One‐Stage Synthesis of Raffinose Fatty Acid Polyesters

Akoh, Casimir C.; Swanson, Barry G.

doi:10.1111/j.1365-2621.1987.tb05881.x

Cited by 37 publications

(33 citation statements)

References 24 publications

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“…Absorption bands were observed at 3450 cm-' (overtone stretching vibrations), 3000-2860 cm-' (C-H stretch in CH, and/or CH,), 1740 cm-' (ester carbonyl), 1460 cm-' (C-H deformation in CH, and/or CH,), 1380 cm-r (C-H deformation in CH,), 920 cm-' (pyranose ring) and 730 cm-' [(CH,), Iin fatty acids]. The presence of overtone bands at 3450 cm-' confirmed the presence of carbonyl group (Socrates;1980;Akoh and Swanson, 1987).…”

Section: Structure Confirmation Of Spesupporting

confidence: 73%

Optimized Synthesis of Sucrose Polyesters: Comparison of Physical Properties of Sucrose Polyesters, Raffinose Polyesters and Salad Oils

Akoh

Swanson

1990

Journal of Food Science

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Synthesis and purification of sucrose polyesters (SPE) were optimized to obtain high-yields of SPE. Sucrose octaacetate (SOAC) and fatty acid methvl esters fFAME) of salad oils or FAME blends of homogenous fatty acids and salad'oils were interesterified in the presence gf sodium metal. Yields 99.6-99.8% of purified SPE based on initial weight of SOAC were obtained. SPE structure was confirmed by infrared (IR) and C-13 nuclear magnetic resonance (C-13 NMR) spectroscopy. Physical properties of SPE and raffinose polyesters (RPE) were similar to physical properties of conventional salad oils. The hydrophile-lipophile balance (HLB) of SPE and RPE were between 2:6 HLB uniis.'Differential scanning calorimetry (DSC) was used to determine the meltine nronerties of SPE and RPE. Neither SPE nor RPE was susceptibleyd in'vifro lipolysis.

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Section: Structure Confirmation Of Spesupporting

confidence: 73%

Optimized Synthesis of Sucrose Polyesters: Comparison of Physical Properties of Sucrose Polyesters, Raffinose Polyesters and Salad Oils

Akoh

Swanson

1990

Journal of Food Science

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“…Sorbitan esters and sucrose esters are the most developed esters in this category, with a market size of approximately 20,000 and 4000 tons/year, respectively [10]. The chemical synthesis of biosurfactants requires protection and de-protection steps to avoid diester and triester formation as by-products, which affect the surfactant quality [11]. With enzymatic synthesis, monoester production can be increased because of enzymes' high regioselectivity [12,13].…”

Section: Biosurfactant Estersmentioning

confidence: 99%

“…Page 13 of 74 A c c e p t e d M a n u s c r i p t 11 Optimization of parameters that affect the biocatalytic synthesis of cosmetic esters is important to obtain maximum possible conversion. Operating parameters such as temperature, enzyme dose, and molar ratio of alcohol and acid have a great impact on the activity of enzymes and eventually conversion in the synthesis of cosmetic esters.…”

Section: Parameters Affecting Biocatalytic Synthesis Of Cosmetic Estersmentioning

confidence: 99%

Enzyme catalyzed synthesis of cosmetic esters and its intensification: A review

Khan

Rathod

2015

Process Biochemistry

195

130

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“…Raffinose, trehalose and stachyose polyesters have been synthesized and analyzed for their performance as lowcalorie food products (100,101). The polyesters were synthesized by solvent-free interesterification, utilizing fatty acid methyl esters.…”

Section: Other Carbohydrate Derivativesmentioning

confidence: 99%

Carbohydrate‐alkyl ester derivatives as biosurfactants

Allen

Tao

1999

J Surfact & Detergents

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Reaction of carbohydrates with long-chain plantderived lipids yields carbohydrate-alkyl ester surfactants with a polyol structure. Their renewability, low cost, and environmental acceptability make carbohydrate-alkyl ester surfactants an excellent alternative to petrochemically derived products. This article reviews developments in the synthesis and surface-active properties of carbohydrate-alkyl ester surfactants.Paper no. S1150 in JSD 2, 383-390 (July 1999). KEY WORDS:Biosurfactants, carbohydrate esters, sugar esters.Surfactants are critical to the cleaning, emulsifying, wetting, and foaming properties of many products. Surfactants are found in a host of applications, including cosmetics, textiles, pharmaceuticals, foods, ore flotation, soaps and detergents, pulp and paper manufacturing, lubricating and metalworking, agrichemicals, and petroleum mining fields. In most industrial cases, surfactants are used as processing aids and are disposed of following usage. Issues regarding disposal have created interest in more biologically acceptable alternatives and more focused use of renewable vs. nonrenewable resources.In this context, carbohydrate-based surfactants are gaining attention. Carbohydrates in the form of polysaccharides are produced naturally in plants and account for approximately three-quarters of the dry weight of the biological world and nearly 80% of the human caloric diet (1). Corn, potatoes, tapioca, and wheat are currently processed and constitute common sources of starch. Polysaccharides are of interest because of the number of reactive hydroxyl groups they carry. Condensation of one of the reactive groups of a saccharide with a fatty acid produces a surfactant. The saccharide provides the hydrophilic component, whereas the fatty acid provides the hydrophobic component. Various types of saccharides that have been used to furnish the required hydrophilicity are outlined in Scheme 1. Carbohydrate-based surfactants have been used primarily in the cosmetic, detergent, food, and pharmaceutical industries (2-4) as they are physiologically, dermatologically, and biologically acceptable (5,6). Because they are odorless, tasteless, nonionic, and biodegradable, they compare well in overall performance (i.e., emulsification, detergency, foam power, wetting power, and other related properties) with other surface-active compounds (7).To date, several major types of carbohydrate-based surfactants are used worldwide. Sucrose esters and sorbitan esters as well as other carbohydrate derivatives are highlighted here. SUCROSE ESTERSSucrose esters are synthesized primarily by combining the primary hydroxyl group of the nonreducing glucose moiety with a methyl ester of a fatty acid (Scheme 2). Synthesis of sucrose fatty acid derivatives was first considered by Herzfeld in 1880 (5). Sucrose octaesters were later synthesized and their physical properties measured (8,9). In 1924, a patent disclosing the condensation of fatty acid chlorides with sucrose in pyridine was awarded to Rosenthal (5), and in 1950 Zief (10) desc...

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One‐Stage Synthesis of Raffinose Fatty Acid Polyesters

Cited by 37 publications

References 24 publications

Optimized Synthesis of Sucrose Polyesters: Comparison of Physical Properties of Sucrose Polyesters, Raffinose Polyesters and Salad Oils

Optimized Synthesis of Sucrose Polyesters: Comparison of Physical Properties of Sucrose Polyesters, Raffinose Polyesters and Salad Oils

Enzyme catalyzed synthesis of cosmetic esters and its intensification: A review

Carbohydrate‐alkyl ester derivatives as biosurfactants

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