Sweetener for electronic cigarette liquids

Abstract

The invention relates to a composition intended for use as an electronic cigarette e-liquid or for addition to an electronic cigarette e-liquid, characterized in that it comprises N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester, a storage device comprising such a composition, an electronic cigarette comprising such a device, and the use of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester as a sweetener or as a flavor enhancer in an electronic cigarette e-liquid composition.

Description

Title of the invention: Sweetener for electronic cigarette liquids Field of the invention

[0001] The present invention relates to the field of electronic cigarettes and, more specifically, to the use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester as a sweetener and / or flavor enhancer for an electronic cigarette composition. State of the art

[0002] The harmful effects of cigarettes on human health have been known for several decades. Now, the high addictive potential of these cigarettes makes the fight against smoking particularly difficult.

[0003] As a result, the advent of the electronic cigarette, or "e-cigarette", has considerably helped to reduce smoking in the sense that it has allowed the consumer to maintain the smoking gestures while eliminating a significant portion of the toxic compounds it contains.

[0004] This electronic cigarette works by vaporizing a liquid, known as "e-liquid", using an electrical resistance, which may or may not be flavored and may or may not contain nicotine. This vaporization produces a thick smoke comparable to that of a conventional cigarette, but free of most of the toxic compounds resulting from the combustion of tobacco. Studies demonstrate the reduction in the impact of this smoke on human health due to the absence of tars, carbon monoxide and many other carcinogenic substances.

[0005] Overall, the main components of e-liquids correspond to:

[0006] - propylene glycol (synthetic or vegetable);

[0007] - glycerol;

[0008] - nicotine;

[0009] - flavorings and colorings;

[0010] - water.

[0011] As for flavors, a large majority of those present on the market are sweet flavors due to a greater appetite for them among consumers. For example, we find flavored e-liquids imitating the flavors of fruits, desserts or even sweets.

[0012] Taste, in the common sense of the term, actually combines olfaction and gustation. Indeed, when food is taken into the mouth, the sapid molecules dissolve in the saliva and stimulate the taste buds located in the papillae of the tongue: the The perceived sensation is called flavor. As for odorant molecules, which are volatile, they rise towards the nasal cavity through the back of the soft palate to stimulate our olfactory system. This is called olfactory stimulation via the retronasal route.

[0013] Human beings, like most animals, are capable of perceiving and distinguishing five different primary flavors, also referred to as fundamental: sweet, sour, bitter and salty, and a fifth flavor, less known to the general public, called umami flavor.

[0014] Among the sweet compounds, we find of course natural sugars (sucrose, fructose and glucose), but also other very different chemically compounds such as certain amino acids (glycine), polyols (sorbitol, xylitol), or certain elements such as lead or beryllium (originally called glucinium, from the Greek Yàwùç (glykys), sweet). Artificial or natural sweeteners, used in the food industry, are also very diverse chemically. We can find modified peptides (aspartame), halogenated sugars (sucralose), glycosides (stevia), sulfamates (saccharin) or rare sweet plant proteins (thaumatin and brazzein, for example).

[0015] The first generation of e-liquids contained sugars such as glucose or fructose. While these provided the sweet taste sought by consumers, several scientific studies have established that their thermal degradation generated toxic compounds. It has thus been established that their degradation is accompanied by the formation of furans, including hydroxymethylfurfural (HMF) and furfural (FA) at levels comparable to those found in a conventional cigarette.

[0016] As these two compounds generate possible carcinogens, AFNOR banned the use of glucose and fructose in e-liquids in 2015.

[0017] In response, these sugars were substituted from 2016 by sucralose, or 4-chloro-4-deoxy-aD-galactose of l,6-dichloro-l,6-dideoxy-[3-D-fructofurannosyl], which is a synthetic sweetener with high sweetening power. This sweetener, which is a food additive (E955) authorized by the European Commission, was then widely used in the formulation of vaping flavors intended for electronic cigarettes.

[0018] Now, it has become apparent that sucralose is also subject to thermal degradation generating irritant products. We thus observe a first stage of degradation, which takes place between 119°C and 137°C, and which corresponds to the decomposition of sucralose with the loss of two molecules of water and one molecule of hydrochloric acid. A recent study on the degradation of e-liquids containing sucralose during vaporization shows that this sucralose is subject to thermal degradation in the presence of propylene glycol and glycerol and that it alters and increases the degradation of these solvents. Finally, the presence of sucralose in vaporized e-liquids would lead to the production of potentially dangerous organochlorine compounds and make its use potentially dangerous for the health of consumers.

[0019] Also, it would be important today to find a molecule with a sweetening power that can be used in e-liquids. Now, identifying such a molecule is not easy since it would have to meet complex specifications, namely to be vaporizable, to have a strong sweetening power (after vaporization) that remains in the mouth and without aftertaste, to be soluble in propylene glycol, not to clog fibers or cottons or resistances and finally not to produce toxic compounds. Summary of the invention#:

[0020] The inventors have now accidentally demonstrated that while N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester has a similar structure to aspartame, its use as a sweetener in an e-cigarette liquid surprisingly has none of the disadvantages associated with the use of aspartame.

[0021] Accordingly, a first subject of the invention relates to a composition intended to be used as an electronic cigarette e-liquid or to be added to an electronic cigarette e-liquid, comprising N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester.

[0022] A second subject of the invention relates to a storage device for electronic cigarette liquid comprising a composition as described above.

[0023] A third object of the invention relates to an electronic cigarette comprising such a storage device.

[0024] A fourth subject relates to a use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester as a sweetener in a composition for electronic cigarettes.

[0025] A fifth object of the invention relates to a method for obtaining vapors having a sweet flavor comprising the steps of:

[0026] i) placing, in an electronic cigarette, a storage device comprising a composition as defined above,

[0027] ii) switching on the electronic cigarette so as to allow heating and vaporization of the composition;

[0028] characterized in that the vaporized composition comprises N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester and has a sweet flavor.

[0029] A sixth subject of the invention relates to a use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester as a flavor enhancer in a composition for electronic cigarettes. Detailed description of the invention

[0030] The term “electronic cigarette” or “e-cigarette” means all electrical devices capable of generating an aerosol intended to be inhaled and delivering nicotine and / or one or more flavors. This definition includes all models of personal vaporizers (VP), electronic nicotine delivery systems (ENDS for “Electronic Nicotine Deliver System” or ENDD for “Electronic Nicotine Delivery Device”), as well as electronic cigars, electronic pipes and electronic hookahs.

[0031] By “e-liquid” is meant a liquid or composition intended to be used in connection with an electronic cigarette so as to allow its vaporization and inhalation by a subject.

[0032] N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester, is a dipeptide which has the following general formula:

[0033] [Chem.l] X) ï \ m, HOOC YYY i H II YJH O H3C ch3

[0034] While similar to aspartame, N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester has an additional (3,3-dimethylbutyl) group on the primary amine function of aspartic acid and provides a sweetness 8,000 times greater than sucrose (on a mass basis). This sweetener and its preparation are described in US patents 5,480,688, US 5,510,508 and US 5,728,862.

[0035] Now, the N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester used in the invention can be found in different forms.

[0036] N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester can thus be found in the form of a salt such as those described for example in international patent applications WO 99 / 012955, WO 99 / 012957, WO 00 / 69282 or WO 01 / 70049.

[0037] N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester can also be found in the form of a complex such as for example a cyclodextrin complex as described in US patent 6,214,402 or erythritol as described in patent application CN 110215732A.

[0038] The content of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester of the composition according to the invention is between 0.00001% and 5% (by mass relative to the total mass of the composition), preferably between 0.0005 and 1% and, particularly preferably, between 0.005% and 0.5%.

[0039] The composition according to the invention may further comprise propylene glycol, or an isomer thereof, which may be of synthetic or plant origin. In the latter case, the propylene glycol may in particular be obtained by hydrogenolysis of sorbitol or plant glycerol or by hydrogenation of plant lactic acid.

[0040] The propylene glycol content of the composition according to the invention may represent from 0 to 80% by mass (relative to the final mass of the composition), preferably from 10 to 60% by mass and, in a particularly preferred manner, from 20 to 50% by mass, relative to the total mass of the composition.

[0041] In the case where the composition according to the invention is presented in a separate form (a concentrate), to be diluted in a second stage in order to then form an e-liquid, the propylene glycol content could reach up to 99.95% by mass, relative to the total mass of the composition.

[0042] The composition may further comprise glycerol, of synthetic or vegetable origin.

[0043] Now, and according to a preferred embodiment, the composition according to the invention comprises from 0 to 99.95% by mass of glycerol (relative to the final mass of the composition), preferably from 0 to 80% by mass of glycerol and, in a particularly preferred manner, from 0 to 50% by mass of glycerol.

[0044] In a particular embodiment, the composition according to the invention does not comprise glycerol. It has in fact been observed that the absence of glycerol makes it possible to avoid the formation of undesirable by-products (e.g. acrolein) resulting from the heating of glycerol.

[0045] Advantageously, the composition according to the invention further comprises nicotine.

[0046] The nicotine may be of synthetic or plant origin (extracted from tobacco leaves).

[0047] The nicotine concentration of the composition according to the invention is between 0 and 50 mg / mL, preferably between 0 and 20 mg / mL.

[0048] Advantageously also, the composition according to the invention further comprises at least one aroma.

[0049] In accordance with European legislation, and as defined by Regulation 1334 / 2008, "flavorings" means products not intended to be consumed as is, which are added to foodstuffs to give them an odor and / or a taste or to modify them. These flavorings are derived from or made up of the components following: flavoring substances, flavoring preparations, smoke flavorings, flavorings obtained by heat treatment, flavor precursors and other flavorings. The labeling of flavorings on finished products is defined by INCO Regulation (Consumer Information) 1169 / 2011. Examples of flavorings include flavoring substances as authorized by Regulation No. 872 / 2012 of October 1, 2012 and in the current American (USP) and European (EP) Pharmacopoeias.

[0050] The content of flavoring(s) is between 0.01 and 15% by mass and, particularly preferably, from 0.1 to 5% by mass (relative to the total mass of the composition) concerning a ready-to-consume formula. Concerning a concentrated flavoring formula, which will be diluted for consumption, the flavoring content can vary between 0 and 99% by mass due to the application dosages which will lead to a concentration in the ready-to-consume product as indicated above.

[0051] The composition according to the invention may also comprise at least one colorant.

[0052] A colorant is a substance used to provide a color to an object to be tinted. Typically, the coloring used is a food coloring as defined by European Directive 94 / 36 / EC.

[0053] The colorant content of the composition according to the invention is such that it makes it possible to obtain the desired coloration. Typically, the colorant content of the composition according to the invention is between 0.00001 and 0.001% by mass of colorant(s) relative to the total mass of the composition, preferably between 0.00001 and 0.0001%.

[0054] Now, the composition according to the invention can comprise other compounds such as water and / or alcohol (e.g. ethanol)

[0055] A second subject of the invention relates to a storage device for electronic cigarette liquid comprising a composition as described above.

[0056] By storage device for electronic cigarette liquid, we mean a cartridge (e.g. silicone, PMMA or stainless metal) or a reservoir (e.g. PMMA / polyethylene, borosilicate glass or stainless metal), possibly supplemented by a device for capturing the liquid by capillarity (e.g. silica, fiberglass, ceramic metal fabric, nylon threads or borosilicate fibers) in contact with the vaporizer system.

[0057] A third object of the invention relates to an electronic cigarette comprising a storage device as described previously.

[0058] A fourth subject of the invention relates to the use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester as a sweetener in a composition for electronic cigarettes as described above.

[0059] By "sweetener" we mean a product or substance having a sweet taste. Sweeteners provide few or no calories. Some have the advantage of not being cariogenic and some have a sweetening power greater than sugar (sucrose).

[0060] Advantageously, the content of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester of the composition according to the invention is between 0.00001% and 5% (by mass relative to the total mass of the composition), preferably between 0.0005 and 1% and, particularly preferably, between 0.005% and 0.5%.

[0061] A fifth object of the invention relates to a process for obtaining vapors having a sweet flavor comprising the steps of:

[0062] i) placing, in an electronic cigarette, a storage device comprising a composition as defined above,

[0063] ii) switching on the electronic cigarette so as to allow heating and vaporization of the composition;

[0064] characterized in that the vaporized composition comprises N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester and has a sweet flavor.

[0065] Preferably, the vaporized composition does not comprise toxic degradation products resulting from the vaporization of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester, preferably no degradation products resulting from the vaporization of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester.

[0066] Advantageously, step ii) of energizing allows heating of the composition to a temperature between 150 and 300°C.

[0067] Advantageously, the method according to the invention further comprises a step iii) of inhalation by a subject of the vapors generated in step ii).

[0068] A sixth subject of the invention relates to the use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester as a flavor enhancer in a composition for electronic cigarettes as described above.

[0069] A “flavor enhancer” (or aroma enhancer) is a substance which, without having a pronounced flavor of its own, does not modify the taste but increases the intensity of the olfactory-gustatory perception of a foodstuff.

[0070] Advantageously, the content of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester of the composition according to the invention is between 0.00001% and 5% (by mass relative to the total mass of the composition), preferably between 0.0005 and 1% and, particularly preferably, between 0.005% and 0.5%.

[0071] Although it is also known to use N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester as a flavor enhancer, there was no indication that its good vaporization would allow this use to be maintained following its vaporization.

[0072] According to a preferred embodiment, N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester is used as a flavor enhancer for buttery notes. Note that the latter makes it possible to avoid using diacetyl and / or acetyl propionyl.

[0073] The invention will be better understood in light of the following examples, which are given purely for illustrative purposes and are not intended to limit the scope of the invention, defined by the appended claims. Examples

[0074] Example 1: Search for possible sweeteners for use in connection with the electronic cigarette:

[0075] In order to identify possible components that could be used as sweeteners for electronic cigarette liquid, a large number of molecules were tested.

[0076] A trained panel of 12 people carried out a sensory evaluation by vaporization using electronic cigarettes (Box Aegis Solo marketed by Geek Vape and dripper Puise 24 marketed by Vandyvape). The vaping conditions were as follows: 3 puffs spaced 5 seconds apart induced by heating for 2 seconds at 35 watts. A new resistance is used and the cotton is replaced for each formula tested. Between each tasting, the panelists rinse their mouths with water. A rest period is observed between the series so as not to be influenced by the persistence of perception of the previous formula.

[0077] Table 1 below lists some of the molecules tested and the perception of sweet flavor after vaporization on a graduated scale from 1 to 10.

[0078] [Tableauxl] Sweeteners Theoretical sweetening power CA S number Dilution of sweetener in the mixture Dilution used in tests Mean sensory test (rating / 10) N-[N-[3-(3-Hyd roxy-4-methoxy phenyl)propyl]-aL-aspartyl]-L-phenylalanine 1-methyl ester 30000 714229-20- 6 0.4% 1% (PG) 1.21 (7.0,3 8 Sucralose 1160 56038-13-2 0.2% 10% (PG) 1.83 (7.0.6 5) Acesulfame potassium (Acesulfame K) 200 55589-62-3 0.2% 1% (PG) 2.52 (7.0.83) Aspartame 200 22839-47-0 0.2% 1% (water) 0.97 (7.0.51) Saccharin 500 81-07-2 0.2% 1% (PG) 0.84 (7.0.4 1) Thaumatin 3000 53850-34-3 0.2% 1% (PG) 2.03 (7.0.77) Neohesperidine dihydrochalcone 3600 20702-77-6 0.2% 10% (PG) 2.5 (7.1.05 ) Stevioside 300 57817-89-7 0.2% Insoluble in PG, unstable in water at sufficient concentration for testing Not suitable for electronic cigarettes L-phenylalanine - 63-91-2 0.2% 1% (water) 0

[0079] All the molecules tested revealed low sweetening powers. These would therefore need to be incorporated into e-liquids in large quantities. In addition, some of the sweeteners had to be diluted in water, an ingredient that is not conventionally used in electronic cigarette preparations. It should be noted that, among the molecules tested, Neohesperidine dihydrochalcone had a strong licorice-like aftertaste, which constitutes a hindrance during formulation in the presence of flavoring.

[0080] Now, and in the context of carrying out these experiments, N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester was used once by mistake instead of N-[N-[3-(3-Hydroxy-4-methoxyphenyl)propyl]-aL-aspartyl]-L-phenylalanine 1-methyl ester, which molecules both correspond to N-substituted derivatives of aspartame. It turned out, during this experiment, that the sweet taste appeared significant even though it was very weak for N-[N-[3-(3-Hydroxy-4-methoxyphenyl)propyl]-aL-aspartyl]-L-phenylalanine 1-methyl ester.

[0081] The ratings were then performed using this formula as the upper reference limit. For the lower reference limit, a mixture of 50% (m / m) propylene glycol and 50% (m / m) glycerol was used.

[0082] Example 2: Determination of the sweetening power of N-[N-(3.3-dimethylbutyl)-La-aspartyll-L-phenylalanine 1-methyl ester in an e-liquid after vaporization

[0083] In a glass beaker, different quantities of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester (CAS: 165450-17-9) are diluted in propylene glycol (CAS: 57-55-6) marketed by the company BRENNTAG (under the reference propylene glycol - USP / EP) and glycerol (CAS: 56-81-5) marketed by the company Ami Chimie (under the reference Glycerin 99.5% AMI). The different dilutions are presented in Table 2 below.

[0084] [Tables2] Amount (g) of each ingredient in the formula Formula Formula 1 b Formula Formula 1 d N-[N-(3,3-dimethylbutyl)-L-a-aspartyl]-L-phenylalanine 1-methyl ester 0.05 0.5 2 4 Propylene glycol 499.975 499.75 499 498 Glycerin 499.975 499.75 499 498

[0085] The dissolution of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester and the homogenization of each composition is then obtained by the action of a stirrer for 20 minutes at 200 rpm.

[0086] As controls, e-liquid formulations comprising equivalent concentrations of N-[N-[3-(3-Hydroxy-4-methoxyphenyl)propyl]-aL-aspartyl]-L-phenylalanine 1-methyl ester (Formulas 2a, 2b, 2c and 2d) and concentrations of sucralose generally used in e-liquids (Formulas 3a, 3b and 3c) were prepared according to the same protocol.

[0087] The different e-liquids were then each evaluated by a trained panel of 12 people.

[0088] For the taste test, 0.035 grams of each example was diluted in a 10 ml glass of Evian brand water. Between each tasting, the panelists rinsed their mouths with water. The evaluation of sweetness perception, in the taste test, is carried out on a graduated scale ranging from 1 to 10. For the upper reference limit, the score 10 was awarded to the composition having shown the strongest sweet flavor. For the lower reference limit, a mixture of 50% (m / m) propylene glycol and 50% (m / m) glycerol is used.

[0089] For sensory evaluation by spraying, the conditions are those indicated in Example 1.

[0090] The evaluation of the sweet perception by vaping was carried out on a graduated scale ranging from 1 to 10. For the upper reference limit, the score of 10 was assigned to the composition giving the most intense sweet flavor. For the lower reference limit, a mixture of 50% (m / m) propylene glycol and 50% (m / m) glycerol is used as previously.

[0091] The results are presented in the following Table 3.

[0092] [Tables3] Product Taste test: Average intensity of sweet perception Taste test: Standard deviation Vaping test: Average intensity of sweet perception Vaping age test: Standard deviation Formula 1a 1.91 0.60 2.63 0.96 Formula 1b 5.08 1.06 4.46 0.66 Formula 1b 7.79 0.62 7.54 0.94 Formula 1d 9.42 0.60 10 (REF MAX) - Formula 2a 1.63 0.83 - - Formula 2b 6.67 0.65 - - Formula 2c 9.29 0.66 - - Formula 2d 10 (REF MAX) - 1.21 0.38 Formula 3a 1.08 0.47 0.92 0.47 Formula 3b 3.33 0.81 1.83 0.65 Formula 3c 4.83 0.83 2.92 0.73

[0093] The results confirm that N-[N-[3-(3-Hydroxy-4-methoxyphenyl)propyl]-aL-aspartyl]-L-phenylalanine 1-methyl ester is not suitable for vaping. Indeed, although it obtains the maximum sweetness intensity scores in the taste test, it is almost not perceived (score 1 / 10) at its maximum concentration in the vaping test or for the other concentrations used. Similarly, a significant difference is observed for sucralose between taste and vaping perceptions. Thus, sucralose seems to lose some of its sweetening power during vaporization. It is therefore not very suitable for vaporization.

[0094] Conversely and unexpectedly, N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester provides a high sweetness both in taste testing and by vaping. As a result, vaporizing N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester does not result in a significant decrease in its sweetness, making it an ideal solution for use in electronic cigarettes.

[0095] Example 4:

[0096] Vaping test on two formulas containing raspberry flavor (Aroma Sense Reference 96096), sucralose or N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester, propylene glycol and glycerin.

[0097] In a glass beaker are precisely mixed 5 grams of sucralose (CAS: 56038-13-2), 70 grams of “Raspberry” flavoring (Aroma Sense Reference 96096), 462.5 grams of propylene glycol (CAS: 57-55-6) and 462.5 grams of glycerol (CAS: 56-81-5) (Formula 4a). A mechanical stirrer then allows dissolution and homogenization for 20 minutes at 200 rpm.

[0098] Another formula is then prepared according to the same process: 0.08 grams of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester (CAS: 165450-17-9), 70 grams of “Raspberry” flavoring (Aroma Sense Reference 96096), 464.96 grams of propylene glycol (CAS: 57-55-6) and 464.96 grams of glycerol (CAS: 56-81-5) (Formula 4b) are mixed and homogenized.

[0099] In taste tests, formula 4a was perceived as much sweeter than formula 4b. Now, the same intensity of the sweet note was perceived in vaping tests.

[0100] Finally, from a sensory point of view, the use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester is therefore much more suitable for vaporization because for small quantities present in the formula, the sweetening power in vapors is important and similar to using more sucralose.

[0101] Example 5: Preparation of an e-liquid composition containing N-[N-(3,3-dimethylbutyl)-La-aspartyl1-L-phenylalanine 1-methyl ester and a fruity aroma

[0102] In a glass beaker are mixed precisely 0.004 grams of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester (CAS: 165450-17-9), 120 grams of fruity aroma “Mixed fruit” (Aroma Sense Reference 87289), 439.998 grams of propylene glycol (CAS: 57-55-6) and 439.998 grams of glycerol (CAS: 56-81-5) (example 5b). A mechanical stirrer then allows dissolution and homogenization for 20 minutes at 200 rpm.

[0103] Another formula is then prepared according to the same process: 150 grams of “Mixed fruit” fruit flavoring (Aroma Sense Reference 87289), 425 grams of propylene glycol (CAS: 57-55-6) and 425 grams of glycerol (CAS: 56-81-5) (example 5a) are mixed and homogenized.

[0104] Formulas 5a and 5b were evaluated by our panel trained by vaping on an electronic cigarette according to the vaping conditions presented in example 1. On the “fruity” characteristic, it appears that these two formulas present similar intensity notes although the aroma is integrated in lower concentration in formula 5b.

[0105] It appears that in e-liquid formulas containing N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester, a synergistic effect occurs between taste and aromatic perceptions. In this case, it allows to accentuate the “fruity” pole of the formula. Finally, the use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester allows to reinforce aromatic notes and thus to use lower concentrations of aromas in the e-liquid formulation.

[0106] Example 6: Preparation of an e-liquid composition containing N-[N-(3.3-dimethylbutyl)-La-aspartyll-L-phenylalanine 1-methyl ester and a Chewing gum flavor.

[0107] In a glass beaker are mixed precisely 0.2 grams of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester (CAS: 165450-17-9), 75 grams of “Malabar” fruity aroma (Aroma Sense Reference 07352), 462.4 grams of propylene glycol (CAS: 57-55-6) and 462.4 grams of glycerin (CAS: 56-81-5) (example 6a).

[0108] A mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm.

[0109] Another formula is then prepared using the same process: 150 grams of “Malabar” fruity aroma (Aroma Sense Reference 07352), 425 grams of propylene glycol (CAS: 57-55-6) and 425 grams of glycerin (CAS: 56-81-5) (example 6b) are mixed and homogenized for 20 min at 200 rpm.

[0110] Formulas 6a and 6b were evaluated by vaping on an electronic cigarette by our trained panel according to the conditions presented in example 3. On the “confectionery” characteristic, it appears that these two formulas present similar intensity notes although the aroma is integrated in lower concentration in formula 6a.

[0111] Here again, and as for the previous example, it appears that the presence of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester enhances the organoleptic characteristics of a formula containing a flavor. The use of this allows the use of lower concentrations of flavor in the e-liquid formulation or the provision of improved, more powerful organoleptic characteristics.

[0112] Example 7: Preparation of an e-liquid composition containing N-[N-(3.3-dimethylbutyl)-La-aspartyll-L-phenylalanine l-methyl ester and a gourmet flavoring

[0113] In a glass beaker are precisely mixed 100 grams of vanilla-popcorn cream flavoring “Movie” (Aroma Sense Reference 93278), 450 grams of propylene glycol (CAS: 57-55-6) and 450 grams of glycerin (CAS: 56-81-5) (example 7 a).

[0114] A mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm.

[0115] In the vape flavor market, a vanilla popcorn cream flavor is often formulated with diacetyl and acetyl propionyl, which provide buttery notes. But these molecules have demonstrated harmful effects on health at high doses.

[0116] A vanilla cream - popcorn flavor (Movie v2 Aroma Sense Reference 93279) was produced with diacetyl (CAS: 431-03-8) and acetyl propionyl (CAS: 600-14-6).

[0117] In a glass beaker are mixed precisely 100 grams of vanilla-popcorn cream flavor V2 “Movie V2” (Aroma Sense Reference 93279), 450 grams of propylene glycol (57-55-6) and 450 grams of glycerin (56-81-5) (example 7b).

[0118] A mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm.

[0119] In a glass beaker are then mixed precisely 0.05 grams of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester (CAS: 165450-17-9), 100 grams of vanilla-popcorn cream flavor “Movie” (Aroma Sense Reference 93278), 449.975 grams of propylene glycol (CAS: 57-55-6) and 449.975 grams of glycerin (CAS: 56-81-5) (formula 7c).

[0120] A mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm.

[0121] Formulas 7a and 7b (containing the movie and movie V2 flavors) were tested by our trained panel. The Movie V2 flavor (formula 7b) is rated as significantly more “gourmet” and more “creamy”. However, examples 7b and 7c (formula containing N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester) tested by our trained panel have the same intensity ratings on the “gourmet” characteristic and closer ratings on the “creamy” characteristic.

[0122] It therefore appears that the use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester in a formula induces an increased perception of the “gourmet” notes of an aroma. This allows the use of fewer potentially problematic compounds.

[0123] Example 8: notation of the note “grilled”, “caramelized” associated with a browning of the cotton.

[0124] In a glass beaker are mixed precisely 4 grams of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester (CAS: 165450-17-9), 498 grams of propylene glycol (CAS: 57-55-6) and 498 grams of glycerin (CAS: 56-81-5) (Formula 8a).

[0125] In another glass beaker are mixed precisely 4 grams of 4-chloro-4-deoxy-aD-galactose of l,6-dichloro-l,6-dideoxy-[3-D-fructofurannosyl (sucralose) (56038-13-2), 498 grams of propylene glycol (CAS: 57-55-6) and 498 grams of glycerin (CAS: 56-81-5) (Formula 7b).

[0126] A mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm. These e-liquid compositions are tested on a vaping robot with the parameters presented in Table 4.

[0127] [Tables4] Puff / Vaporization Duration 3.0 s 7.0.1 s Puff Period 30.0 s 7.0.5 s Number of Puffs per Set 20 Delay Between Sets 300 s Maximum Flow Rate 18.5 mL / s 7.1.0 m L / s Pressure Drop Outside Trapping < 50 hPa Number of Sets 5 Total number of puffs 100 Total vaporization time 300 s

[0128] At the end of the tests, the resistors and cottons are dismantled.

[0129] It appears that the coil used for the vaping series of the formula containing sucralose is blackened. When rubbed with absorbent paper, a significant amount of black residue comes off. The cotton is also blackened and breaks at the contact with the coil (blackest area) when removed. Conversely, the coil used for the vaping series of the formula containing N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester does not have any residue and the cotton when removed is not broken in two or dirty.

[0130] Consequently, this example confirms that N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester allows, in addition to improving the organoleptic characteristics, and in particular sweetness, to limit the presence of degradation products linked to its use in an electronic cigarette.

[0131] Example 9: Identification of components resulting from the use of N-[N-(3.3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester and sucralose in an electronic cigarette

[0132] N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester and sucralose in powder form were placed under an oxidizing atmosphere (artificial air) and a temperature gradient between 30 and 350°C, at a rate of 10°C / min.

[0133] The DSC (Differential Scanning Calorimetry) thermogram obtained for N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester does not show any exothermic peak in this temperature range, which tends to prove the very low oxidation capacity of the organic constituents of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester. A major endothermic peak is also observed, ranging between 80 and 85°C, which corresponds to the melting of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester (coupled with its dehydration). Indeed, the theoretical melting temperature of this product is theoretically between 81 and 84°C. A second weak and very widespread endothermic phenomenon occurs between 130 and 350°C.It is very likely that this phenomenon corresponds to the volatilization of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester, of compounds close to N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester, or of its synthetic residues.

[0134] For Sucralose, a large exothermic peak is visible on the DSC thermogram, between 130 and 150°C. This tends to prove a degradation (oxidation, molecular rupture, etc.) of the product. A second, very spread-out endothermic phenomenon occurs produced between 170 and 360°C. It is very likely that this phenomenon corresponds to the volatilization of compounds resulting from the degradation of sucralose.

[0135] Finally, these DSC analyses show stability of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester, when heated up to 300°C. Conversely, the analysis of sucralose tends to prove its chemical instability when heated between 120 and 350°C.

[0136] Other TGA analyses (ThermoGravimetric Analyses) were carried out under an oxidizing atmosphere (artificial air) and in a temperature gradient between 30 and 400°C, at 10°C / min.

[0137] For this analysis, N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester shows a first mass loss between 70 and 110°C, corresponding to the dehydration of the powder. This is followed by a second stage of slow and regular mass loss between 130 and 380°C, of ​​the order of 80%. It could be linked to the evaporation of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester.

[0138] On the ATG carried out on sucralose, we observe a sudden loss of mass at 135°C which can be coupled with the exothermic peak visible in DSC: this tends to confirm the phenomenon of degradation of sucralose, from 130 / 140°C. From 150°C, the loss of mass is regular and could be attributed to the evaporation of the degradation compounds of sucralose.

[0139] Consequently, these ATG analyses confirm that N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester does not show a sudden chemical decomposition phenomenon between 100 and 350°C. The mass loss is slow and regular between 120 and 350°C, which seems to prove an evaporation of the product in this temperature range. For Sucralose, a sudden mass loss is observed between 140 and 160°C which corresponds to the exothermic peak visible in DSC, and which confirms a chemical degradation of sucralose from these temperatures.

[0140] In conclusion, these results support the superiority of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester over sucralose for its use in e-liquids.

[0141] .

Claims

Claims

1. A composition for use as an electronic cigarette e-liquid or for addition to an electronic cigarette e-liquid, characterized in that it comprises N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester and in that the water content is less than 65% (mass / mass).

2. The composition according to claim 1, characterized in that it further comprises nicotine.

3. The composition according to any one of claims 1 or 2, characterized in that the content of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester is between 0.005% and 0.5% (mass / mass).

4. A storage device for electronic cigarette liquid characterized in that it comprises a composition comprising N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester and having a water content of less than 65% (mass / mass).

5. An electronic cigarette comprising a storage device characterized in that said storage device comprises a composition comprising N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester and having a water content of less than 65% (mass / mass).

6. A method for obtaining vapors having a sweet flavor comprising the steps of: i) placing in an electronic cigarette a storage device comprising a composition as defined in any one of claims 1 to 3, ii) switching on the electronic cigarette so as to allow heating and vaporization of the composition; characterized in that the vaporized composition comprises N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester, a water content of less than 65% (mass / mass) and has a sweet flavor and in that the heating of the composition is carried out at a temperature of between 150 and 300°C.

7. A use of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine 1-methyl ester as a flavor enhancer in an electronic cigarette composition as defined in any one of claims 1 to 3.

8. The use according to the preceding claim characterized in that N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester is used as a flavor enhancer for buttery notes.

9. The use according to any one of claims 7 to 8, characterized in that the content of N-[N-(3,3-dimethylbutyl)-La-aspartyl]-L-phenylalanine l-methyl ester is between 0.005% and 0.5% (mass / mass).