Classifications

• • A—HUMAN NECESSITIES
  • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
  • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
  • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
  • A24B15/10—Chemical features of tobacco products or tobacco substitutes
  • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
  • A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes

Definitions

• the present invention relates to the field of electronic cigarettes and, more specifically, to the use of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester as a sweetener and / or flavor enhancer for an electronic cigarette composition.
• This electronic cigarette works by vaporization by means of an electrical resistance of a liquid, we speak of “e-liquid”, which is flavored or not and which contains, or not, nicotine.
• e-liquid which is flavored or not and which contains, or not, nicotine.
• This vaporization produces a thick smoke comparable to that of a conventional cigarette, but free of most of the toxic compounds from the combustion of tobacco. Studies show in fact the reduction of the impact on human health of this smoke due to the absence of tar, carbon monoxide and many other carcinogenic substances.
• aromas In terms of aromas, a large majority of those on the market are sweet aromas due to the greater appetite of consumers for them. For example, there are flavored e-liquids imitating the flavors of fruit, dessert or even candy.
• Taste in the common sense of the term, actually combines olfaction and taste.
• the sapid molecules dissolve in the saliva and stimulate the taste buds located in the taste buds of the tongue: the perceived sensation is called flavor.
• the odorous molecules which are volatile, they go up towards the nasal cavity by the back of the soft palate to go to stimulate our olfactory system. This is referred to as olfactory stimulation via the retro-nasal route.
• the human being like most animals is able to perceive and distinguish five different primary flavors also qualified as fundamental: sweet, sour, bitter and salty and a fifth flavor, less known to the general public, called umami flavor.
• sweet compounds we naturally find natural sugars (sucrose, fructose and glucose), but also other very different chemically different compounds such as certain amino acids (glycine), polyols (sorbitol, xylitol), or certain elements such than lead or beryllium (originally named glucinium, from the Greek ⁇ (glykys), sweet).
• Artificial or natural sweeteners used in the food industry, are also chemically very diverse. You can find modified peptides (aspartame), halogenated sugars (sucralose), glycosides (stevia), sulfamates (saccharin) or rare sweet vegetable proteins (thaumatin and brazzéin, for example).
• e-liquids contained sugars such as glucose or fructose. If the latter made it possible to give the sweet taste sought by consumers, several scientific studies have established that their thermal degradation generates 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.
• HMF hydroxymethylfurfural
• FA furfural
• sucralose was also subject to thermal degradation generating irritants.
• a first degradation step is thus observed, which takes place between 119 ° C and 137 ° C, and which corresponds to the decomposition sucralose with the loss of two water molecules and one hydrochloric acid molecule.
• 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.
• the presence of sucralose in vaporized e-liquids would lead to the production of potentially dangerous organochlorine compounds and would make its use potentially dangerous for the health of consumers.
• a first object 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) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester.
• a second subject of the invention relates to a storage device for electronic cigarette liquid comprising a composition as described above.
• a third object of the invention relates to an electronic cigarette comprising such a storage device.
• a fourth object relates to a use of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester as a sweetener in a composition for electronic cigarettes.
• a sixth subject of the invention relates to a use of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester as a flavor enhancer in a composition for an electronic cigarette.
• electrosenor cigarette or “e-cigarette” is understood to mean all the electrical devices making it possible to generate an aerosol intended to be inhaled and delivering nicotine and / or one or more aromas.
• This definition encompasses all models of personal vaporizers (PV), 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 hookahs. electronic.
• e-liquid is understood to mean a liquid or composition intended to be used in connection with an electronic cigarette so as to allow its vaporization and its inhalation by a subject.
• N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester is a dipeptide which has the following general formula:
• the N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester has an additional (3,3-dimethylbutyl) group.
• This sweetener and its preparation are described in the patents US 5,480,688 , US 5,510,508 and US 5,728,862 .
• N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester used in the invention can be in different forms.
• N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester can thus be in the form of a salt such as those described for example in international patent applications.
• N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester can also be in the form of a complex such as for example a cyclodextrin complex as described in the patent US 6,214,402 or erythritol as described in the patent application CN 110215732A .
• the N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester content of the composition according to the invention is between 0.00001% and 5% (in mass relative to the total mass of the composition), preferably between 0.0005 and 1% and, particularly preferably between 0.005% and 0.5%.
• composition according to the invention can also comprise propylene glycol, or an isomer thereof, which can be of synthetic or vegetable origin.
• the propylene glycol can in particular be obtained by hydrogenolysis of sorbitol or of vegetable glycerol or by hydrogenation of vegetable lactic acid.
• the propylene glycol content of the composition according to the invention can represent from 0 to 80% by mass (relative to the final mass of the composition), preferably from 10 to 60% by mass and, particularly preferably, of 20 to 50% by mass, relative to the total mass of the composition.
• the propylene glycol content could reach up to 99, 95% by mass, relative to the total mass of the composition.
• composition can also comprise glycerol, of synthetic or vegetable origin.
• 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 , particularly preferably, from 0 to 50% by weight of glycerol.
• the composition according to the invention does not comprise glycerol. It has in fact been observed that the absence of glycerol made it possible to avoid the formation of undesirable by-products (eg acrolein) resulting from the heating of the glycerol.
• composition according to the invention further comprises nicotine.
• Nicotine can be of synthetic or vegetable origin (extracted from tobacco leaves).
• the nicotine concentration of the composition according to the invention is between 0 and 50 mg / mL, preferably between 0 and 20 mg / mL.
• composition according to the invention further comprises at least one flavoring.
• flavorings means products not intended to be consumed as they are, which are added to foodstuffs to give them an odor and / or a taste. or modify these. These flavors are derived from or consist of the following components: flavoring substances, flavoring preparations, smoke flavors, flavors obtained by heat treatment, flavor precursors and other flavors.
• the labeling of flavors on finished products is defined by the INCO Regulation (Consumer Information) 1169/2011.
• INCO Regulation Conser Information
• the flavor content (s) is between 0.01 to 15% by mass and, particularly preferably from 0.1 to 5% by mass (relative to the total mass of the composition) relating to a ready-to-use formula. consumed.
• the aroma content can vary between 0 and 99% by mass due to the application dosages which will lead to a concentration in the ready-to-eat product as indicated. above.
• composition according to the invention can also comprise at least one dye.
• a dye is a substance used to add color to an object to be tinted.
• the colorant used is a food colorant as defined by European Directive 94/36 / EC.
• the dye content of the composition according to the invention is such as to make it possible to obtain the desired coloring.
• the content of dye (s) in 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%.
• composition according to the invention can comprise other compounds such as water and / or alcohol (eg ethanol)
• a second subject of the invention relates to a storage device for electronic cigarette liquid comprising a composition as described above.
• storage device for electronic cigarette liquid is meant a cartridge (eg silicone, PMMA or stainless metal) or a reservoir (eg PMMA / polyethylene, borosilicate glass or stainless metal), possibly completed with a capture device of liquid by capillary action (eg silica, fiberglass, ceramic metallic fabric, nylon threads or borosilicate fibers) in contact with the vaporizer system.
• a cartridge eg silicone, PMMA or stainless metal
• a reservoir eg PMMA / polyethylene, borosilicate glass or stainless metal
• a capture device of liquid by capillary action eg silica, fiberglass, ceramic metallic fabric, nylon threads or borosilicate fibers
• a third object of the invention relates to an electronic cigarette comprising a storage device as described above.
• a fourth object of the invention relates to the use of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester as a sweetener in a composition for electronic cigarettes such as previously described.
• sweetener is meant a product or substance having a sweet taste. Sweeteners provide little or no calories. Some have the advantage of not being cariogenic and some have a sweetening power greater than sugar (sucrose).
• the N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester content 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%.
• the vaporized composition does not include toxic degradation products resulting from the vaporization of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester, preferably not degradation products resulting from the vaporization of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester.
• step ii) of putting under tension allows heating of the composition to a temperature of between 150 and 300 ° C.
• the method according to the invention further comprises a step iii) of inhalation by a subject of the vapors generated in step ii).
• a sixth object of the invention relates to the use of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester as a flavor enhancer in a composition for an electronic cigarette. as described above.
• flavor enhancer is a substance which, without having a distinct distinct flavor, does not modify the taste but increases the intensity of the olfactory-taste perception of a foodstuff.
• the N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester content 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%.
• N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester is used as a flavor enhancer for buttery notes. Note that the latter makes it possible not to use diacetyl and / or acetyl propionyl.
• Example 1 search for possible sweeteners for use in connection with electronic cigarettes :
• a trained panel of 12 people carried out a sensory evaluation by vaporization using electronic cigarettes (Box Aegis Solo marketed by Geek Vape and Pulse 24 dripper marketed by Vandyvape).
• the vaping conditions were as follows: 3 puffs spaced 5 seconds apart induced by a 2 second heating 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 time is observed between the series so as not to be influenced by the perceptual persistence of the previous formula.
• Table 1 below lists some molecules tested and the perception of the sweet flavor after vaporization on a graduated scale ranging from 1 to 10.
• Example 2 determination of the sweetening power of N- [N- (3,3-dimethylbutyl) -L- ⁇ - aspartyl] -L-phenylalanine 1-methyl ester in an e-liquid after vaporization
• e-liquid formulations comprising equivalent concentrations of N- [N- [3- (3-Hydroxy-4-methoxyphenyl) propyl] - ⁇ -L-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.
• 0.035 grams of each example was diluted in a 10 ml glass of Evian brand water. Between each tasting, the panelists rinse their mouths with water. The assessment of sweetness perception, in a taste test, is carried out on a graduated scale ranging from 1 to 10. For the upper reference limit, a score of 10 was attributed to the composition which showed the strongest sweet flavor. For the lower reference limit, a mixture of 50% (m / m) of propylene glycol and 50% (m / m) of glycerol is used.
• Example 1 For the sensory evaluation by vaporization, the conditions are those indicated in Example 1.
• the evaluation of the sweetness perception by vaping was carried out on a graduated scale ranging from 1 to 10. For upper reference limit, a 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) of propylene glycol and 50% (m / m) of glycerol is used as above.
• N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester makes it possible to obtain a high sweet taste whether in test taste or by vaping. Consequently, the vaporization of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester does not cause a significant decrease in its sweetening power, which makes it a ideal solution for use in electronic cigarette.
• Formula 4a was perceived to be much sweeter than Formula 4b. Now, the same intensity of the sweet note was perceived during the vaping tests.
• Example 5 preparation of an e-liquid composition containing N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester and a fruity aroma
• 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 have very similar intensity notes. that the aroma is integrated in a lower concentration in formula 5b.
• Example 6 preparation of an e-liquid composition containing N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester and a flavoring Chewing gum.
• a mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm.
• Formulas 6a and 6b were evaluated by souping on an electronic cigarette by our panel trained according to the conditions presented in Example 3. On the "confectionery” characteristic, it appears that these two formulas have similar intensity notes although the aroma is integrated in a lower concentration in formula 6a.
• N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester enhances the organoleptic characteristics of a formula containing an aroma.
• the use of this makes it possible to use lower aroma concentrations in the formulation of e-liquid or to provide improved, more powerful organoleptic characteristics.
• Example 7 preparation of an e-liquid composition containing N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester and a flavoring greedy
• vanilla-popcorn cream flavor "Movie” (Aroma Sense Reference 93278), 450 grams of propylene glycol ( CAS: 57-55-6 ) and 450 grams of glycerin ( CAS: 56-81-5 ) (example 7a).
• a mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm.
• vanilla cream flavor - popcorn (Reference Movie v2 Aroma Sense 93279) was produced with diacetyl ( CAS: 431-03-8 ) and acetyl propionyl ( CAS: 600-14-6 ).
• vanilla-popcorn cream flavor V2 "Movie V2" (Aroma Sense reference 93279)
• 450 grams of propylene glycol 57-55-6)
• 450 grams of glycerin 56- 81-5) (example 7b).
• a mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm.
• a mechanical stirrer allows dissolution and homogenization for 20 minutes at 200 rpm.
• 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 "greedy” and more "creamy”.
• Examples 7b and 7c (formula containing N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester) tested by our trained panel show the same notes of intensity on the "greedy” characteristic and closer notes on the "creamy” characteristic.
• Example 8 notation of the "grilled”, “caramelized” note associated with browning cotton.
• the resistance used for the vaping series of the sucralose-containing formula is blackened. When rubbed with absorbent paper, a significant amount of black residue comes off. The cotton is also blackened and breaks at contact with resistance (blackest area) when removed. Conversely, the resistance used for the vaping series of the formula containing N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester does not present any residue. and the cotton when pulled out is not broken in half or fouled.
• this example confirms that the N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-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.
• Example 9 Identification of the components resulting from the use of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester and sucralose in an electronic cigarette
• N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester and sucralose in powder form were placed in an oxidizing atmosphere (artificial air) and in a temperature gradient. between 30 and 350 ° C, at a rate of 10 ° C / min.
• the DSC thermogram (Differential Scanning Calorimetry) obtained for N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester shows no 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) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester.
• a major endothermic peak is also observed extending between 80 and 85 ° C, which corresponds to the fusion of N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester (coupled with its dehydration).
• the theoretical melting point of this product is theoretically between 81 and 84 ° C.
• a second weak and very widespread endothermic phenomenon occurs between 130 and 350 ° C.
• Sucralose For Sucralose, a large exothermic peak is visible on the DSC thermogram, between 130 and 150 ° C. This tends to prove degradation (oxidation, rupture molecular ...) of the product. A second very widespread endothermic phenomenon occurs between 170 and 360 ° C. It is very probable that this phenomenon corresponds to the volatilization of compounds resulting from the degradation of sucralose.
• ATG analyzes (ThermoGravimetric Analyzes) were carried out under an oxidizing atmosphere (artificial air) and in a temperature gradient between 30 and 400 ° C, at 10 ° C / min.
• the N- [N- (3,3-dimethylbutyl) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester shows a first loss of mass between 70 and 110 ° C, corresponding to the dehydration of the powder. This results in a second level 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) -L- ⁇ -aspartyl] -L-phenylalanine 1-methyl ester.

Landscapes

• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Seasonings (AREA)
• Manufacture Of Tobacco Products (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=70978001

Family Applications (1)

Country Status (2)

Cited By (1)

Citations (13)

• 2019
  • 2019-10-22 FR FR1911826A patent/FR3102041B1/fr active Active
• 2020
  • 2020-10-22 EP EP20203272.8A patent/EP3811791A1/de active Pending

Patent Citations (13)

Also Published As

Similar Documents

Legal Events