Photophysics of the sunscreen ingredient menthyl anthranilate and its precursor methyl anthranilate: A bottom-up approach to photoprotection

Rodrigues, Natércia d. N.; Cole-Filipiak, Neil C.; Horbury, Michael D.; Staniforth, Michael; Karsili, Tolga N. V.; Peperstraete, Yoann; Stavros, Vasilios G.

doi:10.1016/j.jphotochem.2017.11.042

Cited by 26 publications

(62 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Losantos et al [ 89 ] chose molecules 6 and 8 for non-adiabatic molecular dynamics simulations to predict their S 1 lifetimes. These were determined as ~190 and 240 fs for molecules 6 and 8, respectively, which is remarkably faster than the lifetimes known for some commercial UV filters [ 105 , 130 , 131 ]. Losantos et al’s theoretical work guided the synthesis of 20 different molecules derived from molecules 6 and 8; molecules 9–12 in Figure 14 are a few of these [ 89 ].…”

Section: Case Studiesmentioning

confidence: 85%

Unravelling the Photoprotective Mechanisms of Nature-Inspired Ultraviolet Filters Using Ultrafast Spectroscopy

2020

View full text Add to dashboard Cite

There are several drawbacks with the current commercially available ultraviolet (UV) filters used in sunscreen formulations, namely deleterious human and ecotoxic effects. As a result of the drawbacks, a current research interest is in identifying and designing new UV filters. One approach that has been explored in recent years is to use nature as inspiration, which is the focus of this review. Both plants and microorganisms have adapted to synthesize their own photoprotective molecules to guard their DNA from potentially harmful UV radiation. The relaxation mechanism of a molecule after it has been photoexcited can be unravelled by several techniques, the ones of most interest for this review being ultrafast spectroscopy and computational methods. Within the literature, both techniques have been implemented on plant-, and microbial-inspired UV filters to better understand their photoprotective roles in nature. This review aims to explore these findings for both families of nature-inspired UV filters in the hope of guiding the future design of sunscreens.

show abstract

Section: Case Studiesmentioning

confidence: 85%

Unravelling the Photoprotective Mechanisms of Nature-Inspired Ultraviolet Filters Using Ultrafast Spectroscopy

2020

View full text Add to dashboard Cite

show abstract

“…The trans-cis photoisomerization of PIC (56.19 ps) is longer than RSV (19.62 ps), suggesting that the trans-cis photoisomerization are much slower for PIC. Because the trans-cis photoisomerization lifetimes of the two stilbenoids are both at ultrafast levels, they are preferred as photoprotection molecules, [15] especially RSV.…”

Section: Resultsmentioning

confidence: 99%

Ultrafast Nonadiabatic Photoisomerization Dynamics Mechanism for the UV Photoprotection of Stilbenoids in Grape Skin

Shi

Zhao

Wang

et al. 2020

Chemistry An Asian Journal

View full text Add to dashboard Cite

Natural UV photoprotection plays a vital role in physiological protection. It has been reported that UVC radiation can make resveratrol (RSV) and piceatannol (PIC) accumulate in grape skin. In this work, we demonstrated that RSV and PIC could significantly absorb UVA and UVB, and confirmed their satisfactory photostability. Furthermore, we clarified the UV photoprotection mechanism of typical stilbenoids of RSV and PIC for the first time by using combined femtosecond transient absorption (FTA) spectroscopy and time-dependent density functional theory (TD-DFT) calculations. RSV and PIC can be photoexcited to the excited state after UVA and UVB absorption. Subsequently, the photoisomerized RSV and PIC quickly relax to the ground state via nonadiabatic transition from the S 1 state at a conical intersection (CI) position between potential energy surfaces (PESs) of S 1 and S 0 states. This ultrafast trans-cis photoisomerization will take place within a few tens of picoseconds. As a result, the UV energy absorbed by RSV and PIC could be dissipated by an ultrafast nonadiabatic photoisomerization process.

show abstract

“…This lifetime is shorter than that of current commercial filters such as menthyl anthranilate and avobenzone. [54][55][56] The shorter excited state lifetime is beneficial to potential sunscreen filters; the probability for competing (reactive) pathways within the sunscreen filter itself, or side reactions between the electronically excited sunscreen filter and additional compounds (within a commercial formulation) is minimised. These competing side reactions can also induce unfavourable reactions some of which have been known to cause skin irritation.…”

Section: Case Studiesmentioning

confidence: 99%

Unravelling photoprotection in microbial natural products

Woolley

Stavros

2019

Science Progress

View full text Add to dashboard Cite

Mycosporine-like amino acids have long been known as a natural form of photoprotection for fungi and cyanobacteria. This review will highlight the key time-resolved experimental and theoretical techniques unravelling their photochemistry and photophysics, and directly link this to their use in commercial skin-care products, namely as sunscreen filters. Three case studies have been selected, each having aided advancement in this burgeoning field of research. We discuss these studies in the context of photoprotection and conclude by evaluating the necessary future steps towards translating the photochemistry and photophysics insight of these nature derived sunscreen filters to commercial application.

show abstract

Photophysics of the sunscreen ingredient menthyl anthranilate and its precursor methyl anthranilate: A bottom-up approach to photoprotection

Cited by 26 publications

References 51 publications

Unravelling the Photoprotective Mechanisms of Nature-Inspired Ultraviolet Filters Using Ultrafast Spectroscopy

Unravelling the Photoprotective Mechanisms of Nature-Inspired Ultraviolet Filters Using Ultrafast Spectroscopy

Ultrafast Nonadiabatic Photoisomerization Dynamics Mechanism for the UV Photoprotection of Stilbenoids in Grape Skin

Unravelling photoprotection in microbial natural products

Contact Info

Product

Resources

About