Amino Acids, Lactic Acid and Ascorbic Acid as Raw Materials for Biocompatible Surfactants

Morán, Carmen; Pérez, Lourdes; Pinazo, Aurora; Infante, M. R.

doi:10.1002/9780470686607.ch5

Cited by 5 publications

(4 citation statements)

References 118 publications

(137 reference statements)

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“…It is a powerful antioxidant but it is highly fragile and poorly soluble in organic solvents, which limits its applications to aqueous environments. This problem can be overcome by the synthesis of hydrophobic derivatives (ascorbate esters and their alkali salts for example), which increases the solubility of ascorbic acid and its stability (Moran et al, ). APPS (Ascorbyl 6‐Palmitate 2‐Phosphate triSodium) is a vitamin C derivative that has been successfully used in skin care by many cosmetic companies (Fig.…”

Section: Surfactants Based On a Natural Polar Head Groupmentioning

confidence: 99%

Renewable Surfactants for Biochemical Applications and Nanotechnology

Guenic

Chaveriat

Lequart

et al. 2018

J Surfact & Detergents

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Surfactants find applications in almost every chemical industry, such as household and industrial cleaning, paper, inks, agrochemicals, and personal care or pharmaceuticals. However, their production and use can have a negative impact on the environment and health. Increasing environmental concerns and the strong interest in renewable resources have led to the development of innovative and environmentally friendly surfactants produced by clean and/or sustainable technologies. The aim of this review is to explore the different types of surfactants and their architectures. Then, it will describe the two categories of renewable surfactants: biosurfactants obtained by fermentation, and bio‐based surfactants containing either a bio‐sourced polar head group or a bio‐sourced hydrophobic tail. Finally, this review will focus on highly specialized applications of surfactants (protein crystallization, transfection, and nanotechnology), which are closely related to the ability of surfactants to organize themselves in supramolecular architectures.

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Section: Surfactants Based On a Natural Polar Head Groupmentioning

confidence: 99%

Renewable Surfactants for Biochemical Applications and Nanotechnology

Guenic

Chaveriat

Lequart

et al. 2018

J Surfact & Detergents

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“…The type of application is determined by the balance between the hydrophilic and hydrophobic regions in the surfactant molecule. Petrochemical-based surfactants represent the large majority of surfactants in the market today [2,3]. The huge consumption of surfactants worldwide calls for sustainable surfactant production from natural renewable sources in order to reduce the impact on the environment, answers consumers' demand, and keeps up with increasing regulatory pressure.…”

Section: Introductionmentioning

confidence: 99%

Amino Acid-Based Surfactants for Biomedical Applications

Pinheiro¹,

Faustino²

2017

Application and Characterization of Surfactants

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The growing demand for surfactants worldwide has a profound impact on the environment and public health. The quest for environmentally friendly "green" surfactants has driven research toward bio-based surfactants from renewable sources with improved performances and low toxicity. Amino acid-based surfactants (AAS) are a promising class of biocompatible and biodegradable surfactants for biomedical applications due to their improved safety profiles that meet the requirements of both physiological and ecological compatibility. Natural amino acids are chiral compounds and important raw materials for production of AAS. The amino acid pool allows the synthesis of multifunctional surfactants with chiral properties that can be tailored for specific technological and/or biomedical applications. The nature of the amino acid residue, the chirality, and the ability for hydrogen bond formation strongly influences the surface active properties and self-assembly behavior of AAS. This review summarizes recent developments in AAS structure-property relationships providing valuable information for modulation of the surface active and biological properties of AAS to meet specific biomedical applications. The interaction of AAS with biointerfaces and biological molecules is also addressed concerning cellular toxicity and potential therapeutic applications of AAS as antimicrobial agents, drug delivery vehicles, and a promising alternative to viral vectors in gene therapy.

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“…Most chiral gemini surfactants have been derived from natural chiral resources such as tartaric acid, amino acids, and alkyl glucosides [24][25][26][27][28][29][30][31][32][33]. Nakanishi et al [31] investigated the P-A isotherms of stereoisomers of l-and meso-O,O 0 -dialkanoyl tartaric acid on aqueous CdCl 2 /KHCO 3 solutions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Succinic Gemini Surfactants and the Effect of Stereochemistry on Their Monolayer Behaviors

Kawase

Kagawa-Ohara

Aisaka

et al. 2015

J Surfact & Detergents

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In this work, succinic gemini surfactants, dl‐ and meso‐2,3‐bis(alkyl)succinic acids (alkyl: C6H13–C13H27), were successfully synthesized by oxidative coupling of enolates of fatty acid tert‐butyl esters with copper(II) bromide followed by treatment with CF3COOH. Focusing on the influence of stereochemistry (dl‐ and meso‐) of succinic geminis, their monolayer behaviors at the air–water interface were explored using surface pressure–area (Π–A) isotherms, the compression modulus of monolayers (εs), and Brewster angle microscope (BAM) analysis. meso‐2,3‐Bis(undecyl)succinic acid showed a unique isotherm where the surface pressure drastically decreased at A = ~0.56 nm2 (Π = 21.9 mN m−1) regardless of compression rates and subphase temperatures, while dl‐isomer showed the common isotherm of gas → liquid‐expanded → liquid‐condensed phase transitions. BAM analysis on meso‐2,3‐bis(undecyl)succinic acid films at the air–water interface showed that small islands of aggregates appear just after the maximum pressure (A = ~0.56 nm2), and on further compression needle‐shaped assemblies appear that can grow in size. It was reasonably concluded that hydrophobic interactions can operate more effectively in meso‐isomers than in dl‐isomers, and that meso‐molecules can “jump up” to cause a transition from monolayer to bilayer. This is the first finding of the “jumping‐up” phenomenon of gemini surfactants having meso‐stereochemistry.

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Amino Acids, Lactic Acid and Ascorbic Acid as Raw Materials for Biocompatible Surfactants

Cited by 5 publications

References 118 publications

Renewable Surfactants for Biochemical Applications and Nanotechnology

Renewable Surfactants for Biochemical Applications and Nanotechnology

Amino Acid-Based Surfactants for Biomedical Applications

Synthesis of Succinic Gemini Surfactants and the Effect of Stereochemistry on Their Monolayer Behaviors

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