TW202128603A - 醛化合物及其製造方法、以及香料組成物 - Google Patents
醛化合物及其製造方法、以及香料組成物 Download PDFInfo
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- TW202128603A TW202128603A TW109135899A TW109135899A TW202128603A TW 202128603 A TW202128603 A TW 202128603A TW 109135899 A TW109135899 A TW 109135899A TW 109135899 A TW109135899 A TW 109135899A TW 202128603 A TW202128603 A TW 202128603A
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- Prior art keywords
- fragrance
- formula
- methyl
- compound
- aldehyde
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- 239000003205 fragrance Substances 0.000 title claims abstract description 128
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- -1 Aldehyde compound Chemical class 0.000 title abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 22
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 16
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000005882 aldol condensation reaction Methods 0.000 claims description 4
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- 239000002994 raw material Substances 0.000 abstract description 10
- 239000004480 active ingredient Substances 0.000 abstract description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 25
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
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- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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Abstract
本發明提供作為香料及調合香料素材或其原料係有用且新穎的醛化合物及其製造方法、以及含有上述化合物並將其作為有效成分之香料組成物、以及將該化合物作為香料使用之用途。有關以下列式(1)表示之化合物。
Description
本發明有關作為香料係有用且新穎的第一醛化合物及其製造方法、以及含有該醛化合物之香料組成物,又有關作為上述第一醛化合物之原料係有用的第二醛化合物。
具有香氣、香味之化合物,作為香料成分係極其有用,一直以來,烷基苯甲醛、其衍生物作為香料用途、香料原料之利用係受到注目。
專利文獻1揭示3-(4-(第二丁基)-2-甲基苯基)丙醛、及3-(4-異丁基-2-甲基苯基)-2-甲基丙醛具有香氣。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開2018-138550號公報
[發明所欲解決之課題]
本發明之課題為提供作為香料及調合香料素材係有用且新穎的第一醛化合物及其製造方法、以及含有上述第一醛化合物並將其作為有效成分之香料組成物、以及將該化合物作為香料使用之用途。又,本發明之課題為提供作為上述第一醛化合物之原料係有用且新穎的第二醛化合物。
[解決課題之手段]
本案發明人,在合成各種化合物並針對其香氣進行研究之後,發現特定的醛化合物具有鈴蘭(Muguet)調的香氣而完成了本發明。
本發明,提供以下之<1>~<6>。
<1>一種化合物,以下列式(1)表示。
<2>如<1>之化合物,其中,R為氫原子。
<3>一種香料組成物,含有如<1>或<2>之化合物。
<4>一種化合物之用途,將如<1>或<2>之化合物作為香料使用之用途。
<5>一種化合物,以下列式(2)表示。
<6>一種式(1)表示之化合物之製造方法,按順序具有以下步驟:
將式(2)表示之化合物與乙醛或丙醛進行醛醇縮合,獲得式(3)表示之化合物,
將式(3)表示之化合物予以氫化,獲得以式(1)表示之化合物。
根據本發明,可提供作為香料及調合香料素材係有用且新穎的第一醛化合物及其製造方法、以及含有上述第一醛化合物並將其作為有效成分之香料組成物、以及將該化合物作為香料使用之用途。又,根據本發明,可提供作為上述第一醛化合物之原料係有用且新穎的第二醛化合物。
以下,利用實施形態針對本發明進行說明。另外,在以下說明中,表示數值範圍之「A~B」的記載,係代表「A以上B以下」(A<B時)、或「A以下B以上」(A>B時)。亦即,代表包含了係端點之A及B的數值範圍。
又,質量份及質量%,係各自與重量份及重量%同義。
式(1)中,R為氫原子或甲基。它們之中,考量香氣性的觀點,為氫原子較為理想。
以式(1)表示之醛化合物,在R為甲基時,係具有不對稱碳。此時,亦可僅有光學異構體中之任一者,又,亦可為以任意之比例包含複數之光學異構體的混合物。
以式(1)表示之化合物,係新穎的化合物。
以式(1)表示之本發明之第一醛化合物,作為香料及調合香料素材係有用,具有鈴蘭調之香氣,除此之外,亦同時具有白花調、醛調、綠香調等香氣。
以式(1)表示之化合物,因為其自身具有如後述之優異的香氣所以對香料而言係有用。又,一般來說香料很少會以單品的形式被使用,多數情況係以配合目的而摻合複數之香料而成之調合香料(香料組成物)的形式來使用。本發明之第一醛化合物,作為摻合於調合香料(香料組成物)中之香料(亦稱作「調合香料素材」)係有用。就香料而言,亦可單獨地使用一種以式(1)表示之化合物,亦可將兩種併用。
又,本發明之以式(1)表示之化合物,在不損及本發明之效果的範圍內,不排除包含了少量雜質、副產物、及夾雜物等的情況。
以式(1)表示之化合物,如上所述,在具有鈴蘭調之香氣的同時亦具有白花調、醛調、綠香調等香氣,且擴散性亦優異。
亦可單獨地將本發明之以式(1)表示之化合物作為香料而添加使用於各種香妝品類、以保健衛生材料為首之醫藥品、日用雜貨品、及食品等之中藉此賦予香氣、香味,又,亦可將本發明之以式(1)表示之化合物與其他調合香料素材等進行混合,調製如後述之香料組成物(調合香料),並將其摻合於各種製品中來賦予香氣、香味。這些當中,考量以獲得香氣、香味為目的之觀點,將本發明之化合物作為調合香料素材而摻合於香料組成物中,並將該香料組成物摻合於製品中藉此賦香較為理想。
[香料組成物]
本發明之香料組成物(調合香料),含有以式(1)表示之化合物(本發明之第一醛化合物)並將其作為有效成分。另外,只要至少含有本發明之第一醛化合物之一種以上的話並無特別限定,亦可含有兩種之本發明之第一醛化合物。另外,所謂香料,係指賦予香氣及香味(flavor)中之至少任一項者(以下,亦將「香氣及香味中之至少任一項」稱作「香氣等」)。
本發明之香料組成物,只要含有本發明之第一醛化合物並將其作為有效成分即可,就其他成分而言並不特別限定,更含有其他調合香料素材(以下,亦稱作「習知香料」。)較為理想。
另外,所謂「香料組成物(調合香料)」,係指將該香料組成物添加於各種香妝品類、醫藥品、食品、飲料等中藉此賦予香氣等之組成物,或是其自身被使用於香水等中之組成物,除了習知香料以外,視需要亦可含有溶劑等添加劑。
本發明之第一醛化合物之摻合量,雖根據本發明之第一醛化合物之種類、目的之香氣等之種類及香氣等之強度等而有所不同,但以式(1)表示之本發明之第一醛化合物的量在香料組成物中為0.001質量%以上較為理想,為0.01質量%以上更為理想,為0.1質量%以上更甚理想,為90質量%以下較為理想,為70質量%以下更為理想,為50質量%以下更甚理想。
習知香料,只要是一直以來公知的香料成分的話並無特別限制,可使用廣範圍之香料,例如可從下列所述者中單獨使用,或以任意的混合比例予以選擇使用兩種以上。
例如檸檬烯、α-蒎烯、β-蒎烯、萜品烯、雪松烯、長葉烯、瓦倫烯(valencene)等烴類;芳樟醇、香茅醇、香葉醇、橙花醇、萜品醇、二氫月桂烯醇、乙基芳樟醇、菌綠烯醇(Farnesol)、橙花叔醇、順式-3-己醛、雪松醇、薄荷醇、冰片、β-苯基乙基醇、苄基醇、苯基己醇、2,2,6-三甲基環己基-3-己醇、1-(2-第三丁基環己氧基)-2-丁醇、4-異丙基環己甲醇、4-第三丁基環己醇、4-甲基-2-(2-甲基丙基)四氫-2H-吡喃-4-醇、2-甲基-4-(2,2,3-三甲基-3-環戊烯-1-基)-2-丁烯-1-醇、2-乙基-4-(2,2,3-三甲基-3-環戊烯-1-基)-2-丁烯-1-醇、異樟腦環己醇(Isocamphyl cyclohexanol)、3,7-二甲基-7-甲氧基辛烷-2-醇等醇類;丁香油酚、百里酚、香草精(Vanillin)等苯酚類;甲酸芳樟酯、甲酸香茅酯、甲酸香葉酯、乙酸正己酯、乙酸順-3-己烯酯、乙酸芳樟酯、乙酸香茅酯、乙酸香葉酯、乙酸橙花酯、乙酸萜品酯、乙酸諾卜酯(Nopyl acetate)、乙酸冰片酯、乙酸異冰片酯、乙酸鄰第三丁基環己酯、乙酸對第三丁基環己酯、乙酸三環癸烯酯、乙酸苄基酯、乙酸蘇合香酯(Styrallyl acetate)、乙酸桂皮酯、乙酸二甲基苄基甲酯、3-戊基四氫吡喃-4-基乙酸酯、丙酸香茅酯、丙酸三環癸烯酯、丙酸烯丙基環己酯、丙酸乙基-2-環己酯、丙酸苄酯、丁酸香茅酯、正丁酸二甲基苄基甲酯、異丁酸三環癸烯酯、2-壬烯酸甲酯、苯甲酸甲酯、苯甲酸苄酯、肉桂酸甲酯、水楊酸甲酯、水楊酸正己酯、水楊酸順式-3-己烯酯、惕各酸香葉酯、惕各酸順式-3-己烯酯、茉莉酸甲酯、二氫茉莉酸甲酯、2,4-二羥基-3,6-二甲基苯甲酸甲酯、甲基苯基環氧丙酸乙酯、鄰胺苯甲酸甲酯、果香酯(FRUITATE)等酯類;正辛醛、正癸醛、正十二烷醛、2-甲基十一烷醛、10-十一烯醛、香茅醛、檸檬醛、羥香茅醛、二甲基四氫苯甲醛、4(3)-(4-羥基-4-甲基戊基)-3-環己烯-1-甲醛、2-環己基丙醛、對第三丁基-α-甲基氫桂皮醛、對異丙基-α-甲基氫桂皮醛、對乙基-α,α-二甲基氫桂皮醛、α-戊基桂皮醛、α-己基桂皮醛、向日花香醛、α-甲基-3,4-亞甲二氧基氫桂皮醛等醛類;甲基庚烯酮、4-亞甲基-3,5,6,6-四甲基-2-庚酮、戊基環戊酮、3-甲基-2-(順式-2-戊烯-1-基)-2-環戊烯-1-酮、甲基環戊烯醇酮、玫瑰酮、γ-甲基香堇酮、α-香堇酮、香芹酮、薄荷酮、樟腦、諾卡酮、苄基丙酮、大茴香基丙酮、甲基β-萘基酮、2,5-二甲基-4-羥基-3(2H)-呋喃酮、麥芽醇、7-乙醯基-1,2,3,4,5,6,7,8-八氫-1,1,6,7-四甲基萘、麝香酮、靈貓酮、環十五酮、環十六烯酮等酮類;乙醛乙基苯基丙基縮醛、檸檬醛二乙基縮醛、苯乙醛甘油縮醛、乙醯乙酸乙酯乙二醇縮酮類之縮醛類及縮酮類;茴香腦、β-萘基甲醚、β-萘基乙醚、氧化檸檬烯、氧化玫瑰、1,8-桉醚、外消旋混合物或具光學活性之十二氫-3a,6,6,9a-四甲基萘并[2,1-b]呋喃等醚類;香茅腈等腈類;γ-壬內酯、γ-十一碳內酯、σ-癸內酯、γ-茉莉內酯、香豆素、環十五碳內酯、環十六碳內酯、黃葵內酯、巴西酸乙二醇酯、11-氧雜十六碳內酯等內酯類;橙、檸檬、香檸檬、橘、薄荷、留蘭香、薰衣草、洋甘菊、迷迭香、桉樹、鼠尾草、羅勒、玫瑰、天竺葵、茉莉花、依蘭、茴芹、丁香、薑、肉豆蔻、小豆蔻、雪松、日本扁柏、檀木、香根草、廣藿香、岩玫瑰等的天然精油、天然萃取物等其他香料物質等。
又,香料組成物,就調合香料素材以外的構成成分而言,亦可含有聚氧乙烯月桂基硫酸醚等界面活性劑;二丙二醇、苯二甲酸二乙酯、乙二醇、丙二醇、肉豆蔻酸甲酯、檸檬酸三乙酯等溶劑;BHT(二第三丁基羥基甲苯)、維生素E(tocopherol)等抗氧化劑;著色劑等,至少含有抗氧化劑較為理想。
以式(1)表示之本發明之第一醛化合物,因為在具有鈴蘭調之香氣的同時亦具有白花調、醛調、綠香調等香氣,所以藉由與習知香料進行組合便能夠賦予鈴蘭調以及自然的白花調、醛調、綠香調,所以在添加於各種香妝品類、以保健衛生材料為首之醫藥品、日用雜貨品、及食品等中並賦予香氣等之方面而言係有用。
就賦予香氣等之用途、以及進行摻合對象物之香氣等之改良的用途而可添加含有以式(1)表示之本發明之第一醛化合物的香料組成物者而言,可列舉如香妝品類、健康衛生材料、雜貨、飲料、食品、準醫藥品、醫藥品等各種製品,例如可作為對香水、古龍水類等芳香製品;洗髮精、潤絲精類、護髮油、髮乳類、慕斯、凝膠、髮蠟、定型噴霧、其他毛髪用化妝料;化妝水、美容液、乳霜、乳液、面膜、粉底、白粉、口紅、各種化妝類等肌用化妝料;洗碗劑、洗衣劑、柔軟劑類、消毒用洗劑類、消臭洗劑類、室內芳香劑、家具保養劑、玻璃清潔劑、家具清潔劑、地板清潔劑、消毒劑、殺蟲劑、漂白劑、殺菌劑、忌避劑、其他各種健康衛生用洗劑類;牙膏、漱口水、入浴劑、止汗製品、燙髮液等醫藥部外品;衛生紙、面紙等雜貨;醫藥品等;食品等賦予香氣等的成分而被使用。
上述製品中之香料組成物的摻合量並無特別限定,根據用於賦香之製品之種類、性質及官能的效果等,可廣範圍地選擇香料組成物之摻合量。例如0.00001質量%以上,0.0001質量%以上較為理想,0.001質量%以上更為理想,在例如香水等芳香的情況中亦可為100質量%,80質量%以下較為理想,60質量%以下更為理想,40質量%以下更甚理想。
[式(2)表示之化合物]
本發明之第二醛化合物,係以下列式(2)表示。
以上述式(2)表示之化合物,作為上述本發明之第一醛化合物的合成中間體(或合成原料)係有用。
又,除了以式(1)表示之化合物以外,亦可期待從以式(2)表示之化合物合成其他作為香料係有用的化合物。
有關以式(1)表示之化合物的合成方法、以及以式(2)表示之化合物作為以式(1)表示之化合物的合成中間體(或合成原料)的使用方法,參閱下述。
另外,在本發明中以式(1)表示之化合物的合成中,以式(2)表示之化合物在不損及本發明之效果的範圍內,不排除包含有少量的雜質、副產物、及夾雜物等的情況。
<式(2)表示之化合物的製造方法> 本發明中,以式(2)表示之化合物的製造方法並無特別限定,例如在3-新戊基甲苯中於三氟甲磺酸(triflic acid、trifluoromethanesulfonic acid)的存在下以加壓條件與一氧化碳進行反應的方法,但藉由使3-新戊基甲苯在氟化氫及三氟化硼的存在下與一氧化碳進行反應來製造較為理想。
具體而言,係以下式表示。
另外,上述反應中,3-新戊基甲苯的4號位及6號位容易受到甲醯基化,使位置選擇性改善而進行6號位的甲醯基化較為理想。甲醯基化的位置選擇性,如下所述,會因氟化氫及三氟化硼相對於3-新戊基甲苯的量、一氧化碳的壓力、反應時間、反應溫度等而有所變化,藉由將它們最佳化,可改善位置選擇性。
氟化氫(HF),亦具有作為反應溶劑的功能。就氟化氫而言,考量反應性的觀點為實質上無水的氟化氫較為理想。另外,所謂實質上無水,係指水的含量為5質量%以下,為1質量%以下較為理想,為0.1質量%以下更為理想。
考量與一氧化碳的反應性及抑制副反應的觀點,氟化氫相對於3-新戊基甲苯的莫耳比(氟化氫/3-新戊基甲苯)為1.5以上較為理想,為3.0以上更為理想,為5.0以上更甚理想,然後,考量經濟性及生產效率的觀點,為30.0以下較為理想,為20.0以下更為理想,為12.0以下更甚理想。
又,考量具位置選擇性地進行甲醯基化的觀點,三氟化硼(BF3
)相對於3-新戊基甲苯的莫耳比(三氟化硼/3-新戊基甲苯)為0.1以上較為理想,為0.5以上更為理想,為1.0以上更甚理想,為1.2以上又更甚理想,然後,為5.0以下較為理想,為3.0以下更為理想,為2.0以下更甚理想。
考量使反應性改善,抑制副反應,並使甲醯基被導入之位置的選擇性改善的觀點,反應時之使一氧化碳作用的溫度為-50℃以上較為理想,為-40℃以上更為理想,然後,為30℃以下較為理想,為10℃以下更為理想,為5℃以下更甚理想。
3-新戊基甲苯與一氧化碳的反應係在加壓下進行較為理想。
考量使反應性改善,且抑制副反應的觀點,反應時之壓力,就一氧化碳之分壓而言為1.0MPaG以上較為理想,為1.5MPaG以上更為理想,為1.8MPaG以上更甚理想,然後,為3.0MPaG以下較為理想,為2.5MPaG以下更為理想,為2.2MPaG以下更甚理想。
本發明中,反應時間並不特別限定,考量使反應充分地進行,且在抑制副反應、產物之分解的同時亦有效率地進行製造的觀點,為10分鐘以上較為理想,為20分鐘以上更為理想,為30分鐘以上更甚理想,然後,為24小時以下較為理想,為12小時以下更為理想,為5小時以下更甚理想。
又,本發明之製造方法,亦可在溶劑的存在下進行。就使用之溶劑而言,只要反應原料之溶解性良好,且對於氟化氫及三氟化硼而言係鈍性的溶劑的話並無特別限定。例如己烷、庚烷、癸烷等飽和脂肪族烴;苯、甲苯等芳香族烴;氯仿、二氯甲烷、二氯乙烷等鹵化脂肪族烴。這些溶劑亦可單獨地使用一種,亦可將兩種以上予以併用。
溶劑之使用量,並無特別限定,可考量反應之均勻性、反應速度、及溶劑除去的觀點而適宜地選擇。
另外,本發明中,因為反應時存在的氟化氫亦可發揮作為溶劑之功能,所以亦可不使用溶劑。
上述反應,雖可為批次式、半批次式、及連續式等之中任一之方法,但考量觸媒之回收、再利用之可能、及生產效率的觀點,為連續式較為理想。
又,製造方法中使用之裝置,係可在加壓下一邊調整溫度,一邊將液相與氣相充分混合的反應裝置。
例如,連續式中,先將氟化氫及三氟化硼進料於附攪拌裝置之反應器中,攪拌內容物並將液溫設定成較佳的溫度,並調整成使溫度保持穩定的狀態之後,利用一氧化碳昇壓至較佳的反應壓力,並調整成能以使壓力保持穩定的方式供給一氧化碳的狀態。之後,執行供給視需要溶於溶劑中的3-新戊基甲苯之半批次式的反應。接著再更進一步開始供給氟化氫、三氟化硼、及視需要溶於溶劑中的3-新戊基甲苯,並將反應生成液連續地取出。
從獲得之包含2-甲基-4-新戊基苯甲醛的反應液中去除氟化氫及三氟化硼之後,可利用蒸餾、萃取等一般方法進行精製。又,為了從反應液中去除氟化氫,亦可使用氫氧化鈉水溶液進行中和水洗。
另外,以上式(a)表示之化合物(3-新戊基甲苯)亦能以如下之方式進行合成。
使新戊基苯在氟化氫及三氟化硼的存在下與一氧化碳進行反應,將新戊基的對位進行甲醯基化,獲得4-新戊基苯甲醛。
然後,將獲得之4-新戊基苯甲醛在鈀觸媒的存在下進行還原,將甲醯基還原成甲基。
然後,在氟化氫及三氟化硼的存在下於獲得之4-新戊基甲苯發生異構化反應,將藉由異構化反應生成之3-新戊基甲苯予以單離,藉此獲得3-新戊基甲苯。
[式(1)表示之化合物的製造方法]
以式(1)表示之化合物,亦能以任一之方法進行製造,例如將3-新戊基甲苯之6號位進行溴化,然後在第二級胺及鈀觸媒的存在下以烯丙基醇進行反應,並將獲得之化合物的丙醇側鏈進行氧化的方法等。關於上述方法,可參照日本特表2017-533926號公報。
本發明中,根據以下之製造方法製造以式(1)表示之化合物較為理想。具體而言,係按順序具有以下步驟(i)及步驟(ii)的製造方法。
步驟(i):將上述式(2)表示之化合物與乙醛或丙醛進行醛醇縮合,獲得下述式(3)表示之化合物。
步驟(ii):將下述式(3)表示之化合物予以氫化,獲得以上述式(1)表示之化合物。
反應式係如下所示。
<步驟(i)>
步驟(i)為將上述式(2)表示之化合物與乙醛或丙醛進行醛醇縮合,獲得上述式(3)表示之化合物的步驟。
更具體而言,在係觸媒之鹼性化合物的存在下使乙醛或丙醛於以式(2)表示之化合物進行反應較為理想。
就作為觸媒使用之鹼性化合物而言,可例示如氫氧化鈉、氫氧化鉀、重碳酸鈉、或它們的混合物等。
相對於以式(2)表示之化合物之1當量,鹼性化合物的量為0.05當量以上較為理想,為0.1當量以上更為理想,為0.2當量以上更甚理想,然後,為3當量以下較為理想,為1當量以下更為理想,為0.5當量以下更甚理想。
又,相對於以式(2)表示之化合物之1當量,乙醛或丙醛的添加量為1.0當量以上較為理想,為1.05當量以上更為理想,然後,為1.5當量以下較為理想,為1.1當量以下更為理想。
乙醛或丙醛之添加,係逐次地或連續地經時進行較為理想,例如藉由滴加進行添加較為理想。
上述反應,在溶劑中進行較為理想,就使用之溶劑而言,可例示如水混合性之各種有機溶劑,具體而言,例如甲醇、乙醇、1-丙醇、2-丙醇、第三丁醇、烯丙醇、乙二醇、丙二醇、二乙二醇等醇類較為理想,為甲醇、乙醇、1-丙醇、2-丙醇、第三丁醇、乙二醇、丙二醇、二乙二醇更為理想。
反應溫度並不特別限定,考量反應速度的觀點,為0℃以上較為理想,為3℃以上更為理想,為5℃以上更甚理想,然後,考量抑制副反應的觀點,為50℃以下較為理想,為40℃以下更為理想,為30℃以下更甚理想。
反應時間並無特別限定,只要是能充分地進行縮合的時間即可,但為10分鐘以上較為理想,為30分鐘以上更為理想,為1小時以上更甚理想,然後,為24小時以下較為理想,為12小時以下更為理想,為6小時以下更甚理想,為3小時以下又更甚理想。
反應之停止,可藉由中和來進行,例如可藉由添加乙酸等酸來使反應停止。
又,從反應溶液將以式(3)表示之化合物予以單離的方法並無特別限定,可適宜地組合分液及萃取操作、層析法等來進行。例如,可在反應液中添加低極性或無極性之有機溶劑,將以式(3)表示之化合物移相至油相中,並將獲得之油相以例如硫酸鎂進行乾燥後,將過濾而獲得之濾液濃縮,再以管柱層析法藉由精製來進行單離。
<步驟(ii)>
步驟(ii)為將在步驟(i)獲得之以上述式(3)表示之化合物予以氫化,獲得上述式(1)表示之化合物的步驟。
氫化之方法並不特別限定,可藉由使用氫化觸媒之公知的方法來進行。
就氫化觸媒而言,並無特別限定,可使用公知的觸媒,例如使碳、二氧化矽、氧化鋁、矽藻土等載持Ni、Pt、Pd、Ru等金屬而得之載持型不均勻系氫化觸媒;使用Ni、Co、Fe、Cr等的有機酸鹽或乙醯丙酮鹽等過渡金屬鹽與有機鋁等還原劑之所謂的齊格勒(Ziegler)型氫化觸媒;使用Ti、Ru、Rh、Zr等的有機金屬化合物等所謂的有機金屬錯合物等均勻系氫化觸媒。
考量反應性及抑制副反應的觀點,氫化反應之溫度為0℃以上較為理想,為10℃以上更為理想,為20℃以上更甚理想,然後,為200℃以下較為理想,為150℃以下更為理想,為100℃以下更甚理想。
於氫化反應中使用之氫氣的壓力,為0.01MPaG以上較為理想,為0.03MPaG以上更為理想,為0.05MPaG以上更甚理想,然後,為10MPaG以下較為理想,為3MPaG以下更為理想,為1MPaG以下更甚理想,為0.5MPaG以下又更甚理想。
反應時間,並不特別限定,為3分鐘以上較為理想,為10分鐘以上更為理想,為30分鐘以上更甚理想,然後,為24小時以下較為理想,為12小時以下更為理想,為8小時以下更甚理想。
氫化反應,亦可在溶劑之存在下進行。就使用之溶劑而言,只要不妨礙氫化反應的話並不特別限定,可例示如戊烷、己烷、異戊烷、庚烷、辛烷、異辛烷等脂肪族烴;環戊烷、甲基環戊烷、環己烷、甲基環己烷、乙基環己烷等脂環式烴;苯、甲苯、乙基苯、二甲苯等芳香族烴等烴溶劑。這些亦可單獨地使用一種,亦可將兩種以上予以併用。
從反應液將以式(1)表示之化合物予以單離精製的方法並無特別限定,可適宜地選擇公知的方法來進行。具體而言,可例示如過濾、層析法、蒸餾精製等,可適宜地組合它們來進行精製。
[實施例]
以下,使用實施例及比較例對本發明更具體地進行說明,但本發明並不受這些實施例所限制。
<NMR光譜分析>
裝置:JEOL JNM-AL-400 400MHz(JEOL製)
溶劑:氘代氯仿(CDCl3
)
測定模式:1
H、13
C
內部標準物質:四甲基矽烷(TMS)
<質量分析>
裝置:GCMS-QP2010 Ultra(島津製作所製)
離子化法:EI
<香調評價>
獲得之化合物的香調,係將其含浸於寬8mm、長15cm的濾紙中,以專門的小組成員進行聞嗅的方法來予以評價。
[實施例]
以下之實施例中,當合成量不足以作為下一合成之原料時,係藉由多次重複同樣的合成來合成出必要的量。
<4-新戊基苯甲醛之合成>
使用具備NAC DRIVE式攪拌機並在頂部具備3個入口管嘴、在底部具備1個出口管嘴且可利用夾套控制內部溫度之500mL的高壓釜作為甲醯基化反應器。
於夾套中流通冷媒,並將氟化氫134.2g(6.71莫耳)進料於已冷卻至-25℃的高壓釜中。
之後,一邊攪拌,一邊以不使溫度超過-25℃的方式進行調整,並加入三氟化硼70.6g(1.04莫耳)。
加入三氟化硼之後,在將高壓釜內之溫度保持在-25℃的狀態下,利用一氧化碳昇壓至2MPaG,加入新戊基苯(東京化成工業製)100.0g(0.67莫耳)。
一邊保持溫度-25℃、壓力2MPaG一邊攪拌90分鐘之後,將高壓釜內之反應混合液抽液至冰水中。將抽液後所得者進行充分搖晃混合後,使油層分液。將獲得之油層部中和水洗後,將獲得之油層部進行蒸餾精製(131℃、15Torr),以無色透明之液体的形式獲得4-新戊基苯甲醛87.5g(0.50莫耳)。
獲得之4-新戊基苯甲醛之結構式、NMR光譜、及質量分析的測定結果係如下所述。
[4-新戊基苯甲醛]1
H NMR (400 MHz, CDCl3
) δ 0.92 (9H, s), 2.58 (2H, s), 7.28-7.30 (2H, d, J=8.0Hz), 7.78-7.80 (2H, d, J=8.0Hz), 9.99 (1H, s)13
C NMR (100 MHz, CDCl3
) δ 29.5, 32.1, 50.4, 129.3, 131.1, 134.5, 147.4, 192.2
MS(EI):m/z (%) 57(50), 91(45), 120(100), 161(10), 176(M+・
, 5)
<4-新戊基甲苯之合成>
將4-新戊基苯甲醛50.0g(0.28莫耳)、庚烷25.0g及10% Pd/C 2.5g(5wt%)加入200mL之高壓釜中,將反應器內進行氮氣沖洗後,再進行氫氣沖洗。以氫氣昇壓至1.0MPaG,並一邊攪拌一邊昇溫至50℃。昇溫後保持1.0MPaG及50℃,使其反應10小時。
將獲得之粗反應液進行過濾並去除觸媒,在旋轉蒸發器中將濾液進行濃縮。將獲得之濃縮物進行蒸餾精製(97℃、20Torr),以無色透明之液體的形式獲得4-新戊基甲苯33.9g(0.21莫耳)。
獲得之4-新戊基甲苯之結構式、NMR光譜、及質量分析的測定結果,係如下述。
[4-新戊基甲苯]1
H NMR (400 MHz, CDCl3
) δ 0.89 (9H, s), 2.31 (3H, s), 2.45 (2H, s), 6.99-7.02 (2H, d, J=8.4Hz), 7.05-7.07 (2H, d, J=8.4Hz)13
C NMR (100 MHz, CDCl3
) δ 21.2, 29.5, 31.8, 50.0, 128.5, 130.5, 135.2, 136.8
MS(EI):m/z (%) 57(88), 77(12), 91(41), 106(100), 147(17), 162(M+・
, 48)
<3-新戊基甲苯之合成>
使用具備NAC DRIVE式攪拌機並在頂部具備3個入口管嘴、在底部具備1個出口管嘴且可利用夾套控制內部溫度之500mL的高壓釜作為異構化反應器。
於夾套中流通冷媒,並將氟化氫191.5g(9.57莫耳)進料於已冷卻至0℃的高壓釜中。
之後,一邊攪拌,一邊以不使溫度超過15℃的方式進行調整,並加入三氟化硼47.7g(0.70莫耳)。
加入三氟化硼之後,在將高壓釜內之溫度保持在15℃的狀態下,加入4-新戊基甲苯38.5g(0.24莫耳)及己烷38.5g的混合溶液。
一邊保持溫度15℃一邊攪拌4小時之後,將高壓釜內之反應混合液抽液至冰水中。將抽液後所得者進行充分搖晃混合後,使油層分液,進行中和水洗。
實施這些操作3次,將獲得之油層部的總合於旋轉蒸發器中進行濃縮。將獲得之濃縮物進行蒸餾精製(93℃、20Torr),以無色透明之液體的形式獲得3-新戊基甲苯87.0g(0.53莫耳)。
獲得之3-新戊基甲苯之結構式、NMR光譜、及質量分析的測定結果,係如下述。
[3-新戊基甲苯]1
H NMR (400 MHz, CDCl3
) δ 0.90 (9H, s), 2.33 (3H, s), 2.45 (2H, s), 6.91-6.93(1H, d, J=8.0Hz), 6.93 (1H, s), 7.00-7.02 (1H, d, J=7.6Hz), 7.13-7.17 (1H, t, J=7.6Hz)13
C NMR (100 MHz, CDCl3
) δ 21.6, 29.6, 31.8, 50.3, 126.6, 127.6, 127.7, 131.4, 137.1, 139.8
MS(EI):m/z (%) 57(96), 77(13), 91(45), 106(100), 147(16), 162(M+・
, 48)
<2-甲基-4-新戊基苯甲醛之合成>
使用具備NAC DRIVE式攪拌機並在頂部具備3個入口管嘴、在底部具備1個出口管嘴且可利用夾套控制內部溫度之500mL的高壓釜作為甲醯基化反應器。
於夾套中流通冷媒,並將氟化氫43.0g(2.15莫耳)進料於已冷卻至-25℃的高壓釜中。
之後,一邊攪拌,一邊以不使溫度超過-25℃的方式進行調整,並加入三氟化硼29.5g(0.44莫耳)。
加入三氟化硼之後,在將高壓釜內之溫度保持在-25℃的狀態下,利用一氧化碳昇壓至2MPaG,加入3-新戊基甲苯47.1g(0.29莫耳)及庚烷47.1g的混合溶液。
一邊保持溫度-25℃、壓力2MPaG一邊攪拌120分鐘之後,將高壓釜內之反應混合液抽液至冰水中。將抽液後所得者進行充分搖晃混合後,使油層分液,將獲得之油層部進行中和水洗。
實施這些操作2次,將獲得之油層部的總合於旋轉蒸發器中進行濃縮之後,將濃縮物進行蒸餾精製(139℃、15Torr),以無色透明之液體的形式獲得2-甲基-4-新戊基苯甲醛82.1g(0.43莫耳)。
獲得之2-甲基-4-新戊基苯甲醛之結構式、NMR光譜、及質量分析的測定結果,係如下述。
[2-甲基-4-新戊基苯甲醛]1
H NMR (400 MHz, CDCl3
) δ 0.92 (9H, s), 2.52 (2H, s), 2.65 (3H, s), 7.01 (1H, s), 7.11-7.13 (1H, d, J=7.6Hz), 7.69-7.71 (1H, d, J=7.6Hz), 10.23 (1H, s)13
C NMR (100 MHz, CDCl3
) δ 19.7, 29.5, 32.1, 50.3, 128.5, 131.8, 132.3, 133.9, 139.9, 146.4, 192.5
MS(EI):m/z (%) 57(65), 77(8), 91(26), 105(40), 134(100), 175(11), 190(M+・
, 29)
<(E)-3-(2-甲基-4-新戊基苯基)丙烯醛之合成>
將2-甲基-4-新戊基苯甲醛15.0g(0.08莫耳)、作為溶劑之甲醇15g、及作為觸媒之50%NaOH水溶液2.1g(0.03莫耳)添加至100mL之丸底圓底燒瓶中,並冷卻至10℃。
之後,一邊攪拌,一邊以不超過15℃的方式進行調整並滴加乙醛3.9g(0.09莫耳),反應2小時後加入乙酸2.0g(0.03莫耳)進行淬滅。
淬滅後使用庚烷進行萃取、分液操作,將獲得之油層部以硫酸鎂進行乾燥,並將過濾獲得之濾液在旋轉蒸發器中進行濃縮。
將獲得之濃縮物以管柱層析法(矽膠、己烷:乙酸乙酯=93:7)進行精製,以黃色之固體的形式獲得(E)-3-(2-甲基-4-新戊基苯基)丙烯醛5.0g(0.02莫耳)。
獲得之(E)-3-(2-甲基-4-新戊基苯基)丙烯醛之結構式、NMR光譜、及質量分析的測定結果,如下所述。
[(E)-3-(2-甲基-4-新戊基苯基)丙烯醛]1
H NMR (400 MHz, CDCl3
) δ 0.92 (9H, s), 2.47 (3H, s), 2.49 (2H, s), 6.63-6.69(1H, dd, J=7.6Hz, 16Hz), 7.01 (1H, s), 7.01-7.03 (1H, d, J=9.6Hz), 7.51-7.53 (1H, d, J=7.6Hz), 7.74-7.78 (1H, d, J=16Hz), 9.70-9.72 (1H, d, J=7.6Hz)13
C NMR (100 MHz, CDCl3
) δ 19.9, 29.6, 32.1, 50.2, 126.3, 128.8, 129.0, 130.5, 133.3, 137.4, 143.7, 150.6, 194.1
MS(EI):m/z (%) 57(71), 91(11), 115(16), 131(17), 145(100), 160(70), 201(29), 216(M+・
, 16)
<3-(2-甲基-4-新戊基苯基)丙醛之合成>
將(E)-3-(2-甲基-4-新戊基苯基)丙烯醛0.7g(0.003莫耳)、作為溶劑之庚烷35.0g、及作為觸媒之10% Pd/C 0.07g(10wt%)添加至200mL之高壓釜中,將反應器內進行氮氣沖洗後,再進行氫氣沖洗。之後,以氫氣昇壓至0.1MPaG,並進行攪拌。昇壓後保持0.1MPaG及25℃,使其反應1小時。
將獲得之粗反應液進行過濾並去除觸媒,在旋轉蒸發器中將濾液進行濃縮。將獲得之濃縮物以管柱層析法(矽膠、己烷:乙酸乙酯=96:4)進行精製,以無色透明之液體的形式獲得3-(2-甲基-4-新戊基苯基)丙醛0.4g(0.002莫耳)。
獲得之3-(2-甲基-4-新戊基苯基)丙醛之結構式、NMR光譜、及質量分析的測定結果、以及香調,係如下述。
[3-(2-甲基-4-新戊基苯基)丙醛]1
H NMR (400 MHz, CDCl3
) δ 0.89 (9H, s), 2.29 (3H, s), 2.42 (2H, s), 2.71-2.75 (2H, t, J=7.8Hz), 2.90-2.94 (2H, t, J=7.8Hz), 6.89-6.91 (1H, d, J=7.6Hz),6.91 (1H, s), 7.00-7.02 (1H, d, J=7.2Hz), 9.85 (1H, s)13
C NMR (100 MHz, CDCl3
) δ 19.5, 25.2, 29.5, 31.8, 44.2, 49.8, 127.8, 128.4, 132.7, 135.1, 135.7, 138.0, 202.0
MS(EI):m/z (%) 57(100), 77(7), 91(19), 105(19), 118(57), 129(28), 144(90), 162(25), 203(8), 218(M+・
, 30)
香調:鈴蘭、白花、醛、綠香
另外,香調係比鈴蘭醛有略強的海洋調的油脂感,係介於鈴蘭醛及銀醛中間的香調。
<(E)-3-(2-甲基-4-新戊基苯基)-2-甲基丙烯醛之合成>
將2-甲基-4-新戊基苯甲醛15.0g(0.08莫耳)、作為溶劑之甲醇15.0g、及作為觸媒之50%NaOH水溶液2.0g(0.03莫耳)加入100mL之圓底燒瓶中,並保持25℃。
之後,一邊攪拌,一邊以不超過25℃的方式進行調整,並滴加丙醛5.0g(0.09莫耳),反應2小時後加入乙酸1.6g(0.03莫耳)進行淬滅。
淬滅後使用庚烷進行萃取、分液操作,將獲得之油層部以硫酸鎂進行乾燥,並將過濾獲得之濾液在旋轉蒸發器中進行濃縮。
將獲得之濃縮物以管柱層析法(矽膠、己烷:乙酸乙酯=95:5)進行精製,以黃色之液體的形式獲得(E)-3-(2-甲基-4-新戊基苯基)-2-甲基丙烯醛13.3g(0.06莫耳)。
獲得之(E)-3-(2-甲基-4-新戊基苯基)-2-甲基丙烯醛之結構式、NMR光譜、及質量分析的測定結果,係如下述。
[(E)-3-(2-甲基-4-新戊基苯基)-2-甲基丙烯醛]1
H NMR (400 MHz, CDCl3
) δ 0.93 (9H, s), 1.98 (3H, s), 2.35 (3H, s), 2.49 (2H, s), 7.01-7.03 (1H, d, J=6.4Hz), 7.03 (1H, s), 7.28-7.30 (1H, d, J=8.4Hz), 7.43 (1H, s), 9.63 (1H, s)13
C NMR (100 MHz, CDCl3
) δ 11.0, 19.9, 29.4, 31.8, 50.0, 127.9, 128.3, 131.4, 132.6, 136.5, 138.5, 141.3, 148.3, 195.5
MS(EI):m/z (%) 57(56), 91(7), 105(7), 115(10), 128(12), 145(11), 159(100), 174(33), 215(46), 230(M+・
,12)
<3-(2-甲基-4-新戊基苯基)-2-甲基丙醛之合成>
將(E)-3-(2-甲基-4-新戊基苯基)-2-甲基丙烯醛13.3g(0.06莫耳)、5wt%Na2
CO3
水溶液40.0g、及5% Pd/C 0.3g(2wt%)加入200mL之高壓釜中,將反應器內進行氮氣沖洗之後,進行氫氣沖洗。之後,以氫氣昇壓至0.4MPaG,一邊攪拌一邊昇溫至75℃。昇溫後保持0.4MPaG及75℃,使其反應7小時。
將獲得之粗反應液進行過濾並去除觸媒,在旋轉蒸發器中將濾液進行濃縮。將獲得之濃縮物以管柱層析法(矽膠、己烷:乙酸乙酯=96:4)進行精製之後,進行蒸餾精製(102℃、1Torr)並以無色透明之液體的形式獲得3-(2-甲基-4-新戊基苯基)-2-甲基丙醛6.7g(0.03莫耳)。
獲得之3-(2-甲基-4-新戊基苯基)-2-甲基丙醛之結構式、NMR光譜、及質量分析的測定結果、以及香調,係如下述。
[3-(2-甲基-4-新戊基苯基)-2-甲基丙醛]1
H NMR (400 MHz, CDCl3
) δ 0.89 (9H, s), 1.10-1.12 (3H, d, J=6.8Hz), 2.29 (3H, s), 2.43 (2H, s), 2.54-2.57 (1H, dd, J=8.4Hz, 14.0Hz), 2.63-2.68 (1H, m), 3.05-3.10 (1H, dd, J=6.0Hz, 14.0Hz), 6.89-6.91 (1H, d, J=7.6Hz), 6.92 (1H, s), 6.99-7.01 (1H, d, J=7.6Hz), 9.72 (1H, s)13
C NMR (100 MHz, CDCl3
) δ 13.6, 19.6, 29.5, 31.8, 33.7, 47.0, 49.8, 128.2, 129.0, 032.8, 134.4, 135.3, 138.0, 204.7
MS(EI):m/z (%) 57(93), 77(6), 91(12), 105(27), 119(100), 131(8), 143(24), 158(64), 175(25), 214(8), 232(M+・
,38)
香調:鈴蘭、白花、綠香、木質
另外,其香調,像鈴蘭醛那樣的海洋調的油脂感、醛感弱,係偏木質琥珀調的乾淨的鈴蘭調。在香調方面,被認為隱含有非常大的潛能。
<調合香料評價-1>
從香調的評價結果,可得知3-(2-甲基-4-新戊基苯基)丙醛具有鈴蘭醛(Lilial)、及銀醛(Silvial)那樣的香調。在此,針對係鈴蘭醛之模式處方之以下3處方,添加3-(2-甲基-4-新戊基苯基)丙醛來替代鈴蘭醛並進行評價。
處方1~3係顯示於以下表中。另外,處方1係花粉系之香調、處方2係鈴蘭(Muguet)系之香調、處方3係果花系之香調。
[表1-1]
處方1 | |||||
No. | 成分 | 質量份 | No. | 成分 | 質量份 |
1 | 乙醯異丁香酚 (ACETYL ISO EUGENOL) | 8 | 15 | 二氫茉莉酮酸甲酯(HEDIONE) | 100 |
2 | 醛C-14(ALDEHYDE C-14) | 8 | 16 | 新洋茉莉醛(HELIONAL) | 4 |
3 | 檀香208(BACDANOL) | 25 | 17 | 天芥菜精(HELIOTROPINE) | 5 |
4 | 乙酸芐酯(BENZYL ACETATE) | 6 | 18 | 義大利檸檬油(LEMON OIL ITALY) | 10 |
5 | 水楊酸芐酯 (BENZYL SALICYLATE) | 60 | 19 | γ-甲基紫羅蘭酮 (METHYL IONONE GAMMA) | 40 |
6 | 香茅醇(CITRONELLOL) | 10 | 20 | 麝香(50 IPM)(MUSK 50 IPM) | 120 |
7 | 香豆素(COUMARIN) | 40 | 21 | 苯乙醇 (PHENYL ETHYL ALCOHOL) | 20 |
8 | 仙客來醛 (CYCLAMEN ALDEHYDE) | 15 | 22 | 结晶玫瑰(ROSACETOL) | 5 |
9 | 乙酸二甲基芐基甲醇酯 (D.M.B.C. ACETATE) | 3 | 23 | 乙酸萜品酯 (TERPINYL ACETATE) | 5 |
10 | 二氫月桂烯醇 (DIHYDRO MYRCENOL) | 50 | 24 | 香草精(VANILLIN) | 10 |
11 | 二苯醚(DIPHENYL OXIDE) | 3 | 25 | 乙酸4-叔丁基環己酯(VERTENEX) | 40 |
12 | 玫瑰醇(ETHYL LINALOOL) | 35 | 26 | 鈴蘭醛(LILIAL) | 320 |
13 | 香葉醇(GERANIOL) | 8 | 合計 | 1000 | |
14 | 環十五烯內酯(HABANOLIDE) | 50 |
[表1-2]
處方2 | |||||
No. | 成分 | 質量份 | No. | 成分 | 質量份 |
1 | 乙酸芐酯(BENZYL ACETATE) | 20 | 11 | 新洋茉莉醛(HELIONAL) | 10 |
2 | 無光敏香檸檬油 (BERGAMOT OIL FREE) | 30 | 12 | 羥香茅醛(HYDROXYCITRONELLAL) | 40 |
3 | 肉桂醇(CINNAMIC ALCOHOL) | 40 | 13 | 吲哚(純)(INDOLE PURE) | 2 |
4 | 順式-3-己烯醇(CIS-3-HEXENOL) | 3 | 14 | 芳樟醇(LINALOOL) | 50 |
5 | 順式-3-己烯醇乙酸酯 (CIS-3-HEXENYL ACETATE) | 2 | 15 | 苯乙醇(PHENYL ETHYL ALCOHOL) | 60 |
6 | 水楊酸順式-3-己烯酯 (CIS-3-HEXENYL SALICYLATE) | 20 | 16 | 保加利亞玫瑰油 (ROSE OIL BULGARIAN) | 2 |
7 | 香茅醇(CITRONELLOL) | 80 | 17 | STEMONE(註冊商標) | 3 |
8 | 二磷酸甘油酸(DPG) | 108 | 18 | 科摩羅特級依蘭 (YLANG YLANG EXTRA COMORES) | 10 |
9 | FLOROL(註冊商標) | 70 | 19 | 鈴蘭醛(LILIAL) | 350 |
10 | 二氫茉莉酮酸甲酯(HEDIONE) | 100 | 合計 | 1000 |
[表1-3]
處方3 | |||||
No. | 成分 | 質量份 | No. | 成分 | 質量份 |
1 | 醛C-10(ALDEHYDE C-10) | 2 | 19 | β-香堇酮(IONONE BETA) | 2 |
2 | 11-十一酸 (ALDEHYDE C-11 UNDECYLIC) | 2 | 20 | 女貞(LIGUSTRAL) | 10 |
3 | 醛C-14(ALDEHYDE C-14) | 20 | 21 | 芳樟醇(LINALOOL) | 45 |
4 | 烯丙基乙醇酸戊酯 (ALLYL AMYL GLYCOLATE) | 2 | 22 | 母菊酯(MANZANATE) | 60 |
5 | 八氫四甲基萘基乙酮 (AMBERONNE) | 60 | 23 | 肉桂酸甲酯 (METHYL CINNAMATE) | 1 |
6 | 水楊酸戊酯(AMYL SALICYLATE) | 10 | 24 | γ-甲基紫羅蘭酮 (METHYL IONONE GAMMA) | 20 |
7 | 苯甲醛(BENZALDEHYDE) | 1 | 25 | 苯乙酸甲酯 (METHYL PHENYL ACETATE) | 1 |
8 | 乙酸芐酯(BENZYL ACETATE) | 20 | 26 | γ-壬內酯 (NONALACTONE GAMMA) | 2 |
9 | 順式-3-己烯醇乙酸酯 (CIS-3-HEXENYL ACETATE) | 4 | 27 | 甜橙萜烯(ORANGE TERPENES) | 250 |
10 | 香茅醇(CITRONELLOL) | 10 | 28 | 對甲基苯甲醚 (PARA CRESOL METHYL ETHER) | 1 |
11 | CYCLAPROP(註冊商標) | 10 | 29 | 梨醇酯(PRENYL ACETATE) | 5 |
12 | 乙酸二甲基芐基甲醇酯 (D.M.B.C. ACETATE) | 4 | 30 | 氧化玫瑰(ROSE OXIDE) | 6 |
13 | δ-大馬士革(DAMASCONE DELTA) | 4 | 31 | 乙酸蘇合香酯 (STYRALLYL ACETATE) | 6 |
14 | γ-癸內酯 (DECALACTONE GAMMA) | 6 | 32 | 甲基癸烯醇(UNDECAVERTOL) | 1 |
15 | 鄰胺苯甲酸甲酯 (DIMETHYL ANTHRANILATE) | 1 | 33 | 乙酸鄰第三丁基環己酯(VERDOX) | 100 |
16 | 二磷酸甘油酸(DPG) | 84 | 34 | 乙酸4-叔丁基環己酯(VERTENEX) | 50 |
17 | 乙酸己酯(HEXYL ACETATE) | 10 | 35 | 鈴蘭醛(LILIAL) | 50 |
18 | 己基肉桂醛 (HEXYL CINNAMIC ALDEHYDE) | 140 | 合計 | 1000 |
[處方1:實施例1-1及1-2]
實施例1-1中,係在處方1中添加320質量份之3-(2-甲基-4-新戊基苯基)丙醛來替代320質量份之鈴蘭醛,除此以外,係以同樣的方式製作調合香料,並對其香調進行評價。
又,實施例1-2中,係在處方1中添加120質量份之3-(2-甲基-4-新戊基苯基)丙醛及200質量份之二丙二醇來替代320質量份之鈴蘭醛,除此以外,係以同樣的方式製作調合香料,並對其香調進行評價。亦即,實施例1-2中,係將添加量減少至鈴蘭醛之37.5%並進行評價。
另外,二丙二醇係無臭,係為了稀釋3-(2-甲基-4-新戊基苯基)丙醛而添加。
[處方2:實施例2-1及2-2]
實施例2-1中,係在處方2中添加350質量份之3-(2-甲基-4-新戊基苯基)丙醛來替代350質量份之鈴蘭醛,除此以外,係以同樣的方式製作調合香料,並對其香調進行評價。
又,實施例2-2中,係在處方2中添加150質量份之3-(2-甲基-4-新戊基苯基)丙醛及200質量份之二丙二醇來替代350質量份之鈴蘭醛,除此以外,係以同樣的方式製作調合香料,並對其香調進行評價。亦即,實施例2-2中,係將添加量減少至鈴蘭醛之42.9%並進行評價。
[處方3:實施例3-1及3-2]
實施例3-1中,係在處方3中添加50質量份之3-(2-甲基-4-新戊基苯基)丙醛來替代50質量份之鈴蘭醛,除此以外,係以同樣的方式製作調合香料,並對其香調進行評價。
又,實施例3-2中,係在處方3中添加20質量份之3-(2-甲基-4-新戊基苯基)丙醛及30質量份之二丙二醇來替代50質量份之鈴蘭醛,除此以外,係以同樣的方式製作調合香料,並對其香調進行評價。亦即,實施例3-2中,係將添加量減少至鈴蘭醛之40%並進行評價。
[香調評價]
調合香料之香調的評價,係使用9000份之檸檬酸三乙酯將上述處方1~3稀釋至10倍來進行。
含浸於寬8mm、長15cm之濾紙,以專門的小組成員進行嗅聞的方法來予以評價。
對調合香料之香調進行評價,將在實施例1-1、2-1、3-1中製作之調合香料與處方1~3分別進行對比,結果感受到與係添加有鈴蘭醛之調合香料之處方1~3同樣的香調,但香氣的強度更強。
又,對添加量減少之實施例1-2、2-2、3-2之香調進行評價,結果感受到與添加鈴蘭醛時相同程度之強度的香氣,顯示3-(2-甲基-4-新戊基苯基)丙醛係效價比鈴蘭醛更優異的香料。
<殘香性評價>
殘香性係藉由與鈴蘭醛比較來進行評價。將3-(2-甲基-4-新戊基苯基)丙醛及鈴蘭醛分別含浸於寬8mm、長15cm之濾紙之前端約1cm的部位,並對剛含浸後之香氣的強度進行評價。之後,在室溫下放置,對6小時後及18小時後之香氣的強度進行評價。
對殘香性進行評價,結果感受到3-(2-甲基-4-新戊基苯基)丙醛即便在6小時後仍具有充分的香氣,比鈴蘭醛更強烈。又,18小時後,3-(2-甲基-4-新戊基苯基)丙醛仍具有香氣,反觀鈴蘭醛係幾乎無法感受到之弱的香氣。
<調合香料評價-2>
針對鈴蘭醛之替代香料,日本特開2018-138550號公報中揭示有以下之化合物(以下,稱作睡蓮醛(Nympheal))。在此,針對係上述睡蓮醛之模式處方之以下2處方,添加3-(2-甲基-4-新戊基苯基)丙醛來替代睡蓮醛並進行評價。
處方4及5係顯示於以下表中。另外,處方4係綠花系之香調,處方5係花果系之香調。
[表2-1]
處方4 | |||||
No. | 成分 | 質量份 | No. | 成分 | 質量份 |
1 | 八氫四甲基萘基乙酮 (AMBERONNE) | 20 | 15 | FLOROL(註冊商標) | 35 |
2 | 龍涎香醚(AMBROXAN) | 0.1 | 16 | 香葉醇(GERANIOL) | 18 |
3 | 檀香208(BACDANOL) | 20 | 17 | 二氫茉莉酮酸甲酯(HEDIONE) | 200 |
4 | 樟腦醇晶體 (BORNEOL LAEVO CRISTAL) | 0.1 | 18 | β-香堇酮(IONONE BETA) | 30 |
5 | 順式茉莉酮(CIS JASMONE) | 1.2 | 19 | 女貞(LIGUSTRAL) | 0.2 |
6 | 順式-3-己烯醇(CIS-3-HEXENOL) | 8 | 20 | 芳樟醇(LINALOOL) | 100 |
7 | 順式-3-己烯醇乙酸酯 (CIS-3-HEXENYL ACETATE) | 2 | 21 | 佳樂麝香(50 IPM) (GALAXOLIDE 50 IPM) | 120 |
8 | 檸檬醛二甲縮醛 (CITRAL DIMETHYL ACETAL) | 0.4 | 22 | 苯乙醇(PHENYL ETHYL ALCOHOL) | 60 |
9 | 合成檸檬醛(CITRAL SYNTH) | 0.2 | 23 | 氧化玫瑰(ROSE OXIDE) | 1 |
10 | 香茅醛(CITRONELLAL) | 0.1 | 24 | 蘇合香醇(STYRALLYL ALCOHOL) | 0.1 |
11 | 香茅醇(CITRONELLOL) | 25 | 25 | 乙酸鄰第三丁基環己酯(VERDOX) | 70 |
12 | 二氫月桂烯醇 (DIHYDRO MYRCENOL) | 30 | 26 | 睡蓮醛(NYMPHEAL) | 50 |
13 | 二磷酸甘油酸(DPG) | 128.6 | 合計 | 1000 | |
14 | 巴西酸乙二醇酯 (ETHYLENE BRASSYLATE) | 80 |
[表2-2]
處方5 | |||||
No. | 成分 | 質量份 | No. | 成分 | 質量份 |
1 | 醛 C-10(ALDEHYDE C-10) | 4 | 16 | 新洋茉莉醛(HELIONAL) | 4 |
2 | 己酸烯丙酯(ALLYL CAPROATE) | 4 | 17 | 乙酸己酯(HEXYL ACETATE) | 4 |
3 | 乙酸芐酯(BENZYL ACETATE) | 15 | 18 | 己基肉桂醛 (HEXYL CINNAMIC ALDEHYDE) | 80 |
4 | 順式茉莉酮(CIS JASMONE) | 0.4 | 19 | 水楊酸己酯(HEXYL SALICYLATE) | 40 |
5 | 香茅醇(CITRONELLOL) | 30 | 20 | β-香堇酮(IONONE BETA) | 20 |
6 | 仙客來醛 (CYCLAMEN ALDEHYDE) | 20 | 21 | 乙酸三環癸烯酯 (JASMACYCLENE) | 45 |
7 | 丙酸三環癸烯酯(CYCLAPROP) | 25 | 22 | 芳樟醇(LINALOOL) | 80 |
8 | 乙酸二甲基芐基甲醇酯 (D.M.B.C. ACETATE) | 1.5 | 23 | 母菊酯(MANZANATE) | 0.8 |
9 | 二苯醚(DIPHENYL OXIDE) | 0.4 | 24 | 甜瓜醛(MELONAL) | 0.8 |
10 | 二磷酸甘油酸(DPG) | 270.7 | 25 | γ-甲基紫羅蘭酮 (METHYL IONONE GAMMA) | 35 |
11 | 水楊酸乙酯(ETHYL SALICYLATE) | 0.4 | 26 | 苯乙醇 (PHENYL ETHYL ALCOHOL) | 50 |
12 | 海風醛(FLORALOZONE) | 8 | 27 | 乙酸蘇合香酯 (STYRALLYL ACETATE) | 20 |
13 | FOLIONE(註冊商標) | 0.2 | 28 | 甲基癸烯醇(UNDECAVERTOL) | 0.8 |
14 | 香葉醇(GERANIOL) | 20 | 29 | 睡蓮醛(NYMPHEAL) | 180 |
15 | 乙酸香葉酯(GERANYL ACETATE) | 40 | 合計 | 1000 |
[處方4:實施例4]
實施例4中,係在處方4中添加50質量份之3-(2-甲基-4-新戊基苯基)丙醛來替代50質量份之睡蓮醛,除此以外,係以同樣的方式製作調合香料,並對其香調進行評價。
[處方5:實施例5]
實施例5中,係在處方5中添加180質量份之3-(2-甲基-4-新戊基苯基)丙醛來替代180質量份之睡蓮醛,除此以外,係以同樣的方式製作調合香料,並對其香調進行評價。
[香調評價]
調合香料之香調的評價,係以上述處方4及5來進行。
含浸於寬8mm、長15cm之濾紙,以專門的小組成員進行嗅聞的方法來予以評價。
對調合香料之香調進行評價,將在實施例4及實施例5中製作之調合香料與處方4及5分別進行對比,結果發現實施例4及5在中調的衝擊性、強度的方面係更優異。更具體而言,在大約30分鐘後~3小時後,能更強烈地感受到其堅實而強力的綠花感。
[產業上利用性]
本發明之以式(1)表示之化合物,就香料(調合香料原料)而言係有用,又,可期待其使用作為鈴蘭醛之替代香料。另外,可得知本發明之以式(1)表示之化合物,與鈴蘭醛相比係效價及殘香性更優異的香料。又,可得知即便與係鈴蘭醛之其他替代香料之睡蓮醛進行比較,仍屬特別具有優異的中調強度之優異的香料。
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WO2016074118A1 (en) * | 2014-11-10 | 2016-05-19 | Givaudan Sa | Improvements in or relating to organic compounds |
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