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Tetrahexyldecyl Ascorbate
"Descrizione"
by Al222 (19780 pt)
2023-Aug-30 16:42

Tetrahexyldecyl Ascorbate is a chemical compound, a fat-soluble form of vitamin C and is a precursor of L-ascorbic acid, esterified with branched-chain fatty acid (2-hexyldecanoic acid).

The name describes the structure of the molecule

  • "Tetrahexyldecyl" indicates a particular alkyl ester and refers to a specific alkyl structure that's attached to the main molecule to enhance its solubility and skin penetration.
  • "Ascorbate". Refers to the salt or ester of ascorbic acid, better known as vitamin C. Vitamin C is a potent antioxidant known for its skin-beneficial properties, such as promoting collagen production and protecting against free radical damage.

Description of raw materials used in production

  • Ascorbic acid (Vitamin C) - A pure form of vitamin C.
  • Tetrahexyldecyl alcohol - A fatty alcohol used for its lipophilic affinity.

Step-by-step summary of industrial chemical synthesis process

  • Activation - The ascorbic acid is activated, making it more reactive.
  • Reaction - The activated ascorbic acid is then reacted with tetrahexyldecyl alcohol. This is an esterification reaction that binds the acid to the alcohol.
  • Purification - The crude product of the reaction is purified to remove impurities or unreacted compounds.
  • Quality control - After purification, tetrahexyldecyl ascorbate is tested to make sure it is pure and stable.

It appears in the form of a white powder. 

What it is for and where

Medical

Tetrahexyldecyl Ascorbate has shown antioxidant properties but degrades in the presence of singlet oxygen (1).

Cosmetics

Antioxidant agent. Ingredient that counteracts oxidative stress and prevents cell damage. Free radicals, pathological inflammatory processes, reactive nitrogen species and reactive oxygen species are responsible for the ageing process and many diseases caused by oxidation.

Skin conditioning agent. It is the mainstay of topical skin treatment as it has the function of restoring, increasing or improving skin tolerance to external factors, including melanocyte tolerance. The most important function of the conditioning agent is to prevent skin dehydration, but the subject is rather complex and involves emollients and humectants that can be added in the formulation.

CAS   183476-82-6 1445760-15-5

References_____________________________________________________________________

(1) Swindell WR, Randhawa M, Quijas G, Bojanowski K, Chaudhuri RK. Tetrahexyldecyl Ascorbate (THDC) Degrades Rapidly under Oxidative Stress but Can Be Stabilized by Acetyl Zingerone to Enhance Collagen Production and Antioxidant Effects. Int J Mol Sci. 2021 Aug 15;22(16):8756. doi: 10.3390/ijms22168756. PMID: 34445461; PMCID: PMC8395926.

Abstract. Tetrahexyldecyl Ascorbate (THDC) is an L-ascorbic acid precursor with improved stability and ability to penetrate the epidermis. The stability and transdermal penetration of THDC, however, may be compromised by the oxidant-rich environment of human skin. In this study, we show that THDC is a poor antioxidant that degrades rapidly when exposed to singlet oxygen. This degradation, however, was prevented by combination with acetyl zingerone (AZ) as a stabilizing antioxidant. As a standalone ingredient, THDC led to unexpected activation of type I interferon signaling, but this pro-inflammatory effect was blunted in the presence of AZ. Moreover, the combination of THDC and AZ increased expression of genes associated with phospholipid homeostasis and keratinocyte differentiation, along with repression of MMP1 and MMP7 expression, inhibition of MMP enzyme activity, and increased production of collagen proteins by dermal fibroblasts. Lastly, whereas THDC alone reduced viability of keratinocytes exposed to oxidative stress, this effect was completely abrogated by the addition of AZ to THDC. These results show that AZ is an effective antioxidant stabilizer of THDC and that combination of these products may improve ascorbic acid delivery. This provides a step towards reaching the full potential of ascorbate as an active ingredient in topical preparations.

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