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59-02-9

Basic Information
CAS No.: 59-02-9
Name: 2H-1-Benzopyran-6-ol,3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-,[2R-[2R*(4R*,8R*)]]-
Molecular Structure:
Molecular Structure of 59-02-9 (2H-1-Benzopyran-6-ol,3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-,[2R-[2R*(4R*,8R*)]]-)
Formula: C29H50O2
Molecular Weight: 430.79
Synonyms: (+)-a-Tocopherol;(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol;(2R,4'R,8'R)-a-Tocopherol;(R,R,R)-a-Tocopherol;(all-R)-a-Tocopherol;5,7,8-Trimethyltocol;Covitol F 1000;Covitol F 1300;Covitol IK 00069;Denamone;Endo E;Eprolin;Eprolin S;Epsilan;Esorb;Etavit;NSC 20812;NatAlc;Natur-E micelle;Phytogermin;Spavit E;Syntopherol;Tenox GT 1;Tokopharm;Vascuals;Verrol;Viteolin;alpha-Tocopherol;a-Vitamin E;Vitamin E;
EINECS: 200-412-2
Density: 0.93 g/cm3
Melting Point: 2.5-3.5 °C
Boiling Point: 485.856 °C at 760 mmHg
Flash Point: 210.229 °C
Solubility: insoluble in water
Appearance: light yellow liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 23-24/25-37/39-26
Transport Information:
PSA: 29.46000
LogP: 8.84020
Synthetic route
titanium montmorillonite

titanium montmorillonite

505-32-8

isophytol

700-13-0

Trimethylhydroquinone

59-02-9

Tocopherol

Conditions
ConditionsYield
In octane100%
32466-45-8

(2R,4'R,8'R)-α-tocopheryl methyl ether

59-02-9

Tocopherol

Conditions
ConditionsYield
Stage #1: (2R,4'R,8'R)-α-tocopheryl methyl ether With triethylsilane; tris(pentafluorophenyl)borate at 20℃;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃;
100%
With aluminum (III) chloride; boron dimethyl-trifluoro sulphide In dichloromethane; acetonitrile at 20℃;84%
With aluminum (III) chloride; boron trifluoride dimethyl sulfide In dichloromethane; acetonitrile at 0 - 20℃; for 6h;78%
505-32-8

isophytol

700-13-0

Trimethylhydroquinone

59-02-9

Tocopherol

Conditions
ConditionsYield
With hydrogenchloride; Zinc chloride In tetrachloromethane99.1%
With hydrogenchloride; sodium dithionite; Zinc chloride In toluene99.8%
With hydrogenchloride; zinc dibromide; zinc98.6%
110-19-0

2-methylpropyl acetate

505-32-8

isophytol

700-13-0

Trimethylhydroquinone

59-02-9

Tocopherol

Conditions
ConditionsYield
With hydrogenchloride; Zinc chloride In water; toluene99.6%
With hydrogenchloride; Zinc chloride In water; toluene98.6%
505-32-8

isophytol

700-13-0

Trimethylhydroquinone

105-58-8

Diethyl carbonate

59-02-9

Tocopherol

Conditions
ConditionsYield
With hydrogenchloride; sodium chloride; Zinc chloride In water; toluene99.2%
With hydrogen bromide; zinc dibromide In water99.1%
With hydrogenchloride; Zinc chloride In water; toluene98.9%
505-32-8

isophytol

700-13-0

Trimethylhydroquinone

78-93-3

butanone

59-02-9

Tocopherol

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride; scandium tris(trifluoromethanesulfonate) In ethyl acetate; toluene99%
505-32-8

isophytol

700-13-0

Trimethylhydroquinone

71-36-3

butan-1-ol

59-02-9

Tocopherol

Conditions
ConditionsYield
With hydrogenchloride; Zinc chloride In hexane; water; toluene98.1%
With hydrogenchloride; Zinc chloride In hexane; water; toluene98.1%
With hydrogenchloride; Zinc chloride In hexane; water; toluene95.9%
With hydrogenchloride; Zinc chloride In hexane; water; toluene95.9%
700-13-0

Trimethylhydroquinone

isophytol

59-02-9

Tocopherol

Conditions
ConditionsYield
aluminum ion-exchanged montmorilonites In octane for 3h; Product distribution; Heating; var. metal ion-exchanged montmorilonites, var. solvents, var. reaction time;98%

scandium fluorosulfonate

505-32-8

isophytol

700-13-0

Trimethylhydroquinone

59-02-9

Tocopherol

Conditions
ConditionsYield
With sodium chloride In ethyl acetate; toluene98%
14745-36-9

2-((7R,11R)-3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylbenzene-1,4-diol

59-02-9

Tocopherol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 80℃; for 1.25h;95%
With toluene-4-sulfonic acid In benzene Heating;
With toluene-4-sulfonic acid In toluene at 45℃;
6991-51-1

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

59-02-9

Tocopherol

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In 2-methyl-propan-1-ol for 9h; Heating;95%
scandium bentonite

scandium bentonite

505-32-8

isophytol

700-13-0

Trimethylhydroquinone

59-02-9

Tocopherol

Conditions
ConditionsYield
In hexane; toluene93%
1402580-98-6

4-methoxybenzyl (R,R,R)-α-tocopheryl ether

59-02-9

Tocopherol

Conditions
ConditionsYield
With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 6h;93%
505-32-8

isophytol

59-02-9

Tocopherol

Conditions
ConditionsYield
In toluene91%
88.7%
7559-04-8

2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione

59-02-9

Tocopherol

Conditions
ConditionsYield
90.3%

(2R,4'R,8'R)-1',2'-dehydro-α-tocopheryl benzyl ether

59-02-9

Tocopherol

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide at 20℃; under 760 Torr;86%

europium trifluoromethanesulfonate

505-32-8

isophytol

700-13-0

Trimethylhydroquinone

59-02-9

Tocopherol

Conditions
ConditionsYield
With sodium chloride In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; ethyl acetate84%
505-32-8

isophytol

700-13-0

Trimethylhydroquinone

yttrium(III) trifluoromethanesulfonate

59-02-9

Tocopherol

Conditions
ConditionsYield
With sodium chloride In diethyl ether; nitromethane; ethyl acetate82%
6991-51-1

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

tetrabutylammonium borohydride

A

n-butyl α-tocopheryl ether

B

59-02-9

Tocopherol

Conditions
ConditionsYield
In 2-methyl-propan-1-ol for 4h; Heating;A n/a
B 77%
113348-75-7

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

59-02-9

Tocopherol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetic acid under 760 Torr;75%

(2R,6R)-1-chloro-2,6,10-trimethyl-undecane

dilithium tetrachlorocuprate

(2R,6R)-2,6,10-trimethyl-1-undecyl-magnesium chloride

75-16-1

methylmagnesium bromide

94353-04-5

(2S)-(-)-2-(2-bromoethyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol

59-02-9

Tocopherol

Conditions
ConditionsYield
In tetrahydrofuran75%
527-18-4

Durohydroquinone

2-methylbut-3-en-2-ol

59-02-9

Tocopherol

Conditions
ConditionsYield
Molecular sieve;72%
(2RS,6RS)-2,6,10-trimethyl-1-undecylmagnesium chloride

(2RS,6RS)-2,6,10-trimethyl-1-undecylmagnesium chloride

(2RS,6RS)-1-chloro-2,6,10-trimethylundecane

dilithium tetrachlorocuprate

75-16-1

methylmagnesium bromide

130266-62-5

2-(2-bromoethyl)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran

59-02-9

Tocopherol

Conditions
ConditionsYield
In tetrahydrofuran64%

scandium(III) nitrate

scandium(III) nitrate tetrahydrate

505-32-8

isophytol

700-13-0

Trimethylhydroquinone

59-02-9

Tocopherol

Conditions
ConditionsYield
With sodium chloride In ethyl acetate; toluene62%
700-13-0

Trimethylhydroquinone

2-methylbut-3-en-2-ol

A

151716-51-7

trimethyl-((7R:11R)-trans-phytyl)-benzoquinone-(1.4)

B

59-02-9

Tocopherol

Conditions
ConditionsYield
With CuAl-SBA-15 In cyclohexane at 85℃; for 16h;A 25%
B 61%

ytterbium trifluoromethanesulfonate

505-32-8

isophytol

700-13-0

Trimethylhydroquinone

59-02-9

Tocopherol

Conditions
ConditionsYield
With sodium chloride In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetate59%
2283-11-6

hexaethylphosphoric triamide

59-02-9

Tocopherol

562828-32-4

bis(N,N-diethylamido)-O-tocopherylphosphite

Conditions
ConditionsYield
at 90 - 100℃; for 5h;100%
110-52-1

1,4-dibromo-butane

59-02-9

Tocopherol

1451385-71-9

(R)-6-(4-bromobutoxy)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; Inert atmosphere; Darkness;100%
Stage #1: Tocopherol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
50%
Stage #1: Tocopherol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃;
47%
124-63-0

methanesulfonyl chloride

59-02-9

Tocopherol

1261156-27-7

2-(4,8,12-trimethyltridecyl)-2,5,7,8-tetramethyl-chroman-6-ylmethanesulfonate

Conditions
ConditionsYield
Stage #1: Tocopherol With triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: methanesulfonyl chloride In dichloromethane for 1h;
96%
With pyridine; dmap In dichloromethane at 20℃; for 24h;85.1%
With pyridine; dmap In dichloromethane at 20℃; for 12h;85.1%

2,3-O-isopropylidene-4-O-benzyl-α-L-rhamnopyranosyl diphenylphosphate

59-02-9

Tocopherol

C45H70O6

Conditions
ConditionsYield
With C53H57F11N6O4S2 In di-isopropyl ether at 30℃; for 24h; Molecular sieve; Sealed tube; stereoselective reaction;96%
824-94-2

p-methoxybenzyl chloride

59-02-9

Tocopherol

1402580-98-6

4-methoxybenzyl (R,R,R)-α-tocopheryl ether

Conditions
ConditionsYield
Stage #1: Tocopherol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h;
Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 20℃;
95%

2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl diphenylphosphate

59-02-9

Tocopherol

C41H68O7

Conditions
ConditionsYield
With C53H57F11N6O4S2 In di-isopropyl ether at 50℃; for 24h; Molecular sieve; Sealed tube; stereoselective reaction;95%
20826-04-4

5-bromo-3-pyridinecarboxylic acid

59-02-9

Tocopherol

(R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl 5-bromonicotinate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran Inert atmosphere;95%
108-30-5

succinic acid anhydride

59-02-9

Tocopherol

4345-03-3

vitamin E succinate

Conditions
ConditionsYield
With pyridine; dmap at 25℃;94%
With sodium hydroxide In butanone at 40℃; for 6h; Reagent/catalyst; Temperature; Solvent;93.6%
dmap; triethylamine In dichloromethane at 25℃;85%
598-21-0

2-Bromoacetyl bromide

59-02-9

Tocopherol

(R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl 2-bromoacetate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 3h;93.82%
With pyridine In dichloromethane at 0℃; for 3h;93.82%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; Sealed tube;86%
With pyridine In dichloromethane at 20℃; Inert atmosphere;59%
With pyridine In dichloromethane at 0℃; for 3h;1 g
10533-83-2

N-benzoyl-N-methyl-4-methylbenzenesulfonamide

59-02-9

Tocopherol

102734-34-9

(R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl benzoate

Conditions
ConditionsYield
With potassium phosphate In tetrahydrofuran at 23℃; for 15h; Inert atmosphere; Schlenk technique;93%
59-02-9

Tocopherol

7559-04-8

2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione

Conditions
ConditionsYield
With bromine In ethanol at 0 - 20℃; for 1.16667h; pH=6; Mechanism; Solvent; Time; Temperature; pH-value; aq. phosphate buffer;92%
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 25℃; for 10h;90%
With iron(III) chloride In methanol; diethyl ether; water for 0.5h;89%
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  • Casno:

    59-02-9

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Chemistry


IUPAC Name: (2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol 
Empirical Formula: C29H50O2
Molecular Weight: 430.7061
EINECS: 200-412-2
Classification Code: Antioxidants; Growth Substances; Micronutrients; Mutation data; Protective Agents; Reproductive Effect; Vitamins
Melting Point: 2.5-3.5 °C
Index of Refraction: 1.495
Molar Refractivity: 135.06 cm3
Molar Volume: 462.7 cm3
Surface Tension: 34.6 dyne/cm
Density: 0.93 g/cm3
Flash Point: 210.2 °C
Enthalpy of Vaporization: 78 kJ/mol
Boiling Point: 485.9 °C at 760 mmHg
storage temp.: 2-8 °C
alpha: 24 °(c=2, in isooctane 25 °C)
Water Solubility:  INSOLUBLE
Appearance: Clear yellow oil
Vapour Pressure of alpha-Tocopherol (CAS NO.59-02-9): 4.59E-10 mmHg at 25 °C

Uses

 alpha-Tocopherol (CAS NO.59-02-9) is the most important lipid-soluble antioxidant and that it protects cell membranes from oxidation by reacting with lipid radicals produced in the lipid peroxidation chain reaction. alpha-Tocopherol is a nucleophile that may react with electrophilic mutagens.

Toxicity Data With Reference

1.    

dnd-rat-ivn 27 nmol/kg

    EXPEAM    Experientia. 31 (1975),1023.
2.    

dni-rat:lvr 100 µmol/L

    CNREA8    Cancer Research. 45 (1985),337.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: FlammableF
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-24/25-37/39-26 
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes. 
S37/39:Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 1
F: 8-10-23
RTECS:  DJ2900000

Specification

  alpha-Tocopherol (CAS NO.59-02-9), its Synonyms are 2H-1-Benzopyran-6-ol,3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)- ; 2H-1-Benzopyran-6-ol,3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-,[2R-[2R*(4R*,8R*)]]- ; (+)-a-Tocopherol ; (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol .