Tocopherol Acetate

Tocopherol Acetate

Tocopheroll Acetate, also known as vitamin E acetate, is a synthetic form of vitamin E. 

CAS NO:58-95-7
EC NO:200-405-4

IUPAC NAMES:
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-yl acetate
.alpha.-Tocopheryl acetate
2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-yl acetate
[(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] acetate
alpha-Tocopherol acetate

SYNONYMS:

Tocopheryl acetate
O-acetyl--tocopherol
CHEMBL3989859
2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]chroman-6-ol acetate
[2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] acetate
(+)-α-Tocopherol acetate
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-yl acetate [ACD/IUPAC Name]
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-yl-acetat [German] [ACD/IUPAC Name]
[2R*(4R*,8R*)]-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol Acetate
200-405-4 [EINECS]
231-710-0 [EINECS]
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, acetate, (2R)- [ACD/Index Name]
54-22-8 [RN]
58-95-7 [RN]
7695-91-2 [RN]
A7E6112E4N
Acétate de (2R)-2,5,7,8-tétraméthyl-2-[(4R,8R)-4,8,12-triméthyltridécyl]-3,4-dihydro-2H-chromén-6-yle [French] [ACD/IUPAC Name]
all-rac-α-tocopheryl acetate
a-Tocopherol Acetate
a-Tocopheryl Acetate
D-?-tocopherol acetate
Eprolin [Trade name]
E-Vimin
Evion
GA8747000
GP8280000
MFCD00072042 [MDL number]
MFCD00072052
O-Acetyl-α-tocopherol
TOCOPHEROL ACETATE [JP15]
Tocopheryl acetate [Wiki]
Tocopheryl Acetate, a
Vitamin E acetate
Vitamin- E acetate
α Tocopheryl Acetate
α-tocopherol acetate
α-Tocopherol acetate
α-Tocopherylis acetas
α-Tocopherol acetate

Tocopherol Acetate

Use in cosmetics
Tocopheryl Acetate is often used in dermatological products such as skin creams. It is not oxidized and can penetrate through the skin to the living cells, where about 5% is converted to free tocopherol. Claims are made for beneficial antioxidant effects.[6] α-Tocopheryl acetate is used as an alternative to tocopherol itself because the phenolic hydroxyl group is blocked, providing a less acidic product with a longer shelf life. It is believed that the acetate is slowly hydrolyzed after it is absorbed into the skin, regenerating tocopherol and providing protection against the sun's ultraviolet rays.[7] Tocopheryl acetate was first synthesized in 1963 by workers at Hoffmann-La Roche.[8]

Although there is widespread use of Tocopherol Acetate as a topical medication, with claims for improved wound healing and reduced scar tissue,[9] reviews have repeatedly concluded that there is insufficient evidence to support these claims.[10][11] There are reports of vitamin E-induced allergic contact dermatitis from use of vitamin E derivatives such as tocopheryl linoleate and tocopherol acetate in skin care products. Incidence is low despite widespread use.[12]

Chemistry
At room temperature, Tocopherol Acetate is a fat-soluble liquid. It has 3 chiral centers and thus 8 stereoisomers. It is made by esterifying α-tocopherol with acetic acid. 2R,4R,8R-isomer, also known as RRR-α-tocopheryl acetate, is the most common isomer used for various purposes. This is because α-tocopherol occurs in the nature primarily as RRR-α-tocopherol.[2]

α-Tocopherol acetate does not boil at atmospheric pressure and begins to degrade at 240 °C.[2] It can be vacuum distilled: it boils at 184 °C at 0.01 mmHg, at 194 °C (0.025 mmHg) and at 224 °C (0.3 mmHg). In practice, it is not degraded notably by air, visible light or UV-radiation. It has a refractive index of 1.4950–1.4972 at 20 °C.[1]

It has effective anti-inflammatory and antioxidant properties.
DL-Alpha tocopheryl acetate or Vitamin-E acetate is frequently preferred in cosmetic formulations due to its stable structure. Vitamin E protects cell membranes from free radical damage. Therefore, it can prevent premature aging of the skin caused by UV light and lipid peroxidation.

What’s tocopheryl acetate?

Tocopherol Acetate (ATA) is a specific form of vitamin E that’s often found in skin care products and dietary supplements. It’s also known as tocopheryl acetate, tocopherol acetate, or vitamin E acetate.

Vitamin E is known for its antioxidant properties. Antioxidants help to protect your body from damaging compounds called free radicals. Normally, free radicals form when your body converts food into energy. However, free radicals can also come from UV light, cigarette smoke, and air pollution.

In nature, vitamin E comes in the form of tocopheryl or tocotrienol. Both tocopherol and tocotrienol have four forms, known as alpha, beta, gamma, and delta. Alpha-tocopheryl (AT) is the most active form of vitamin E in humans.

Tocopherol Acetate is more stable than Tocopherol Acetate, meaning it can better withstand environmental stresses such as heat, air, and light. This makes it ideal for use in supplements and fortified foods because it has a longer shelf life.

Where can I find Tocopherol Acetate?
Cosmetics and supplements
You’ll find Tocopherol Acetate in a variety of skin care products. The antioxidant properties of vitamin E can help to prevent damage to skin caused by free radicals from UV exposure. Vitamin E may also have an anti-inflammatory effect on the skin.

Due to its higher stability, Tocopherol Acetate is also used in vitamin E dietary supplements. When taken orally,Tocopherol Acetate is converted to AT within the intestine. Vitamin E is in most multivitamins, so be sure to check how much is in your multivitamin if you take one, before adding a supplement.

Foods
In addition to dietary supplements and cosmetic products, you can find vitamin E in the following foods:

green leafy vegetables, such as broccoli and spinach
oils, such as sunflower oil, wheat germ oil, and corn oil
sunflower seeds
nuts, such as almonds and peanuts
whole grains
fruits, such as kiwi and mango
Vitamin E is also added to fortified foods, such as cereals, fruit juices, and many spreads. You can check food labels to see if vitamin E has been added. If you want to increase your vitamin E intake, you should start by first increasing your intake of these foods.

Tocopherol Acetate is a specific type of vitamin E, in a class of organic chemical compounds known as tocopherols. These compounds are considered fat-soluble antioxidants, but are also said to have many other functions in the body. Tocopheryl acetate is “A natural tocopherol and one of the most potent antioxidant tocopherols,” according to the U.S. National Library of Medicine’s publication, “PubChem.” The antioxidants in vitamin E are known to protect the cell from damage that naturally occurs from free radicals. These free radicals are formed in the body during normal processes (such as energy production). Other free radicals come from various sources, like radiation from X-rays, air pollution, smoking, and industrial chemicals.

Note, there are eight different types of natural vitamin E; alpha tocopherol is the most abundant type in human tissue. It is the only variation of vitamin E used to treat vitamin E deficiencies.

Tocopherol Acetate is commonly used to formulate dietary supplements as well as skin care products.

Tocopherol Acetate (Alpha-tocopheryl acetate) is also known as:

Alpha Tocopherol Acetate (ATA)
Vitamin E acetate
Tocopherol acetate
A-tocopherol
Alpha tocopherol
D-alpha tocopherol
Health Benefits 
There are many benefits that are claimed to be offered by tocopheryl acetate, these include:

Treating vitamin E deficiency
Promoting healthy skin (such as moisturizing and preventing wrinkles)
Helping with wound healing
Reducing inflammation
Slowing the progression of age-related macular degeneration (AMD)
 

But what does the research say?

This means that the studies were performed in cell cultures, outside of the body. But according to Oregon State University’s Micronutrient Information Center, “These models do not recreate the complex structure of skin tissues. Therefore, in vivo [performed inside of a living organism] studies are needed.”

While there are some promising study results regarding the benefits of tocopheryl acetate, much of the research on the success of tocopheryl acetate supplementation is mixed. 

General description
α-Tocopherol is a predominant form of vitamin E in human and animal tissues[1] and also in leaf chloroplasts.[3] It is the major form in supplements.[1] DL-α-Tocopherol acetate is considered as the only storage form of vitamin E.[2]

Biochem/physiol Actions
Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble antioxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by homo sapiens. Tocopherol acetate has properties similar but not identical to α-tocopherol.

A natural tocopherol and one of the most potent antioxidant tocopherols. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. It has four methyl groups on the 6-chromanol nucleus. The natural d form of alpha-tocopherol is more active than its synthetic dl-alpha-tocopherol racemic mixture.

It’s the most commonly used version of pure vitamin E in cosmetics. You can read all about the pure form here. This one is the so-called esterified version. 

According to famous dermatologist, Leslie Baumann while tocopheryl acetate is more stable and has a longer shelf life, it’s also more poorly absorbed by the skin and may not have the same awesome photoprotective effects as pure Vit E.

What is it?
Tocopherol acetate is a fat-soluble vitamin from a class of organic compounds, many of which are known to have vitamin E activity.  Vitamin E is an antioxidant - naturally occurring chemicals that help prevent cell damage by fighting off highly reactive free radicals.   Antioxidants can be found in a variety of places in nature: fruits, vegetables, marine plants, even some seafood. In the diet of many Americans, the most significant sources of vitamin E is their breakfast cereal and tomato sauce.

What does it do?
Tocopherol acetate is used as an alternative to free tocopherol because it is more stable in formulation.   The tocopheryl acetate in our products serves as an antioxidant for the product and for its skin conditioning properties.
Tocopherol acetate is a derivative of Vitamin E. It acts in cosmetics as an antioxidant. It can be produced synthetically or of natural origin, extract of soybean oil or sunflower for example. It is often used in cosmetics as an alternative to pure tocopherol because it is considered more stable and less acidic.It is authorized in organic, when it is of vegetable origin.

Tocopherol and its several ester and ether derivatives all function as antioxidants in cosmetic formulations; they also have other functions, such as skin conditioning. Tocopheryl Acetate, Tocopherol, and Tocopheryl Linoleate are used in 2673 formulations, generally at concentrations of up to 36%, 5%, and 2%, respectively, although Tocopheryl Acetate is 100% of vitamin E oil. Tocophersolan, Tocopheryl Linoleate/Oleate, Tocopheryl Nicotinate, Tocopheryl Succinate, Dioleyl Tocopheryl Methylsilanol, and Potassium Ascorbyl Tocopheryl Phosphate, combined, are used in 36 formulations at concentrations lower than those reported for the frequently used ingredients. Tocopherol may be isolated from vegetable oils or synthesized using isophytol and methylhydroquinone.

What Is It?
Tocopherol, or vitamin E, a fat-soluble vitamin is a naturally occuring antioxidant which can be isolated from vegetable oil. When isolated Tocopherol, is a viscous oil that varies in color from yellow to brownish red. Rather than Tocopherol itself, esters of Tocopherol are often used in cosmetic and personal care products. These esters include, Tocopheryl Acetate, the acetic acid ester of Tocopherol; Tocopheryl Linoleate, the linoleic acid ester of Tocopherol; Tocopheryl Linoleate/Oleate, a mixture of linoleic and oleic acid esters of Tocopherol; Tocopheryl Nicotinate, the nicotinic acid ester of Tocopherol; and Tocopheryl Succinate, the succinic acid ester of Tocopherol. Potassium Ascorbyl Tocopheryl Phosphate, a salt of both vitamin E (Tocopherol) and vitamin C (Ascorbic Acid) may also be used in cosmetic products.

Other Tocopherol-derived ingredients that may be found in cosmetic products include Dioleyl Tocopheryl Methylsilanol, which is the dioleyl ether of Tocopheryl Acetate monoether with methylsilanetriol, and Tocophersolan, which is also called Tocopheryl Polyethylene Glycol 1000 Succinate. The addition of succinic acid and an average of 22 ethylene oxide groups to Tocopheryl makes Tocophersolan a water-soluble form of Tocopherol.

In cosmetics and personal care products, Tocopherol and other ingredients made from Tocopherol, including Tocopherol esters are used in the formulation of lipstick, eye shadow, blushers, face powders and foundations, moisturizers, skin care products, bath soaps and detergents, hair conditioners, and many other products.

Why is it used in cosmetics and personal care products?
Tocopherol, Tocophersolan, Tocopheryl Acetate, Tocopheryl Linoleate, Tocopheryl Linoleate/Oleate, Tocopheryl Nicotinate, Tocopheryl Succinate, Dioleyl Tocopheryl Methylsilanol and Potassium Ascorbyl Tocopheryl Phosphate all function as antioxidants. Tocopherol, Tocopheryl Acetate, Tocopheryl Linoleate, Tocopheryl Linoleate/Oleate, Tocopheryl Nicotinate and Dioleyl Tocopheryl Methylsilanol also function as skin-conditioning agents - miscellaneous.

Scientific Facts: 
Tocopherol, a fat-soluble vitamin, is found in vegetable fats and oils, dairy products, meat, eggs, cereals, nuts, and leafy green and yellow vegetables. It is usually present in these foods as mixtures of different forms: alpha-, beta-, gamma-, and delta-Tocopherol. The alpha form has the same biological activity as vitamin E.Tocopherols can be produced from vegetable oils or can be synthesized. Tocopherol Acetate, made by the esterification of Tocopherol with acetic acid, is frequently the source of vitamin E in dietary supplements.

alpha-Tocopherol acetate, also known as a-tocopherol acetic acid or D-vitamin e acetate, belongs to the class of organic compounds known as vitamin e compounds. These are a group of fat-soluble compounds containing or derived either from a tocopherol or a tocotrienol skeleton. alpha-Tocopherol acetate is an extremely weak basic (essentially neutral) compound.

Tocopherol acetate is often used rather than vitamin E as an ingredient of skin care products and dermatological preparations, because it lacks the free phenolic OH group. However, because of this the acetate as such is biologically inactive. In spite of this intrinsic inactivity, the skin is protected against the harmful effects of sunlight after topical application of Tocopherol acetate. Therefore it is supposed that hydrolysis takes place in the skin and that the reaction product, the radical scavenger vitamin E, is responsible for the protection observed.

Alpha-tocopherol is the primary form of vitamin E that is preferentially used by the human body to meet appropriate dietary requirements. In particular, the RRR-alpha-tocopherol (or sometimes called the d-alpha-tocopherol stereoisomer) stereoisomer is considered the natural formation of alpha-tocopherol and generally exhibits the greatest bioavailability out of all of the alpha-tocopherol stereoisomers. Moreover, RRR-alpha-tocopherol acetate is a relatively stabilized form of vitamin E that is most commonly used as a food additive when needed.

 At the same time, vitamin E deficiency is generally quite rare but may occur in premature babies of very low birth weight (< 1500 grams), individuals with fat-malabsorption disorders (as fat is required for the digestive tract to absorb vitamin E), or individuals with abetalipoproteinemia - a rare, inherited disorder that causes poor absorption of dietary fat - who require extremely large doses of supplemental vitamin E daily (around 100 mg/kg or 5-10 g/day) 5. In all such cases, alpha-tocopherol is largely the preferred form of vitamin E to be administered.

Tocopherol  acetate is used as a fortifying agent and dietary supplement in food. It is used in dermatological products such as skin creams. It is an alternative to tocopherol and provides protection against the sun’s ultraviolet rays.

Active agent suitable as anti-oxidant for cosmetic emulsions, such as sunscreen preparations, body lotions, hand and facial creams.

Application
After Sun
Baby Care and Cleansing 
Body Care
Color Care
Conditioning
Face Care
Face Cleansing 
Personal Care
Wipes Self Tanning 
Sun Protection 
Toothpaste/Mouthwash

Vitamin E Acetate (Tocopherol) is the stable form of Vitamin E most often used in cosmetic formulations for its skin care benefits. It protects the cells against free radicals and prevents the peroxidation of body fats as an in-vivo antioxidant.

What Is Tocopherol acetate?
A form of vitamin E, tocopheryl acetate is an ester of tocopherol. Tocopherol, or vitamin E, is found in many plants, dairy products, meat, eggs, cereals, and nuts.[1,2]

What Does Tocopherol acetate Do in Our products?
Tocopherol acetate is a skin-conditioning agent and antioxidant.[3] It is found in thousands of personal care products, including lipstick, sunscreen, moisturizer, conditioner, shampoo, makeup, nail polish, lip balm, and other products.

Why Puracy Uses Tocopherol acetate
We use tocopherol acetate in several of our products as a moisturizer. The FDA has deemed tocopherols generally recognized as safe (GRAS).[9] A study shows tocopherol acetate is generally not irritating or sensitizing to the skin.[10,11]Whole Foods has deemed the ingredient acceptable in its body care and cleaning product quality standards.[12,13] The Cosmetics Ingredient Review has also determined that tocopherol acetate is safe for use in cosmetics. In a 2002 assessment, it was initially concerned with possible irritation and sensitization due to a large number of outbreaks reported in Switzerland with the release of a line of cosmetics containing tocopheryl linoleate; however, the researchers thought the outbreaks were caused by contamination or a metabolite. According to the Cosmetic Ingredients Review, irritation and sensitization data available since the 2002 report indicated that tocopheryl acetate is not an irritant or sensitizer.[14]

How Tocopherol acetate Is Made
Tocopherol acetate is an ester of tocopherol, which is vitamin E.[7] Tocopherol production can begin by drying out oil seeds to remove some of their moisture. After removing the shells or hulls, the seeds are usually ground, then mixed with hot water and boiled to allow some of the oil to float. The milled seed is then turned into a paste and kneaded or pressed to separate the oil. At that point, the oil can be refined to remove flavor or odor.

Tocopherol acetate is the most widely used active ingredient in Personal Care. Its central role in Personal Care is that of a strong antioxidant, capturing free oxygen radicals generated by exposure to UV-light or pollution and preventing further damage. Generally, the addition of vitamin antioxidants (vitamin E and vitamin C) improves the photoprotection provided by sunscreens as a biological second line of defense against UV-induced premature skin ageing.

In the form of Tocopherol Acetate, vitamin E is extremely stable in formulations. Indeed, this is the vitamin compound of choice for cosmetic preparations to deliver maximum vitamin efficacy. In the form of Tocopherols, it is mostly used to stabilise oxygen sensitive ingredients in formulations.

Tocopherol  Acetate provides all of the benefits of Vitamin E with the added benefit of sustainability. The most widely used active ingredient in the beauty industry, Vitamin E has proven antioxidant effects, enhances moisturization and strengthens the skin barrier. Vitamin E helps to counteract the appearance of inflammation linked to oxidative processes through downregulation of its mediators. Tocopherol Acetate (dl-alpha-tocopheryl acetate) also has the lowest carbon footprint for Vitamin E in the personal care industry, assessed via Lifecycle analysis. dl-a-Tocopheryl Acetate is a colorless to yellow or greenish yellow, practically odorless viscous oil. It is practically insoluble in water, and freely soluble in alcohol, chloroform, acetone, ether, and vegetable oils.

Tocopherol  Acetate is an active ingredient for use in cosmetic products for the skin and the hair. As an in-vivo antioxidant, it protects the cells against free radicals and prevents the peroxidation of body fats. It is also an effective moisturizing agent and improves the elasticity and smoothness of the skin. It is particularly suitable for use in sun-protection products and products for daily personal care.
Natural source Vitamin E isolated from edible vegetable oil. The ester of d-alpha Tocopherol is white to off-white free flowing powder.

Product description
Vit E Acetate (Tocopheryl Acetate) is the more stable acetic acid ester of Tocopherol. Tocopheryl Acetate is absorbed easily by the skin, where it is cleaved enzymatically into Tocopherol.

Tocopherol is an in vivo antioxidant, scavenges free radicals induced by UV radiation. Tocopherol increases the moisture-retaining ability of the epidermis.

Tocopherol slows down the photooxidative processes of decomposition in hair pigment (melanin) and hair protein (keratin).

Ideal ingredient to add to sun screen and after sun formulations at 0.3 to 5%.

What is TOCOPHERYL ACETATE and where is it found?
This chemical is used mainly as an antioxidant in pharmaceutical, cosmetic and food
formulations. It is found in many personal care products such as skin creams,
moisturizers, medicated lotions, skin and eye cosmetics, hair care and hair styling
products, baby wipes, lip balms and cold sore products, shaving creams, soap &
cleansers, sunscreens, and antifungal products. Further research may identify additional
product or industrial usages of this chemical.

TOCOPHERYL ACETATE
A synthetic vitamin E acetate. Proven antioxidant effects, enhances moisturization and strengthens the skin barrier. Helps to counteract the appearance of inflammation linked to oxidative processes. Without preservative.

Antioxidant to create and protect alluring skin every day. DL-α-Tocopherol Acetate is synthetic vitamin E acetate. Vitamin E is a building block in cosmetic formulations: it has proven antioxidant effects, enhances moisturization and strengthens the skin barrier. Vitamin E helps to counteract the appearance of inflammation linked to oxidative processes through downregulation of its mediators. As one of the most powerful oil-soluble antioxidants and free-radical scavengers available today, Vitamin E plays a crucial role in oxidative regeneration of skin exposed to stressors.

Tocopheryl acetate is obtained from vegetable oils. It is a high quality vitamin E, which in cosmetic products promotes cell respiration and renewal. It also binds free radicals and protects the skin from harmful environmental influences.

Extraction: tocopherol acetate is a form of vitamin E than can be isolated from plant-derived oils. It is used in food and cosmetics.

Benefits: it has antioxidant, moisturising and anti-inflammatory properties. It is a suitable ingredient to achieve anti-ageing benefits, by promoting the protection and repair of skin.

What is it?
Tocopheryl acetate is a fat-soluble vitamin from a class of organic compounds, many of which are known to have vitamin E activity.  Vitamin E is an antioxidant - naturally occurring chemicals that help prevent cell damage by fighting off highly reactive free radicals.   Antioxidants can be found a variety of places in nature: fruits, vegetables, marine plants, even some seafood. In the diet of many people, the most significant sources of vitamin E is their breakfast cereal and tomato sauce.

What does it do?
Tocopheryl acetate is used as an alternative to free tocopherol because it is more stable in formulation. The tocopheryl acetate in our products serves as an antioxidant for the product and for its skin conditioning properties.

Tocopherol and tocopheryl acetate can be made naturally from vegetable oils or synthetically from petroleum products.  The tocopherol we use is naturally derived from either soybean or rapeseed oil.  The tocopheryl acetate is produced when this naturally derived d-alpha tocopherol is combined with acetic acid in a process known as esterification.