Tocopherol and Tocopheryl Acetate as antioxidants; Is there any difference?

tecnico3viniatecnico3vinia Member
in Formulating
Hello,

I just watched a video () that says that the Tocopheryl Acetate won't protect a cosmetic formulation against oxidation. Does it make sense?

I did a quick research afterwards and didn't find anything besides this from DSM (https://www.dsm.com/personal-care/en_US/products/vitamins/vitamin-e.html).

I tend to use Tocopheryl Acetate as a antioxidant for my formulations and it always worked. Anyone else do it too?

Thanks in advance.

Kind regards,

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Comments

  • SerMig1111SerMig1111 Member
    Hi, I also use tocopheryl acetate in my cosmetic formulations. Actually, it seems to be the most common way to add Vitamin E to a cosmetic. As described in the technical sheet of the known manufacturer BASF: "Vitamin E acetate is stable towards heat and oxygen, in contrast to Vitamine E alcohol (tocopherol)". I think that's the main reason.
  • AbdullahAbdullah Member
    What does it do in your formula?
    How do you know it works? 
    What happens to your formula if you don't add tocopheryl acetate? 
  • SerMig1111SerMig1111 Member
    Tocopherols protect natural oils with double bonds against rancidity since it works as an antioxidant (double bonds are prone to oxidation).

  • MarkBroussardMarkBroussard Member, Professional Chemist
    Simply look at the chemical structure of the molecules Tocopherol and Tocopheryl Acetate.

    In Tocopheryl Acetate, the only active site on the molecule Tocopherol that can readily serve as a proton donor to quench free radicals has been modified to the acetate form which is realatively unreactive or needs to first undergo a conversion to the tocopherol form to be active as a proton donor.

    Yes, Tocopheryl Acetate may be more stable towards heat and oxygen than tocopherol, but the ability to serve as a proton donor is its whole essence in Tocopherol functioning as an antioxidant, so the modification of Tocopherol to Tocopheryl Acetate essentially disables Tocopherol's ability to be a functional molecular antioxidant. 
    Chemist/Microbiologist formulating in the Clean Beauty and Naturals arena under Clean At Sephora/Credo Clean Beauty/ECOCert/Natural Products Assn/Whole Foods/National Organic Program/NSF.
     
    Highly functional skincare formulations for Indie Beauty Brands, Dermatologists, Estheticians & Beatuy Entrepreneurs.

    See website for details https://desertinbloomcosmeticslab.com
    Or read the Blog for my insights on Cosmetic Chemistry & Skincare https://desertinbloomcosmeticslab.com/cosmetic-chemist-skincare-blog/
  • MicroformulationMicroformulation Member, Professional Chemist
    Tocopheryl Acetate will NOT protect your Formulation from oxidation. Again. these are some pretty broad and rudimentary subjects that one should explore on one's own through credible (not online most likely) sources. Feed a man, teach them to fish and all that...
    markfuller@microformulation.com Microformulation.com Microformulation Cosmetic Consulting provides Custom Formulations for both large Commercial accounts as well as smaller entrepreneurs. We can provide Naturally compliant Formulations under the NSF, NPA, Whole Foods and USDA Organic Certifications. BS.Pharm Albany College of Pharmacy, Union University.
  • EVchemEVchem Member
    @tecnico3vinia - you are saying tocopheryl acetate "works" as an antioxidant in the formula, how are you evaluating that? Are you going based off appearance/smell, or do you test something quantitative like peroxide content?

    Totally agree with Mark and micro here

    Vitamin E Acetate is more stable than tocopherol, and that's exactly why it is not a good antioxidant. In rough terms, antioxidants should be unstable- they take the hit of free radicals and react so that your other materials aren't undergoing those chemical reactions, resulting in odor or color change.

    As far as studies here's a quick one

    https://www.researchgate.net/publication/10607302_Comparison_of_antioxidant_activites_of_tocopherols_alone_and_in_pharmaceutical_formulations
  • tecnico3viniatecnico3vinia Member
    MarkBroussard said:
    Simply look at the chemical structure of the molecules Tocopherol and Tocopheryl Acetate.

    In Tocopheryl Acetate, the only active site on the molecule Tocopherol that can readily serve as a proton donor to quench free radicals has been modified to the acetate form which is realatively unreactive or needs to first undergo a conversion to the tocopherol form to be active as a proton donor.

    Yes, Tocopheryl Acetate may be more stable towards heat and oxygen than tocopherol, but the ability to serve as a proton donor is its whole essence in Tocopherol functioning as an antioxidant, so the modification of Tocopherol to Tocopheryl Acetate essentially disables Tocopherol's ability to be a functional molecular antioxidant. 
    Thanks. I did more research on the topic and finally understood why Tocopheryl Acetate isn't a good option for the formulation protection.
  • tecnico3viniatecnico3vinia Member
    EVchem said:
    @tecnico3vinia - you are saying tocopheryl acetate "works" as an antioxidant in the formula, how are you evaluating that? Are you going based off appearance/smell, or do you test something quantitative like peroxide content?

    Totally agree with Mark and micro here

    Vitamin E Acetate is more stable than tocopherol, and that's exactly why it is not a good antioxidant. In rough terms, antioxidants should be unstable- they take the hit of free radicals and react so that your other materials aren't undergoing those chemical reactions, resulting in odor or color change.

    As far as studies here's a quick one

    https://www.researchgate.net/publication/10607302_Comparison_of_antioxidant_activites_of_tocopherols_alone_and_in_pharmaceutical_formulations
    Thank you. Great article. It really helped me to understand why tocopheryl acetate isn't a good option for formulations' protection. 
  • tecnico3viniatecnico3vinia Member
    Microformulation said:
    Tocopheryl Acetate will NOT protect your Formulation from oxidation. Again. these are some pretty broad and rudimentary subjects that one should explore on one's own through credible (not online most likely) sources. Feed a man, teach them to fish and all that...
    Did more research and finally understood it. Thanks ;)
  • tecnico3viniatecnico3vinia Member
    Hi, I also use tocopheryl acetate in my cosmetic formulations. Actually, it seems to be the most common way to add Vitamin E to a cosmetic. As described in the technical sheet of the known manufacturer BASF: "Vitamin E acetate is stable towards heat and oxygen, in contrast to Vitamine E alcohol (tocopherol)". I think that's the main reason.
    After some research I can finally understand that Tocopheryl Acetate isn't a great option to protect the formulation against oxidantion. Here's some articles that I found that helped me understand it: 

    https://pubmed.ncbi.nlm.nih.gov/23600381/;
    https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1524-4725.2005.31724;
    https://www.researchgate.net/publication/10607302_Comparison_of_antioxidant_activites_of_tocopherols_alone_and_in_pharmaceutical_formulations.
  • MicroformulationMicroformulation Member, Professional Chemist
    Buy some texts or take a course like Perry's. Don't use place a great deal of weight on online citations.
    markfuller@microformulation.com Microformulation.com Microformulation Cosmetic Consulting provides Custom Formulations for both large Commercial accounts as well as smaller entrepreneurs. We can provide Naturally compliant Formulations under the NSF, NPA, Whole Foods and USDA Organic Certifications. BS.Pharm Albany College of Pharmacy, Union University.
  • SerMig1111SerMig1111 Member
    It is true that the -OH functional group allows the antioxidant activity of tocopherol; however, tocopheryl acetate is actually intended to work as a prodrug, with tocopherol being slowly released as the ester group es hydrolyzed. The process is slow, but there is actually evidence that it occurs. I am currently checking more information on the topic, particularly in the book Cosmetic Creams - Development, manufacture, and marketing of effective skincare products, which I think is a reliable source.  I wouldn't directly eliminate tocopheryl acetate as a useful antioxidant, not only to the formulation but also to the skin. I'll let you know if  I find some interesting information.
  • HenryHenry Member
    I would like to thank the members that provided a detail explanation on what is happening with raw materials like the example here. I didn't have any idea about the protonation of the molecule and such. (I hope I don't sound to silly here). Now and days the focus on why something works gets lost in the middle of "make it work" or "add this to make the label claim."  The act of finding something functional or making something functional gets lost too.  Often times I have asked co workers how or why something does or does not work and they don't know.  Sometimes people are working with folks that don't have a true experienced senior colleague to ask or provide assistance.

    On my soap box.... This is what make us (Chemists) different from the DIY folks who are basically taking the "short cut" to creating good chemistry.
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