TW201429415A - Flavor precursors - Google Patents

Abstract

A smoking composition comprises an aerosol-generating substrate and a phenolic glycoside. Cleavage of the glycosidic bond releases a phenolic compound having a smoky note. The smoking composition may be incorporated into a smoking article that is configured to cause the glycosidic bond to be cleaved during use. The smoking article may include tobacco and may be configured to heat, but does not combust, tobacco. Such articles typically are lacking in smoky flavor relative to smoking articles in which tobacco is combusted. Inclusion of the phenolic glycoside helps bridge the flavor gap.

Description

香料前驅物 Spice precursor

本發明係關於可用於香煙組成物之香料前驅物，以及與此類香煙組成物相關之製品和方法。 This invention relates to perfume precursors useful in cigarette compositions, as well as articles and methods relating to such cigarette compositions.

加熱煙草而非燃燒煙草的吸煙製品已經被提出。此類製品可產生能夠將尼古丁和其它煙草成分傳遞給使用者的氣溶膠。然而，由於在使用此類製品的過程中並沒有燃燒煙草，使用者可能感受到的煙味香韻(smoky note)會比傳統吸煙製品(如香煙)明顯減少。 Smoking articles that heat tobacco rather than burn tobacco have been proposed. Such articles can produce an aerosol capable of delivering nicotine and other tobacco components to a user. However, since tobacco is not burned during the use of such articles, the smoky note that the user may feel is significantly less than that of conventional smoking articles such as cigarettes.

因此，可能希望將化合物摻入用於非燃燒型吸煙物品中所用的煙草中，以使其與抽吸傳統香煙所伴隨的經驗更為接近。有許多種化合物已知可產生煙味香韻。然而，此類化合物的揮發性會使得將該化合物摻入煙草或吸煙製品時帶來挑戰。例如，在生產或儲存過程中可能會因為化合物的揮發性而發生損耗。此外，摻入此類化合物但尚未使用的製品將可能讓人感受到不悅的焦臭或煙味。 Therefore, it may be desirable to incorporate the compound into the tobacco used in non-combustible smoking articles to bring it closer to the experience associated with smoking conventional cigarettes. There are many compounds known to produce a scent of smoke. However, the volatility of such compounds can present challenges when incorporating such compounds into tobacco or smoking articles. For example, losses may occur due to the volatility of the compound during production or storage. In addition, articles incorporating such compounds but not yet used may result in an unpleasant burnt or smoke odor.

如本文所述，其中煙草或其它材料係被加熱 而非燃燒的吸煙製品，可提供使用者一種含有本發明化合物之氣溶膠，而讓使用者可感受到類似於抽吸傳統香煙的感覺。此種製品含有一種包括酚糖苷的香煙組成物，其不會產生明顯的氣味。酚糖苷的糖苷鍵會在加熱時斷裂，以產生提供煙味香韻的酚類化合物。因此，煙草製品的使用者可感受到抽吸傳統香煙的類似感覺。 As described herein, wherein tobacco or other materials are heated The non-combustible smoking article provides the user with an aerosol containing the compound of the invention, allowing the user to feel a feeling similar to smoking a conventional cigarette. Such articles contain a composition of cigarettes including phenol glycosides that do not produce significant odors. The glycosidic linkage of the phenol glycoside breaks upon heating to produce a phenolic compound that provides a scent of smoke. Therefore, users of tobacco products can feel a similar feeling of smoking a conventional cigarette.

本文所描述的吸煙製品可提供優於舊有非燃燒煙草之吸煙製品的一或多項優點。例如前面所述，相對於未包括具有煙味香韻之化學固定化酚類化合物的吸煙製品，本文所述的吸煙製品可提供增強的香氣或感官體驗。因為酚類化合物能夠從糖苷中解離，並且因為糖苷不會揮發或是比酚類化合物的揮發性低，因此可以減緩在生產過程中的損耗，而製品可以具有更長的儲存壽命。此外，由於糖苷的氣味比酚類化合物為低，其製品在未使用時不會產生焦臭或煙味。 The smoking articles described herein can provide one or more advantages over smoking articles of the old non-combustible tobacco. For example, as previously described, the smoking articles described herein provide an enhanced aroma or sensory experience relative to smoking articles that do not include a chemically immobilized phenolic compound having a scent of smoke. Because the phenolic compound is capable of dissociating from the glycoside, and because the glycoside does not volatilize or is less volatile than the phenolic compound, it can slow the loss in the production process, and the article can have a longer shelf life. Further, since the glycoside has a lower odor than the phenolic compound, the product does not produce a burnt smell or a smoke smell when not used.

就本發明而言，「香料化合物」乙詞可與「具有煙味香韻的酚類化合物」交替使用。 For the purposes of the present invention, the term "fragrance compound" can be used interchangeably with "a phenolic compound having a scent of smoke".

如本文中所使用的「煙味(smoky)」乙詞對於有經驗的調香師而言是容易理解的，即指伴隨著木材燃燒所帶來的香味。這個名詞被用於許多參考書中，包括Gary Reineccius所著的「香料、化學和技術(Flavor,Chemistry and Technology)」，第二版，以及Steffen Arctander所著的「香水和香料化學品(Perfume and Flavor Chemicals」，1969年。 The term "smoky" as used herein is readily understood by an experienced perfumer, meaning the aroma associated with wood burning. This term is used in many reference books, including "Flavor, Chemistry and Technology" by Gary Reineccius, Second Edition, and "Perfume and Fragrance Chemicals by Steffen Arctander" (Perfume and Flavor Chemicals", 1969.

任何適合的香料化合物可與還原糖接合以產 生酚糖苷，其可添加至煙草或其它材料中，以產生本文所述之香煙組成物。在糖苷鍵的裂解時，具有煙味香韻的酚類化合物就會被釋放出來。 Any suitable perfume compound can be combined with a reducing sugar to produce A phenol glucoside, which can be added to tobacco or other materials to produce the cigarette composition described herein. When the glycosidic bond is cleaved, the phenolic compound having a scent of smoke is released.

在具體實施例中，香料化合物具有下式之結構： In a particular embodiment, the perfume compound has the structure of:

其中R¹、R²、R³、R⁴和R⁵係各自獨立選自由(i)H和(ii)C1-C5直鏈或支鏈烷基或烷氧基所構成之群組，其中烷基或烷氧基未經取代或是經鹵素或羥基取代。其中一或多個R¹、R²、R³、R⁴和R⁵為C1-C5直鏈或支鏈的烷基或烷氧基。經取代或未經取代之烷基或烷氧基較佳為C1-C3烷基或烷氧基。烷基或烷氧基較佳係未經取代。 Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently selected from the group consisting of (i)H and (ii) a C1-C5 linear or branched alkyl or alkoxy group, wherein the alkane The base or alkoxy group is unsubstituted or substituted by halogen or hydroxy. One or more of R ¹ , R ² , R ³ , R ⁴ and R ⁵ are a C1-C5 linear or branched alkyl or alkoxy group. The substituted or unsubstituted alkyl or alkoxy group is preferably a C1-C3 alkyl group or an alkoxy group. The alkyl or alkoxy group is preferably unsubstituted.

在具體實施例中，一或多個R¹、R²、R³、R⁴和R⁵係選自由甲基、乙基、丙基(例如異丙基)、甲氧基和乙氧基所構成的群組。一或多個R¹、R²、R³、R⁴和R⁵較佳係選自由甲基、乙基、異丙基和甲氧基所構成的群組。在一些具體實施例中，非甲基、乙基、丙基、甲氧基或乙氧基的R¹、R²、R³、R⁴和R⁵為H。 In a particular embodiment, one or more of R ¹ , R ² , R ³ , R ⁴ and R ⁵ are selected from the group consisting of methyl, ethyl, propyl (eg isopropyl), methoxy and ethoxy. The group that is formed. One or more of R ¹ , R ² , R ³ , R ⁴ and R ^{5 are} preferably selected from the group consisting of methyl, ethyl, isopropyl and methoxy. In some embodiments, R ¹ , R ² , R ³ , R ⁴ and R ⁵ of the non-methyl, ethyl, propyl, methoxy or ethoxy group are H.

在具體實施例中，R¹和R⁵其中一個或兩個都是甲氧基。 In a particular embodiment, one or both of R ¹ and R ⁵ are methoxy.

在一些具體實施例中，R³為異丙基。 In some embodiments, R ³ is isopropyl.

在具體實施例中，一或多個R¹、R²和R³為甲基。 In a particular embodiment, one or more of R ¹ , R ² and R ³ are methyl.

在具體實施例中，R²為乙基。 In a particular embodiment, R ² is ethyl.

較佳的香料化合物包括選自由2-甲氧基酚(或癒創木酚，其中式I中的R¹為甲氧基，且R²、R³、R⁴和R⁵為H)、2,6-二甲氧基酚(其中式I中的R¹和R⁵為甲氧基，且R²、R³和R⁴為H)、鄰甲酚(其中式I中的R¹為甲基，且R²、R³、R⁴和R⁵為H)、間甲酚(其中式I中的R²為甲基，且R¹、R³、R⁴和R⁵為H)、對甲酚(其中式I中的R³為甲基，且R¹、R²、R⁴和R⁵為H)、3-乙基酚(其中式I中的R²為乙基，且R¹、R³、R⁴和R⁵為H)、4-異丙基酚(其中式I中的R³為異丙基，且R¹、R²、R⁴和R⁵為H)和2,3-二甲基酚(其中式I中的R¹和R²為甲基，且R³、R⁴和R⁵為H)所構成之群組。更佳的是，香料化合物為癒創木酚(2-甲氧基酚)。 Preferred perfume compounds include those selected from the group consisting of 2-methoxyphenol (or guaiacol wherein R ^{1 in} formula I is methoxy and R ² , R ³ , R ⁴ and R ⁵ are H), 2 , 6-dimethoxyphenol (wherein R ¹ and R ^{5 in} formula I are methoxy, and R ² , R ³ and R ⁴ are H), o-cresol (wherein R ^{1 in} formula I is A) And R ² , R ³ , R ⁴ and R ⁵ are H), m-cresol (wherein R ^{2 in} formula I is methyl, and R ¹ , R ³ , R ⁴ and R ⁵ are H), Cresol (wherein R ^{3 in} formula I is methyl, and R ¹ , R ² , R ⁴ and R ⁵ are H), 3-ethylphenol (wherein R ^{2 in} formula I is ethyl, and R ¹ And R ³ , R ⁴ and R ⁵ are H), 4-isopropylphenol (wherein R ³ in the formula I is isopropyl, and R ¹ , R ² , R ⁴ and R ⁵ are H) and 2, a group consisting of 3-dimethylphenol (wherein R ¹ and R ^{2 in} formula I are methyl groups, and R ³ , R ⁴ and R ⁵ are H). More preferably, the perfume compound is guaiacol (2-methoxyphenol).

依據本文所教示，任何香料化合物可能由糖苷釋出。本文所指的香料化合物是一種芳香族的六員碳環結構，其中環中至少一個碳原子具有羥基取代基。其它的環中成分可經取代或未經取代，只要該化合物可產生煙味香韻。 Any perfume compound may be released from the glycoside, as taught herein. The perfume compound referred to herein is an aromatic six member carbon ring structure in which at least one carbon atom in the ring has a hydroxy substituent. Other cyclic components may be substituted or unsubstituted as long as the compound produces a scent of smoke.

可以使用任何一種適合的測試方法來確定香料化合物是否會產生煙味香韻。例如，可引發主觀感受到煙味香韻、氣味(odour)、味道(smell)、香味(flavor)等類似感覺之化合物即可被認為具有或產生了煙味香 韻。在具體實施例中，受過氣味感訓練的人員可用來確認酚類化合物是否具有煙味香韻。在具體實施例中，也可使用隨機或非隨機選取的人來確認他們是否感受到化合物產生了煙味香韻。舉例而言，如果25%或以上(例如50%或以上、60%或以上、70%或以上，或者是80%或以上)選取的人感受到煙味香韻，或者是一個評判小組使用有關煙味香韻(例如煙味)之描述詞的話，該化合物將被視為有煙味香韻。香料化合物，或其衍生物，可經由糖苷鍵與任何一種適合的還原糖(亦被稱為糖基(glycone))接合，以產生糖苷，其將在糖苷鍵裂解時釋出酚類化合物。糖基可以是任何一種適合的單糖或多醣或其衍生物。舉例而言，多醣可以是纖維素、三醣或雙醣。可做為糖基之三醣的例子包括異麥芽三糖、黑曲霉三糖、麥芽三糖、松三糖、麥芽三酮糖、棉子糖、蔗果三糖等。可做為糖基之雙醣的例子包括蔗糖、麥芽糖、乳糖、纖維二糖、乳酮糖、海藻糖、麴二糖、黑曲霉糖、異麥芽糖、β,β-海藻糖、α,β-海藻糖、槐二糖、海帶二糖、龍膽二糖、松二糖、麥芽酮糖、巴拉金糖、龍膽二酮糖(gentiobiulose)、甘露二糖、蜜二糖、蜜二酮糖(melibiulose)、芸香糖、芸香酮糖(rutinulose)、木二糖等。 Any suitable test method can be used to determine if the fragrance compound will produce a scent of smoke. For example, a compound which induces a subjective feeling of odor, odour, smell, flavor, etc. can be considered to have or produce a scent of smoke. rhyme. In a particular embodiment, a person trained in odor can be used to confirm whether the phenolic compound has a scent of smoke. In particular embodiments, random or non-randomly selected persons may also be used to confirm whether they are aware that the compound produces a scent of smoke. For example, if 25% or more (for example, 50% or more, 60% or more, 70% or more, or 80% or more), the selected person feels the smell of smoke, or a panel uses the relevant smoke. For the description of the flavor (such as smoke), the compound will be considered to have a scent of smoke. The perfume compound, or a derivative thereof, can be joined to any suitable reducing sugar (also known as a glycone) via a glycosidic linkage to produce a glycoside which will liberate the phenolic compound upon cleavage of the glycosidic linkage. The glycosyl group can be any suitable monosaccharide or polysaccharide or a derivative thereof. For example, the polysaccharide can be a cellulose, a trisaccharide or a disaccharide. Examples of the trisaccharide which can be used as the glycosyl group include isomaltotriose, Aspergillus trisaccharide, maltotriose, melezitose, maltotrione, raffinose, canetriose, and the like. Examples of the disaccharide which can be used as a glycosyl group include sucrose, maltose, lactose, cellobiose, lactulose, trehalose, bismuthose, avermose, isomaltose, β, β-trehalose, α, β- Trehalose, bismuth saccharide, kelp disaccharide, gentiobiose, pine disaccharide, maltulose, palatinose, gentiobiulose, mannose, melibiose, melibet Sugar (melibiulose), chewing gum, rutinulose, xylobiose, and the like.

如果單糖為糖基，則單糖較佳為C5-C7單糖。單糖更佳為C6單糖。可以做為糖基之單糖的實例包括葡萄糖、半乳糖、葡糖醛酸、果糖、木糖、核糖、甘露糖、樹膠糖、麥芽糖、塔格糖(tagatose)s等。單糖較佳為葡萄糖。 If the monosaccharide is a glycosyl group, the monosaccharide is preferably a C5-C7 monosaccharide. The monosaccharide is more preferably a C6 monosaccharide. Examples of the monosaccharide which can be used as a glyco group include glucose, galactose, glucuronic acid, fructose, xylose, ribose, mannose, gum sugar, maltose, tagatose s and the like. The monosaccharide is preferably glucose.

可以任何一種適合的方式來合成糖苷。糖化反應的一個實例為Koenigs-Knorr反應，這是糖苷鹵化物與醇的取代反應，其在有重金屬或銀鹽存在的情況下進行，以產生糖苷。其它可使用的糖化方法為Helferich糖化反應，其中的催化劑為如氰化汞之類的汞鹽；Fischer糖化反應；利用乙酸糖苷酯；糖苷基三氯乙醯亞胺酯；糖苷基氟化物；分子內配糖基轉移；等等。 The glycoside can be synthesized in any suitable manner. An example of a saccharification reaction is the Koenigs-Knorr reaction, which is a substitution reaction of a glycoside halide with an alcohol, which is carried out in the presence of a heavy metal or a silver salt to produce a glycoside. Other saccharification methods that can be used are Helferich saccharification, in which the catalyst is a mercury salt such as mercury cyanide; Fischer saccharification reaction; utilization of glycoside glycosyl ester; glycosyltrichloroethylene imidate; glycosyl fluoride; Internal glycosyl transfer; and so on.

在具體實施例中，可以使用或修改例如(i)Dignum等人(2004)，食品科學85：199-205；(ii)Hayasaka等人(2010)，農業食品化學期刊58：10989-10998；(iii)Cai等人(2010)，亞洲化學期刊(2010)22(9)：6647-6651；或(iv)WO 88/09133中所述之糖化反應來製造酚糖苷。 In particular embodiments, for example, (i) Dignum et al. (2004), Food Science 85: 199-205; (ii) Hayasaka et al. (2010), Journal of Agro-Food Chemistry 58: 10989-10998; Iii) The saccharification reaction described in Cai et al. (2010), Asian Chemical Journal (2010) 22(9): 6647-6651; or (iv) WO 88/09133 to produce phenol glycosides.

糖化反應通常包括在催化劑存在的情況下使糖苷基供體與糖苷基受體反應以產生酚糖苷，糖苷基受體在本發明中為酚類化合物或其衍生物。酚類化合物或其衍生物的游離醇將會與糖苷基供體反應，以產生O-糖苷鍵。可以使用任何一種適合的糖苷基供體。通常糖苷基供體為糖苷基鹵化物，如糖苷基溴化物、糖苷基氯化物等。 The saccharification reaction generally involves reacting a glycosyl donor with a glycosyl acceptor in the presence of a catalyst to produce a phenolic glycoside, which in the present invention is a phenolic compound or a derivative thereof. The free alcohol of the phenolic compound or its derivative will react with the glycosyl donor to produce an O-glycosidic linkage. Any suitable glycosyl donor can be used. Typically, the glycosyl donor is a glycosyl halide such as a glycosyl bromide, a glycosyl chloride, and the like.

2,3,4,6-四乙醯基-α-D-葡吡喃糖苷基溴化物(「乙醯溴葡萄糖」)常用來製備衍生自葡萄糖的糖苷。乙醯溴葡萄糖的製備方法通常包括在催化劑(如吡啶、三乙胺和二甲胺基吡啶或乙酸鈉和氯化鋅)存在的情況下，於溶劑(如二氯甲烷)中，使葡萄糖與乙酸酐進行全 乙醯化反應。所得到的1,2,3,4,6-五乙醯基-α-β-D葡吡喃糖苷可在例如二氯甲烷中以HBr-乙酸進行處理，以產生乙醯溴葡萄糖，其可藉由結晶來獲得。氯衍生物可以藉由使用HCl蒸汽、在二甲基甲醯胺(「DMF」)中的SOCl₂、或其類似物來獲得。 2,3,4,6-Tetradecyl-α-D-glucopyranosyl bromide ("Ethyl bromide") is commonly used to prepare glycosides derived from glucose. The preparation method of acetaminophen bromoglucose usually comprises using glucose in a solvent (such as dichloromethane) in the presence of a catalyst such as pyridine, triethylamine and dimethylaminopyridine or sodium acetate and zinc chloride. Acetic anhydride is subjected to a full oximation reaction. The obtained 1,2,3,4,6-pentaethyl-α-β-D-glucopyranoside can be treated with HBr-acetic acid in, for example, dichloromethane to produce ethyl bromide, which can be Obtained by crystallization. The chlorine derivative can be obtained by using HCl vapor, SOCl ₂ in dimethylformamide ("DMF"), or the like.

如果糖含有酸敏性基團(例如疊氮化物)或酸敏性保護基(如丙縮酮或苯亞甲基)，可使用更溫和的鹵化反應條件(如光氣在DMF或三甲基溴矽烷中)來產生糖苷基鹵化物。 If the sugar contains an acid-sensitive group (such as an azide) or an acid-sensitive protecting group (such as acetal or benzylidene), a milder halogenation reaction condition (such as phosgene in DMF or trimethyl) can be used. In bromodecane) to produce a glycosyl halide.

乙醯溴葡萄糖(CAS編號572-09-8)可以依上述方法來合成，或由供應商購買，如Sigma-Aldrich。上述關於乙醯溴葡萄糖的反應可以很容易地修改，以產生三甲基乙醯溴葡萄糖(CAS編號81058-27-7)。或者是，由供應商購買，由如Sigma-Aldrich之類的供應商來購買三甲基乙醯溴葡萄糖。 Ethyl bromide (CAS No. 572-09-8) can be synthesized as described above or purchased by a supplier such as Sigma-Aldrich. The above reaction for acetamidine bromide can be easily modified to produce trimethyl ethane bromide (CAS number 81058-27-7). Alternatively, it is purchased by a supplier to purchase trimethyl ethane bromide from a supplier such as Sigma-Aldrich.

舉例而言，具有葡萄糖或其衍生物做為糖基及香料化合物做為配糖基(aglycone)之糖苷描繪如下式II： For example, a glycoside having glucose or a derivative thereof as a glycosyl group and a perfume compound as an aglycone is depicted by the following formula II:

其中R¹、R²、R³、R⁴和R⁵如前面式I中所 述，並且R⁶、R⁷、R⁸和R⁹係各自獨立為H或是一種保護基，如乙醯基[-C(O)CH₃]、三甲基乙醯基[-C(O)(CH₃)₃，又稱為三甲基乙醯基或2,2-二甲基丙醯基]；等等。在具體實施例中，R⁶、R⁷、R⁸和R⁹為相同。R⁶、R⁷、R⁸和R⁹較佳為H。如果R⁶、R⁷、R⁸或R⁹為保護基，該保護基可被裂解，以產生具有未經取代糖基之酚糖苷。例如，乙醯基或三甲基乙醯基可以在甲醇鈉-甲醇(NaOMe-MeOH)中輕易地發生裂解。其它保護基可以經由任何一種適合的去保護反應而被輕易的去除，其許多為已知的技術。應理解的是，糖基可衍生自異於式II所描繪之葡萄糖的任何一種適合的單糖或是如前所述的多糖。 Wherein R ¹ , R ² , R ³ , R ⁴ and R ^{5 are} as defined in the above formula I, and R ⁶ , R ⁷ , R ⁸ and R ⁹ are each independently H or a protecting group such as ethyl hydrazino. [-C(O)CH ₃ ], trimethylethenyl [-C(O)(CH ₃ ) ₃ , also known as trimethylethenyl or 2,2-dimethylpropanyl]; and many more. In a particular embodiment, R ⁶ , R ⁷ , R ⁸ and R ⁹ are the same. R ⁶ , R ⁷ , R ⁸ and R ^{9 are} preferably H. If R ⁶ , R ⁷ , R ⁸ or R ⁹ is a protecting group, the protecting group can be cleaved to produce a phenolic glycoside having an unsubstituted sugar group. For example, an ethenyl or trimethylethenyl group can be readily cleaved in sodium methoxide-methanol (NaOMe-MeOH). Other protecting groups can be readily removed via any suitable deprotection reaction, many of which are known techniques. It will be understood that the glycosyl group may be derived from any suitable monosaccharide other than the glucose depicted in Formula II or a polysaccharide as previously described.

在一個較佳的具體實施例中，糖苷為癒創木酚糖苷((2R,3S,4S,5R,6S)-2-羥甲基)-6-(2-甲氧苯氧基)四氫-2H-吡喃-3,4,5-三醇)，它具有下式之結構： In a preferred embodiment, the glycoside is guaiacol glucoside ((2R,3S,4S,5R,6S)-2-hydroxymethyl)-6-(2-methoxyphenoxy)tetrahydrogen -2H-pyran-3,4,5-triol), which has the structure of the formula:

本文所指的香料組成物係含有酚糖苷之組成物。本文中的「酚糖苷」乙詞係與「香料前驅化合物」乙詞交替使用。本發明之香料傳遞組成物包含香料前驅化合物，並且其有助於香料前驅化合物以受控的方式釋 放到周圍環境。在各種具體實施例中，酚糖苷是在其添加至香料組成物或香料傳遞組成物之前被合成或純化。 The perfume composition referred to herein contains a composition of a phenol glycoside. In this article, the word "phenolic glycoside" is used interchangeably with the word "perfume precursor compound". The perfume delivery composition of the present invention comprises a perfume precursor compound and which facilitates the release of the perfume precursor compound in a controlled manner Put it in the surrounding environment. In various embodiments, the phenolic glycoside is synthesized or purified prior to its addition to the perfume composition or perfume delivery composition.

如前所述，酚糖苷可以任何一種適合的方式及以任何適合的量內含於香煙組成物中。「香煙組成物」乙詞係用來描述一種當其被燃燒或加熱時可產生煙霧(smoke)之組成物，且被用來做成吸煙製品。「吸煙製品」乙詞包括香煙、雪茄、小雪茄和其它製品，其中香煙組成物(如煙草組成物)被點燃及燃燒，以產生煙霧。「吸煙製品」乙詞還包括香煙組成物並未燃燒的製品，諸如但不限於：直接或間接加熱香煙組成物但未燒毀或燃燒該香煙組成物之吸煙製品，或者是既未燃燒也未加熱香煙組成物而是使用氣流或化學反應來傳遞來自煙草的尼古丁、香料化合物或其它材料之吸煙製品。本文所用的「煙霧」乙詞是用來描述經由燃燒吸煙製品所產生的氣溶膠。由吸煙製品所產生的氣溶膠可能是，例如，由可燃性吸煙製品(例如香煙)所產生的煙霧，或者是由不可燃的吸煙製品(如加熱式吸煙製品或非加熱式吸煙製品)所產生的氣溶膠。 As stated previously, the phenol glycoside can be contained in the cigarette composition in any suitable manner and in any suitable amount. The term "cigarette composition" is used to describe a composition that produces smoke when it is burned or heated and is used to make a smoking article. The term "smoking articles" includes cigarettes, cigars, cigarillos and other products in which cigarette constituents (such as tobacco constituents) are ignited and burnt to produce smoke. The term "smoking article" also includes articles in which the composition of the cigarette is not burned, such as, but not limited to, a smoking article that directly or indirectly heats the composition of the cigarette but does not burn or burn the composition of the cigarette, or neither burns nor heats. A cigarette composition is a smoking article that uses a gas stream or chemical reaction to deliver nicotine, a fragrance compound, or other material from tobacco. As used herein, the term "smoke" is used to describe an aerosol produced by burning a smoking article. The aerosol produced by the smoking article may be, for example, smoke produced by a flammable smoking article (such as a cigarette) or by a non-combustible smoking article (such as a heated smoking article or a non-heated smoking article). Aerosol.

除了香料前驅化合物之外，本發明之香料組成物可包含一或多種本領域已知的香味劑，包括但不限於，薄荷醇、綠薄荷、薄荷、桉樹、香草、可可、巧克力、咖啡、茶、香辛料(如肉桂、丁香和薑)、水果萃取物，及其組合。在具體實施例中，香料組成物還含有薄荷醇或丁香酚。此類香味劑經常用來使得吸煙製品之煙霧具有清涼芳香的氣味。 In addition to the perfume precursor compound, the perfume composition of the present invention may comprise one or more flavoring agents known in the art including, but not limited to, menthol, spearmint, mint, eucalyptus, vanilla, cocoa, chocolate, coffee, tea. , spices (such as cinnamon, cloves and ginger), fruit extracts, and combinations thereof. In a particular embodiment, the perfume composition further contains menthol or eugenol. Such fragrances are often used to impart a cool, aromatic scent to the smoke of smoking articles.

香料傳遞組成物可藉由任何一種適當的方法將香料前驅化合物控制釋放到周圍環境中，例如使香料傳遞組成物變形或者是改變溫度等方式。香料前驅化合物隨著時間間隔的釋放量，以及間隔的開始或結束都是可以控制的。在每一段時間間隔期間所釋放香料前驅化合物的量，以及時間間隔的長度並不需要相等。 The perfume delivery composition can be controlled to release the perfume precursor compound to the surrounding environment by any suitable means, such as by modifying the perfume delivery composition or by changing the temperature. The amount of fragrance precursor compound released over time intervals, as well as the beginning or end of the interval, is controllable. The amount of perfume precursor compound released during each time interval, as well as the length of the time interval, need not be equal.

在具體實施例中，香料傳遞組成物可以是任何一種適合的形式，只要其能夠使香料組成物維持在該組成物的結構中，直到需要被釋放為止。香料傳遞組成物較佳係包括一種封閉式基質或網狀結構，其可將香料前驅化合物鎖在該封閉結構中。例如，香料組成物可以鎖在基質結構內的區域中。在材料受壓縮或變形時，香料前驅組成物將由基質結構中被擠出，例如，經由周圍結構的斷裂。在具體實施例中，香料傳遞組成物包括一種包含一或多種基質形成聚合物的聚合物基質。例如，聚合物基質隨著壓縮力量、溫度或兩者同時的增加而逐漸崩解，使得香料前驅化合物由香料傳遞組成物中控制釋放出來。因此，香料前驅化合物的釋放可作為溫度或施加於香料傳遞組成物上的壓縮或剪切力所引起的變形之函數而改變。香料傳遞組成物可有利的以各種不同的形式配置於吸煙製品內，因而使得該組成物摻入吸煙製品的方式具有相當的靈活性。在具體實施例中，香料傳遞組成物的形式可以是顆粒、珠粒或膠囊狀。這些顆粒、珠粒或膠囊可以被製成任何適合的形狀，但最好是實質上為圓柱形或球形。 In a particular embodiment, the perfume delivery composition can be in any suitable form so long as it is capable of maintaining the fragrance composition in the structure of the composition until it needs to be released. Preferably, the perfume delivery composition comprises a closed matrix or network structure that locks the perfume precursor compound in the closed structure. For example, the perfume composition can be locked in a region within the matrix structure. When the material is compressed or deformed, the perfume precursor composition will be extruded from the matrix structure, for example, via a fracture of the surrounding structure. In a particular embodiment, the perfume delivery composition comprises a polymeric matrix comprising one or more matrix forming polymers. For example, the polymer matrix gradually disintegrates as the compressive strength, temperature, or both increase, such that the perfume precursor compound is controlled to be released from the perfume delivery composition. Thus, the release of the perfume precursor compound can be varied as a function of temperature or deformation caused by compression or shear forces applied to the perfume delivery composition. The perfume delivery composition can advantageously be disposed in the smoking article in a variety of different forms, thereby providing considerable flexibility in the manner in which the composition is incorporated into the smoking article. In a particular embodiment, the flavor delivery composition can be in the form of granules, beads or capsules. These granules, beads or capsules can be formed into any suitable shape, but are preferably substantially cylindrical or spherical.

本發明之香煙組成物包括香料前驅化合物、香料組成物或香料傳遞組成物。香煙組成物可包含例如，粉末、細粒、丸粒、碎片、細條或細片等一或多種形式之一或多種的香草葉、菸葉、煙桿、煙梗碎片、均化煙草、再造煙草、加工煙草、擠壓煙草和膨脹煙草。香煙組成物可以是鬆散的形式，或者可以裝置在適合的容器或筒匣中。例如，香煙組成物可以內含於紙或捲紙中，並且具有栓塞的形式。 The cigarette composition of the present invention comprises a fragrance precursor compound, a fragrance composition or a fragrance delivery composition. The cigarette composition may comprise, for example, vanilla leaves, tobacco leaves, tobacco stems, stem fragments, homogenized tobacco, reconstituted tobacco, one or more of one or more forms such as powder, granules, pellets, chips, thin strips or flakes, Processing tobacco, extruded tobacco and expanded tobacco. The cigarette composition can be in a loose form or can be placed in a suitable container or cartridge. For example, the cigarette composition can be contained in paper or roll paper and have the form of a plug.

包括氣溶膠產生裝置的吸煙製品通常包括一種氣溶膠產生基材，其經常與其它成分組裝成桿狀的形式。一般而言，這種桿子的形狀和尺寸會被設計成能***一種氣溶膠產生裝置中，該裝置包含一種用於加熱氣溶膠產生基材的加熱元件。本文中所指的「氣溶膠產生基材」是一種香煙組成物的類型，其可用於氣溶膠產生裝置中以產生氣溶膠。氣溶膠產生基材可以在燃燒或加熱時釋放出香料化合物。氣溶膠產生基材可以是固體形式或液體形式。基材可同時包括液體和固體成分。氣溶膠產生基材可包括煙草和香料組成物，其中香料前驅化合物或解離的香料化合物在加熱時由基材中釋出。在具體實施例中，氣溶膠產生基材不包括煙草，但包括一種香料組成物以及選用的尼古丁，於該香料組成物中如本文所述的酚糖苷或解離的香料化合物在加熱時由基材中釋放出來。氣溶膠產生基材還可進一步包含氣溶膠形成劑。適合之氣溶膠形成劑的例子為甘油和丙二醇。選擇性地，氣溶膠產生基材可裝置在或嵌入一種載體中，其 可以是粉末、細粒、丸粒、碎片、義大利麵條、細條或細片等形式。氣溶膠產生基材可以例如薄片、泡沫、凝膠或漿料等形式沈積於載體的表面上。氣溶膠產生基材可以被沈積在載體的整個表面上，或者是選擇性地，為了在使用時提供非均勻的香料傳遞而以圖案沈積。 Smoking articles comprising an aerosol generating device typically comprise an aerosol generating substrate which is often assembled into a rod-like form with other ingredients. In general, such a rod will be shaped and sized to be inserted into an aerosol generating device comprising a heating element for heating the aerosol generating substrate. As used herein, "aerosol-generating substrate" is a type of cigarette composition that can be used in an aerosol generating device to produce an aerosol. The aerosol-generating substrate can release the fragrance compound upon burning or heating. The aerosol-generating substrate can be in solid form or in liquid form. The substrate can include both liquid and solid components. The aerosol-generating substrate can include a tobacco and perfume composition wherein the perfume precursor compound or the dissociated perfume compound is released from the substrate upon heating. In a particular embodiment, the aerosol-generating substrate does not include tobacco, but includes a perfume composition and selected nicotine in which the phenolic glycoside or dissociated perfume compound as described herein is heated by the substrate. Released in the middle. The aerosol-generating substrate may further comprise an aerosol former. Examples of suitable aerosol formers are glycerin and propylene glycol. Optionally, the aerosol generating substrate can be mounted or embedded in a carrier, It may be in the form of powder, granules, pellets, chips, pasta, thin strips or flakes. The aerosol-generating substrate can be deposited on the surface of the carrier in the form of, for example, a sheet, foam, gel or slurry. The aerosol-generating substrate can be deposited on the entire surface of the carrier or, alternatively, in a pattern for providing non-uniform perfume delivery during use.

吸煙製品可以包括一個濾嘴，它可以是單段濾嘴或是包含兩個或以上之連接或未連接濾嘴段之多組件濾嘴。習於本技術領域者應知道有許多種適合的濾嘴段。一或多個濾嘴段可各自包括香料前驅化合物、香料組成物或香料傳遞組成物。吸煙製品可以包裝在容器中販售，例如軟盒包裝或是翻蓋盒包裝，其內襯塗布或浸漬了香料化合物、香料組成物或香料傳遞組成物。 The smoking article can include a filter that can be a single-stage filter or a multi-component filter that includes two or more connected or unconnected filter segments. Those skilled in the art will recognize that there are many suitable filter segments. The one or more filter segments can each comprise a perfume precursor compound, a perfume composition, or a perfume delivery composition. The smoking article can be packaged and sold in a container, such as a soft box or a flip-top box, the liner being coated or impregnated with a fragrance compound, a fragrance composition or a fragrance delivery composition.

可以使用任何一種適合的技術來製造包含香料前驅化合物、香料組成物或香料傳遞組成物之香煙組成物。例如，可將香料前驅化合物添加至供料到製煙機的捲煙煙絲貨料中，或者是在捲煙紙圍繞煙草柱包裝之前，將其施用於預先形成的煙草柱中。在具體實施例中，用於製造香煙組成物的方法包括以香料前驅化合物噴灑煙草的步驟。為了便於噴灑，可將香料前驅化合物添加到液體載體中，以形成溶液或懸浮液，並且將溶液或懸浮液施用於煙草上。接著可將香煙組成物予以加工，以用於香煙或其它吸煙製品中。含有香料前驅化合物之溶液或懸浮液可包括任何一種適合用來分散或分配(噴灑)含香料前驅化合物之顆粒的液體或液體混合物。較佳的液體為水(例如，去離子水)，但也可使用其它液體，例 如醇類。 Any suitable technique can be used to make a cigarette composition comprising a flavor precursor compound, a perfume composition, or a perfume delivery composition. For example, the flavor precursor compound can be added to the cigarette tobacco stock fed to the cigarette maker, or it can be applied to the preformed tobacco column before the cigarette paper is wrapped around the tobacco column. In a particular embodiment, a method for making a cigarette composition includes the step of spraying tobacco with a flavor precursor compound. To facilitate spraying, the perfume precursor compound can be added to a liquid carrier to form a solution or suspension, and the solution or suspension applied to the tobacco. The cigarette composition can then be processed for use in cigarettes or other smoking articles. The solution or suspension containing the perfume precursor compound can include any liquid or liquid mixture suitable for dispersing or dispensing (spraying) the particles of the fragrance-containing precursor compound. The preferred liquid is water (eg, deionized water), but other liquids may also be used, such as Such as alcohols.

香料前驅化合物在漿料中的濃度可以是適合將溶液或懸浮液分配到煙草上的任何量。在液體中包含香料前驅化合物之分散液的此類溶液或懸浮液可含有約0.1重量%且高達約0.5重量%，或約0.2重量%且高達約1重量%的香料前驅化合物。香料前驅化合物可以是乾燥粉末的形式，並且施用於煙草本身。如果使用的是乾燥粉末，可以將它撒在煙草上。將香料前驅化合物摻入煙草香煙組成物的另一種技術係關於將香料前驅化合物添加至用於製造再造煙草之成分的漿料中。該種含有香料前驅化合物的漿料可形成再造煙草薄片，並且可將該薄片切成碎片，以併入香煙組成物桿或其它形式的吸煙製品作為切面填料。 The concentration of the perfume precursor compound in the slurry can be any amount suitable for dispensing the solution or suspension onto the tobacco. Such solutions or suspensions comprising a dispersion of a perfume precursor compound in a liquid may contain from about 0.1% by weight and up to about 0.5% by weight, or from about 0.2% by weight and up to about 1% by weight of the perfume precursor compound. The perfume precursor compound can be in the form of a dry powder and applied to the tobacco itself. If you are using a dry powder, you can sprinkle it on the tobacco. Another technique for incorporating a flavor precursor compound into a tobacco cigarette composition relates to the addition of a perfume precursor compound to a slurry used to make the ingredients of the reconstituted tobacco. The slurry containing the perfume precursor compound can form a reconstituted tobacco sheet, and the sheet can be cut into pieces to incorporate a cigarette composition rod or other form of smoking article as a face filler.

也可以使用均化煙草來製造用於吸煙製品中之氣溶膠產生基材，其在氣溶膠產生裝置中會被加熱。本文中所用的「均化煙草」乙詞係表示由黏聚微粒狀煙草所形成的材料。在船運和製造期間因煙草破損所產生的煙草灰、葉片、莖幹和其它煙草副產品，在精細研磨之後，可與黏合劑混合，以使得煙草微粒黏聚。均化煙草除了香料組成物或香料傳遞組成物之外，可包含其它添加劑，其包括但不限於，氣溶膠形成劑、塑化劑、保濕劑、以及非煙草纖維、填料、水性和非水性溶劑及其組合。均化煙草可以被鑄型、擠壓或滾軋。在本技術領域中已知有數種用於製造均化煙草的再造方法。這些方法包括，但不限於：在例如US 5,724,998中所描述的造 紙方法；在例如US 5,724,998中所描述的鑄型方法；在例如US 3,894,544中所描述的麵糰重組方法；以及在例如GB 983,928中所描述的擠壓方法。 Homogenized tobacco can also be used to make an aerosol-generating substrate for use in smoking articles that can be heated in an aerosol generating device. As used herein, the term "homogenized tobacco" means a material formed by cohesive particulate tobacco. Tobacco ash, leaves, stems and other tobacco by-products resulting from tobacco breakage during shipping and manufacturing may be mixed with the binder after fine grinding to cause the tobacco particles to coagulate. Homogenized tobacco may contain, in addition to the perfume composition or perfume delivery composition, other additives including, but not limited to, aerosol formers, plasticizers, humectants, and non-tobacco fibers, fillers, aqueous and non-aqueous solvents. And their combinations. Homogenized tobacco can be cast, extruded or rolled. Several methods of reconstituting tobacco for making homogenized tobacco are known in the art. These methods include, but are not limited to, those described in, for example, US 5,724,998 A paper process; a casting process as described in, for example, US 5,724,998; a dough reconstitution process as described, for example, in US Pat. No. 3,894,544; and an extrusion process as described, for example, in GB 983,928.

應理解的是，氣溶膠產生基材可具有不同的形狀和大小，其取決於，例如，擬使用之吸煙製品的類型。氣溶膠產生基材可以大致上為三維。例如，氣溶膠產生基材可以是包括複數個本發明之均化煙草材料束的磚或栓塞。或者是，氣溶膠產生基材可以大致上為二維。例如，本發明之氣溶膠產生基材可以是包括複數個均化煙草束的蓆網或薄片。 It should be understood that the aerosol-generating substrate can have different shapes and sizes depending on, for example, the type of smoking article to be used. The aerosol-generating substrate can be substantially three-dimensional. For example, the aerosol-generating substrate can be a brick or plug comprising a plurality of bundles of homogenized tobacco material of the present invention. Alternatively, the aerosol-generating substrate can be substantially two-dimensional. For example, the aerosol-generating substrate of the present invention may be a mesh or sheet comprising a plurality of homogenized tobacco bundles.

香煙組成物中所需之香料前驅化合物的量可以有所變動，其係取決於內含香煙組成物的最終產品。例如，可以將酚糖苷添加到煙草中，以提升傳統吸煙製品(例如香煙、雪茄等)的煙味或香氣。由於此類製品在吸煙時可能已經產生了煙味或香氣，因此可以相對較低的濃度或量來添加本文所述的酚類化合物。相反地，可能希望添加更高濃度或量的酚糖苷至香煙組成物，例如含煙草的氣溶膠產生基材，其將用於組成被氣溶膠化或加熱而未燃燒的吸煙製品中。與傳統的香煙相比，具有氣溶膠產生基材(其含有煙草並且係與氣溶膠產生裝置一起使用)的吸煙製品通常可提供使用者較不強烈的煙味或香氣。它也可能希望在未包括煙草的香煙組成物(如包含非煙草的氣溶膠產生基材)中包含更高濃度或量的酚糖苷。酚糖苷較佳係內含於用於吸煙製品的香煙組成物中，其量可提供使用者類似於傳統吸煙製品(如香煙) 之感受強度。例如，酚糖苷可內含於一種非燃燒式的吸煙製品或是不含煙草的吸煙製品中，其含量係可導致酚類化合物以類似於傳統吸煙製品(如香煙)傳遞給使用者的感受濃度或量釋放或傳遞。 The amount of perfume precursor compound required in the composition of the cigarette may vary depending on the final product containing the composition of the cigarette. For example, phenol glycosides can be added to tobacco to enhance the smoke or aroma of traditional smoking articles such as cigarettes, cigars, and the like. Since such articles may have produced a smoke or aroma when smoking, the phenolic compounds described herein may be added in relatively low concentrations or amounts. Conversely, it may be desirable to add a higher concentration or amount of phenol glycoside to a cigarette composition, such as a tobacco-containing aerosol-generating substrate, which will be used to make up a smoking article that is aerosolized or heated to be unburned. Smoking articles having an aerosol-generating substrate (which contains tobacco and are used with an aerosol generating device) generally provide a less intense smoke or aroma to the user than conventional cigarettes. It may also be desirable to include a higher concentration or amount of phenol glycoside in a cigarette composition that does not include tobacco, such as an aerosol-generating substrate comprising non-tobacco. The phenol glycoside is preferably contained in a cigarette composition for smoking articles in an amount that provides a user with a similar smoking article (such as a cigarette). The intensity of the feeling. For example, a phenolic glycoside may be contained in a non-combustible smoking article or a tobacco-free smoking article in an amount that results in a perceived concentration of the phenolic compound being delivered to the user in a manner similar to conventional smoking articles (eg, cigarettes). Or release or deliver.

在具體實施例中，傳遞給使用者的酚類香料化合物之量可以每次噴煙為基礎來測定。可以使用任何一種適合的方法來測定每次噴煙所傳遞香料化合物的量。例如，可以使用或修改ISO、加拿大衛生部深度抽吸標準(Health Canada Intense)，或者是其它標準或自動化程序來測定每次噴煙的內含量。可使用或修改之ISO方法的實例包括：(i)ISO 4387：1991香煙-使用常規分析吸煙機來測定全部及無尼古丁乾燥物質，1991-10-15；(ii)ISO 8454：1995香煙-測定香煙煙氣氣相中之一氧化碳-NDIR法，1991-11-15；(iii)ISO 10315：1991香煙-測定煙氣冷凝物中之尼古丁-氣相色層分析法，1991-08-01；和(iv)ISO 10362-1：1991香煙-測定煙氣冷凝物中之水分-第1部分：氣相色層分析法，1991-09-15。加拿大衛生部深度抽吸方法是指：加拿大衛生部-官方方法T-115，測定煙草主流煙氣中的「焦油」、尼古丁和一氧化碳，1999年12月。無論採用何種方法，可能希望能測定傳統香煙每一次噴煙所傳遞之香料化合物的量，然後再配製非傳統的吸煙物品，其係在未燃燒的情況下使煙草或其它成分氣溶膠化，而可在每次噴煙時傳遞出類似量的香料化合物。添加至用於此類製品之香煙組成物中的酚糖苷量可以加以改變及測試，以確定需要多少酚糖苷來 傳遞類似量的香料化合物。 In a particular embodiment, the amount of phenolic perfume compound delivered to the user can be determined on a per smoke basis. Any suitable method can be used to determine the amount of perfume compound delivered per puff. For example, the ISO, Health Canada Intense, or other standard or automated procedures can be used or modified to determine the internal content of each puff. Examples of ISO methods that can be used or modified include: (i) ISO 4387: 1991 cigarettes - determination of all and no nicotine dry matter using conventional analytical smoking machines, 1991-10-15; (ii) ISO 8454: 1995 cigarettes - determination One of the carbon oxides in the gas phase of cigarette smoke - NDIR method, 1991-11-15; (iii) ISO 10315: 1991 cigarette - determination of nicotine in gas condensate - gas chromatography, 1991-08-01; (iv) ISO 10362-1:1991 - Determination of moisture in flue gas condensate - Part 1: Gas chromatographic analysis, 1991-09-15. Health Canada's deep pumping method refers to: Health Canada - Official Method T-115, measuring "tar", nicotine and carbon monoxide in tobacco mainstream smoke, December 1999. Regardless of the method used, it may be desirable to determine the amount of perfume compound delivered by each cigarette in a conventional cigarette, and then formulate a non-traditional smoking article that aerosolizes tobacco or other ingredients in the unburned condition. A similar amount of perfume compound can be delivered at each puff. The amount of phenol glycoside added to the cigarette composition used in such articles can be varied and tested to determine how much phenol glycoside is needed A similar amount of perfume compound is delivered.

經由舉例及以下更詳盡的討論，已經發現，當使用加拿大衛生部深度抽吸方法來測量時，傳統香煙可傳遞給抽煙者的癒創木酚量約為每次噴煙100奈克至每次噴煙約300奈克之間。因此，對於非傳統吸煙製品而言，如氣溶膠化煙草成分或其它成分而未燃燒者，希望其含有能夠達到每次噴煙傳遞50奈克或更多的癒創木酚之酚糖苷量，例如每次噴煙約50奈克癒創木酚至約500奈克癒創木酚，或者是每次噴煙約100奈克癒創木酚至約300奈克癒創木酚。 By way of example and more detailed discussion below, it has been found that when measured by the Canadian Department of Health's deep aspiration method, the amount of guaiacol that a conventional cigarette can deliver to a smoker is about 100 ng per squirt per spurt. About 300 Nike. Therefore, for non-traditional smoking articles, such as aerosolized tobacco constituents or other ingredients that are not burned, it is desirable to have a phenolic glycoside amount capable of achieving 50 ng or more of guaiacol per squirt, for example Each smog is about 50 ng guaiacol to about 500 ng guaiacol, or about 100 ng per gram of guaiacol to about 300 ng guaiacol.

當然，每次噴煙所需傳遞香料化合物的量將取決於香料化合物本身。在具體實施例中，吸煙製品被設計為每次噴煙傳遞約5奈克或更多的香料化合物。在具體實施例中，吸煙製品被設計為傳遞每次噴煙約10奈克至1毫克的香料化合物，例如約50奈克/噴煙至約750奈克/噴煙，或者是約75奈克/噴煙至約500奈克/噴煙。 Of course, the amount of perfume compound required to deliver each puff will depend on the perfume compound itself. In a particular embodiment, the smoking article is designed to deliver about 5 nanograms or more of perfume compound per puff. In a particular embodiment, the smoking article is designed to deliver from about 10 ng to 1 mg of perfume compound per puff, such as from about 50 Ng/smoke to about 750 Ng/smoke, or about 75 Ng/smoke to About 500 ng / puff.

添加到香煙組成物中以將所需量之解離香料化合物傳遞給使用者的香料前驅化合物用量係由該製品的成分和設計方式及酚糖苷來決定。 The amount of the perfume precursor compound added to the cigarette composition to deliver the desired amount of the dissociated perfume compound to the user is determined by the composition and design of the article and the phenol glycoside.

當然，可以任何適當的量或濃度將酚糖苷添加到香煙組成物中。在具體實施例中，香煙組成物包含約0.001重量%，更佳為約0.005重量%，還要更佳為約0.01重量%的酚糖苷。在具體實施例中，香煙組成物可包括高達約2重量%的酚糖苷，還要更佳為高達約1重量%的酚糖苷，還要更佳為高達約0.5重量%的酚糖苷， 以及還要更佳為高達約0.02重量%的酚糖苷(所有的重量%係指乾重)。 Of course, the phenol glycoside can be added to the cigarette composition in any suitable amount or concentration. In a particular embodiment, the cigarette composition comprises about 0.001% by weight, more preferably about 0.005% by weight, still more preferably about 0.01% by weight phenol glycoside. In a particular embodiment, the cigarette composition can include up to about 2% by weight phenol glycoside, still more preferably up to about 1% by weight phenol glycoside, still more preferably up to about 0.5% by weight phenol glycoside, And still more preferably up to about 0.02% by weight of phenol glycoside (all % by weight refers to dry weight).

一或多種添加的酚糖苷可能是天然存在於熟化煙草或未熟化煙草中。舉例而言，已發現癒創木酚糖苷[((2R,3S,4S,5R,6S)-2-(羥甲基)-6-(2-甲氧苯氧基)四氫-2H-吡喃-3,4,5-三醇)]存在於煙草中。因此，將合成或純化的酚糖苷添加到煙草中，相對於煙草本身，其將會提高含有煙草之香煙組成物中的酚糖苷濃度。在具體實施例中，合成或純化的酚糖苷被添加到煙草中以形成香煙組成物，其具有酚糖苷的濃度係煙草本身中之濃度的1.5倍或以上。例如，香煙組成物之酚糖苷濃度可以是煙草本身中之的濃度的2倍或以上、2.5倍或以上、3倍或以上、3.5倍或以上、4倍或以上、4.5倍或以上、5倍或以上，7.5倍或以上，或者是10倍或以上。 One or more added phenol glycosides may be naturally present in matured or unripened tobacco. For example, guaiacol glucoside [((2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)tetrahydro-2H-pyridyl has been discovered Anthracene-3,4,5-triol)] is present in tobacco. Thus, the addition or purification of a synthetic or purified phenol glycoside to tobacco will increase the concentration of phenolic glycoside in the tobacco-containing cigarette composition relative to the tobacco itself. In a particular embodiment, the synthetic or purified phenol glycoside is added to the tobacco to form a cigarette composition having a concentration of phenol glycoside that is 1.5 times or more the concentration in the tobacco itself. For example, the concentration of the phenolic glycoside of the cigarette composition may be 2 times or more, 2.5 times or more, 3 times or more, 3.5 times or more, 4 times or more, 4.5 times or more, 5 times of the concentration in the tobacco itself. Or more, 7.5 times or more, or 10 times or more.

一或多種香料前驅物可以任何一種適合的方式添加到香煙組成物中。例如，可將含有香料前驅化合物的香料組成物以溶液、懸浮液或分散液的形式噴灑在煙草上；可將煙草浸漬在酚糖苷的溶液、懸浮液或分散液中；可將酚糖苷的粉末或晶體添加到煙草中；等等。香料前驅化合物可在任何適合的時間添加至煙草中，例如在將煙草處理以摻入吸煙製品等之前或是期間加入。糖苷較佳是能夠在處理期間穩定(亦即，糖苷鍵不會斷裂)。 One or more flavor precursors can be added to the cigarette composition in any suitable manner. For example, the perfume composition containing the perfume precursor compound may be sprayed onto the tobacco in the form of a solution, suspension or dispersion; the tobacco may be impregnated in a solution, suspension or dispersion of the phenol glycoside; the powder of the phenol glycoside may be Or crystals added to tobacco; and so on. The flavor precursor compound can be added to the tobacco at any suitable time, such as before or during the processing of the tobacco to incorporate the smoking article or the like. The glycoside is preferably capable of being stable during processing (i.e., the glycosidic linkage does not break).

舉例而言，煙草的再造可以藉由將煙草粉末、水、甘油、膠豆和纖維素纖維之均質漿料予以乾燥 和鑄型的方式來進行。這種類型的方法被稱為鑄葉方法(cast leaf process)，且其廣泛用於煙草產業以製造用於傳統香煙的再造或均化煙草。鑄葉方法可能涉及施用200℃以下、150℃以下、或在約100至150℃，或100至200℃的範圍內之溫度。因此，如果在鑄葉方法中欲製造包含香料前驅化合物之香煙組成物，該香料前驅化合物較佳是能夠在該溫度下穩定。 For example, tobacco can be reconstituted by drying a homogeneous slurry of tobacco powder, water, glycerin, gum beans and cellulose fibers. And the way of casting. This type of process is known as the cast leaf process and is widely used in the tobacco industry to make reconstituted or homogenized tobacco for use in conventional cigarettes. The cast leaf process may involve application of temperatures below 200 °C, below 150 °C, or in the range of from about 100 to 150 °C, or from 100 to 200 °C. Therefore, if a cigarette composition containing a flavor precursor compound is to be produced in the cast leaf method, the flavor precursor compound is preferably stable at this temperature.

香料前驅化合物的糖苷鍵較佳是在摻入香煙組成物之製品的一般使用條件下進行裂解。舉例而言，加熱而非燃燒煙草以使得煙草成分氣溶膠化的吸煙製品通常是在約200℃下至約300℃的溫度下加熱煙草。因此，當此類製品中含有具有糖苷之香煙組成物時，香料前驅化合物的糖苷鍵較佳是在低於約200℃至約300℃的溫度下裂解。舉另一個例子，煙草的燃燒通常是發生在約400℃的溫度下。因此，當傳統的吸煙製品(如香煙或雪茄)中含有具有糖苷之煙草組成物時，香料前驅化合物的糖苷鍵較佳是在低於約400℃的溫度下裂解。 Preferably, the glycosidic linkage of the perfume precursor compound is cleaved under the general conditions of use of the article incorporating the composition of the cigarette. For example, a smoking article that heats rather than combusts tobacco to aerosolize the tobacco component typically heats the tobacco at a temperature of from about 200 °C to about 300 °C. Thus, when such an article contains a cigarette composition having a glycoside, the glycosidic linkage of the perfume precursor compound is preferably cleaved at a temperature below about 200 ° C to about 300 ° C. As another example, the burning of tobacco typically occurs at a temperature of about 400 °C. Thus, when a conventional smoking article (such as a cigarette or cigar) contains a tobacco composition having a glycoside, the glycosidic linkage of the flavor precursor compound is preferably cleaved at a temperature below about 400 °C.

在具體實施例中，香料前驅化合物的糖苷鍵是在約150℃或更高的溫度下裂解，以釋放出本發明之香料化合物。在具體實施例中，香料前驅化合物的糖苷鍵是在約400℃或更低的溫度下裂解。在具體實施例中，香料前驅化合物的糖苷鍵是在約100℃至約400℃的溫度下裂解，如約150℃至約300℃之間，或約200℃至約300℃之間。 In a particular embodiment, the glycosidic linkage of the perfume precursor compound is cleaved at a temperature of about 150 ° C or higher to liberate the perfume compound of the present invention. In a particular embodiment, the glycosidic linkage of the perfume precursor compound is cleaved at a temperature of about 400 ° C or less. In a particular embodiment, the glycosidic linkage of the perfume precursor compound is cleaved at a temperature of from about 100 ° C to about 400 ° C, such as between about 150 ° C to about 300 ° C, or between about 200 ° C to about 300 ° C.

本文中所使用之煙草組成物係指稱包含煙草 和香料前驅化合物之香煙組成物，且其可以用來製造任何一種希望能具有較強烈煙味香韻之適合的吸煙製品。例如，煙草組成物可以用於傳統的吸煙製品中，或者是使用氣溶膠產生基材的吸煙製品中。煙草組成物可以是含有各種不同來源之煙草類型及黏合劑和保濕劑之再造煙草。保濕劑有利於氣溶膠的產生。當加熱時，保濕劑蒸發並且重新冷凝成小液滴，以產生可見的氣溶膠。香料前驅組成物的糖苷鍵較佳是在使用的情況下裂解，而不是在儲存、加工或製造的情況下裂解。 The tobacco composition used herein refers to tobacco And a cigarette composition of a flavor precursor compound, and which can be used to make any suitable smoking article that is desired to have a strong smoke flavor. For example, the tobacco composition can be used in a conventional smoking article or in a smoking article that uses an aerosol-generating substrate. The tobacco composition can be a reconstituted tobacco containing a variety of different types of tobacco types and binders and humectants. Humectants are good for aerosol production. When heated, the humectant evaporates and recondenses into small droplets to produce a visible aerosol. The glycosidic linkage of the perfume precursor composition is preferably cleavable in the case of use, rather than cleavage in the case of storage, processing or manufacture.

如果是可燃燒的吸煙製品，如香煙，則香煙組成物可以用於具有煙草基材之吸煙製品的任何部分，例如傳統香煙的煙桿、或是傳統香煙的一或多段濾嘴中。如果是其中香煙組成物或其成分並未燃燒的吸煙製品，則香煙組成物可以用於具有氣溶膠產生基材之吸煙製品的任何部分。 In the case of a flammable smoking article, such as a cigarette, the cigarette composition can be used in any part of a smoking article having a tobacco substrate, such as a tobacco rod of a conventional cigarette, or one or more filters of a conventional cigarette. If it is a smoking article in which the cigarette composition or component thereof is not burned, the cigarette composition can be applied to any portion of the smoking article having the aerosol-generating substrate.

101‧‧‧吸煙製品 101‧‧‧Smoking products

102‧‧‧吸煙製品 102‧‧‧Smoking products

103‧‧‧前端栓塞 103‧‧‧ front end embolization

104‧‧‧熱源 104‧‧‧heat source

105‧‧‧口件濾嘴 105‧‧‧ mouthpiece filter

106‧‧‧氣溶膠產生基材 106‧‧‧Aerosol generating substrate

107‧‧‧傳送段 107‧‧‧Transport

108‧‧‧膨脹室 108‧‧‧Expansion room

109‧‧‧中空醋酸纖維素管 109‧‧‧ hollow cellulose acetate tube

110‧‧‧口件 110‧‧‧ mouthpieces

111‧‧‧氣溶膠產生基材 111‧‧‧Aerosol generating substrate

112‧‧‧捲煙紙 112‧‧‧cigarette paper

113‧‧‧加熱元件 113‧‧‧ heating elements

114‧‧‧耐熱塗層 114‧‧‧heat resistant coating

115‧‧‧捲煙紙 115‧‧‧cigarette paper

116‧‧‧中央氣流通道 116‧‧‧Central airflow channel

117‧‧‧隔熱套管 117‧‧‧Insulation casing

118‧‧‧均化煙草材料 118‧‧‧Homogeneous tobacco materials

119‧‧‧氣溶膠產生裝置 119‧‧‧Aerosol generating device

120‧‧‧栓塞捲紙 120‧‧‧ Embossed roll paper

121‧‧‧鞘 121‧‧‧sheath

122‧‧‧導熱元件 122‧‧‧thermal element

124‧‧‧開口式硬紙管 124‧‧‧Open cardboard tube

126‧‧‧醋酸纖維素絲束 126‧‧‧cellulose acetate tow

128‧‧‧濾嘴栓塞捲紙 128‧‧‧Filter plug paper

第1圖顯示一種其中香煙組成物並未燃燒的吸煙製品之示意圖；第2圖顯示一種當與吸食裝置接合時係藉由電熱源加熱之吸煙製品；第3圖顯示癒創木酚糖苷在熱脫附器中加熱之離子偵測結果；第4圖顯示被捕集的氣溶膠藉由穩定同位素稀釋分析(SIDA)法測定癒創木酚濃度之結果。 Figure 1 shows a schematic view of a smoking article in which the composition of the cigarette is not burned; Figure 2 shows a smoking article which is heated by an electric heat source when engaged with the smoking device; Figure 3 shows that the guaiacol glucoside is in heat The ion detection results of heating in the desorber; Figure 4 shows the results of the guaiacol concentration determined by the stable isotope dilution analysis (SIDA) method for the trapped aerosol.

藉由參考第1圖來做舉例說明，其顯示一個非限制性吸煙製品102(其中香煙組成物並未燃燒)的示意圖。如第1圖所示，吸煙製品102包括可燃熱源104、氣溶膠產生基材106、細長的膨脹室108及同軸對接之口件110，其皆被低透氣性捲煙紙112的外包裝所包覆。 By way of example with reference to Figure 1, it shows a schematic representation of a non-limiting smoking article 102 in which the cigarette composition is not burned. As shown in FIG. 1, the smoking article 102 includes a combustible heat source 104, an aerosol generating substrate 106, an elongated expansion chamber 108, and a coaxially butted mouthpiece 110, both of which are covered by an outer package of the low permeability cigarette paper 112. .

可燃熱源104是一種熱解的多孔碳系熱源。可燃熱源104為圓柱形，且包括一個中央氣流通道116，其係縱向延伸穿過可燃熱源104。在中央氣流通道116的內表面上配置一種實質上不透氣的氧化鐵耐熱塗層114。氣溶膠產生基材106緊接著位於可燃熱源104的下游處，並且其包含均化煙草材料118的圓柱形栓塞並且被栓塞捲紙120所環繞，該均化煙草材料118含有香料前驅化合物及做為氣溶膠形成劑的甘油。均化煙草材料118係由縱向排列之擠壓煙草材料細絲所構成。 The combustible heat source 104 is a pyrolyzed porous carbon-based heat source. The combustible heat source 104 is cylindrical and includes a central airflow passage 116 that extends longitudinally through the combustible heat source 104. A substantially gas impermeable iron oxide heat resistant coating 114 is disposed on the inner surface of the central gas flow passage 116. The aerosol-generating substrate 106 is located immediately downstream of the combustible heat source 104 and includes a cylindrical plug of homogenized tobacco material 118 surrounded by a plug wrap 120 that contains a flavor precursor compound and Aerosol forming agent glycerin. The homogenized tobacco material 118 is comprised of longitudinally aligned extruded tobacco material filaments.

導熱元件122係由環繞的鋁箔管所構成，並且其係與可燃熱源104的後段及氣溶膠產生基材106鄰接的前段接觸。如第1圖所示，氣溶膠產生基材106的後段並未被導熱元件122所包圍。 The thermally conductive element 122 is comprised of a circumferential aluminum foil tube and is in contact with the anterior segment of the combustor heat source 104 and the aerosol generating substrate 106. As shown in FIG. 1, the rear section of the aerosol-generating substrate 106 is not surrounded by the heat-conducting element 122.

細長的膨脹室108係位於氣溶膠產生基材106的下游，並且包含開口式硬紙管124。吸煙製品102的口件110係位於膨脹室108的下游，其包含過濾效率非常低的醋酸纖維素絲束126圓柱形栓塞，其係被濾嘴栓塞捲紙128所環繞。口件110可被外層紙(tipping paper)(圖中未顯示)環繞。吸煙製品102的尺寸可與傳統 的香煙類似。 The elongated expansion chamber 108 is located downstream of the aerosol-generating substrate 106 and includes an open cardboard tube 124. The mouthpiece 110 of the smoking article 102 is located downstream of the expansion chamber 108 and contains a cylindrical plug of cellulose acetate tow 126 having a very low filtration efficiency, which is surrounded by the filter plug wrap 128. The mouthpiece 110 can be surrounded by a tipping paper (not shown). The size of the smoking article 102 can be compared to the traditional The cigarettes are similar.

使用時，使用者將可燃碳系熱源104點燃，接著經由中央氣流通道116向下游口件110處抽吸空氣。氣溶膠產生基材106的前段主要是經由鄰接可燃熱源104之未燃燒後段及導熱元件122的傳導來加熱。當吸入之空氣通過中央氣流通道116時將被加熱，接著經由對流來加熱氣溶膠產生基材106。氣溶膠產生基材106之加熱將釋放出揮發及半揮發性的化合物，包括解離的香料化合物以及來自氣溶膠形成基材118的甘油，其在受熱的吸入之空氣流過氣溶膠產生基材時被挾帶在其中。 In use, the user ignites the combustible carbon-based heat source 104 and then draws air through the central airflow passage 116 to the downstream mouthpiece 110. The front section of the aerosol-generating substrate 106 is primarily heated via conduction adjacent the unburned rear section of the combustible heat source 104 and the thermally conductive element 122. The inhaled air will be heated as it passes through the central airflow passage 116, and then the aerosol-generating substrate 106 is heated via convection. Heating of the aerosol-generating substrate 106 will release volatile and semi-volatile compounds, including dissociated perfume compounds and glycerol from the aerosol-forming substrate 118, as the heated inhaled air flows through the aerosol-generating substrate. Being taken in it.

受熱的空氣和挾帶的化合物向下游通過膨脹室108，冷卻和冷凝，形成通過口件而(在大約室溫之下)進入使用者口中的氣溶膠。 The heated air and entrained compounds pass downstream through the expansion chamber 108, cool and condense, forming an aerosol that enters the user's mouth through the mouthpiece (at about room temperature).

為了製作吸煙製品102，將矩形的導熱元件122黏在捲煙紙112上。將熱源104、氣溶膠產生基材106的栓塞和膨脹室108適當地對準，並且定位於已黏貼導熱元件122的捲煙紙112上。已黏貼導熱元件122的捲煙紙112係包圍著熱源104的後段、氣溶膠產生基材106和膨脹室108，並且予以膠合。口件110係使用已知的濾嘴接合技術附接於膨脹室的開口端。 To make the smoking article 102, a rectangular thermally conductive element 122 is adhered to the cigarette paper 112. The heat source 104, the plug of the aerosol-generating substrate 106, and the expansion chamber 108 are properly aligned and positioned on the cigarette paper 112 that has been adhered to the thermally conductive element 122. The cigarette paper 112 to which the heat conductive member 122 has been attached surrounds the rear portion of the heat source 104, the aerosol generating substrate 106, and the expansion chamber 108, and is glued. The mouthpiece 110 is attached to the open end of the expansion chamber using known filter joining techniques.

在加熱吸煙物品的另一個實施例中，包含香料前驅化合物的香煙組成物係與如電熱源等未燃燒的熱源直接接觸。第2圖顯示的是一種當與吸食裝置接合時係藉由電熱源加熱之吸煙製品。吸煙製品101包括前端 栓塞103、氣溶膠產生基材111、中空醋酸纖維素管109、傳送段107、及口件濾嘴105。這五種元件係依序且同軸對準排列，並且係藉由捲煙紙115來組裝，以形成煙桿。煙桿具有嘴端和遠端，使用者在使用時將嘴端***他或她的口內，而遠端則是位於煙桿嘴端的另一端。在組裝時，煙桿15為52毫米長，並有直徑為7.2毫米。前端栓塞103為圓柱狀的醋酸纖維素絲束。氣溶膠產生基材111位於前端栓塞103的下游，並且包括包在濾嘴紙內的一束捲曲的鑄葉煙草。鑄葉煙草包括添加劑，其包含甘油做為氣溶膠形成劑。管109緊接著位於氣溶膠產生基材111的下游處，並且係由醋酸纖維素所形成。傳送段107可讓包括氣溶膠產生基材111釋放之香料化合物的揮發性物質經由煙桿朝向嘴端通過。揮發性物質可在傳送段107內冷卻，以形成氣溶膠。口件濾嘴105係由醋酸纖維素絲束形成的傳統口件濾嘴。上述指定的元件係藉由緊密包裹在捲煙紙115中的方式來組合。 In another embodiment of heating a smoking article, the cigarette composition comprising the flavor precursor compound is in direct contact with an unburned heat source such as an electric heat source. Figure 2 shows a smoking article that is heated by an electric heat source when engaged with a smoking device. Smoking article 101 includes a front end The plug 103, the aerosol generating substrate 111, the hollow cellulose acetate tube 109, the transfer section 107, and the mouthpiece filter 105. The five components are sequentially and coaxially aligned and assembled by cigarette paper 115 to form a tobacco rod. The tobacco rod has a mouth end and a distal end, the user inserts the mouth end into his or her mouth when in use, and the distal end is located at the other end of the mouth end of the tobacco rod. When assembled, the tobacco rod 15 is 52 mm long and has a diameter of 7.2 mm. The front end plug 103 is a cylindrical cellulose acetate tow. The aerosol-generating substrate 111 is located downstream of the front end plug 103 and includes a bundle of crimped cast tobacco that is wrapped within the filter paper. Cast leaf tobacco includes an additive comprising glycerin as an aerosol former. The tube 109 is located immediately downstream of the aerosol-generating substrate 111 and is formed of cellulose acetate. The transfer section 107 allows the volatile substance including the fragrance compound released from the aerosol-generating substrate 111 to pass through the tobacco rod toward the mouth end. The volatile material can be cooled in the transfer section 107 to form an aerosol. The mouthpiece filter 105 is a conventional mouthpiece filter formed of cellulose acetate tow. The above-specified elements are combined by being tightly wrapped in the cigarette paper 115.

氣溶膠產生裝置119包括用來承接吸煙製品101以利吸食之鞘121。加熱元件113位於鞘121內且定位在可與吸煙製品101的遠端接合的位置。加熱元件113的形狀為末端為尖點的刀刃狀。當吸煙製品101被壓入鞘時，加熱元件113的尖點將首先與前端栓塞103接合，然後刺入氣溶膠產生基材111中。當吸煙製品101與氣溶膠產生裝置119適當的接合時，加熱元件113係位於氣溶膠產生基材111內。由加熱元件113產生的熱經由傳導和對流傳遞到含有香料前驅化合物的氣溶膠產生基 材111內。絕緣套管117可圍繞加熱元件113的一部分，其係與前端栓塞103接觸，並保護其不會燒毀或燒熔。當然，應理解的是，有關第1圖和第2圖所述之吸煙製品僅為可使用包含本文所述香料前驅化合物之香煙組成物的兩個吸煙製品實例。可進一步理解的是，也可以使用不同於第1圖和第2圖所述之相關方法來製造包括具有香料前驅化合物之香煙組成物的吸煙製品。 The aerosol generating device 119 includes a sheath 121 for receiving the smoking article 101 for ingestion. The heating element 113 is located within the sheath 121 and is positioned in a position engageable with the distal end of the smoking article 101. The shape of the heating element 113 is a blade shape having a pointed end. When the smoking article 101 is pressed into the sheath, the sharp point of the heating element 113 will first engage the front end plug 103 and then penetrate into the aerosol generating substrate 111. When the smoking article 101 is properly engaged with the aerosol generating device 119, the heating element 113 is located within the aerosol generating substrate 111. The heat generated by the heating element 113 is transferred via conduction and convection to an aerosol generating base containing a perfume precursor compound. Inside the material 111. The insulating sleeve 117 can surround a portion of the heating element 113 that is in contact with the front end plug 103 and protects it from burning or burning. Of course, it should be understood that the smoking articles described in Figures 1 and 2 are merely examples of two smoking articles in which a cigarette composition comprising a flavor precursor compound described herein can be used. It will be further appreciated that smoking articles comprising a cigarette composition having a flavor precursor compound can also be made using methods other than those described in Figures 1 and 2.

可以使用任何一種適合的方法來製造包括具有香料前驅化合物之香煙組成物的吸煙製品。一般而言，用於製造包括具有香料前驅化合物之香煙組成物的吸煙製品之方法包括：將香料前驅化合物或香料傳遞組成物添加或摻入香煙組成物中，如煙草或其它基材；以及將香煙組成物摻入吸煙物品中。 Any suitable method can be used to make a smoking article comprising a cigarette composition having a flavor precursor compound. In general, a method for making a smoking article comprising a cigarette composition having a flavor precursor compound comprises: adding or incorporating a flavor precursor compound or a perfume delivery composition into a cigarette composition, such as tobacco or other substrate; The cigarette composition is incorporated into a smoking article.

一般而言及如本文所述，為了增進香煙組成物之香煙氣味或香韻的方法包括將香料前驅化合物或香料傳遞組成物添加至香煙組成物中。香料前驅化合物的糖苷鍵在加熱時被水解，而造成香料化合物的解離。當吸煙者使用(燃燒或加熱)吸煙製品時，香料前驅化合物就會被加熱。 In general and as described herein, a method for enhancing the odor or aroma of a cigarette of a cigarette composition comprises adding a flavor precursor compound or a perfume delivery composition to the composition of the cigarette. The glycosidic bond of the perfume precursor compound is hydrolyzed upon heating to cause dissociation of the perfume compound. When a smoker uses (burns or heats) a smoking article, the flavor precursor compound is heated.

除非另有說明，本文所使用的所有科學及技術名詞係具有本技術領域通常使用的意涵。本文所提供的定義是為了便於瞭解本文頻繁使用的某些術語。 Unless otherwise indicated, all scientific and technical terms used herein have the meaning commonly employed in the art. The definitions provided in this article are intended to facilitate the understanding of certain terms used frequently in this article.

在本發明說明書及附帶的專利申請範圍中所用的「一個」和「該」之單數形式，除非內容中清楚的明確指出，其係涵蓋具有複數對象的具體實施例。 The singular forms "a", "the", and "the"

在本發明申請書及附帶的專利申請範圍中所用的「或」乙詞，除非內容中清楚的明確指出，否則一般通常係包括「和/或」的意思。 The word "or" used in the scope of the present application and the accompanying patent application generally includes the meaning of "and/or" unless the context clearly dictates otherwise.

在本文中所使用的「具有」、「包括」、「包含」等用語係代表開放式的意涵，並且通常是指「包括，但不限於」。應理解的是，「基本上由......組成」、「由......組成」等用語均歸入「包含」等範疇內。 The terms "having", "including" and "including" as used herein mean an open-ended meaning and generally mean "including, but not limited to". It should be understood that terms such as "consisting essentially of" and "consisting of" are all included in the category of "including".

以下提供的是說明在此所揭示之化合物、組成物、方法及製品的某些方面之非限制性實施例。 Provided below are non-limiting examples illustrating certain aspects of the compounds, compositions, methods, and articles of manufacture disclosed herein.

實施例Example

實施例1：具有煙味香韻的化合物之評估Example 1: Evaluation of Compounds with Smoke Flavor

將文獻和其它來源中描述過的四十五種化合物列為具有煙味香韻特性之候選材料。某些化合物是由感官專家小組來進行測試，並且相對於癒創木酚之煙味香韻進行比較，癒創木酚已被測定為最能夠正確觸發煙味感覺。雖然有一些化合物也能夠引起煙味香韻，但會呈現出其它干擾或削弱煙味香韻的額外香韻。例如，2-甲氧基硫酚具有一些煙味特性，但同時具有更重的肉類香韻。許多其它化合物經測定並無法引起煙味的感覺。 Forty-five compounds described in the literature and other sources are listed as candidate materials with smoke flavor characteristics. Certain compounds were tested by a panel of sensory experts and compared to the scent of guaiacol, guaiacol has been determined to best trigger the scent of smoke. Although some compounds can also cause aromas of smoke, they present additional scent that interferes with or weakens the scent of smoke. For example, 2-methoxythiophenol has some smoke odor characteristics, but at the same time has a heavier meat flavor. Many other compounds have been tested and do not give a feeling of smoke.

雖然以癒創木酚做為領先測試的例子，也可指定具有類似所需煙味特性的其它酚類化合物。這些化合物包括2,6-二甲氧基酚(CAS 91-10-1)；鄰-甲酚、間-甲酚或對-甲酚；3-乙基酚(CAS 123-07-9)；4-異丙基酚(CAS 99-89-8)；及2,3-二甲基酚(CAS 526-75-0)。 Although guaiacol is used as an example of leading testing, other phenolic compounds having similar desirable flavor characteristics can also be specified. These compounds include 2,6-dimethoxyphenol (CAS 91-10-1); o-cresol, m-cresol or p-cresol; 3-ethylphenol (CAS 123-07-9); 4-isopropylphenol (CAS 99-89-8); and 2,3-dimethylphenol (CAS 526-75-0).

實施例2：由吸煙製品中的癒創木酚糖苷釋放出癒創木酚Example 2: Release of guaiacol from guaiacol glucoside in smoking articles

合成癒創木酚((2R,3S,4S,5R,6S)-2-(羥甲基)-6-(2-甲氧苯氧基)四氫-2H-吡喃-3,4,5-三醇)的糖苷，並且以熱脫附器初始測試的結果顯示其會在加熱時釋放出癒創木酚。如第3圖所示，其係顯示當癒創木酚糖苷在熱脫附器中加熱時(尤其是)對於癒創木酚離子的偵測，癒創木酚由糖苷釋出的起始溫度約為222℃。這種釋放溫度非常適合加熱而非燃燒煙草的吸煙製品，以增加此種製品所產生之氣溶膠中的煙味香韻。 Synthesis of guaiacol ((2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5 - Triol) glycoside, and as a result of initial testing with a thermal desorber, it shows that guaiacol is released upon heating. As shown in Figure 3, it shows the initial temperature at which guaiacol is released from glycosides when guaiacol glycoside is heated in a thermal desorber (especially) for the detection of guaiacol ions. It is about 222 °C. This release temperature is well suited for smoking, rather than smoking, smoking articles to increase the smell of smoke in the aerosols produced by such products.

同樣如第3圖中所示，較低量的乙酸離子會在約250℃的起始溫度下被偵測到。 As also shown in Figure 3, a lower amount of acetate ions will be detected at an initial temperature of about 250 °C.

其次，將各種不同濃度的癒創木酚糖苷摻入煙草中。摻料煙草的栓塞被內含於加熱但非燃燒煙草的吸煙製品中。第一吸煙製品包括第一煙草摻混物(摻混物A，無熱交換器)，且第二吸煙製品包括第二煙草摻混物(摻混物B，具有熱交換器)。 Second, various concentrations of guaiacols glycosides were incorporated into the tobacco. The plug incorporating tobacco is contained in a smoking article that is heated but not burned. The first smoking article comprises a first tobacco blend (blend A, no heat exchanger) and the second smoking article comprises a second tobacco blend (blend B, with a heat exchanger).

依加拿大衛生部深度抽吸方法之規範抽吸該物品，並且將超過12次噴煙所產生的氣溶膠收集於冷阱中。被捕集的氣溶膠的癒創木酚濃度已藉由穩定同位素稀釋分析(SIDA)法來測定。其結果呈現於第4圖。 The article was aspirated according to the Canadian Department of Health's deep suction method and the aerosol produced by more than 12 soots was collected in a cold trap. The guaiacol concentration of the trapped aerosol has been determined by the stable isotope dilution analysis (SIDA) method. The result is presented in Figure 4.

如第4圖所示，當藉由在第一吸煙製品中之煙草內的電性裝置加熱時，癒創木酚-糖苷傳遞高的癒創木酚產量(摻混物A，無熱交換器，HX)，(第4圖中的上半部曲線)。在第一吸煙製品上添加1毫克癒創木酚糖苷 可導致超過3000奈克/噴煙的癒創木酚釋出，此數值超過於市售品牌的傳統香煙中所觀察之癒創木酚濃度(未顯示於第4圖中)的10倍。另外，第二吸煙製品(摻混物B，具有熱交換器，HX)(第4圖中的下半部綠色曲線)顯示其癒創木酚的釋放量相對於市售品牌的傳統香煙為較高的情形，但明顯低於無熱交換器之吸煙製品。從前面的實驗中可知，具有羥基的化合物(特別是酚類化合物(如癒創木酚))會被熱交換器所捕集。 As shown in Figure 4, guaiacol-glycoside delivers high guaiacol yield when heated by electrical means in the tobacco in the first smoking article (blend A, no heat exchanger) , HX), (the upper half of the curve in Figure 4). Add 1 mg of guaiacol glucoside to the first smoking article Can be caused to release more than 3000 ng/smoke of guaiacol, which is more than 10 times the guaiacol concentration (not shown in Figure 4) observed in conventional cigarettes of the commercial brand. In addition, the second smoking article (blend B, with heat exchanger, HX) (the lower half of the green curve in Figure 4) shows that the release of guaiacol is comparable to that of a commercial brand of traditional cigarettes. High, but significantly lower than smoking articles without heat exchangers. It has been known from previous experiments that compounds having a hydroxyl group (especially phenolic compounds such as guaiacol) are trapped by a heat exchanger.

接著，考慮在加拿大衛生部深度抽吸方法的規範下，於12次噴煙所傳遞的癒創木酚量，計算相對於每個栓塞所摻入的前驅物之初始量的轉化產率(以莫耳%來表示)。雖然沒有熱交換器之吸煙製品的轉化產率約為10莫耳%，但具有熱交換器的吸煙製品卻只有1莫耳%。然而，加入相當低量的癒創木酚糖苷卻仍可達到癒創木酚的目標濃度(150-250奈克/噴煙，其係於市售品牌傳統香煙所觀察到者)。 Next, consider the amount of guaiacol delivered in 12 puffs under the Canadian Department of Health's deep pumping method, and calculate the conversion yield relative to the initial amount of precursor incorporated into each plug. % of the ear to indicate). Although the conversion yield of a smoking article without a heat exchanger is about 10 mol%, the smoking article with a heat exchanger is only 1 mol%. However, the addition of a relatively low amount of guaiacol glucoside can still achieve the target concentration of guaiacol (150-250 Ng/spray, which is observed in commercial brands of conventional cigarettes).

由於只有部分的煙草被加熱且只有部分的前驅物在12次噴煙期間被降解，轉化產率明顯低於100%。結果如下表1所示。 Since only a portion of the tobacco was heated and only a portion of the precursor was degraded during 12 puffs, the conversion yield was significantly less than 100%. The results are shown in Table 1 below.

*氣溶膠中的濃度(12次噴煙/吸煙製品的總和)與每個栓塞摻入量之間的關係，以莫耳單位表示。該栓塞包含280毫克的煙草。 * The relationship between the concentration in the aerosol (the sum of 12 puff/smoking articles) and the amount of each embedding, expressed in mole units. The plug contains 280 mg of tobacco.

102‧‧‧吸煙製品 102‧‧‧Smoking products

104‧‧‧熱源 104‧‧‧heat source

106‧‧‧氣溶膠產生基材 106‧‧‧Aerosol generating substrate

108‧‧‧膨脹室 108‧‧‧Expansion room

110‧‧‧口件 110‧‧‧ mouthpieces

112‧‧‧捲煙紙 112‧‧‧cigarette paper

114‧‧‧耐熱塗層 114‧‧‧heat resistant coating

116‧‧‧中央氣流通道 116‧‧‧Central airflow channel

118‧‧‧均化煙草材料 118‧‧‧Homogeneous tobacco materials

120‧‧‧栓塞捲紙 120‧‧‧ Embossed roll paper

122‧‧‧導熱元件 122‧‧‧thermal element

124‧‧‧開口式硬紙管 124‧‧‧Open cardboard tube

126‧‧‧醋酸纖維素絲束 126‧‧‧cellulose acetate tow

128‧‧‧濾嘴栓塞捲紙 128‧‧‧Filter plug paper

Claims (14)

一種香煙組成物，包括：化學合成的酚糖苷化合物，其中該酚糖苷之糖苷鍵裂解造成具有以下結構之酚類化合物的釋出： 其中R¹、R²、R³、R⁴和R⁵係各自獨立選自由(i)H和(ii)C1-C5直鏈或支鏈烷基或烷氧基所構成之群組，其中該烷基或烷氧基未經取代或是經鹵素或羥基取代，其中一或多個R¹、R²、R³、R⁴和R⁵為C1-C5直鏈或支鏈的烷基或烷氧基，其中該酚類化合物具有煙味香韻(smoky flavor note)。 A cigarette composition comprising: a chemically synthesized phenol glycoside compound, wherein the cleavage of the glucoside of the phenolic glycoside results in the release of a phenolic compound having the following structure: Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently selected from the group consisting of (i)H and (ii) a C1-C5 linear or branched alkyl or alkoxy group, wherein Alkyl or alkoxy is unsubstituted or substituted by halogen or hydroxy, wherein one or more of R ¹ , R ² , R ³ , R ⁴ and R ⁵ are C1-C5 straight or branched alkyl or alkane An oxy group wherein the phenolic compound has a smoky flavor note. 如請求項1之香煙組成物，其中R¹、R²、R³、R⁴和R⁵係各自獨立選自由(i)氫和(ii)C1-C5直鏈或支鏈烷基或烷氧基所構成之群組，其中該烷基或烷氧基未經取代。 The cigarette composition of claim 1, wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently selected from (i) hydrogen and (ii) C1-C5 linear or branched alkyl or alkoxy A group consisting of a group in which the alkyl or alkoxy group is unsubstituted. 如請求項1之香煙組成物，其中該酚類化合物為癒創木酚。 The cigarette composition of claim 1, wherein the phenolic compound is guaiacol. 如請求項1之香煙組成物，其中該酚類化合物係選自由2,6-二甲氧基酚、3-乙基酚、鄰甲酚、間甲酚、對甲酚、4-異丙基酚和2,3-二甲基酚所構成之群組。 The cigarette composition of claim 1, wherein the phenolic compound is selected from the group consisting of 2,6-dimethoxyphenol, 3-ethylphenol, o-cresol, m-cresol, p-cresol, 4-isopropyl A group consisting of phenol and 2,3-dimethylphenol. 如前述請求項中任一項之香煙組成物，其中該酚糖苷的糖基(glycone)部分是單醣基團、雙醣基團、三醣基團，或其衍生物，其中一或多個保護基被用來取代該單醣、雙醣或三醣基團的一或多個羥基中的一或多個氫原子。 A cigarette composition according to any one of the preceding claims, wherein the glyco moiety of the phenol glycoside is a monosaccharide group, a disaccharide group, a trisaccharide group, or a derivative thereof, wherein one or more A protecting group is used to replace one or more of the one or more hydroxyl groups of the monosaccharide, disaccharide or trisaccharide group. 如前述請求項中任一項之香煙組成物，其中該單醣基團為葡萄糖基團。 A cigarette composition according to any of the preceding claims, wherein the monosaccharide group is a glucose group. 如請求項1之香煙組成物，其中該酚糖苷為癒創木酚葡萄糖苷。 The cigarette composition of claim 1, wherein the phenol glycoside is guaiacol glucoside. 如前述請求項中任一項之香煙組成物，其中該酚糖苷之糖苷鍵裂解係在約140℃以上的溫度下發生。 A cigarette composition according to any one of the preceding claims, wherein the glucoside linkage cleavage of the phenol glycoside occurs at a temperature above about 140 °C. 如前述請求項中任一項之香煙組成物，其中該酚糖苷之糖苷鍵裂解係在約400℃以下的溫度下發生。 A cigarette composition according to any of the preceding claims, wherein the glucoside linkage cleavage of the phenol glycoside occurs at a temperature below about 400 °C. 如前述請求項中任一項之香煙組成物，其中該酚糖苷的糖苷鍵裂解係在約200℃至約300℃的溫度下發生。 A cigarette composition according to any of the preceding claims, wherein the glycosidic linkage cleavage of the phenolic glycoside occurs at a temperature of from about 200 °C to about 300 °C. 如前述請求項中任一項之香煙組成物，其還進一步包含煙草。 A cigarette composition according to any of the preceding claims, which further comprises tobacco. 一種吸煙製品，其包含前述請求項中任一項之組成物。 A smoking article comprising the composition of any of the preceding claims. 如請求項12之吸煙製品，其包含一種氣溶膠形成基材，其中該基材包含該香煙組成物。 A smoking article according to claim 12, which comprises an aerosol-forming substrate, wherein the substrate comprises the cigarette composition. 如請求項13之吸煙製品，其中該製品被設計為傳遞 每次噴煙約10奈克的香料化合物至每次噴煙1毫克的香料化合物。 The smoking article of claim 13, wherein the article is designed to be delivered Approximately 10 ng of perfume compound per squirt to 1 mg of perfume compound per squirt.