7695-91-2

Basic information

• Product Name: Tocopheryl acetate
• Synonyms: 3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-yl acetate;[2r-[2r*(4r*,8r*)]]-3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-ol acetate;ALPHA-TOCOPHERYL ACETATE;ALPHA-TOCOPHERYLIS ACETAS;(+/-)-ALPHA-TOCOPHEROL ACETATE;ALL-RAC-ALPHA-TOCOPHERYL ACETATE;(+)-A-TOCOPHEROL;DL-TOCOPHRIN
• CAS NO: 7695-91-2
• Molecular Formula: C₃₁H₅₂O₃
• Molecular Weight: 472.74
• EINECS: 231-710-0
• Product Categories: Organics;Antioxidant;Biochemistry;Vitamins;Vitamins and derivatives;Vitamin series;food additives
• Mol File: 7695-91-2.mol

Chemical Properties

• Melting Point: -28°C
• Boiling Point: 224 °C0.3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.96 g/mL at 20 °C(lit.)
• Vapor Density: 16.3 (vs air)
• Vapor Pressure: 1.42E-09mmHg at 25°C
• Refractive Index: n20/D 1.497
• Storage Temp.: 2-8°C
• Solubility: Practically insoluble in water, freely soluble in acetone, in anhydrous ethanol and in fatty oils.
• Water Solubility: Immiscible with water.
• Sensitive: Air & Light Sensitive
• Merck: 14,9495
• BRN: 97512
• CAS DataBase Reference: Tocopheryl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Tocopheryl acetate(7695-91-2)
• EPA Substance Registry System: Tocopheryl acetate(7695-91-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: GA8747000
• F: 8-10-23
• TSCA: Yes
• Hazardous Substances Data: 7695-91-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to yellow clear liquid

Uses

Different sources of media describe the Uses of 7695-91-2 differently. You can refer to the following data:
1. anti-Altzheimer therapeutic
2. vitamin E acetate (tocopherol acetate) is an anti-oxidant with skinmoisturizing activity. given its free-radical scavenging properties, it is useful in uV protective products. Vitamin e acetate is commonly used to replace vitamin e because it is more stable and is converted to vitamin e by the body.
3. Vitamin E (α-tocopherol) occurs naturally in most vegetable oils. The highest concentrations are found in com, soybean oils, sunflower seed, wheat germ, rapeseed, alfalfa, and lettuce. It is claimed to have age-retardant properties. May produce erythemamultiforme-like eruptions. It is used in a number of cosmetic products; creams are used for scars, striae, and bums; in pharmaeeutical ereams and deodorants; as an antioxidant in foods.
4. All-rac-alpha-tocopheryl acetate for peak identification may be used as an analytical reference standard for the determination of the analyte in pharmaceutical formulations by liquid chromatography.

General Description

DL-α-Tocopherol acetate is a stable ester form of vitamin E, widely used in the formulation of cosmetics for the prevention or correction of skin damage.

Hazard

A reproductive hazard.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by Homosapiens. DL-α-Tocopherol acetate can inhibit oxidation of linoleate.

Purification Methods

It is a viscous liquid which is purified by distillation under high vacuum under N2 or Ar and stored in sealed ampoules in the dark. It is considerably more stable to light and air than the parent unacetylated vitamin. It is insoluble in H2O but freely soluble in organic solvents. All eight stereoisomers have been synthesised. The commercially pure d-tocopheryl acetate (2R,4'R,8'R) has b 180-200o/0.7mm and [] D 20 +3.9o (c 5, EtOH); see above. [Cohen et al. Helv Chim Acta 64 1158 1981, Beilstein 17/4 V 169.]

InChI:InChI=1/C31H52O3/c1-21(2)13-10-14-22(3)15-11-16-23(4)17-12-19-31(9)20-18-28-26(7)29(33-27(8)32)24(5)25(6)30(28)34-31/h21-23H,10-20H2,1-9H3/t22-,23+,31+/m0/s1

Upstream product

• 59-02-9 vitamin E 
• 108-24-7 acetic anhydride 
• 1721-51-3 α-tocotrienol 
• 505-32-8 isophytol 
• 36592-62-8 4-acetoxy-2,3,5-trimethylphenol 
• 935-92-2 2,3,5-Trimethyl-1,4-benzoquinone 
• 700-13-0 Trimethylhydroquinone 
• 64-19-7 acetic acid 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 60018-13-5 3,7-dimethyl-1-octanal 
• 80370-69-0 citronellylmagnesium chloride 
• 728894-66-4 (E,Z)-(all-rac)-3-phytyl-2,5,6-trimethylhydroquinone-1-acetate 
• 696597-97-4 (all-rac)-acetic acid 4-hydroxy-2,3,6-trimethyl-5-[3-(4,8,12-trimethyltridecyl)-but-3-enyl]phenyl ester 
• 286476-98-0 β-springene 

Downstream Products

• 588-46-5 N-(phenylmethyl)acetamide 
• 527-17-3 Duroquinone 
• 59-02-9 vitamin E 

Relevant articles and documents

SYNTHESIS OF CHROMANOL AND 2-METHYL-1,4-NAPHTHOQUINONE DERIVATIVES

The present invention relates to a process for the production of chromanol and 2-methyl-1,4-naphthoquinone derivatives, more specifically to a process for preparing a compound of the general formula (I) or (II) wherein the variables are as defined in the claims and the description.

Method for preparing vitamin E acetate

The invention provides a method for preparing vitamin E acetate. The method has the characteristic of high product selectivity; a catalyst used in the method provided by the invention facilitates recovery and reutilization and has less corrosion to equipment; and a product has good stability. The method for preparing the vitamin E acetate provided by the invention prepares the vitamin E acetate through a reaction of 2,3,5-trimethylhydroquinone diester and isophytol, wherein the reaction is carried out in the presence of the catalyst; and with a molecular sieve as a carrier, the catalyst is prepared by loading Bronsted acid, metal halide, metallocene and a metal element onto the molecular sieve.

Vitamin E acetate preparation method (by machine translation)

The invention relates to a technical field of chemical synthesis, in particular relates to a vitamin E acetate preparation method, in order to trimethyl [...][...] as raw materials, innovative in a sulfuric acid and paratoluene sulfonic acid under acidic conditions, using magnesium sulfate as a catalyst, greatly improves the catalytic efficiency; in addition, in concentrated hydrochloric acid and ethyl acetate under the reaction environment, esterification synthetic vitamin E acetate efficiency is higher; and, synthetic route of this invention relates to the reaction of the routine chemical reaction, mild reaction conditions, simple operation, is suitable for industrial. (by machine translation)

dl-alpha tocopherol acetate preparation method

The present invention relates to a dl-alpha tocopherol acetate preparation method, wherein trimethyl hydroquinone diethyl ester or trimethyl hydroquinone-4-ethyl ester is adopted as a raw material, Bronsted acid and Lewis acid are adopted as catalysts, the raw material and phytol or isophytol or a phytol derivative are directly subjected to a condensation reaction in an ester solvent to obtain the product dl-alpha tocopherol acetate or an intermediate dl-alpha tocopherol, wherein the intermediate dl-alpha tocopherol is subjected to further esterification to obtain the product dl-alpha tocopherol acetate. According to the present invention, the process route is simple, the production cost is reduced, the quality of the obtained product is good, the yield is high, and the method is suitable for large-scale industrial production.

Method for preparing d1-alpha tocopheryl acetate

The invention relates to a method for preparing d1-alpha tocopheryl acetate. According to the method, d1-alpha tocopherol or a mixture of d1-alpha tocopherol and d1-alpha tocopheryl acetate serves as a raw material, nitrogen-containing alkaline matter is adopted as a catalyst, acetic acid or acetic anhydride or a mixture of acetic acid and acetic anhydride serves as an acylating agent, and a d1-alpha tocopheryl acetate product is obtained through an esterification reaction. The preparation method is simple as a whole, operability is good, the yield is high, product quality is good, and besides risks in the aspects of the environment and safety are small.

ACYLATIONS IN MICRO REACTION SYSTEMS

A method for acylating tertiary alcohols and phenolic compounds with carboxylic acids or their anhydrides in micro-reaction systems wherein the acylation is effected in the absence of any catalyst including water at residence times of at most 30 minutes.

A Convenient access to (All-rac)-α-tocopherol acetate from linalool and dihydromyrcene

Refluxing trimethylhydroquinone 2 in 10:1 dodecane/CH2Cl 2 with linalool 3b (two-fold excess) and camphorsulfonic acid, then treating the crude condensation product (consisting of a mixture of the chromanols 1b and 1c, alongside the tricyclic compounds 9 and 10) sequentially with Ac2O and m-CPBA afforded, after removal by column chromatography of the 9/10 acetates, a mixture of the regioisomeric epoxides 1jOAc and 1kOAc (ratio 9:1, total 60%). Treatment of this mixture with Al(O-i-Pr)3 followed by CuI-catalysed Wurtz coupling of the acetates of the resulting allylic alcohols with citronellylmagnesium chloride 12a, and finally hydrogenation then provided the title acetate (overall 46% from 2).

METHOD OF MAKING PURIFIED ODOR FREE TOCOPHEROL ACETATE

A process for producing odor free tocopherol acetate is disclosed. This process comprises forming a solution of tocopherol acetate in a suitable solvent, e.g., isopropyl alcohol, subjecting said solution to a sufficient amount of low pressure and heat to remove said solvent and sparging sufficient amount of an inert gas through said solution to remove traces of remaining solvent.

PROCESS FOR THE ACYLATION OF ORGANIC HYDROXY COMPOUNDS

A process for acylating organic hydroxy compounds, characterized in that the acylation is effected in the presence of a metal oxide which does not carry a catalyst and the use of such metal oxides for acylating organic hydroxy compounds.

MANUFACTURE OF TOCOPHEROLS USING A BISMUTH CATALYST

The present invention is concerned with a novel process for the manufacture of tocols and tocopherols, especially α-tocopherol, and cc-tocopheryl acetate by the reaction of a hydroquinone comprising 0 to 3 methyl groups, especially 2,3,5-trimethylhydroquinone, or 2,3,6--trimethylhydroquinone- 1 -acetate, respectively, with isophytol, phytol or a(n) (iso)phytol derivative, most preferably with isophytol, in the presence of bismuth trifluoromethanesulphonate, Bi(OS02CF3)3, as the catalyst in an organic solvent or a biphasic solvent system. A further object of the invention is the use of bismuth trifluoromethanesulphonate, Bi(OS02CF3)3, as the catalyst in Friedel-Crafts type alkylation reactions and ring-closure reactions in organic solvents.