Tetrahexyldecyl Ascorbate (THDC) Degrades Rapidly under Oxidative Stress but Can Be Stabilized by Acetyl Zingerone to Enhance Collagen Production and Antioxidant Effects

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.

Vitamin C, lactoferrin and elastin—Advancing the science

“…This added benefit to an antioxidant formulation that includes multiple antioxidants has the capacity to effectively quench free oxygen radicals, stimulate collagen fibers, and also uniquely stimulate elastin fibers in contrast to products that use L-ascorbate as their Vitamin C active or use other actives such as tetrahexyldecyl ascorbate, which is an L-ascorbic acid precursor that degrades to L-Ascorbate with the same issues. 15 Limitations to the study include the fact that the full formulation was not tested against the comparator full formulation. However, the point here was to try to identify the active components responsible for the elastin stimulation seen when the full formulation was used.…”

“…Thus, the solution to the in vitro, ex vivo, and histological observations in clinical studies may have been uncovered, namely, SAC, together with lactoferrin synergistically stimulates elastin fiber formation. This added benefit to an antioxidant formulation that includes multiple antioxidants has the capacity to effectively quench free oxygen radicals, stimulate collagen fibers, and also uniquely stimulate elastin fibers in contrast to products that use L‐ascorbate as their Vitamin C active or use other actives such as tetrahexyldecyl ascorbate, which is an L‐ascorbic acid precursor that degrades to L‐Ascorbate with the same issues 15 …”

Acetyl Zingerone: A Photostable Multifunctional Skincare Ingredient That Combats Features of Intrinsic and Extrinsic Skin Aging

“…One of the most popular AA-esters used today in cosmetic formulations is tetrahexyldecyl ascorbate (THDC), an ester that is structurally similar to VC-IP [ 79 , 80 ]. While THDC exhibits improved chemical stability compared with AA within formulation matrices and enhanced penetration through stratum corneum (due to its lipophilicity), it was reported recently that THDC is highly susceptible to facile degradation in the presence of 1 O 2 , an entity of ROS that commonly forms within skin that is associated with significant levels of oxidative damage [ 81 ]. For example, exposure to 1 O 2 degraded TDHC by 94% within 2 min and completely within 6 min.…”

Properties, forms and biological effects of vitamin C in skin therapies

“…Wykazuje efektywne działanie nawet przy niskich stężeniach. Stosowana w celu opóźnienia procesów starzenia się skóry [12,15].…”