Ultralong Fatty Acyl Derivatives As Occlusive Structure Lipids for Cosmetic Applications: Synthesis and Characterization

Bianca Pérez; Pallav Bulsara; Anothony Vincent Rawlings; Wei Wei; Mads Mørk Jensen; Zegao Wang; Jason Dickens; Shuai Zhang; Russell P. Elliot; Marianne Glasius; MD Dong; Martyn Clarke; Zheng Guo

doi:10.1021/acssuschemeng.6b02021

Ultralong Fatty Acyl Derivatives As Occlusive Structure Lipids for Cosmetic Applications: Synthesis and Characterization

Bianca Pérez, Pallav Bulsara, Anothony Vincent Rawlings, Wei Wei, Mads Mørk Jensen, Zegao Wang, Jason Dickens, Shuai Zhang, Russell P. Elliot, Marianne Glasius, MD Dong, Martyn Clarke, Zheng Guo

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

10 Citations (Scopus)

Abstract

Finding sustainable and commercially viable sources of occlusive materials, as an alternative to petroleum, is of great interest. Inspired by the fundamental role of long chain fatty acids in maintaining skin barrier, ultralong fatty acyl derivatives with diverse structures (varied acyl chain length and different polar head; i.e. glycerol, ethylene glycol, and diethylene glycol) were synthesized. These molecules can be feasibly obtained via enzymatic esterification of fatty acids or fractionated from commercial glycerides mixture via short path distillation. The molecular packing behaviors of compounds were characterized via differential scanning calorimetry, Fourier transform infrared, and Langmuir isotherm measurements. The structure-property relationship study reveals that a glycerol molecule monoacylated with an ultralong fatty acyl is the derivative which entails the most occlusive properties of the series of ultralong chain fatty acid derivatives. Fast Fourier transform filtering (FFTF) analysis of atomic force microscopy images verified a homogeneous monolayer packing of glyceryl monobehenate monolayer, and the water vapor transmission study demonstrated that the formulation of glyceryl monobehenate at 3% w/w in a phospholipid-containing emulsion generates an occlusive film significantly superior to a 3% w/w petrolatum formulation. This work demonstrated that natural glyceryl monobehenate can be a novel source of sustainable occlusive structuring agents and green replacements for petrolatum.

Original language	English
Journal	ACS Sustainable Chemistry & Engineering
Volume	4
Issue	12
Pages (from-to)	7137–7146
Number of pages	10
ISSN	2168-0485
DOIs	https://doi.org/10.1021/acssuschemeng.6b02021
Publication status	Published - 5 Dec 2016

Keywords

Glyceryl monobenhenate
Occlusive materials
Orthorhombic lateral packing
Petrolatum
Stratum corneum
Water vapor transmission rate

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10.1021/acssuschemeng.6b02021

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Pérez, B., Bulsara, P., Rawlings, A. V., Wei, W., Jensen, M. M., Wang, Z., Dickens, J., Zhang, S., P. Elliot, R., Glasius, M., Dong, MD., Clarke, M., & Guo, Z. (2016). Ultralong Fatty Acyl Derivatives As Occlusive Structure Lipids for Cosmetic Applications: Synthesis and Characterization. ACS Sustainable Chemistry & Engineering, 4(12), 7137–7146. https://doi.org/10.1021/acssuschemeng.6b02021

@article{c13567c5975946dfa90337b0dca32d38,

title = "Ultralong Fatty Acyl Derivatives As Occlusive Structure Lipids for Cosmetic Applications: Synthesis and Characterization",

abstract = "Finding sustainable and commercially viable sources of occlusive materials, as an alternative to petroleum, is of great interest. Inspired by the fundamental role of long chain fatty acids in maintaining skin barrier, ultralong fatty acyl derivatives with diverse structures (varied acyl chain length and different polar head; i.e. glycerol, ethylene glycol, and diethylene glycol) were synthesized. These molecules can be feasibly obtained via enzymatic esterification of fatty acids or fractionated from commercial glycerides mixture via short path distillation. The molecular packing behaviors of compounds were characterized via differential scanning calorimetry, Fourier transform infrared, and Langmuir isotherm measurements. The structure-property relationship study reveals that a glycerol molecule monoacylated with an ultralong fatty acyl is the derivative which entails the most occlusive properties of the series of ultralong chain fatty acid derivatives. Fast Fourier transform filtering (FFTF) analysis of atomic force microscopy images verified a homogeneous monolayer packing of glyceryl monobehenate monolayer, and the water vapor transmission study demonstrated that the formulation of glyceryl monobehenate at 3% w/w in a phospholipid-containing emulsion generates an occlusive film significantly superior to a 3% w/w petrolatum formulation. This work demonstrated that natural glyceryl monobehenate can be a novel source of sustainable occlusive structuring agents and green replacements for petrolatum.",

keywords = "Glyceryl monobenhenate, Occlusive materials, Orthorhombic lateral packing, Petrolatum, Stratum corneum, Water vapor transmission rate",

author = "Bianca P{\'e}rez and Pallav Bulsara and Rawlings, {Anothony Vincent} and Wei Wei and Jensen, {Mads M{\o}rk} and Zegao Wang and Jason Dickens and Shuai Zhang and {P. Elliot}, Russell and Marianne Glasius and MD Dong and Martyn Clarke and Zheng Guo",

year = "2016",

month = dec,

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doi = "10.1021/acssuschemeng.6b02021",

language = "English",

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journal = "ACS Sustainable Chemistry & Engineering",

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Pérez, B, Bulsara, P, Rawlings, AV, Wei, W, Jensen, MM, Wang, Z, Dickens, J, Zhang, S, P. Elliot, R, Glasius, M , Dong, MD, Clarke, M & Guo, Z 2016, 'Ultralong Fatty Acyl Derivatives As Occlusive Structure Lipids for Cosmetic Applications: Synthesis and Characterization', ACS Sustainable Chemistry & Engineering, vol. 4, no. 12, pp. 7137–7146. https://doi.org/10.1021/acssuschemeng.6b02021

Ultralong Fatty Acyl Derivatives As Occlusive Structure Lipids for Cosmetic Applications: Synthesis and Characterization. / Pérez, Bianca; Bulsara, Pallav; Rawlings, Anothony Vincent et al.
In: ACS Sustainable Chemistry & Engineering, Vol. 4, No. 12, 05.12.2016, p. 7137–7146.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Ultralong Fatty Acyl Derivatives As Occlusive Structure Lipids for Cosmetic Applications

T2 - Synthesis and Characterization

AU - Pérez, Bianca

AU - Bulsara, Pallav

AU - Rawlings, Anothony Vincent

AU - Wei, Wei

AU - Jensen, Mads Mørk

AU - Wang, Zegao

AU - Dickens, Jason

AU - Zhang, Shuai

AU - P. Elliot, Russell

AU - Glasius, Marianne

AU - Dong, MD

AU - Clarke, Martyn

AU - Guo, Zheng

PY - 2016/12/5

Y1 - 2016/12/5

N2 - Finding sustainable and commercially viable sources of occlusive materials, as an alternative to petroleum, is of great interest. Inspired by the fundamental role of long chain fatty acids in maintaining skin barrier, ultralong fatty acyl derivatives with diverse structures (varied acyl chain length and different polar head; i.e. glycerol, ethylene glycol, and diethylene glycol) were synthesized. These molecules can be feasibly obtained via enzymatic esterification of fatty acids or fractionated from commercial glycerides mixture via short path distillation. The molecular packing behaviors of compounds were characterized via differential scanning calorimetry, Fourier transform infrared, and Langmuir isotherm measurements. The structure-property relationship study reveals that a glycerol molecule monoacylated with an ultralong fatty acyl is the derivative which entails the most occlusive properties of the series of ultralong chain fatty acid derivatives. Fast Fourier transform filtering (FFTF) analysis of atomic force microscopy images verified a homogeneous monolayer packing of glyceryl monobehenate monolayer, and the water vapor transmission study demonstrated that the formulation of glyceryl monobehenate at 3% w/w in a phospholipid-containing emulsion generates an occlusive film significantly superior to a 3% w/w petrolatum formulation. This work demonstrated that natural glyceryl monobehenate can be a novel source of sustainable occlusive structuring agents and green replacements for petrolatum.

AB - Finding sustainable and commercially viable sources of occlusive materials, as an alternative to petroleum, is of great interest. Inspired by the fundamental role of long chain fatty acids in maintaining skin barrier, ultralong fatty acyl derivatives with diverse structures (varied acyl chain length and different polar head; i.e. glycerol, ethylene glycol, and diethylene glycol) were synthesized. These molecules can be feasibly obtained via enzymatic esterification of fatty acids or fractionated from commercial glycerides mixture via short path distillation. The molecular packing behaviors of compounds were characterized via differential scanning calorimetry, Fourier transform infrared, and Langmuir isotherm measurements. The structure-property relationship study reveals that a glycerol molecule monoacylated with an ultralong fatty acyl is the derivative which entails the most occlusive properties of the series of ultralong chain fatty acid derivatives. Fast Fourier transform filtering (FFTF) analysis of atomic force microscopy images verified a homogeneous monolayer packing of glyceryl monobehenate monolayer, and the water vapor transmission study demonstrated that the formulation of glyceryl monobehenate at 3% w/w in a phospholipid-containing emulsion generates an occlusive film significantly superior to a 3% w/w petrolatum formulation. This work demonstrated that natural glyceryl monobehenate can be a novel source of sustainable occlusive structuring agents and green replacements for petrolatum.

KW - Glyceryl monobenhenate

KW - Occlusive materials

KW - Orthorhombic lateral packing

KW - Petrolatum

KW - Stratum corneum

KW - Water vapor transmission rate

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U2 - 10.1021/acssuschemeng.6b02021

DO - 10.1021/acssuschemeng.6b02021

M3 - Journal article

SN - 2168-0485

VL - 4

SP - 7137

EP - 7146

JO - ACS Sustainable Chemistry & Engineering

JF - ACS Sustainable Chemistry & Engineering

IS - 12

ER -

Ultralong Fatty Acyl Derivatives As Occlusive Structure Lipids for Cosmetic Applications: Synthesis and Characterization

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