Role Evaluation of Active Groups in Lignin on UV-Shielding Performance
Abstract
The contribution of the active groups in lignin to ultraviolet (UV)-shielding performance still remains unclear. In this study, we employed 16 lignin model compounds and theoretical calculations to ascertain the contribution of different functional groups to UV-shielding performance. These results showed that the order of UV-shielding performance on functional groups was -C=C–CHO > -C=C–COOH > -C=C–CH2OH > --C=C > quinone > -COOH > -OCH3 ≈ -OH. Moreover, the synergism between the para-substituted electron-donating group -OH and the electron-withdrawing group allyl on the aromatic ring played a major role in UV-shielding performance of lignin models, whereas the additive effect of meta/ortho-substituted -OCH3 played a secondary role. Furthermore, we found that the hydrophile–lipophile balance (HLB) value of lignin models also greatly affected the sunscreen protection factor (SPF) of lignin model-based sunscreens. A closer HLB value of lignin to 8.89 corresponded with a higher SPF of the lignin model-based sunscreen. The commercial photoprotective ingredient ethylhexyl methoxycinnamate (EHMC) and lignin models had a synergistic effect on UV-shielding performance caused by the π–π stacking interaction between the parallel-displaced stacked aromatic rings of lignin models and EHMC. Additionally, the UV irradiation test showed that these sunscreens prepared using lignin models and EHMC exhibited good photostability.
- Authors:
-
[3];
[5];
[7];
- Guangxi Univ., Nanning (China); Provincial and Ministerial Collaborative Innovation Center for Sugar Industry, Nanning (China); Engineering Research Center for Sugar Industry and Comprehensive Utilization, Ministry of Education, Nanning (China)
- Guangxi Univ., Nanning (China); Key Laboratory of Clean Pulp & Papermaking and Pollution Control, Nanning (China)
- Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Guangxi Univ., Nanning (China)
- Tianjin Univ. of Technology, Tianjin (China)
- China Univ. of Mining and Technology, Xuzhou, Jiangsu (China)
- Guangxi Univ., Nanning (China); Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control, Nanning (China)
- Publication Date:
- Research Org.:
- Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE; National Key Research and Development Program of China; Natural Science Foundation of Guangxi Province, China; Guangxi Innovation Driven Development Special Fund Project, China; National Natural Science Foundation of China (NSFC); Foundation of Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control
- OSTI Identifier:
- 1885231
- Grant/Contract Number:
- AC05-00OR22725; 2021YFE0114400; 2021GXNSFDA196006; AA17204092; 21766002; 2021KF02; 2021KF32; 2021KF20
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Sustainable Chemistry & Engineering
- Additional Journal Information:
- Journal Volume: 10; Journal Issue: 36; Journal ID: ISSN 2168-0485
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Sunscreen; Lignin models; Functional groups; UV-shielding performance; π-π stacking interaction
Citation Formats
Li, Yarong, Zhao, Siyu, Hu, Dongbin, Ragauskas, Arthur J., Cao, Danyu, Liu, Wenqing, Si, Chuanling, Xu, Ting, Zhao, Peitao, Song, Xueping, and Li, Kai. Role Evaluation of Active Groups in Lignin on UV-Shielding Performance. United States: N. p., 2022.
Web. doi:10.1021/acssuschemeng.2c02714.
Li, Yarong, Zhao, Siyu, Hu, Dongbin, Ragauskas, Arthur J., Cao, Danyu, Liu, Wenqing, Si, Chuanling, Xu, Ting, Zhao, Peitao, Song, Xueping, & Li, Kai. Role Evaluation of Active Groups in Lignin on UV-Shielding Performance. United States. https://doi.org/10.1021/acssuschemeng.2c02714
Li, Yarong, Zhao, Siyu, Hu, Dongbin, Ragauskas, Arthur J., Cao, Danyu, Liu, Wenqing, Si, Chuanling, Xu, Ting, Zhao, Peitao, Song, Xueping, and Li, Kai. Tue .
"Role Evaluation of Active Groups in Lignin on UV-Shielding Performance". United States. https://doi.org/10.1021/acssuschemeng.2c02714. https://www.osti.gov/servlets/purl/1885231.
@article{osti_1885231,
title = {Role Evaluation of Active Groups in Lignin on UV-Shielding Performance},
author = {Li, Yarong and Zhao, Siyu and Hu, Dongbin and Ragauskas, Arthur J. and Cao, Danyu and Liu, Wenqing and Si, Chuanling and Xu, Ting and Zhao, Peitao and Song, Xueping and Li, Kai},
abstractNote = {The contribution of the active groups in lignin to ultraviolet (UV)-shielding performance still remains unclear. In this study, we employed 16 lignin model compounds and theoretical calculations to ascertain the contribution of different functional groups to UV-shielding performance. These results showed that the order of UV-shielding performance on functional groups was -C=C–CHO > -C=C–COOH > -C=C–CH2OH > --C=C > quinone > -COOH > -OCH3 ≈ -OH. Moreover, the synergism between the para-substituted electron-donating group -OH and the electron-withdrawing group allyl on the aromatic ring played a major role in UV-shielding performance of lignin models, whereas the additive effect of meta/ortho-substituted -OCH3 played a secondary role. Furthermore, we found that the hydrophile–lipophile balance (HLB) value of lignin models also greatly affected the sunscreen protection factor (SPF) of lignin model-based sunscreens. A closer HLB value of lignin to 8.89 corresponded with a higher SPF of the lignin model-based sunscreen. The commercial photoprotective ingredient ethylhexyl methoxycinnamate (EHMC) and lignin models had a synergistic effect on UV-shielding performance caused by the π–π stacking interaction between the parallel-displaced stacked aromatic rings of lignin models and EHMC. Additionally, the UV irradiation test showed that these sunscreens prepared using lignin models and EHMC exhibited good photostability.},
doi = {10.1021/acssuschemeng.2c02714},
journal = {ACS Sustainable Chemistry & Engineering},
number = 36,
volume = 10,
place = {United States},
year = {Tue Aug 30 00:00:00 EDT 2022},
month = {Tue Aug 30 00:00:00 EDT 2022}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Photoprotection assessment of olive (Olea europaea L.) leaves extract standardized to oleuropein: In vitro and in silico approach for improved sunscreens
journal, April 2019
- da Silva, Anne C. P.; Paiva, Juliana P.; Diniz, Raiane R.
- Journal of Photochemistry and Photobiology B: Biology, Vol. 193
Synergistic Antioxidant Performance of Lignin and Quercetin Mixtures
journal, August 2017
- Liu, Di; Li, Ying; Qian, Yong
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 9
Fabrication of Light-Colored Lignin Microspheres for Developing Natural Sunscreens with Favorable UV Absorbability and Staining Resistance
journal, July 2019
- Zhang, Hui; Liu, Xinxin; Fu, Shiyu
- Industrial & Engineering Chemistry Research, Vol. 58, Issue 31
Current Understanding of the Correlation of Lignin Structure with Biomass Recalcitrance
journal, November 2016
- Li, Mi; Pu, Yunqiao; Ragauskas, Arthur J.
- Frontiers in Chemistry, Vol. 4
Occurrence, Distribution, and Fate of Organic UV Filters in Coral Communities
journal, April 2017
- Tsui, Mirabelle M. P.; Lam, James C. W.; Ng, T. Y.
- Environmental Science & Technology, Vol. 51, Issue 8
New Opportunities in the Valorization of Technical Lignins
journal, January 2021
- Balakshin, Mikhail Yu.; Capanema, Ewellyn A.; Sulaeva, Irina
- ChemSusChem, Vol. 14, Issue 4
Long-Acting and Safe Sunscreens with Ultrahigh Sun Protection Factor via Natural Lignin Encapsulation and Synergy
journal, September 2018
- Qiu, Xueqing; Li, Ying; Qian, Yong
- ACS Applied Bio Materials, Vol. 1, Issue 5
Theoretical insights on flavanones as antioxidants and UV filters: A TDDFT and NLMO study
journal, May 2017
- Ajmala Shireen, P.; Abdul Mujeeb, V. M.; Muraleedharan, K.
- Journal of Photochemistry and Photobiology B: Biology, Vol. 170
Photostability of sunscreens
journal, March 2012
- Kockler, Jutta; Oelgemöller, Michael; Robertson, Sherryl
- Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 13, Issue 1
Towards lignin-based functional materials in a sustainable world
journal, January 2016
- Kai, Dan; Tan, Mein Jin; Chee, Pei Lin
- Green Chemistry, Vol. 18, Issue 5
Fabrication of uniform lignin colloidal spheres for developing natural broad-spectrum sunscreens with high sun protection factor
journal, July 2017
- Qian, Yong; Zhong, Xiaowen; Li, Ying
- Industrial Crops and Products, Vol. 101
Review on lignin modifications toward natural UV protection ingredient for lignin-based sunscreens
journal, January 2021
- Tran, My Ha; Phan, Dieu-Phuong; Lee, Eun Yeol
- Green Chemistry, Vol. 23, Issue 13
Non-adiabatic Dynamics Mechanism in Excited State of Novel UV Protective Sunscreen in Rice: Conical Intersection Promotes Internal Conversion
journal, August 2020
- Zhao, Xiaoying; Wu, Yanqing; Shi, Yanan
- Journal of Cluster Science, Vol. 32, Issue 4
Photoprotection: extending lessons learned from studying natural sunscreens to the design of artificial sunscreen constituents
journal, January 2017
- Baker, Lewis A.; Marchetti, Barbara; Karsili, Tolga N. V.
- Chemical Society Reviews, Vol. 46, Issue 12
UV‐Shielding Performance and Color of Lignin and its Application to Sunscreen
journal, November 2021
- Li, Yarong; Zhao, Siyu; Song, Xueping
- Macromolecular Materials and Engineering, Vol. 307, Issue 2
The Nature and Applications of π–π Interactions: A Perspective
journal, January 2019
- Thakuria, Ranjit; Nath, Naba K.; Saha, Binoy K.
- Crystal Growth & Design, Vol. 19, Issue 2
Repurposing of Drug Candidates for Treatment of Skin Cancer
journal, January 2021
- Cortés, Hernán; Reyes-Hernández, Octavio D.; Alcalá-Alcalá, Sergio
- Frontiers in Oncology, Vol. 10
Atomic Force Microscopy Measurement in the Lignosulfonate/Inorganic Silica System: From Dispersion Mechanism Study to Product Design
journal, August 2021
- Wang, Jingyu; Qian, Yong; Zhou, Yijie
- Engineering, Vol. 7, Issue 8
Challenges and future of chemical assisted heavy oil recovery processes
journal, January 2020
- Ahmadi, Mohammadali; Chen, Zhangxin
- Advances in Colloid and Interface Science, Vol. 275
The nature of .pi.-.pi. interactions
journal, July 1990
- Hunter, Christopher A.; Sanders, Jeremy K. M.
- Journal of the American Chemical Society, Vol. 112, Issue 14
Physico-chemical characterization of lignins from different sources for use in phenol–formaldehyde resin synthesis
journal, May 2007
- Tejado, A.; Peña, C.; Labidi, J.
- Bioresource Technology, Vol. 98, Issue 8
Sunscreen Performance of Lignin from Different Technical Resources and Their General Synergistic Effect with Synthetic Sunscreens
journal, May 2016
- Qian, Yong; Qiu, Xueqing; Zhu, Shiping
- ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 7
A practicable process for lignin color reduction: fractionation of lignin using methanol/water as a solvent
journal, January 2017
- Zhang, Hui; Bai, Youcan; Yu, Boming
- Green Chem., Vol. 19, Issue 21
Spherical lignin particles: a review on their sustainability and applications
journal, January 2020
- Österberg, Monika; Sipponen, Mika H.; Mattos, Bruno D.
- Green Chemistry, Vol. 22, Issue 9
Revisiting lignin: a tour through its structural features, characterization methods and applications
journal, January 2021
- Melro, Elodie; Filipe, Alexandra; Sousa, Dora
- New Journal of Chemistry, Vol. 45, Issue 16
Phenol and Toluene Stacking Interactions, Including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces
journal, December 2019
- Živković, Jelena M.; Stanković, Ivana M.; Ninković, Dragan B.
- Crystal Growth & Design, Vol. 20, Issue 2
Lignin for white natural sunscreens
journal, February 2019
- Lee, Sang Cheon; Tran, Thi Minh Thu; Choi, Joon Weon
- International Journal of Biological Macromolecules, Vol. 122
Sunscreen Products as Emerging Pollutants to Coastal Waters
journal, June 2013
- Tovar-Sánchez, Antonio; Sánchez-Quiles, David; Basterretxea, Gotzon
- PLoS ONE, Vol. 8, Issue 6
Current advancement on the isolation, characterization and application of lignin
journal, November 2020
- Liao, Jing Jing; Latif, Nur Hanis Abd; Trache, Djalal
- International Journal of Biological Macromolecules, Vol. 162
Quantifying Direct DNA Damage in the Basal Layer of Skin Exposed to UV Radiation from Sunbeds
journal, June 2018
- Barnard, Isla Rose Mary; Tierney, Patrick; Campbell, Catherine Louise
- Photochemistry and Photobiology, Vol. 94, Issue 5
A review on biopolymer production via lignin valorization
journal, October 2019
- Rajesh Banu, J.; Kavitha, S.; Yukesh Kannah, R.
- Bioresource Technology, Vol. 290
Lignin: a nature-inspired sun blocker for broad-spectrum sunscreens
journal, January 2015
- Qian, Yong; Qiu, Xueqing; Zhu, Shiping
- Green Chemistry, Vol. 17, Issue 1
Review of environmental effects of oxybenzone and other sunscreen active ingredients
journal, January 2019
- Schneider, Samantha L.; Lim, Henry W.
- Journal of the American Academy of Dermatology, Vol. 80, Issue 1
Mechanisms of sunscreen failure
journal, May 2001
- Wright, Mandy Wartha; Wright, Steven T.; Wagner, Richard F.
- Journal of the American Academy of Dermatology, Vol. 44, Issue 5
Molecular Modeling Studies of the Structural, Electronic, and UV Absorption Properties of Benzophenone Derivatives
journal, November 2012
- Corrêa, Bianca A. M.; Gonçalves, Arlan S.; de Souza, Alessandra M. T.
- The Journal of Physical Chemistry A, Vol. 116, Issue 45