3-O-ethyl-l-ascorbic acid: Characterisation and investigation of single solvent systems for delivery to the skin

Iliopoulos, Fotis; Sil, Bruno C.; Moore, David J.; Lucas, Robert A.; Lane, Majella E.

doi:10.1016/j.ijpx.2019.100025

Cited by 33 publications

(58 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The solubility parameters of the solvent mixtures were estimated by the Van-Krevelen and Hoftyzer approach using Molecular Modelling Pro ® software (Version 7.0.8, 2016, Norgwyn Montgomery Software, Inc., North Wales, PA, USA), as explained previously [12]. Solubility studies were conducted at 32 ± 1 • C and samples were analysed using the previously reported and validated HPLC method [5].…”

Section: Miscibility Solubility Parameter Calculation and Solubilitmentioning

confidence: 99%

“…All formulations were prepared to contain EA 2% (w/w), because neat solvents containing EA at this concentration were previously reported to promote penetration of the active across pig skin [5]. Permeation studies were conducted in full thickness porcine ear skin in vitro, using Franz-type cells of a diffusion area of approximately 1 cm 2 and were followed by mass balance studies.…”

Section: Porcine Skin Permeation and Mass Balance Studies Of Eamentioning

confidence: 99%

“…Permeation studies were conducted in full thickness porcine ear skin in vitro, using Franz-type cells of a diffusion area of approximately 1 cm 2 and were followed by mass balance studies. The experiments were performed as previously described [5,13,14]. For the receptor medium, freshly prepared PBS solution was used, with a pH value of 7.3.…”

Section: Porcine Skin Permeation and Mass Balance Studies Of Eamentioning

confidence: 99%

“…Structurally, the molecule has an ethyl group on the 3-OH group of the ascorbic acid structure. EA has been found to have good stability in several commonly used solvents, with a reported recovery of greater than 90% after 120 h at 32 ± 1 • C [5].…”

Section: Introductionmentioning

confidence: 99%

“…Despite the improved stability of EA compared with the parent compound [6], topical delivery of this active still presents challenges, given its hydrophilic nature (logP( o/w ) = −1.1) [5]. Even though the ability of some solvents to promote delivery of EA across porcine skin in vitro has been confirmed, the permeability of the compound was comparatively low, with 0.6% to 7.5% of the applied dose delivered after 24 h. Additionally, commonly used excipients and/or penetration enhancers such as ethoxydiglycol, dipropylene glycol, 1,5 pentanediol, and tripropylene glycol did not promote permeation of EA through porcine skin [5]. Generally, it is accepted that skin permeation of actives is vehicle-dependent [7,8] and combinations of solvents have been shown to act synergistically to enhance permeation of compounds [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Topical Delivery of 3-O-ethyl l-ascorbic Acid from Complex Solvent Systems

et al. 2020

Self Cite

View full text Add to dashboard Cite

3-O-ethyl l-ascorbic acid (EA), an ether derivative of Vitamin C, is widely used in skincare formulations. Previously, we reported the effects of neat solvents on EA percutaneous absorption and observed that 0.6–7.5% of the applied EA was delivered through the skin over 24 h. In this work, we designed complex formulations using combinations of solvents that may act synergistically and examined their impact on EA permeation in porcine skin in vitro under finite dose conditions. Binary combinations of propylene glycol (PG) with propylene glycol monolaurate (PGML) were effective in enhancing skin permeation of EA compared with individual solvents (p < 0.05). Combining PGML with 1,2-hexanediol (HEX) did not result in significantly higher EA permeation compared with the neat solvents (p > 0.05). Addition of the volatile solvent isopropyl alcohol (IPA) to PG solutions also did not improve EA skin delivery compared with neat PG. Ternary solvent systems containing PG:PGML were subsequently prepared by the addition of a lipophilic solvent, either isopropyl myristate (IPM), medium-chain triglycerides (MCT) or isostearyl isostearate (ISIS). The optimum vehicle, PG:PGML:IPM, promoted up to 70.9% skin delivery of EA. The PG:PGML:ISIS vehicles also promoted EA permeation across the skin, but to a significantly lesser extent than the IPM-containing vehicles. No enhancement of EA delivery was noted for the PG:PGML:MCT mixtures. These results will inform the development of targeted formulations for EA in the future.

show abstract

Section: Miscibility Solubility Parameter Calculation and Solubilitmentioning

confidence: 99%

Section: Porcine Skin Permeation and Mass Balance Studies Of Eamentioning

confidence: 99%

Section: Porcine Skin Permeation and Mass Balance Studies Of Eamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Topical Delivery of 3-O-ethyl l-ascorbic Acid from Complex Solvent Systems

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

Comparison of Vitamin C and Its Derivative Antioxidant Activity: Evaluated by Using Density Functional Theory

Liu

2020

ACS Omega

View full text Add to dashboard Cite

Vitamin C (VC) is an essential antioxidant, but its application is limited because of its unstable chemical properties. Hence, a variety of VC derivatives have emerged in practical antioxidant applications. To explore the relationship between the antioxidant properties and the chemical structures of vitamin C and its derivatives, density functional theory (DFT) was used in this work to calculate the reaction enthalpies of the mechanisms related to radical scavenging activity. The structures were optimized at the B3LYP-D3(BJ)/6-31G* level of theory. Single point calculations (SPE) were performed at the PWPB95-D3 (BJ)/def2-QZVPP level. To estimate the solvent effect on antioxidant properties, the SMD (solvation model based on density) method was used. The results showed that in the process of optimizing the chemical structure of vitamin C, the antioxidant capacity of its derivatives decreased slightly in aqueous solvents. In the calculation process, it is also found that in the choice of antioxidant mechanism, these compounds are more inclined to the hydrogen atom transfer (HAT) mechanism, and from the chemical structure point of view, the double bond of the lactone ring is essential for its free radical scavenging activity. In general, it is necessary to continue to optimize the structure of VC to obtain derivatives with better oxidation resistance and more practical value.

show abstract

Detachable dissolvable microneedles: intra-epidermal and intradermal diffusion, effect on skin surface, and application in hyperpigmentation treatment

Sawutdeechaikul

Kanokrungsee

Sahaspot

et al. 2021

Sci Rep

View full text Add to dashboard Cite

Delivering bioactive compounds into skin tissue has long been a challenge. Using ex vivo porcine and rat skins, here we demonstrate that a detachable dissolvable microneedle (DDMN) array, a special dissolvable microneedle that allows needle detachment from the base within 2 min post administration, can effectively embed a model compound into epidermis and dermis. Diffusion of the compound from the needle embedding sites to the nearby skin tissue is demonstrated at various post administration periods. The relationship between the time that a conventional dissolvable microneedle array is left on skin without needle detachment from the base and the degree of skin surface abrasion at each microneedle penetration spot is also demonstrated on skin of human volunteers. Co-loading glutathione with vitamin C (vitC) can stabilize vitC in the DDMN. DDMN loaded with vitC and glutathione can help erasing post-acne-hyperpigmentation spots.

show abstract

3-O-ethyl-l-ascorbic acid: Characterisation and investigation of single solvent systems for delivery to the skin

Abstract: Graphical abstract

Cited by 33 publications

References 44 publications

Topical Delivery of 3-O-ethyl l-ascorbic Acid from Complex Solvent Systems

Topical Delivery of 3-O-ethyl l-ascorbic Acid from Complex Solvent Systems

Comparison of Vitamin C and Its Derivative Antioxidant Activity: Evaluated by Using Density Functional Theory

Detachable dissolvable microneedles: intra-epidermal and intradermal diffusion, effect on skin surface, and application in hyperpigmentation treatment

Contact Info

Product

Resources

About