Synthetic Emulsifying Agents

Fieser, Mary; Fieser, Louis; Toromanoff, E.; Hiratå, Yoshimasa; Heymann, H; Tefft, Melvin; Bhattacharya, Sivaprasad

doi:10.1021/ja01593a049

Cited by 64 publications

(25 citation statements)

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“…Kester (1949) reported that long-chain N-acylglutamic acids could be used as wetting agents, foaming agents, or detergents. The emulsifying property of N-acylamino acids has been examined in a series of synthetic emulsifying agents (Fieser et al, 1956). Aqueous solutions of long-chain N-acylglutamic acids were shown to have low surface tensions and good foaming properties (Takeharaet al, 1972).…”

Section: Discussionmentioning

confidence: 99%

“…Amides of fatty acids, particularly those of amino acids, also possess significant antibacterial properties (Fieser et al, 1956; Takehara et al, 1972;Paquet, 1977;Shibasaki, 1982; Paquet and Rayman, 1987). A series of fatty N-acylamino acids have been prepared (Paquet, 1974(Paquet, ,1979; Paquet and Sarwar, 1980) and investigated as potential food additives.…”

Section: Introductionmentioning

confidence: 99%

“…A series of fatty N-acylamino acids have been prepared (Paquet, 1974(Paquet, ,1979; Paquet and Sarwar, 1980) and investigated as potential food additives. The high nutritive value (Paquet and Sarwar, 1980), antimicrobial activity (Madhosingh et al, 1978; Paquet and Rayman, 19871, and good emulsifying properties (Fieser et al, 1956; Takehara et al, 1972) of these compounds have been recognized. In a previous study (McKellar et al, 1992), the antimicrobial activity of a series of fatty N-acylamino acids against Gram-positive foodborne pathogens was investigated.…”

Section: Introductionmentioning

confidence: 99%

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Effect of fatty N-acylamino acids on some functional properties of two food proteins

Yung¹,

Paquet²,

McKellar³

1993

J. Agric. Food Chem.

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The effect of fatty N-acylamino acids on the foaming, emulsifying, and gelling properties of egg white and whey protein isolate was investigated. The overrun, emulsifying activity, and gelling properties of these two protein products were generally enhanced by the addition of 0.1-0.5 % of the fatty N-acylamino acids, while the foaming stability was lowered. Both lauroyl(C1~) and myristoyl (CU) derivatives were highly effective, particularly the derivatives of phenylalanine and methionine. The palmitoyl (c16) and stearoyl (C16) derivatives were less effective, while the esters of active derivatives did not affect protein functionality. The thermal characteristics of the proteins were modified by fatty N-acylamino acids and were related to changes in functional properties. The results suggest the potential use of fatty N-acylamino acids as multifunctional food additives.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effect of fatty N-acylamino acids on some functional properties of two food proteins

Yung¹,

Paquet²,

McKellar³

1993

J. Agric. Food Chem.

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“…Of the three irradiated groups of mice, one group was treated on the dorsal trunk skin with 100 µL of 0·05% all‐ trans RA (Sigma, St Louis, MO, U.S.A.) in ethanol : propylene glycol (vehicle 70 : 30 v/v). Another group was treated with 0·05% GRA, prepared according to the published procedure 36 from all‐ trans retinoic acid (Sigma) and glucosamine (Sigma) (Fig. 1).…”

Section: Methodsmentioning

confidence: 99%

N-retinoyl-D-glucosamine, a new retinoic acid agonist, mediates topical retinoid efficacy with no irritation on photoaged skin

et al. 2005

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“…Henc~ they find many applications in cosmetic and antibacterial formulations. Fieser et aL (2) synthesized N-acylamino acids for use as fat emulsifying agents Kameda et aL (3) reported on the strong sterilization action of N-lauroyl-DL-phenylalanine Fosdick et aL (4) found sodium N-acyl sa~ cosinate, a commem~ally used antibacterial agent, to possess strong anticaries action. Infante et aL (5) investigated the physicochemical and antimicrobial properties of N-acyl arginine esters of common fatty acids.…”

mentioning

confidence: 99%

N‐acyl‐L‐leucines of biologically active uncommon fatty acids: Synthesis and antibacterial activity

Mhaskar¹,

Lakshminarayana²,

SaiSree³

1993

J Americ Oil Chem Soc

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The effect of structural variation in the fatty acid chain on the antibacterial activity ofN‐acyl‐L‐leucines was investigated. PureN‐acyl leucines of some structurally different and biologically active uncommon fatty acids were synthesized for the first time and tested for antimicrobial activity.N‐Stearoyl‐,N‐oleoyl‐ andN‐ricinoleoyl leucines were also evaluated for comparison. TheN‐acyl leucines exhibited greater activity in acid form than the methyl ester form and against gram positive bacteria than gram‐negative bacteria. The presence of a cyclopropane or a hydroxy group or unsaturation in the acyl chain increased the antibacterial activity. Shifting the hydroxyl group toward the amide linkage resulted in a diminished effect on the antibacterial activity.

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Synthetic Emulsifying Agents

Cited by 64 publications

References 0 publications

Effect of fatty N-acylamino acids on some functional properties of two food proteins

Effect of fatty N-acylamino acids on some functional properties of two food proteins

N-retinoyl-D-glucosamine, a new retinoic acid agonist, mediates topical retinoid efficacy with no irritation on photoaged skin

N‐acyl‐L‐leucines of biologically active uncommon fatty acids: Synthesis and antibacterial activity

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