(12) Patent Application Publication (10) Pub. No.: US 2012/0308486A1 Singer Et Al
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US 2012O3O8486A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0308486A1 Singer et al. (43) Pub. Date: Dec. 6, 2012 (54) FRAGRANCE AND/OR FLAVORING Publication Classification COMPOSITIONS CONTAINING (51) Int. Cl. DOXOLANES A6IR 8/49 (2006.01) C07D 317/12 (2006.01) C07D 31 7/72 (2006.01) (75) Inventors: Emilie Singer, Holzminden (DE); A61O 1704 (2006.01) Bernd Hölscher, Halle (DE) A2.3L 2/56 (2006.01) A61O 15/00 (2006.01) A61O II/00 (2006.01) (73) Assignee: SYMRISE AG, Holzminden (DE) CLID 3/50 (2006.01) A2.3L. I./226 (2006.01) (21) Appl. No.: 13/473,053 A61O 13/00 (2006.01) A61O 19/00 (2006.01) (52) U.S. Cl. ................. 424/49; 512/12: 512/9; 549/430; (22) Filed: May 16, 2012 549/341; 424/59; 514/772; 424/65; 510/103; 426,536 Related U.S. Application Data (57) ABSTRACT (60) Provisional application No. 61/486.998, filed on May The present invention primarily relates to the use of diox olanes of the following Formula (I) as fragrance and/or fla 17, 2011. Voring Substances, certain perfume and/or flavoring compo sitions comprising these dioxolanes and corresponding perfumed and/or flavored items. (30) Foreign Application Priority Data The present invention also relates to a method for producing the dioxolanes of Formula (I) and certain new dioxolanes May 17, 2011 (EP) ................................ 11 166440.5 according to Formula (I). US 2012/030848.6 A1 Dec. 6, 2012 FRAGRANCE AND/OR FLAVORING in the process. In the context of the present invention, there COMPOSITIONS CONTAINING fore, no fragrance Substances are sought which exclusively or DOXOLANES predominantly Smell of pineapple or impart a pineapple note. 0011 Furthermore these fragrance and/or flavoring sub stances preferably have positive secondary characteristics, 0001. The present invention primarily relates to the use of preferably odor-enhancing characteristics and/or have the dioxolanes of Formula (I) defined below as fragrance and/or flavoring Substance, certain fragrance and/or flavoring com capacity to have odor and/or taste-enhancing characteristics positions comprising these dioxolanes and correspondingly and/or in combination with other fragrance and/or flavoring perfumed and/or flavored items. Substances to round offorto increase their naturalness, fresh 0002 The present invention also relates to a method for ness, (mouth)fill, (radiant) power and/or radiance and/or the producing the dioxolanes of Formula (I) and certain new increase the diffusivity of a fragrance mixture. dioxolanes according to Formula (I). 0012. This object was achieved by the use of a compound 0003 Because of the general scarcity of natural fragrance according to Formula (I) components, the changes required to keep up with changing flavor preferences and the ever-increasing need for new fra grances, which on their own or in the form of compositions (I) constitute valuable fragrances or perfumes with interesting scents, there continues also to be a need for compounds with interesting fragrance qualities. 0004 Because of the increasing demand from consumers for new scents the perfume industry has a constant need for new fragrance substances with which to achieve novel effects in perfumes and in this way to create fashion trends. 0005. Despite a whole range of fragrance substances already being available the perfume industry also continues to including the stereosiomers, wherein have a general need for new fragrance Substances, in particu 0013 R1 and R2 in each case and independently of one lar those which, in addition to their primary, that is to say odor, another is either hydrogen or methyl, preferably hydrogen, characteristics also have positive secondary characteristics, and Such as for example a higher stability under certain applica 0014) a) R3 and R4—together with the ketal carbon atom tion conditions, a high extension, a high radiant power, good of the dioxolane ring form a ring with a total of 5, 6, 7 or diffusivity (e.g. a good spatial effect), fullness, power and/or 8 ring carbonatoms, where the ring optionally contains one naturalness, odor-enhancing characteristics or also improved or two double bonds and/or optionally 1 to a maximum of dermatological characteristics compared with fragrance Sub 3 oxygen atoms, and wherein the ring is optionally Substi stances with comparable primary odor characteristics. tuted by one or a plurality of branched or unbranched, 0006. The perfume industry thus has a basic need for more bridged or unbridged, alkyl groups, alkenyl groups, fragrance Substances that are suitable for the production of cycloalkyl groups, cycloalkenyl groups, aryl groups, aryl fragrance compositions or perfumed items. There is in par alkyl groups, alkoxy alkyl groups or alkoxy aryl groups, ticular a need for fragrances which through the abovemen tioned technical characteristics lead to increased use of fra and wherein R3 and R4 together comprise in total 3 grance compositions and perfume oils. through 30 carbon atoms, 0007 WO 02/085294 describes various acetals for block 0.015 or ing or reducing the unpleasant odor of certain acids. The 0016 b) R3 is either hydrogen oran organic radical with 1 acetals disclosed there can, according to WO 02/085294, be through 15 carbon atoms, wherein the organic radical used in various compositions, inter alia in the area of body optionally contains 1 to a maximum of 3 oxygen atoms, care and in cleaning agents. preferably R3 is either hydrogen or a saturated or unsatur 0008 DE 25 41 438 describes dioxolane aldehyde fra ated, aromatic oraliphatic, branched or unbranched, cycli grance substances, which were obtained there by the hydro cal or linear, bridged or unbridged structure element with 1 formylation of the corresponding dioxolanes. The various through 15 carbon atoms, wherein the structure element dioxolanes disclosed in DE 2541 438 served there as starting optionally contains 1 to a maximum of 3 oxygenatoms and materials for the production of the dioxolane aldehyde fra the structure element is optionally substituted by 1 to a grance substances. The only dixolane described in DE 2541 maximum of 3 alkyl- and/or alkenyl groups and/or by one 438 with regard to odor is 2-hexyl-4-vinyl-1,3-dioxolane, or two hydroxy groups, which according to DE 25 41 438 has a fruity odor of pine 0017 and apple. 0018 R4 contains an organic radical with 2 through 15 0009 EP 1992 606A1 discloses certain alkene acetals as carbonatoms, wherein the organic radical optionally contains fragrance Substances. The fragrance Substances disclosed in 1 to a maximum of 3 oxygen atoms, preferably R4 is a EP 1992 606 A1 are derived from 4-pentenals, and have in saturated or unsaturated, aromatic or aliphatic, branched or particular a 2.3,3-trimethyl-4-pentenyl structure element. unbranched, cyclical or linear, bridged or unbridged structure 0010 So the primary object was to find fragrance and/or element with 2 through 15 carbon atoms, wherein the struc flavoring Substances having an interesting sensory profile and ture element optionally contains 1 to a maximum of 3 oxygen which are Suitable for use as fragrance Substances in perfum atoms and the structure element is optionally substituted by 1 ery or as flavoring Substances for flavoring consumable to a maximum of 3 alkyl-and/or alkenyl groups and/or by one preparations, without themselves imparting a pineapple note or two hydroxy groups US 2012/030848.6 A1 Dec. 6, 2012 0019 and wherein at least one of the following conditions 0033 or applies: 0034 2. R4 a mono-, bi- or tricyclic alkyl system, which is 0020 i. where R4 is a branched or unbranched alkyl radi optionally substituted by one, two or a cal with 4 through 15 carbon atoms with optionally one, 0035 plurality of alkyl radicals, hydroxy radicals or two or a plurality of double bonds, at position3 to position alkoxy radicals, wherein the alkyl radicals are preferably 4 of R4 a carbon-carbon single bond is present selected from the group consisting of methyl, ethyl, propyl. 0021 or 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1.1- 0022 ii. where R4 is a branched or unbranched alkyl radi dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-me cal with 2 through 15 carbon atoms with optionally one, thylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1- two or a plurality of double bonds, R3 is not hydrogen, dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 0023 as a fragrance and/or flavoring substance for impart 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dim ing, enhancing and/or modifying one, two or a plurality of ethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dim scents and/or flavors, wherein no scent and/or flavor of pine ethylbutyl, 2,3-dimethylbutyl, 3.3-dimethylbutyl, 1-ethylbu apple is imparted. tyl, 2-ethylbutyl, 1.1.2-trimethylpropyl. 1.2.2- 0024. To clarify: condition i. means that between the two trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2- carbon atoms at positions 3 and 4 of R4 in particular no methylpropyl. carbon-carbon double bond is present. 0036 or 0025 Preference is for compounds of Formula (I), 0037 3. R4 is a branched or unbranched alkyl radical with wherein 2 through 15 carbon atoms with one, two or a plurality of 0026 R1 and R2 in each case and independently of one another is either hydrogen or methyl, preferably hydrogen, double bonds or a ring system with 5, 6 or 7 carbon atoms and with one, two or a plurality of double bonds, 0038 and wherein at least one of the following conditions 0027 a) R3 and R4 together result in a cyclical alkyl applies: system with 5, 6, 7 or 8 carbon atoms, which is optionally substituted by one or a plurality of branched or unbranched 0039 i.