

gamma-tocopherol

B

Tocopherol
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

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

(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

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

C

γ-tocopherol

γ-tocopherol

D

gamma-tocopherol
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.
...Expand
d-γ-tocopheroxyl radical

d-γ-tocopheroxyl radical

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
With sodium L-ascorbate In ethanol; water at 25℃; Kinetics;
5-bromomethyl-3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-chromen-6-ol
2140-91-2

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

gamma-tocopherol
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
Tocopherol
59-02-9

Tocopherol

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Br2 / hexane / 3 h / 20 °C
2: AcOH; H2SO4 / CH2Cl2 / 20 °C
3: N-methylmorpholine N-oxide / acetonitrile / 5 h / 20 °C
4: NH2SO3H; NaClO2 / dioxane; H2O / 0.83 h / 20 °C
5: KOH / methanol / 2 h / 50 °C
6: 91 percent / 3 h / 170 °C
View Scheme
5-(bromomethyl)-2,7,8-trimethyl-2-((4R, 8R)-4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-yl acetate
835613-31-5

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

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-methylmorpholine N-oxide / acetonitrile / 5 h / 20 °C
2: NH2SO3H; NaClO2 / dioxane; H2O / 0.83 h / 20 °C
3: KOH / methanol / 2 h / 50 °C
4: 91 percent / 3 h / 170 °C
View Scheme
5-formyl-2,7,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-yl acetate
835613-32-6

5-formyl-2,7,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-yl acetate

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NH2SO3H; NaClO2 / dioxane; H2O / 0.83 h / 20 °C
2: KOH / methanol / 2 h / 50 °C
3: 91 percent / 3 h / 170 °C
View Scheme
6-O-acetyl-(2R,4'R,8'R)-γ-tocopherol-5-carboxylic acid
835613-33-7

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

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOH / methanol / 2 h / 50 °C
2: 91 percent / 3 h / 170 °C
View Scheme
3,6-dimethoxy-o-xylene
39021-83-5

3,6-dimethoxy-o-xylene

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: N-Bromosuccinimide / dichloromethane / 6 h / Reflux
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -60 °C
3.1: sodium hydroxide / ethanol; water / 0.25 h / 20 °C
4.1: Oxone; sodium bromide / dichloromethane; water / 0 - 20 °C
5.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
6.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
7.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
8.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
9.1: hydrazine hydrate; oxygen / ethanol
10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
10.2: 0.5 h / 20 °C
10.3: 0.5 h / 65 °C
View Scheme
Multi-step reaction with 9 steps
1.1: N-Bromosuccinimide / dichloromethane / 6 h / Reflux
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -60 °C
3.1: sodium hydroxide / ethanol; water / 0.25 h / 20 °C
4.1: Oxone; sodium bromide / dichloromethane; water / 0 - 20 °C
5.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
6.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
7.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
8.1: hydrazine hydrate; oxygen / ethanol
9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
9.2: 0.5 h / 20 °C
9.3: 0.5 h / 65 °C
View Scheme
(4R,8R)-4,8,12-trimethyltridecanylmagnesium bromide

(4R,8R)-4,8,12-trimethyltridecanylmagnesium bromide

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
2.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
3.1: hydrazine hydrate; oxygen / ethanol
4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
4.2: 0.5 h / 20 °C
4.3: 0.5 h / 65 °C
View Scheme
(3R,7R,11R)-(Z)-2-bromo-3,7,11,15-tetramethyl-1-(2,5-dimethoxy-3,4-dimethylphenyl)hexadecen-3-ol

(3R,7R,11R)-(Z)-2-bromo-3,7,11,15-tetramethyl-1-(2,5-dimethoxy-3,4-dimethylphenyl)hexadecen-3-ol

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
2.1: hydrazine hydrate; oxygen / ethanol
3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
3.2: 0.5 h / 20 °C
3.3: 0.5 h / 65 °C
View Scheme
(3R,7R,11R)-(E)-3,7,11,15-tetramethyl-1-(2,5-dimethoxy-3,4-dimethylphenyl)hexadecen-3-ol

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

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrazine hydrate; oxygen / ethanol
2.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
2.2: 0.5 h / 20 °C
2.3: 0.5 h / 65 °C
View Scheme
1-bromo-2,5-dimethoxy-3,4-dimethylbenzene
103323-61-1

1-bromo-2,5-dimethoxy-3,4-dimethylbenzene

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -60 °C
2.1: sodium hydroxide / ethanol; water / 0.25 h / 20 °C
3.1: Oxone; sodium bromide / dichloromethane; water / 0 - 20 °C
4.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
5.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
6.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
7.1: hydrazine hydrate; oxygen / ethanol
8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
8.2: 0.5 h / 20 °C
8.3: 0.5 h / 65 °C
View Scheme
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -60 °C
2.1: sodium hydroxide / ethanol; water / 0.25 h / 20 °C
3.1: Oxone; sodium bromide / dichloromethane; water / 0 - 20 °C
4.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
5.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
6.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
7.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
8.1: hydrazine hydrate; oxygen / ethanol
9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
9.2: 0.5 h / 20 °C
9.3: 0.5 h / 65 °C
View Scheme
2,5-dimethoxy-3,4-dimethylbenzaldehyde
86489-95-4

2,5-dimethoxy-3,4-dimethylbenzaldehyde

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium hydroxide / ethanol; water / 0.25 h / 20 °C
2.1: Oxone; sodium bromide / dichloromethane; water / 0 - 20 °C
3.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
4.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
5.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
6.1: hydrazine hydrate; oxygen / ethanol
7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
7.2: 0.5 h / 20 °C
7.3: 0.5 h / 65 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium hydroxide / ethanol; water / 0.25 h / 20 °C
2.1: Oxone; sodium bromide / dichloromethane; water / 0 - 20 °C
3.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
4.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
5.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
6.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
7.1: hydrazine hydrate; oxygen / ethanol
8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
8.2: 0.5 h / 20 °C
8.3: 0.5 h / 65 °C
View Scheme
(E)-4-(2,5-dimethoxy-3,4-dimethylphenyl)-3-buten-2-one

(E)-4-(2,5-dimethoxy-3,4-dimethylphenyl)-3-buten-2-one

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Oxone; sodium bromide / dichloromethane; water / 0 - 20 °C
2.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
3.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
4.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
5.1: hydrazine hydrate; oxygen / ethanol
6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
6.2: 0.5 h / 20 °C
6.3: 0.5 h / 65 °C
View Scheme
Multi-step reaction with 7 steps
1.1: Oxone; sodium bromide / dichloromethane; water / 0 - 20 °C
2.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
3.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
4.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
5.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
6.1: hydrazine hydrate; oxygen / ethanol
7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
7.2: 0.5 h / 20 °C
7.3: 0.5 h / 65 °C
View Scheme
(Z)-3-bromo-4-(2,5-dimethoxy-3,4-dimethylphenyl)-3-buten-2-one

(Z)-3-bromo-4-(2,5-dimethoxy-3,4-dimethylphenyl)-3-buten-2-one

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
2.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
3.1: hydrazine hydrate; oxygen / ethanol
4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
4.2: 0.5 h / 20 °C
4.3: 0.5 h / 65 °C
View Scheme
(E)-3-bromo-4-(2,5-dimethoxy-3,4-dimethylphenyl)-3-buten-2-one

(E)-3-bromo-4-(2,5-dimethoxy-3,4-dimethylphenyl)-3-buten-2-one

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
2.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
3.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
4.1: hydrazine hydrate; oxygen / ethanol
5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
5.2: 0.5 h / 20 °C
5.3: 0.5 h / 65 °C
View Scheme
C14H18Br2O3

C14H18Br2O3

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
2.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
3.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
4.1: hydrazine hydrate; oxygen / ethanol
5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
5.2: 0.5 h / 20 °C
5.3: 0.5 h / 65 °C
View Scheme
Multi-step reaction with 6 steps
1.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
2.1: triethylamine / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
3.1: copper(I) bromide dimethylsulfide complex; 223121-01-5 / tert-butyl methyl ether; diethyl ether / -78 °C / Schlenk technique; Inert atmosphere
4.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
5.1: hydrazine hydrate; oxygen / ethanol
6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 0 °C
6.2: 0.5 h / 20 °C
6.3: 0.5 h / 65 °C
View Scheme
7,8-dimethyltocol
7616-22-0

7,8-dimethyltocol

A

(2S,4’R,8’R)-γ-tocopherol
162118-42-5

(2S,4’R,8’R)-γ-tocopherol

B

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
With carbon dioxide In methanol; n-heptane at 40℃; under 67506.8 Torr; Supercritical conditions;
(2RS,4'R,8'R)-γ-tocopherol
19625-16-2

(2RS,4'R,8'R)-γ-tocopherol

A

(2S,4’R,8’R)-γ-tocopherol
162118-42-5

(2S,4’R,8’R)-γ-tocopherol

B

gamma-tocopherol
54-28-4

gamma-tocopherol

Conditions
ConditionsYield
With carbon dioxide In methanol; n-heptane at 40℃; under 67506.8 Torr; Supercritical conditions;
allyl bromide
106-95-6

allyl bromide

gamma-tocopherol
54-28-4

gamma-tocopherol

(R,R,R)-6-allyloxy-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman
13027-54-8

(R,R,R)-6-allyloxy-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman

Conditions
ConditionsYield
With potassium carbonate In acetone for 20h; Heating / reflux;100%
butyraldehyde
123-72-8

butyraldehyde

gamma-tocopherol
54-28-4

gamma-tocopherol

7,9,10-trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene
916319-66-9

7,9,10-trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene

Conditions
ConditionsYield
With sulfuric acid; acetic acid for 18h;100%
gamma-tocopherol
54-28-4

gamma-tocopherol

(R,R,R)-5-bromo-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-ol

(R,R,R)-5-bromo-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-ol

Conditions
ConditionsYield
With sulfuric acid; bromine In hexane at 0 - 20℃;100%
With bromine In hexane at 0 - 20℃; Inert atmosphere;72%
morpholine
110-91-8

morpholine

paraformaldehyde-d2
1664-98-8

paraformaldehyde-d2

gamma-tocopherol
54-28-4

gamma-tocopherol

(2R,4'R,8'R)-5-(morpholino[(2)H2]methyl)-γ-tocopherol
936230-71-6

(2R,4'R,8'R)-5-(morpholino[(2)H2]methyl)-γ-tocopherol

Conditions
ConditionsYield
Stage #1: morpholine; paraformaldehyde-d2 at 70 - 80℃; for 2.33333h;
Stage #2: gamma-tocopherol at 20 - 80℃; for 0.75h; Mannich reaction; Further stages.;		98.3%
...Expand
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

gamma-tocopherol
54-28-4

gamma-tocopherol

2,7,8-trimethyl-(2R-(4R,8R,12-trimethyltridecyl)-chroman-6-yloxy) acetic acid
261929-58-2

2,7,8-trimethyl-(2R-(4R,8R,12-trimethyltridecyl)-chroman-6-yloxy) acetic acid

Conditions
ConditionsYield
Stage #1: bromoacetic acid methyl ester; gamma-tocopherol With sodium hydroxide In DMF (N,N-dimethyl-formamide) at 20℃; for 24h;
Stage #2: With hydrogenchloride In DMF (N,N-dimethyl-formamide); water		97%
With sodium hydroxide In DMF (N,N-dimethyl-formamide) at 20℃; for 24h;97%
3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

gamma-tocopherol
54-28-4

gamma-tocopherol

(R,R,R)-2,7,8-trimethyl-6-(2-methyl-allyloxy)-2-(4,8,12-trimethyl-tridecyl)-chroman
916319-71-6

(R,R,R)-2,7,8-trimethyl-6-(2-methyl-allyloxy)-2-(4,8,12-trimethyl-tridecyl)-chroman

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetone for 20h; Heating / reflux;95%
5-bromomethyl-3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-chromen-6-ol
2140-91-2

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

gamma-tocopherol
54-28-4

gamma-tocopherol

bis(5-γ-tocopheryl)methane
849198-82-9

bis(5-γ-tocopheryl)methane

Conditions
ConditionsYield
Stage #1: 5-bromomethyl-3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-chromen-6-ol; gamma-tocopherol With boron trifluoride diacetate; acetic acid at 20℃; for 48h;
Stage #2: With hydrogenchloride In methanol for 0.5h;		94%
succinic acid anhydride
108-30-5

succinic acid anhydride

gamma-tocopherol
54-28-4

gamma-tocopherol

C60H102O4

C60H102O4

Conditions
ConditionsYield
Stage #1: succinic acid anhydride; gamma-tocopherol With boron trifluoride diethyl etherate; chloroformic acid ethyl ester In 1,4-dioxane for 2h; Heating;
Stage #2: With sodium tetrahydroborate; chloroformic acid ethyl ester In 1,4-dioxane at 0℃; for 0.5h;		92%
N,N-Dimethylthiocarbamoyl chloride
16420-13-6

N,N-Dimethylthiocarbamoyl chloride

gamma-tocopherol
54-28-4

gamma-tocopherol

O-dimethylthiocarbamoyl-d-γ-tocopherol
1380511-42-1

O-dimethylthiocarbamoyl-d-γ-tocopherol

Conditions
ConditionsYield
Stage #1: gamma-tocopherol With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.666667h; Inert atmosphere;
Stage #2: N,N-Dimethylthiocarbamoyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;		91%
gamma-tocopherol
54-28-4

gamma-tocopherol

2-bromo-3-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-5,6-dimethyl-[1,4]benzoquinone
1311403-07-2

2-bromo-3-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-5,6-dimethyl-[1,4]benzoquinone

Conditions
ConditionsYield
With bromine In ethanol at 0 - 20℃; for 1.16667h; pH=6; aq. phosphate buffer;88%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

gamma-tocopherol
54-28-4

gamma-tocopherol

C59H100O4

C59H100O4

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate; gamma-tocopherol With boron trifluoride diethyl etherate; chloroformic acid ethyl ester In 1,4-dioxane for 2h; Heating;
Stage #2: With sodium tetrahydroborate; chloroformic acid ethyl ester In 1,4-dioxane at 0℃; for 0.5h;		84%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

gamma-tocopherol
54-28-4

gamma-tocopherol

(2R,4'R,8'R)-γ-tocopheryl trifluoromethanesulfonate
1169840-66-7

(2R,4'R,8'R)-γ-tocopheryl trifluoromethanesulfonate

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at -20 - -10℃; for 3h;82%
glutaric anhydride,
108-55-4

glutaric anhydride,

gamma-tocopherol
54-28-4

gamma-tocopherol

C61H104O4

C61H104O4

Conditions
ConditionsYield
Stage #1: glutaric anhydride,; gamma-tocopherol With boron trifluoride diethyl etherate; chloroformic acid ethyl ester In 1,4-dioxane for 2h; Heating;
Stage #2: With sodium tetrahydroborate; chloroformic acid ethyl ester In 1,4-dioxane at 0℃; for 0.5h;		81%
gamma-tocopherol
54-28-4

gamma-tocopherol

Tocopherol
59-02-9

Tocopherol

bis(5-γ-tocopheryl)methane
849198-82-9

bis(5-γ-tocopheryl)methane

Conditions
ConditionsYield
With silver(l) oxide78%
paraformaldehyde-d2
1664-98-8

paraformaldehyde-d2

gamma-tocopherol
54-28-4

gamma-tocopherol

(2R,4'R,8'R)-[C5-(2)H3]-α-tocopherol
113848-10-5

(2R,4'R,8'R)-[C5-(2)H3]-α-tocopherol

Conditions
ConditionsYield
With hydrogen chloride; tin(ll) chloride In di-isopropyl ether at 88℃; for 2.5h;77%
gamma-tocopherol
54-28-4

gamma-tocopherol

2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-5-nitro-6-chromanol
574732-12-0

2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-5-nitro-6-chromanol

Conditions
ConditionsYield
With acetic acid; sodium nitrite In ethanol at 22℃; for 0.5h;72%
With (2R,4'R,8'R)-α-tocopheramine; silver(l) oxide In hexane
acetic anhydride
108-24-7

acetic anhydride

gamma-tocopherol
54-28-4

gamma-tocopherol

(2R,4'R,8'R)-γ-tocopherol acetate
22373-06-4

(2R,4'R,8'R)-γ-tocopherol acetate

Conditions
ConditionsYield
With sulfuric acid In dichloromethane at 22℃; for 18h; Inert atmosphere;65%
With pyridine
C36H51NO4S

C36H51NO4S

gamma-tocopherol
54-28-4

gamma-tocopherol

C56H94O4S

C56H94O4S

Conditions
ConditionsYield
With triethylamine In chloroform at 60℃;65%
Adipic acid dichloride
111-50-2

Adipic acid dichloride

gamma-tocopherol
54-28-4

gamma-tocopherol

C62H106O4

C62H106O4

Conditions
ConditionsYield
Stage #1: Adipic acid dichloride; gamma-tocopherol With boron trifluoride diethyl etherate In 1,4-dioxane for 2h; Heating;
Stage #2: With sodium tetrahydroborate In 1,4-dioxane at 0℃; for 0.5h;		64%
gamma-tocopherol
54-28-4

gamma-tocopherol

4a,8a-dibromo-2,6,7-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4,4a,8a-tetrahydro-2H-chromene-5,8-dione

4a,8a-dibromo-2,6,7-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4,4a,8a-tetrahydro-2H-chromene-5,8-dione

Conditions
ConditionsYield
With borax; bromine; sodium hydroxide In tetrahydrofuran; hexane; water at 0℃; for 0.25h; pH=11;57%
succinic acid anhydride
108-30-5

succinic acid anhydride

gamma-tocopherol
54-28-4

gamma-tocopherol

γ-tocopheryl succinate

γ-tocopheryl succinate

Conditions
ConditionsYield
With zinc(II) chloride In toluene Heating;51%
With pyridine
gamma-tocopherol
54-28-4

gamma-tocopherol

A

5-(γ-tocopheroxy)-γ-tocopherol
131615-90-2

5-(γ-tocopheroxy)-γ-tocopherol

B

(R)-5,5'-bi-γ-tocopheryl
254972-61-7

(R)-5,5'-bi-γ-tocopheryl

C

(S)-5,5'-bi-γ-tocopheryl
18802-32-9, 67112-52-1, 67112-53-2, 133397-90-7

(S)-5,5'-bi-γ-tocopheryl

Conditions
ConditionsYield
With alkaline aq. ferricyanide In hexane Ambient temperature;A 45%
B 20%
C 20%
...Expand
gamma-tocopherol
54-28-4

gamma-tocopherol

A

C28H46O4

C28H46O4

B

4a,8a-dibromo-2,6,7-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4,4a,8a-tetrahydro-2H-chromene-5,8-dione

4a,8a-dibromo-2,6,7-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4,4a,8a-tetrahydro-2H-chromene-5,8-dione

C

para-γ-tocopherylquinone

para-γ-tocopherylquinone

Conditions
ConditionsYield
With borax; bromine; sodium hydroxide In tetrahydrofuran; hexane; water pH=11; Mechanism;A 13%
B 36%
C 39%
...Expand
formaldehyd
50-00-0

formaldehyd

gamma-tocopherol
54-28-4

gamma-tocopherol

6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-carbaldehyde
113348-75-7

6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-carbaldehyde

Conditions
ConditionsYield
With tributyl-amine; tin(IV) chloride In toluene at 90 - 95℃; for 2h; Vilsmeier-Haack formylation;19%
cyanic acid
420-05-3

cyanic acid

gamma-tocopherol
54-28-4

gamma-tocopherol

(2R,4'R,8'R)-O-Allophanoyl-γ-tocopherol
6197-56-4

(2R,4'R,8'R)-O-Allophanoyl-γ-tocopherol

Conditions
ConditionsYield
With toluene at -50℃;
4-Nitrophenyl isocyanate
100-28-7

4-Nitrophenyl isocyanate

gamma-tocopherol
54-28-4

gamma-tocopherol

(2R,4'R,8'R)-O-(4-Nitro-phenylcarbamoyl)-γ-tocopherol

(2R,4'R,8'R)-O-(4-Nitro-phenylcarbamoyl)-γ-tocopherol

Conditions
ConditionsYield
With benzene
gamma-tocopherol
54-28-4

gamma-tocopherol

(4R,8R,12R)-4-hydroxy-4,8,12,16-tetramethylheptadecanoic acid lactone
96168-15-9

(4R,8R,12R)-4-hydroxy-4,8,12,16-tetramethylheptadecanoic acid lactone

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid

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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