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Okafor O.C.,Stevens Institute of Technology | Tadepalli S.,International Flavors Fragrances Inc. | Tampy G.,International Flavors Fragrances Inc. | Lawal A.,Stevens Institute of Technology
Industrial and Engineering Chemistry Research | Year: 2010

The cycloaddition reaction between isoamylene and α-methylstyrene yields indane compounds 1,1,2,3,3,-pentamethylindane and 3-ethyl-1,1,3- trimethylindane, which are intermediate cyclic products used in the synthesis of musk fragrances. This exothermic reaction is usually carried out industrially in large semibatch reactors. The microreactor, with enhanced heat and mass transfer characteristics, was used for the reaction with aqueous sulfuric acid as catalyst. The dependence of reactant conversion, product yield, and average reaction rates on catalyst concentration, temperature, velocity, residence time, and the molar ratio of the reactants in the feed was investigated. A similar study was also performed in the semibatch reactor to compare its performance with that of the microreactor. Higher product yields were obtained in the microreactor, and the average reaction rates in the microreactor were 3 orders of magnitude greater than those obtained in the semibatch reactor. © 2010 American Chemical Society.


Choi S.J.,University of Massachusetts Amherst | Decker E.A.,University of Massachusetts Amherst | Henson L.,International Flavors Fragrances Inc. | Popplewell L.M.,International Flavors Fragrances Inc. | McClements D.J.,University of Massachusetts Amherst
Food Chemistry | Year: 2010

Citral is a flavour component that is widely used in the beverage, food, and fragrance industries. Citral chemically degrades over time in aqueous solutions due to acid catalysed and oxidative reactions, leading to loss of desirable flavour and the formation of off-flavours. We examined the influence of surfactant micelles (Tween 80) in the aqueous phase and reverse micelles (polyglycerol polyricinoleate, PGPR) in the oil phase on the oil-water partitioning and chemical degradation of citral in medium chain triglyceride oil-in-water emulsions. The percentage of citral in the aqueous phase of the emulsions increased with increasing Tween 80 concentration, which was attributed to its incorporation within surfactant micelles. The rate of citral degradation decreased as the Tween 80 concentration was increased from 1% to 5% w/w in both aqueous solutions and in emulsions, suggesting that citral was protected from degradation once it was incorporated into micelles. The presence of reverse micelles (5% or 10% w/w PGPR) in the oil droplets decreased the percentage of citral present within the aqueous phase of the emulsions, suggesting that citral was preferentially incorporated into the reverse micelles. In addition, the presence of reverse micelles increased the chemical stability of citral, possibly because a greater fraction remained within the oil droplets. These results show that micelle or reverse-micelle structures may be used to improve the chemical stability of citral in beverage emulsions. © 2010 Elsevier Ltd. All rights reserved.


Krause A.J.,University of Minnesota | Henson L.S.,International Flavors Fragrances Inc. | Reineccius G.A.,University of Minnesota
Flavour and Fragrance Journal | Year: 2011

A mechanical device was fabricated to simulate mastication of chewing gum; this device allowed us to perform a mass balance on the volatiles and non-volatiles added to chewing gum during simulated mastication. Model volatiles (ethyl butyrate, isoamyl acetate and limonene) released from the gum into the gas phase were quantified using a proton transfer reaction mass spectrometer (PTR-MS). The chewing device was equipped to simulate salivation (saliva in) and swallowing (saliva out) using water as simulated saliva. The model compounds released into simulated saliva were extracted and quantified using gas chromatography. Sugar alcohols (sorbitol and xylitol) and glycerin were quantified using HPLC-MS. High-potency sweeteners (acesulfame-K, sucralose, rebaudioside A and sodium saccharin) were quantified using UPLC-MS. The model volatiles initially added to the chewing gum were distributed in two or three fractions: the masticated gum (43-84%); the simulated saliva (ethyl butyrate and isoamyl acetate were recovered from the water at 9-11% and 14-17%, respectively) and the gas phase (ethyl butyrate and isoamyl acetate were recovered from the gas phase at 7-10% and 29-40%, respectively). Limonene could not be detected in the simulated saliva, and >80% remained in the gum after mastication. Almost all (>90%) of the water-soluble polyols and high-potency sweeteners were extracted from the gum into the simulated saliva by mastication. Given the presented validation of the device, we feel the device could be used to evaluate and potentially screen and evaluate ingredients in chewing gum formulations. By using a device to circumvent the variability of human subjects, a more consistent and efficient throughput of samples could be achieved. © 2010 John Wiley & Sons, Ltd.


Choi S.J.,University of Massachusetts Amherst | Decker E.A.,University of Massachusetts Amherst | Henson L.,International Flavors Fragrances Inc. | Popplewell L.M.,International Flavors Fragrances Inc. | And 2 more authors.
Food Research International | Year: 2011

There is a growing trend toward utilizing more label friendly ingredients in foods and beverages. In this study, we focused on the utilization of sucrose monopalmitate (SMP) as a non-ionic surfactant for stabilizing acidic beverages. Orange oil-in-water emulsions (5% (w/w) oil) stabilized by SMP were prepared using high pressure homogenization (pH 7). The minimum droplet diameter was around 130nm, while the minimum mass ratio of SMP-to-oil required to produce small droplets was 0.1-to-1. Extensive droplet aggregation occurred when the pH of the emulsions was reduced from pH 7 to 3, with the mean particle diameter increasing from around 0.13 to 7.25μm. This effect was attributed to an appreciable reduction in droplet charge when the pH was reduced (ζ≈-35mV at pH 3 and -2mV at pH 3) thereby decreasing the electrostatic repulsion between droplets. It was proposed that the negative charge on the SMP-coated droplets was due to the presence of anionic substances within the droplets, such as palmitic acid (pKa≈4.9). Palmitic acid may have been an impurity in the original ingredient or it may have been generated due to degradation of SMP during storage. The addition of anionic lyso-lecithin markedly improved the stability of the emulsions to droplet aggregation and phase separation at low pH, which was attributed to an increased electrostatic repulsion between the droplets. This study has important consequences for the formulation of acidic beverage emulsions with improved stability and physicochemical performance. © 2011 Elsevier Ltd.


Lim S.S.,Kyung Hee University | Baik M.Y.,Kyung Hee University | Decker E.A.,University of Massachusetts Amherst | Henson L.,International Flavors Fragrances Inc. | And 3 more authors.
Food Chemistry | Year: 2011

Orange oil-in-water emulsions (5% oil) stabilized by modified starch (2-10%) were prepared using high pressure homogenization. The initial droplet diameter decreased with increasing modified starch concentration, but all emulsions exhibited appreciable droplet growth during storage (15 days). The impact of adding a lipophilic weighting agent (ester gum) to the oil phase prior to homogenization was examined. Droplet growth could be inhibited by ensuring that the oil phase contained >9% ester gum, which was attributed to its ability to inhibit Ostwald ripening through an entropy of mixing effect. There was little effect of ionic strength (0-500 mM NaCl) or thermal treatment (30-90°C) on the stability of modified-starch stabilized emulsions containing orange oil and ester gum. This manuscript demonstrates that the primary role of ester gum (usually considered a weighting agent) in improving the stability of orange oil emulsions is to retard Ostwald ripening, rather than to act simply as a weighting agent. It was also demonstrated that corn oil could be used to retard Ostwald ripening by a similar mechanism in orange oil emulsions. © 2011 Elsevier Ltd. All rights reserved.


Narula A.P.S.,International Flavors Fragrances Inc.
Chemistry and Biodiversity | Year: 2014

There is a constant need for developing new fragrance ingredients in the flavor and fragrance industry, as it allows perfumers to create unique and differentiating perfumes for fine as well as functional products. Among all the categories of notes used in perfume creation, amber notes are indispensible and ubiquitous in their presence in all perfumes. Not only amber notes impart high performance and substantivity to fragrances, but they are paramount in the development of classic and legendary fragrances. This article is based on the plenary lecture delivered at the flavor & fragrance 2013 conference of the German Chemical Society in Leipzig, Germany. The strategy, rationale, and the various synthetic approaches that led to the discovery of two new very powerful, woody, amber materials, Amber Xtreme® (1) and Trisamber® (2), are delineated. © 2014 Verlag Helvetica Chimica Acta AG, Zürich.


Servant G.,Senomyx Inc. | Tachdjian C.,Senomyx Inc. | Li X.,International Flavors Fragrances Inc. | Karanewsky D.S.,Senomyx Inc.
Trends in Pharmacological Sciences | Year: 2011

A diet low in carbohydrates helps to reduce the amount of ingested calories and to maintain a healthy weight. With this in mind, food and beverage companies have reformulated a large number of their products, replacing sugar or high fructose corn syrup with several different types of zero-calorie sweeteners to decrease or even totally eliminate their caloric content. A challenge remains, however, with the level of acceptance of some of these products in the market-place. Many consumers believe that zero-calorie sweeteners simply do not taste like sugar. A recent breakthrough reveals that positive allosteric modulators of the human sweet taste receptor, small molecules that enhance the receptor activity and sweetness perception, could be more effective than other reported taste enhancers at reducing calories in consumer products without compromising on the true taste of sugar. A unique mechanism of action at the receptor level could explain the robust synergy achieved with these new modulators. © 2011 Elsevier Ltd. All rights reserved.


Patent
International Flavors Fragrances Inc. | Date: 2012-09-24

The present invention relates to spray-dried compositions capable of retaining volatile compounds and methods relating to the same. The present invention also relates to the powders produced by such methods.


Patent
International Flavors Fragrances Inc. | Date: 2011-12-21

The present invention is directed to the use of one or more rebaudioside C polymorphs, or stereoisomers thereof, to enhance the sweet taste of a flavoring, such as glucosylated steviol glycoside, rebaudioside A, ammoniated glycyrrhizin, neohespherdin dihydrochalcone or thaumatin.


Li J.,International Flavors Fragrances Inc.
Macromolecules | Year: 2011

Relations between morphology and transport sensitively govern proton conductivity in perfluorsulfonate ionomers (PFSIs) and thus determine useful properties of these technologically important materials. In order to understand such relations, we have conducted a broad systematic study of H+-form PFSI membranes over a range of uniaxial extensions and water uptakes. On the basis of small-angle X-ray scattering (SAXS) and 2H NMR spectroscopy, uniaxial deformation induces a strong alignment of ionic domains along the stretching direction. We correlate ionic domain orientation to transport using pulsed-field-gradient 1H NMR measurements of water diffusion coefficients along the three orthogonal membrane directions. Intriguingly, we observe that uniaxial deformation enhances water transport in one direction (parallel-to-draw direction) while reducing it in the other two directions (two orthogonal directions relative to the stretching direction). We evaluate another important transport parameter, proton conductivity, along two orthogonal in-plane directions. In agreement with water diffusion experiments, orientation of ionic channels increases proton conduction along the stretching direction while decreasing it in the perpendicular direction. These findings provide valuable fodder for optimal application of PFSI membranes as well as for the design of next generation polymer electrolyte membranes. © 2011 American Chemical Society.

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