Fragrance and flavor compositions comprising aromatic derivatives

Abstract

The present application relates to ethyl 3-phenylpropiolate and related compounds, methods for their preparation, and methods of use thereof as flavor and perfume ingredients in food, cosmetic, pharmaceutical, consumer products, and other compositions and products.

Description

[0001] Cross-reference to related applications This application is an international application that claims priority and interest in U.S. Provisional Application No. 63 / 535,728, filed August 31, 2023, and U.S. Provisional Application No. 63 / 624,739, filed January 24, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0002] This application relates to ethyl 3-phenylpropynate and related compounds, methods for their preparation, and methods for using them as flavor and fragrance ingredients in food, cosmetics, pharmaceuticals, consumer products, and other compositions and products. Background Technology Aroma is a crucial factor in imbuing many consumer products with a sense of anticipation, quality, palatability, and safety. For food, flavor is particularly critical. Imbuing products with effective aromas and flavors is a key element in determining their success, contributing to product marketing, increasing customer satisfaction, and enhancing customer loyalty. Aromas such as cereals, floral notes, lily of the valley, iris, fresh notes, fruity notes, apple, and pear may be particularly ideal for specific flavors and fragrances, suitable for toiletries, cosmetics, household cleaners, room sprays, fabric care products, and high-end fragrance applications such as perfumes and eau de toilettes, oral hygiene products (such as toothpaste and mouthwash), oral medications, and food products.

[0003] Numerous researchers are dedicated to identifying novel substances, used alone or in combination, to impart or enhance the aroma or flavor of various consumer materials, such as cosmetics, detergents, and foods. Although there are certain trends in the relationship between the chemical structure of a molecule and the flavor or aroma it produces—for example, low molecular weight aldehydes and alcohols are often used as flavoring agents and fragrances—the specific aroma produced by a molecule remains extremely difficult to predict. Subtle structural changes, such as adding or removing a single carbon atom from a functional group, can have profound and unexpected effects on the flavor or aroma characteristics of a compound. Flavor and aroma prediction techniques are still in their infancy.

[0004] Using proprietary predictive methods, the inventors have identified 3-phenylpropynic acid as a novel flavor and fragrance ingredient. It is believed that this compound has never been previously identified as a flavor or fragrance ingredient, and its odor properties have never been documented. The inventors have also discovered that esters of 3-phenylpropynic acid, such as ethyl 3-phenylpropynate, are promising new flavor and fragrance ingredients.

[0005] This application describes the surprising and unexpected olfactory properties of 3-phenylpropynic acid and its esters (e.g., ethyl 3-phenylpropynic acid), their analogues, and their derivatives, their uses as flavor and fragrance ingredients, and their potential applications. Invention Overview On the one hand, this application relates to compounds of formula I: Formula I in: R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); X is selected from -O-, -CH2-, -C(O)-, -CH(OH)-, and -CH(OR)-; Y is selected from -CH2CH2CH2CH2-, -CH2CH2OCH2-, -CH2OCH2CH2-, -OCH2CH2CH2-, -CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, -OCH2CH2-, -CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2-, -CH2OCH2CH2CH2-, -CH2CH2OCH2CH2-, -CH2CH2CH2OCH2-, -CH2CH 2CH2CH2O-, -CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2-, -CH2OCH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2-, -CH2CH2CH2OCH2CH2-, - CH2CH2CH2CH2OCH2-, -CH2CH2CH2CH2CH2O-, -CH2CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2CH2-, -CH2OCH2CH2CH2CH2CH2-, -CH 2CH2OCH2CH2CH2CH2-, -CH2CH2CH2OCH2CH2CH2-, -CH2CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2CH2OCH2-, and -CH2CH2CH2CH2CH2CH2O-; The group Y can optionally be C 1-3 Alkyl groups (e.g., CH3), OH, CHO, and OC 1-3 One or more groups in an alkyl group (e.g., OCH3) are substituted; Or XY does not exist; R 3 Selected from H, R b OH, OR bOC(O)R b CN, COOH, COOR b C(O)R b and CHO; R 4 R 5 , and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl or optionally substituted benzyl; Optionally, provided that the compound is not ethyl 3-phenylpropynate, methyl 3-phenylpropynate, or 3-phenylpropynic acid.

[0007] In another embodiment, this disclosure provides compounds of formula II: Formula II in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b OH, OR b OC(O)R b CN, COOH, COOR b C(O)R b and CHO; R 4 R 5 , and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl.

[0008] In another embodiment, this disclosure provides compounds of formula III: Formula III in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b OH, OR b OC(O)R b CN, COOH, COOR b C(O)R b and CHO; R 4 R 5 , and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl.

[0009] In some embodiments, the compound of formula I is ethyl 3-phenylpropynate, methyl 3-phenylpropynate, or 3-phenylpropynic acid.

[0010] On the other hand, this application relates to flavor and fragrance compositions comprising compounds of Formula I, Formula II, or Formula III, optionally comprising one or more additives, additional flavor or fragrance components, or combinations of additives with flavor or fragrance components. In some embodiments, this application relates to flavor and fragrance compositions comprising ethyl 3-phenylpropynate, methyl 3-phenylpropynate, or 3-phenylpropynic acid.

[0011] On the other hand, this application relates to products, such as consumer products, that contain flavor and fragrance compositions containing compounds of Formula I or Formula II, such as products containing ethyl 3-phenylpropynate, methyl 3-phenylpropynate, or 3-phenylpropynic acid.

[0012] On the other hand, this disclosure provides methods for preparing compounds of formula I, II or III.

[0013] Details of one or more embodiments of this application are described below. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application pertains. In case of any conflict, this specification shall prevail.

[0014] Other features and advantages of this application can be found in the following detailed description, embodiments and claims.

[0015] Detailed description The inventors have unexpectedly discovered that ethyl 3-phenylpropynate and 3-phenylpropynic acid possess alcoholic, fermented, and / or fruity aromas. Therefore, such compounds have potential uses for products requiring the addition of pleasant aromas or flavors, including but not limited to perfumes, household products, laundry products, personal care products, cosmetics, oral hygiene products, oral medications, and food products. Compounds of Formula I, II, or III can be used in varying amounts depending on the specific fragrance or flavor product application, the nature and amount of other flavor or fragrance components contained therein, and the desired aroma and / or flavor of the product.

[0016] In a first aspect, this disclosure provides a compound of formula I (compound I). Formula I in: R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); X is selected from -O-, -CH2-, -C(O)-, -CH(OH)-, and -CH(OR)-; Y Selected from -CH2CH2CH2CH2-, -CH2CH2OCH2-, -CH2OCH2CH2-, -OCH2CH2CH2-, -CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, -OCH2CH2-, -CH2CH2 CH2CH2CH2-, -OCH2CH2CH2CH2-, -CH2OCH2CH2CH2-, -CH2CH2OCH2CH2-, -CH2CH2CH2OCH2-, -CH2CH2CH2CH2O-, -CH2CH2CH2CH2C H2CH2-, -OCH2CH2CH2CH2CH2-, -CH2OCH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2-, -CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2OCH2-, -CH 2CH2CH2CH2CH2O-, -CH2CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2CH2-, -CH2OCH2CH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2CH2-, -CH2CH2CH2OCH2CH2CH2-, -CH2CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2CH2OCH2-, and -CH2CH2CH2CH2CH2CH2O-; The group Y can optionally be C 1-3 Alkyl groups (e.g., CH3), OH, CHO, and OC 1-3 One or more groups in an alkyl group (e.g., OCH3) are substituted; Or XY does not exist; R 3 Selected from H, R b OH, OR b OC(O)R b CN, COOH, COOR b C(O)R b and CHO; R 4 R 5 , and R 6 Each is independently selected from H and C.1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl or optionally substituted benzyl; Optionally, the condition is that the compound is not ethyl 3-phenylpropynate, methyl 3-phenylpropynate, or 3-phenylpropynic acid.

[0017] In a further embodiment of the first aspect, this disclosure provides: 1.1 Compound 1, wherein the compound is not 3-phenylpropynic acid; 1.2 Compound 1, wherein the compound is not ethyl 3-phenylpropynate or methyl 3-phenylpropynate; 1.3 Compound 1, or 1.2, wherein R 1 For CHO; 1.4 Compound 1, or 1.2, wherein R 1 COOH; 1.5 Compound 1, or 1.2, wherein R 1 For COOR a ; 1.6 Compound 1.5, wherein R a C is an optional replacement 1-6 Alkyl groups (e.g., CH3 or CH2CH3); 1.7 Compound 1.6, where R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 1.8 Compound 1.5, where R a C is an optional replacement 2-6 alkenyl (e.g., allyl); Compound 1.9, 1.8, wherein R a It is allyl or 2-methylpropyl-1-enyl; 1.10 Compound 1.5, wherein R a C is an optional replacement 3-6 cycloalkyl (e.g., cyclopropyl); 1.11 Compound 1.5, wherein R a CH2C as an optional substitute 3-6 cycloalkyl groups (e.g., cyclopropylmethyl); Compound 1.12, 1.5, wherein R a It is an optionally substituted phenyl or an optionally substituted benzyl group; 1.13 Compound 1, or any one of 1.1 to 1.12, wherein R 2 It is H or OH; 1.14 Compound 1, or any one of 1.1 to 1.12, wherein R 2 C 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl (e.g., OCH3), optionally, wherein R 2 It is CH3 or OCH3; 1.15 Compound 1, or any one of 1.1 to 1.12, wherein R 2 For CHO; 1.16 Compound 1, or any one of 1.1 to 1.15, wherein X is -O-; 1.17 Compound 1, or any one of 1.1 to 1.15, wherein X is -CH2-; 1.18 Compound 1, or any one of 1.1 to 1.17, wherein X is -C(O)-; 1.19 Compound 1, or any one of 1.1 to 1.17, wherein X is -CH(OH)-; 1.20 Compound 1, or any one of 1.1 to 1.19, wherein Y is -CH2CH2CH2CH2-, -CH2CH2OCH2-, -CH2OCH2CH2-, or -OCH2CH2CH2-; 1.21 Compound 1, or any one of 1.1 to 1.19, wherein Y is -CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, or -OCH2CH2-; 1.22 Compound 1, or any one of 1.1 to 1.19, wherein Y is -CH2CH2CH2CH2-, or -CH2CH2CH2-; 1.23 Compound 1, or any one of 1.1 to 1.19, wherein Y is -CH2CH2CH2CH2-; 1.24 Compound 1, or any one of 1.1 to 1.19, wherein XY is absent; 1.25 Compound 1, or any one of 1.1 to 1.24, wherein R 3 For H; 1.26 Compound 1, or any one of 1.1 to 1.24, wherein R 3 For R b ; 1.27 Compound 1, or any one of 1.1 to 1.24, wherein R 3 For OH, OR b , or OC(O)R b Optionally, wherein the R b C 1-6 Alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl); 1.28 Compound 1, or any one of 1.1 to 1.24, wherein R 3 For CN, COOH, COOR, C(O)R b , or CHO; 1.29 Compound 1, or any one of 1.1 to 1.28, wherein R b C is an optional replacement 1-6 Alkyl groups (e.g., CH3 or CH2CH3); 1.30 Compound 1, or any one of 1.1 to 1.28, wherein R b Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl; 1.31 Compound 1, or any one of 1.1 to 1.28, wherein R b C is an optional replacement 3-6 cycloalkyl; 1.32 Compound 1, or any one of 1.1 to 1.28, wherein R b It is cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; 1.33 Compound 1, or any one of 1.1 to 1.28, wherein R b CH2C as an optional substitute 3-6 cycloalkyl groups (e.g., cyclopropylmethyl); 1.34 Compound 1, or any one of 1.1 to 1.28, wherein R b C 4-6 Cycloalkenyl (e.g., cyclopentenyl, such as cyclopent-1-en-1-yl); 1.35 Compound 1, or any one of 1.1 to 1.28, wherein R b It is an optionally substituted phenyl or an optionally substituted benzyl group; 1.36 Compound 1, or any one of 1.1 to 1.35, wherein the compound of formula I is a compound of formula Ia: Formula Ia Among them, Ra R 2 R 3 R 4 and R 6 As defined in any of the preceding formulas; Compound 1.37, 1.36, wherein R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 1.38 Compounds 1.36 or 1.37, where R 2 R 4 and R 6 Each independently represents H and C. 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3); Compounds 1.39, 1.36, 1.37, or 1.38, wherein R 3 For R b OR b And R b Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, allyl, or 2-methylprop-1-enyl; 1.40 Compounds 1.36, 1.37, or 1.38, where R 3 For R b OR b And R b It is phenyl, cyclopentenyl or cyclohexenyl; 1.41 Compound 1, or any one of 1.1 to 1.35, wherein the compound of formula I is a compound of formula Ib: Formula Ib Among them, R a R 3 R 4 and R 6 As defined in any of the preceding formulas; Compound 1.42, 1.41, wherein R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 1.43 Compounds 1.41 or 1.42, wherein R 4 and R 6 Each independently represents H and C. 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3); 1.44 Compounds 1.41, 1.42, or 1.43, wherein R 3 For R b OR b And Rb Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, allyl, or 2-methylprop-1-enyl; 1.45 Compounds 1.41, 1.42, or 1.43, wherein R 3 For R b OR b And R b It is phenyl, cyclopentenyl or cyclohexenyl; 1.46 Compound 1, or any one of 1.1 to 1.35, wherein the compound of formula I is a compound of formula Ic: Formula Ic Where R a and R 3 As defined in any of the preceding formulas; Compound 1.47, 1.36, where R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 1.48 Compounds 1.46 or 1.47, where R 3 For R b OR b And R b Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, allyl, and 2-methylprop-1-enyl; Compound 1.49, 1.46, or 1.47, where R 3 For R b OR b And R b It is phenyl, cyclopentenyl or cyclohexenyl; 1.50 Compound 1, or any one of 1.1 to 1.35, wherein the compound of formula I is a compound of formula Id: FormulaId Where R a As defined in any of the preceding equations (e.g., R) a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl). 1.51 Any of the preceding compounds, wherein the molecular weight of said compound is selected from the following ranges: 172 to 500, or 172 to 450, or 172 to 400, or 172 to 350, or 172 to 300, or 172 to 250, or 172 to 225, or 172 to 200, or 172 to 190; 1.52 Any of the preceding compounds, wherein the compound is selected from: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , as well as ; 1.53 Compounds selected from the following groups: , , , , as well as ; 1.54 Any of the preceding compounds, wherein if the compound has an acidic or basic atom or functional group, the compound is in the form of a salt, such as a base addition salt or an acid addition salt; 1.55 Any of the preceding compounds, wherein the compound has a pleasant taste and / or aroma, as assessed by a trained spice or flavor chemist or perfumer (e.g., roasted coconut or other nutty aroma and / or taste).

[0018] In another embodiment of the first aspect, this disclosure provides a compound of formula II (compound 2): Formula II in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b OH, OR b OC(O)R b CN, COOH, COOR b C(O)R b and CHO; R 4 R 5 and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b C can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl.

[0019] In a further embodiment of the first aspect, this disclosure provides: 2.1 Compound 2, wherein the compound is a compound of formula IIa: Formula IIa 2.2. Compound 2, wherein the compound is a compound of formula IIb: Formula IIb; 2.3. Compound 2, wherein the compound is a compound of formula IIc: Formula IIc 2.4. Compound 2, or any one of 2.1 to 2.3, wherein R 1 For CHO; 2.5. Compound 2, or any one of 2.1 to 2.3, wherein R 1 It is COOH; 2.6. Compound 2, or any one of 2.1 to 2.3, wherein R 1 For COOR a ; 2.7. Compound 2.6, where R a C is an optional replacement 1-6 Alkyl groups (e.g., CH3 or CH2CH3); 2.8. Compound 2.7, where R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 2.9. Compound 2.6, where R a C is an optional replacement 2-6 alkenyl (e.g., allyl); 2.10. Compound 2.9, where R a It is allyl or 2-methylpropyl-1-enyl; 2.11. Compound 2.6, where R a C is an optional replacement 3-6 cycloalkyl (e.g., cyclopropyl); 2.12. Compound 2.6, where R a CH2C as an optional substitute 3-6 cycloalkyl groups (e.g., cyclopropylmethyl); 2.13. Compound 2.6, where R a It is an optionally substituted phenyl or an optionally substituted benzyl group; 2.14. Compound 2, or any one of 2.1 to 2.13, wherein R 2 It is H or OH; 2.15. Compound 2, or any one of 2.1 to 2.13, wherein R 2 C 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3), optionally wherein R 2 It is CH3 or OCH3; 2.16. Compound 2, or any one of 2.1 to 2.13, wherein R 2 For CHO; 2.17. Compound 2, or any one of 2.1 to 2.16, wherein R 3 For H; 2.18. Compound 2, or any one of 2.1 to 2.16, wherein R 3 For R b ; 2.19. Compound 2, or any one of 2.1 to 2.16, wherein R 3 For OH, OR b , or OC(O)R b Optionally, wherein the R b C 1-6 Alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl); 2.20. Compound 2, or any one of 2.1 to 2.16, wherein R 3 For CN, COOH, COOR, C(O)R b , or CHO; 2.21. Compound 2, or any one of 2.1 to 2.20, wherein R b C is an optional replacement 1-6 Alkyl groups (e.g., CH3 or CH2CH3); 2.22. Compound 2, or any one of 2.1 to 2.20, wherein R b Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl; 2.23. Compound 2, or any one of 2.1 to 2.20, wherein R b C is an optional replacement 3-6 cycloalkyl; 2.24. Compound 2, or any one of 2.1 to 2.20, wherein R b It is cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; 2.25. Compound 2, or any one of 2.1 to 2.20, wherein R b CH2C as an optional substitute 3-6 cycloalkyl groups (e.g., cyclopropylmethyl); 2.26. Compound 2, or any one of 2.1 to 2.20, wherein R b C 4-6 Cycloalkenyl (e.g., cyclopentenyl, such as cyclopent-1-en-1-yl); 2.27. Compound 2, or any one of 2.1 to 2.20, wherein R b It is an optionally substituted phenyl or an optionally substituted benzyl group; 2.28. Compound 2, or any one of 2.1 to 2.27, wherein the compound of formula II is a compound of formula IId: Formula IId Where R a R 4 and R 6 As defined in any of the preceding formulas; 2.29. Compound 2.28, where R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 2.30. Compounds 2.28 or 2.29, wherein R 4 and R 6 Each independently represents H and C. 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3); 2.31. Compound 2, or any one of 2.1 to 2.27, wherein the compound of formula II is a compound of formula IIe: Formula IIe Where R a R 4 and R 6 As defined in any of the preceding formulas; 2.32. Compound 2.31, wherein R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 2.33. Compounds 2.31 or 2.32, wherein R 4 and R 6 Each independently represents H and C. 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3); 2.34. Compound 2, or any one of 2.1 to 2.27, wherein the compound of formula II is a compound of formula IIf: Formula IIf Where R a R 4 and R 6 As defined in any of the preceding formulas; 2.35. Compound 2.34, where R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 2.36. Compounds 2.34 or 2.35, wherein R 4 and R6 Each independently represents H and C. 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3); 2.37. Any of the preceding compounds, wherein the molecular weight of said compound is selected from the following ranges: 172 to 500, or 172 to 450, or 172 to 400, or 172 to 350, or 172 to 300, or 172 to 250, or 172 to 225, or 172 to 200, or 172 to 190; 2.38. Any of the preceding compounds, wherein the compound is selected from: , , , , ,as well as ; 2.39. Any of the preceding compounds, wherein if the compound has an acidic or basic atom or functional group, the compound is in the form of a salt, such as a base addition salt or an acid addition salt; 2.40. Any of the preceding compounds, wherein the compound has a pleasant taste and / or aroma, as assessed by a trained spice or flavor chemist or perfumer (e.g., roasted coconut or other nutty aroma and / or taste).

[0020] In another embodiment, this disclosure provides a compound of formula III (compound 3): Formula III in, n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b OH, OR b OC(O)R b CN, COOH, COOR b C(O)R b and CHO; R 4 R 5 and R 6 Each is independently selected from H and C.1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); Each R a and R b C can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl.

[0021] In a further embodiment of the first aspect, this disclosure provides: 3.1. Compound 3, wherein the compound is a compound of formula IIIa: Formula IIIa 3.2. Compound 3, wherein the compound is a compound of formula IIIb: Formula IIIb 3.3. Compound 3, wherein the compound is a compound of formula IIIc: Formula IIIc 3.4. Compound 3, or any one of 3.1 to 3.3, wherein R 1 For CHO; 3.5. Compound 3, or any one of 3.1 to 3.3, wherein R 1 It is COOH; 3.6. Compound 3, or any one of 3.1 to 3.3, wherein R 1 For COOR a ; 3.7. Compound 3.6, where R a C is an optional replacement 1-6 Alkyl groups (e.g., CH3 or CH2CH3); 3.8. Compound 3.7, wherein R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 3.9. Compound 3.6, wherein R a C is an optional replacement 2-6 alkenyl (e.g., allyl); 3.10. Compound 3.9, where R a It is allyl or 2-methylpropyl-1-enyl; 3.11. Compound 3.6, where R a C is an optional replacement 3-6 cycloalkyl (e.g., cyclopropyl); 3.12. Compound 3.6, where R a CH2C as an optional substitute 3-6 cycloalkyl groups (e.g., cyclopropylmethyl); 3.13. Compound 3.6, where R a It is an optionally substituted phenyl or an optionally substituted benzyl group; 3.14. Compound 3, or any one of 3.1 to 3.13, wherein R 2 It is H or OH; 3.15. Compound 3, or any one of 3.1 to 3.13, wherein R 2 C 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl group (e.g., OCH3), optionally, wherein R 2 It is CH3 or OCH3; 3.16. Compound 3, or any one of 3.1 to 3.13, wherein R 2 For CHO; 3.17. Compound 3, or any one of 3.1 to 3.16, wherein R 3 For H; 3.18. Compound 3, or any one of 3.1 to 3.16, wherein R 3 For R b ,; 3.19. Compound 3, or any one of 3.1 to 3.16, wherein R 3 For OH, OR b or OC(O)R b Optionally, wherein the R b C 1-6 Alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl); 3.20. Compound 3, or any one of 3.1 to 3.16, wherein R 3 For CN, COOH, COOR, C(O)R b Or CHO; 3.21. Compound 3, or any one of 3.1 to 3.20, wherein R b C is an optional replacement 1-6 Alkyl groups (e.g., CH3 or CH2CH3); 3.22. Compound 3, or any one of 3.1 to 3.20, wherein R b Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl; 3.23. Compound 3, or any one of 3.1 to 3.20, wherein R b C is an optional replacement 3-6 cycloalkyl; 3.24. Compound 3, or any one of 3.1 to 3.20, wherein R b It is cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; 3.25. Compound 3, or any one of 3.1 to 3.20, wherein R b CH2C as an optional substitute 3-6 cycloalkyl groups (e.g., cyclopropylmethyl); 3.26. Compound 3, or any one of 3.1 to 3.20, wherein R b C 4-6 Cycloalkenyl (e.g., cyclopentenyl, such as cyclopent-1-en-1-yl); 3.27. Compound 3, or any one of 3.1 to 3.20, wherein R b It is an optionally substituted phenyl or an optionally substituted benzyl group; 3.28. Compound 3, or any one of 3.1 to 3.27, wherein the compound of formula III is a compound of formula IIId: Formula IIId Where R a and R 6 As defined in any of the preceding formulas; 3.29. Compound 3.28, where R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 3.30. Compounds 3.28 or 3.29, wherein R 6 For H, C 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3); 3.31. Compound 3, or any one of 3.1 to 3.27, wherein the compound of formula III is a compound of formula IIIe: Formula IIIe Where R a and R 6 As defined in any of the preceding formulas; 3.32. Compound 3.31, wherein R aSelected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 3.33. Compounds 3.31 or 3.32, wherein R 6 For H, C 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3); 3.34. Compound 3, or any one of 3.1 to 3.27, wherein the compound of formula III is a compound of formula IIIf: Formula IIIf Where R a and R 6 As defined in any of the preceding formulas; 3.35. Compound 3.34, where R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl; 3.36. Compounds 3.34 or 3.35, wherein R 6 For H, C 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3); 3.37. Any of the preceding compounds, wherein the molecular weight of said compound is selected from the following ranges: 172 to 500, or 172 to 450, or 172 to 400, or 172 to 350, or 172 to 300, or 172 to 250, or 172 to 225, or 172 to 200, or 172 to 190; 3.38. Any one of the preceding compounds, wherein the compound is selected from: , , , as well as ; 3.39. Any of the preceding compounds, wherein if the compound has an acidic or basic atom or functional group, the compound is in the form of a salt, such as a base addition salt or an acid addition salt; 3.40. Any of the preceding compounds, wherein the compound has a pleasant taste and / or aroma, as assessed by a trained spice or flavor chemist or perfumer (e.g., roasted coconut or other nutty aroma and / or taste).

[0022] In a second aspect, this disclosure provides a flavor composition and / or fragrance composition (composition 1) comprising compound 1 or any one of 1.1 to 1.55, compound 2 or any one of 2.1 to 2.40, or compound 3 or any one of 3.1 to 3.40, and mixed with one or more non-toxic, orally acceptable, pharmaceutically acceptable, cosmetically acceptable, or household product acceptable carriers or excipients. In a specific embodiment, the second aspect provides: 1.1 Composition 1, wherein the composition is a fragrance composition.

[0023] 1.2 Composition 1, wherein the composition is a flavor composition.

[0024] 1.3 Composition 1, or any one of 1.1 to 1.2, wherein the composition comprises compound 1 or any one of 1.1 to 1.55, compound 2 or any one of 2.1 to 2.40, or compound 3 or any one of 3.1 to 3.40, in an amount of 0.1% to 100% by weight of the composition, for example, 0.1% to 90%, or 0.1% to 80%, or 0.1% to 70%, or 0.1% to 60%, or 0.1% to 50%, or 0.1% to 40%, or 0.1% to 30%, or 0.1% to 20%, or 0% by weight of the composition. 0.1% to 15%, or 0.1% to 10%, or 0.1% to 7.5%, or 0.1% to 5%, or 0.1% to 4%, or 0.1% to 3%, or 0.1% to 2%, or 0.1% to 1%, or 10% to 100%, or 20% to 100%, or 30% to 100%, or 40% to 100%, or 50% to 100%, or 60% to 100%, or 70% to 100%, or 80% to 100%, or 90% to 100%, or 95% to 100%, or 25% to 75%, or 50% to 75%, or 75% to 95%.

[0025] 1.4 Composition 1, or any one of 1.1 to 1.3, wherein the composition further comprises one or more other flavoring agents or fragrances.

[0026] 1.5 Composition 1, or any one of 1.1 to 1.4, wherein the composition further comprises one or more solvents.

[0027] 1.6 Composition 1.5, wherein the one or more solvents are selected from water, methanol, ethanol, propanol, isopropanol, dimethyl ether, diethyl ether, diisopropyl ether, methyl tert-butyl ether, ethylene glycol, propylene glycol, glycerol, triethyl citrate, triacetyl triacetate, triglycerides, liquid waxes, propylene glycol derivatives (e.g., polypropylene glycol or ethylene oxide / propylene oxide copolymers), ethylene glycol derivatives (e.g., polyethylene glycol or ethylene oxide / propylene oxide copolymers), other alcohols or ethers, or any combination thereof.

[0028] 1.7 Composition 1, or any one of 1.1 to 1.6, wherein the composition is a liquid.

[0029] 1.8 Composition 1, or any one of 1.1 to 1.6, wherein the composition is a soft solid or a waxy solid.

[0030] 1.9 Composition 1, or any one of 1.1 to 1.8, wherein the composition further comprises one or more polymers, gelling agents, powdered matrices, surfactants, emollients, plasticizers, wetting agents, swelling agents or activators (e.g., oral care activators or pharmaceutical activators), or any other additives described herein.

[0031] 1.10 Composition 1, or any one of 1.1 to 1.9, wherein the composition does not contain any ingredient or component that is unsafe for ingestion, oral application or topical application to the skin or hair; 1.11 Composition 1, or any one of 1.1 to 1.10, wherein the composition does not contain any ingredient or component that is unsafe or unapproved for use in food, cosmetic, pharmaceutical, oral care, or consumer cleaning compositions.

[0032] As used herein, the term "fragrance composition" refers to a mixture of fragrance ingredients (e.g., compounds of formula I, II, or III) with one or more non-toxic, cosmetically acceptable, or household product acceptable carriers or excipients (e.g., solvents). For example, the fragrance ingredient may be dissolved in a suitable solvent or mixed with a powdered matrix, with additional excipients (e.g., additives) added as needed. Fragrance compositions are used and intended to provide or impart a desired odor or aroma to products, such as cosmetics or household products (e.g., household cleaners). Thus, fragrance compositions are used as an ingredient or component in the final product, such as cosmetics or consumer products requiring a specific fragrance. Examples of products having fragrance compositions include, but are not limited to, perfumes, soaps, insect repellents and pesticides, detergents, household cleaners, air fresheners, room sprays, aromatherapy, candles, cosmetics, eau de toilette, preshave and aftershave, talcum powder, hair care products, body deodorants, antiperspirants, and pet bedding. The fragrance composition should contain sufficient fragrance ingredients to effectively provide the desired odor or aroma to the final product, which depends on both the concentration of the fragrance ingredients in the composition and the concentration of the composition used in the product.

[0033] As used herein, the term "flavor composition" refers to a mixture of a flavor component (e.g., including compounds of formula I, II, or III) with one or more non-toxic, orally acceptable, or pharmaceutically acceptable carriers or excipients, such as solvents. For example, the flavor component may be soluble in a suitable solvent or mixed with a suitable solid, semi-solid, or liquid excipient, and additional excipients (e.g., additives) may be added as needed. Flavor compositions are used and intended to provide or impart a desired flavor and aroma to products, such as food or oral pharmaceutical products. Thus, flavor compositions are used as an ingredient or component in the final product, such as food or oral pharmaceutical products requiring a specific flavor. Examples of products having flavor compositions include, but are not limited to: oral care compositions (e.g., oral hygiene products such as mouthwash, toothpaste, dental floss, and breath fresheners), pharmaceutical compositions (e.g., oral medications, including liquid formulations, tablets, or capsules), and foods. Flavor compositions should contain sufficient amounts of the flavor component to effectively provide the desired flavor and aroma to the final product, depending both on the concentration of the flavor component in the composition and the concentration of the composition used in the product.

[0034] Flavoring and flavoring components and mixtures thereof that can be combined with the disclosed compounds for the manufacture of flavoring and flavoring compositions include, but are not limited to: natural products (including extracts), animal products and essential oils, absolutes, resinous oils, resins and extracts, and synthetic flavoring substances, including but not limited to alcohols, aldehydes, ketones, ethers, acids, esters, acetals, phenols, ethers, lactones, furanone acetals, nitriles, acids and hydrocarbons, including saturated and unsaturated compounds and aliphatic carbocyclic and heterocyclic compounds, as well as animal products. As used herein, the terms "flavoring component" and "flavoring ingredient" refer to components other than compounds of Formula I used to impart flavor or aroma to a composition or product.

[0035] Examples of esters that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: acrylates (methyl ester, ethyl ester, etc.), acetoacetate esters (methyl ester, ethyl ester, etc.), anisole esters (methyl ester, ethyl ester, etc.), benzoate esters (allyl ester, isoamyl ester, ethyl ester, geraniol ester, linalool ester, phenethyl ester, hexyl ester, cis-3-hexenyl ester, benzyl ester, methyl ester, etc.), anthranilate esters (cinnamyl ester, cis-3-hexenyl ester, methyl ester, ethyl ester, linalool ester, isobutyl ester, etc.), N-methyl anthranilate esters (methyl ester, ethyl ester, etc.), isovalerate esters (pentyl ester, allyl ester, isoamyl ester, isobutyl ester, isopropyl ester, ethyl ester, octyl ester, geraniol ester, cyclohexyl ester, citronellol ester, terpineol ester, linalool ester, cinnamyl ester, phenethyl ester, butyl ester, propyl ester, etc.). Esters, hexyl esters, benzyl esters, methyl esters, rhodane esters, etc.), isobutyrates (isoamyl esters, geraniol esters, citronellol esters, terpineol esters, cinnamyl esters, octyl esters, nerolithyl esters, phenethyl esters, phenylpropyl esters, phenoxyethyl esters, butyl esters, propyl esters, isopropyl esters, hexyl esters, benzyl esters, methyl esters, ethyl esters, linalool esters, rhodane esters, etc.), undecylenoic acid esters (allyl esters, isoamyl esters, butyl esters, ethyl esters, methyl esters, etc.), octyl esters (allyl esters, isoamyl esters, ethyl esters, octyl esters, hexyl esters, butyl esters, methyl esters, linalool esters, etc.), hexanoates (allyl esters, pentyl esters, isoamyl esters, methyl esters, ethyl esters, isobutyl esters, propyl esters, hexyl esters, cis-3-hexenyl esters, trans-2-hexenyl esters, linalool esters, geraniol esters, cyclohexyl esters, etc.), hexyl esters, etc. Acrylates (methyl ester, ethyl ester, etc.), valerates (pentyl ester, isopropyl ester, isobutyl ester, ethyl ester, cis-3-hexenyl ester, trans-2-hexenyl ester, cinnamate, phenethyl ester, methyl ester, etc.), formates (anesinyl ester, isoamyl ester, isopropyl ester, ethyl ester, octyl ester, geraniol ester, citronellol ester, cinnamate, cyclohexyl ester, terpineol ester, phenethyl ester, butyl ester, propyl ester, hexyl ester, cis-3-hexenyl ester, benzyl ester, linalool ester, rhodane ester, etc.), crotonyl esters (isobutyl ester, ethyl ester, cyclohexyl ester, etc.), cinnamic acid esters (allyl ester, ethyl ester, methyl ester, isopropyl ester, propyl ester, 3-phenylpropyl ester, benzyl ester, cyclohexyl ester, methyl ester, etc.), succinates (monomethyl ester, diethyl ester, dimethyl ester, etc.), acetates (anesinyl ester, pentyl ester, α-pentylcinnamate, isoamyl ester, isobutyl ester). Isopropyl ester, isoborneol ester, isoeugenol ester, eugenol ester, 2-ethylbutyl ester, ethyl ester, 3-octyl ester, p-cresol ester, o-cresol ester, geraniol ester, α- or β-santalyl ester, cyclohexyl ester, cycloneryl ester, dihydrocumyl ester, dimethyl benzyl methanol ester, cinnamic acid ester, styrax ester, decyl ester, dodecyl ester, terpineol ester, guaiac ester, nerolithyl ester, nonyl ester, phenethyl ester, phenylethyl ester, propyl ester, butyl ester, furfuryl ester, propyl ester, hexyl ester, cis-3-hexenyl ester, trans-2-hexenyl ester, cis-3-nonenyl ester, cis-6-nonenyl ester, cis-3-cis-6-nonadienyl ester, 3-methyl-2-butenyl ester, heptyl ester, benzyl ester, borneol ester, myrcene ester, dihydromyrcene ester, myrtyl ester, methyl ester, 2-methylbutyl ester, menthyl ester, linalool ester, rhodane ester, etc.Salicylate esters (allyl, isoamyl, phenyl, ethyl, benzyl, ethyl, methyl, etc.), cyclohexylalkyl esters (ethyl cyclohexyl, allyl cyclohexylpropionate, allyl cyclohexylbutyrate, allyl cyclohexylhexanoate, allyl cyclohexyldecanoate, allyl cyclohexylvalerate, etc.), stearates (ethyl, propyl, butyl, etc.), sebacic acid esters (diethyl, dimethyl, etc.), decanoic acid esters (isoamyl, ethyl, butyl, methyl, etc.), dodecanoic acid esters (isoamyl, ethyl, butyl, etc.), lactate esters (isoamyl, ethyl, butyl, etc.), nonanoic acid esters. (Ethyl acetate, phenethyl acetate, methyl acetate, etc.), nonenolates (allyl acetate, ethyl acetate, methyl acetate, etc.), hydroxyhexanoates (ethyl acetate, methyl acetate, etc.), phenylacetic acids (isoamyl acetate, isobutyl acetate, ethyl acetate, geraniol, cis-3-hexenyl acetate, methyl acetate, etc.), phenoxyacetic acids (allyl acetate, ethyl acetate, methyl acetate, etc.), furanylcarboxylic acids (ethyl furanylcarboxylate, methyl furanylcarboxylate, hexyl furanylcarboxylate, isobutylfuran-neopentyl glycol diacetate dipropionate, etc.), propionates (anesinyl acetate, allyl acetate, ethyl acetate, pentyl acetate, isoamyl acetate, propyl acetate, butyl acetate, isobutyl acetate, isopropyl ... Propyl acetate, benzyl acetate, geraniol acetate, cyclohexyl acetate, citronellol acetate, cinnamyl acetate, tetrahydrofurfuryl acetate, tricyclodecenyl acetate, heptayl acetate, borneol acetate, methyl acetate, menthyl acetate, linaloyl acetate, terpineol acetate, α-methylpropionyl acetate, β-methylpropionyl acetate, etc.), heptayl esters (allyl acetate, ethyl acetate, octyl acetate, propyl acetate, methyl acetate, etc.), heptaynyl carboxylic esters (allyl acetate, ethyl acetate, propyl acetate, methyl acetate, etc.), myristate esters (isopropyl acetate, ethyl acetate, methyl acetate, etc.), phenyl glycidyl esters (ethyl phenyl glycidyl acid, ethyl 3-methylphenyl glycidyl acid, ethyl p-methyl-β-phenyl glycidyl acid, etc.). 2-Methylbutyrates (methyl, ethyl, octyl, phenethyl, butyl, hexyl, benzyl, etc.), 3-methylbutyrates (methyl, ethyl, etc.), butyrates (anesinyl, amyl, allyl, isoamyl, methyl, ethyl, propyl, octyl, guaiacyl, linaloyl, geraniol, cyclohexyl, citronellol, cinnamonyl, nerol, terpineol, phenylpropyl, β-phenethyl, butyl, hexyl, cis-3-hexenyl, trans-2-hexenyl, benzyl, rhodane, etc.), and hydroxybutyrates (methyl, ethyl, menthyl, etc. of 3-hydroxybutyrate).

[0036] Examples of alcohols that can be used as flavoring agents, aroma components, or solvents in the compositions and products disclosed herein include, but are not limited to: fatty alcohols (isoamyl alcohol, 2-ethylhexanol, 1-octanol, 3-octanol, 1-octen-3-ol, 1-decanol, 1-dodecanol, 2,6-nonadienol, nonanol, 2-nonanol, cis-6-nonenol, trans-2-cis-6-nonadienol, cis-3-cis-6-nonadienol, butanol, hexanol, cis-3-hexenol, trans-2-hexenol, 1-undecanol, heptanol, 2-heptanol, 3-methyl-1-pentanol, etc.). ); terpenoid alcohols (borneol, isoborneol, carvacrol, geraniol, α- or β-santalol, citronellol, 4-thujol, terpineol, 4-terpineol, nerol, myrceneol, myrtol, dihydromyrceneol, tetrahydromyrceneol, nerolidol, hydroxycitronellol, farnesol, perillol, rhodaneol, linalool, etc.); and aromatic alcohols (anesinol, α-pentylcinnamol, isopropylbenzyl alcohol, carvacrol, cuminol, dimethylbenzyl alcohol, cinnamol, phenylallyl alcohol, phenethyl alcohol, β-phenylethanol, 3-phenylpropanol, benzyl alcohol, etc.).

[0037] Examples of aldehydes that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: aliphatic aldehydes (acetaldehyde, octanal, nonanal, decanal, undecanal, 2,6-dimethyl-5-heptanal, 3,5,5-trimethylhexanal, cis-3-cis-6-nonadienal, trans-2-cis-6-nonadienal, pentanal, propanal, isopropanal, hexanal, trans-2-hexenal, cis-3-hexenal, 2-pentenal, dodecanal, tetradecanal, trans-4-decenal, trans-2-tetadecanal, trans-2-dodecenal, trans-2-undecenal, 2,4-hexadienal, cis-6-nonenal, trans-2-nonenal, 2-methylbutanal, etc.); Aromatic aldehydes (anisinaldehyde, α-pentylcinnamaldehyde, α-methylcinnamaldehyde, cyclamenaldehyde, p-isopropylphenylacetaldehyde, ethyl vanillin, cuminaldehyde, salicylaldehyde, cinnamaldehyde, o-, m- or p-tolualdehyde, vanillin, piperaldehyde, phenylacetaldehyde, jasmine aldehyde, benzaldehyde, 4-methyl-2-phenyl-2-pentenaldehyde, p-methoxycinnamaldehyde, p-methoxybenzaldehyde, etc.); and terpene aldehydes (geranialdehyde, citral, citronellol, α-sweet orange aldehyde, β-sweet orange aldehyde, perillaldehyde, hydroxycitronellol, tetrahydrocitronellol, myrtol, cyclocitronellol, isocyclocitronellol, citronoxyacetaldehyde, neraldehyde, α-methylene citronellol, citric acid aldehyde, vernaldehyde, saffron aldehyde, etc.).

[0038] Examples of ketones that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: cyclic ketones (1-acetyl-3,3-dimethyl-1-cyclohexene, cis-jasmone, α-, β- or γ-irone, ethyl maltol, cycloenone, dihydronorcaconone, 3,4-dimethyl-1,2-cyclopentanedione, sotorone, α-, β-, γ- or δ-damasconone, α-, β- or γ-damasconone, nocaconone, 2-sec-butylcyclohexanone, maltol, α-, β- or γ-ionone, α-, β- or γ-methyl ionone). Ionone, α-, β- or γ-isomethyl ionone, furanone, camphor, etc.; aromatic ketones (acetylnaphthone, acetophenone, anisidine acetone, raspberry ketone, p-methyl acetophenone, anisyl acetone, p-methoxyacetophenone, etc.); and chain ketones (diacetyl, 2-nonanone, diacetyl, 2-heptanone, 2,3-heptanedione, 2-pentanone, methylpentyl ketone, methyl nonyl ketone, β-methylnaphthyl ketone, methyl heptanone, 3-heptanone, 4-heptanone, 3-octanone, 2,3-hexanedione, 2-undecaneone, dimethyloctenone, 6-methyl-5-hepten-2-one, etc.).

[0039] Examples of acetals that can be used as fragrance or flavor components in the compositions and products disclosed herein include, but are not limited to: acetaldehyde diethyl acetal, acetaldehyde dipentane acetal, acetaldehyde dihexyl acetal, acetaldehyde propylene glycol acetal, acetaldehyde ethyl cis-3-hexenyl acetal, benzaldehyde glycerol acetal, benzaldehyde propylene glycol acetal, citral dimethyl acetal, citral diethyl acetal, citral propylene glycol acetal, citral ethylene glycol acetal, phenylacetaldehyde dimethyl acetal, citronellol methyl acetal, acetaldehyde phenylethylpropyl acetal, and hexaldehyde dimethyl acetal. Acetal, hexanal dihexyl acetal, hexanal propylene glycol acetal, trans-2-hexenal diethyl acetal, trans-2-hexenal propylene glycol acetal, cis-3-hexenal diethyl acetal, heptanal diethyl acetal, heptanal ethylene glycol acetal, octanal dimethyl acetal, nonanal dimethyl acetal, decanal dimethyl acetal, decanal diethyl acetal, 2-methylundecanoal dimethyl acetal, citronellol dimethyl acetal, Ambes (produced by Givaudan), ethyl acetoacetate ethylene glycol acetal, and 2-phenylpropanal dimethyl acetal.

[0040] Examples of phenols that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: eugenol, isoeugenol, 2-methoxy-4-vinylphenol, thymol, carvacrol, guaiacol, piperol, and vanillin.

[0041] Examples of ethers and epoxides that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: anethole, 1,4-cineole, dibenzyl ether, linalool oxide, limonene oxide, nerol oxide, rose oxide, isoeugenol methyl ether, tarragon, isopentylphenethyl ether, β-naphthyl methyl ether, phenylpropyl ether, p-cresol methyl ether, vanillyl butyl ether, α-terpineol methyl ether, citronellol ethyl ether, geraniol ethyl ether, rose furan, theanosterane, decyl methyl ether, and methyl phenyl methyl ether.

[0042] Examples of lactones that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: γ- or δ-decyl lactone, γ-heptyl lactone, γ-nonyl lactone, γ- or δ-caprolactone, γ- or δ-octyl lactone, γ- or δ-undecanolactone, δ-dodecyl lactone, δ-2-decenolactone, methyl lactone, 5-hydroxy-8-undecenoic acid δ-lactone, jasmine lactone, menthol lactone, dihydrocoumarin, octahydrocoumarin, and 6-methylcoumarin.

[0043] Examples of furans that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: furan, 2-methylfuran, 3-methylfuran, 2-ethylfuran, 2,5-diethyltetrahydrofuran, 3-hydroxy-2-methyltetrahydrofuran, 2-(methoxymethyl)furan, 2,3-dihydrofuran, furfural, 5-methylfurfural, 3-(2-furanyl)-2-methyl-2-propenal, 5-(hydroxymethyl)furfural, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (furanone), and 4,5-dimethyl-3-hydroxy-2(5H)-furanone (fenugreek lactone). 2-Ethyl-4-hydroxy-5-methyl-3(2H)-furanone (high-furanone), 5-Ethyl-3-hydroxy-4-methyl-2(5H)-furanone (high-trigonolactone), 3-Methyl-1,2-cyclopentanedione (methylcyclopentenolone), 2(5H)-furanone, 4-methyl-2(5H)-furanone, 5-methyl-2(5H)-furanone, 2-methyl-3(2H)-furanone, 5-methyl-3(2H)-furanone, 2-acetylfuranone, 2-acetyl-5-methylfuran, furfuryl alcohol, methyl 2-furancarboxylate, ethyl 2-furancarboxylate, and furfuryl acetate.

[0044] Examples of hydrocarbons that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: α- or β-bisabolene, β-caryophyllene, p-cymene, terpinene, terpinene oil, juniperene, cedrolene, longleafene, farnesene, limonene, ocimene, myrcene, α- or β-pinene, 1,3,5-undecanetriene, and Valencia citrusene.

[0045] Examples of acids that can be used as flavoring or fragrance components in the compositions and products disclosed herein include, but are not limited to: geranilic acid, lauryl acid, myristic acid, stearic acid, lactic acid, phenylacetic acid, pyruvic acid, trans-2-methyl-2-pentenoic acid, 2-methyl-cis-3-pentenoic acid, 2-methyl-4-pentenoic acid, and cyclohexanecarboxylic acid.

[0046] The spice and flavor compositions of this application may contain one or more natural extracts or oils as additional spice or flavor ingredients, including but not limited to: anise, orange, lemon, lime, citrus, petitgrain, bergamot, lemon balm, grapefruit, elemi, frankincense, lemongrass, orange blossom, marjoram, angelica root, star anise, basil, bay leaf, calamus, chamomile, caraway, cardamom, lentil, cinnamon, pepper, perilla, cypress, oregano, quinoa, ginger, parsley, pine needles, sage, hyacinth, tea tree, mustard, horseradish, sage, clove, cognac, coriander, and dragon fruit. Artemisia, eucalyptus, fennel, guaiac wood, dill, melaleuca, sage, allspice, juniper, fenugreek, garlic, bay leaf, nutmeg, myrrh, nutmeg, spruce, geranium, lemongrass, lavender, mixed lavender, palmarosa, rose, rosemary, sandalwood, oakmoss, cedarwood, vetiver, linalool, rosewood, patchouli, rockrose, cumin, thyme, ylang-ylang, birch, chili, celery, toloaf, broom, immortelle, benzoin, jasmine, acacia, tuberose, mignonette, marigold, mimosa, myrrh, orris root, vanilla, and licorice. Each of these natural extracts or oils contains a complex mixture of compounds, possibly including those listed above. Additional flavoring components can be isolated from natural products; for example, geraniol and citronellol can be isolated from citronella oil, citral from lemongrass oil, eugenol from clove oil, and linalool from rosewood oil. Animal products used in the flavoring compositions include, but are not limited to, musk, ambergris, civet, and castoreum. The natural ingredients described herein can also be produced synthetically and may include compounds disclosed herein, used as flavoring and / or flavoring components in the flavoring and flavoring compositions of this application.

[0047] Examples of fragrance ingredients used in perfumes, air fresheners, laundry detergents, pet bedding, cleaning products, liquid soaps and bar soaps, shampoos and conditioners, cosmetics, deodorants, and personal hygiene products include, but are not limited to: hexylcinnamaldehyde; pentylcinnamaldehyde; amyl salicylate; hexyl salicylate; terpineol; 3,7-dimethyl-cis-2,6-octadien-1-ol; 2,6-dimethyl-2-octanol; 2,6-dimethyl-7-octen-2-ol; 3,7-dimethyl-3-octanol; 3,7-dimethyl-trans-2,6-octadien-1-ol; 3,7-dimethyl-6-octen-1-ol; 3,7-dimethyl-1-octanol; 2-methyl- 3-(p-tert-butylphenyl)propanal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde; tricyclodecenyl propionate; tricyclodecenyl acetate; anisaldehyde; 2-methyl-2-(p-isopropylphenyl)propanal; ethyl 3-methyl-3-phenyl glycidyl acid; 4-(p-hydroxyphenyl)-but-2-one; 1-(2,6,6-trimethyl-2-cyclohexene-1-yl)-2-buten-1-one; p-methoxyacetophenone; p-methoxy-α-phenylpropene; methyl 2-hexyl-3-oxocyclopentanecarboxylate; γ-undecyl lactone; geraniol; geraniol acetate; linalool; linalool acetate; tetrahydrolinalool; citronellol; ethyl Citronellol; dihydromyrcenol; dihydromyrcenol acetate; tetrahydromyrcenol; terpineol acetate; nobile alcohol; nobile acetate; 2-phenylethanol; 2-phenylethyl acetate; benzyl alcohol; benzyl acetate; benzyl salicylate; benzyl benzoate; styrax acetate; dimethylbenzyl alcohol; methylphenyl alcohol; trichloromethylphenyl alcohol acetate; isononyl acetate; vetiverol acetate; vetiverol; 2-methyl-3-(p-tert-butylphenyl)propanal; 2-methyl-3-(p-isopropylphenyl)propanal; 3-(p-tert-butylphenyl)propanal; 4-(4-methyl-3-pentenyl)-3-cyclohexenecarboxaldehyde; 4-acetoxy-3-pentyltetrahydropyran; dihydrojasmine Methyl ketoate; 2-n-heptylcyclopentanone; 3-methyl-2-pentylcyclopentanone; n-decanal; n-dodecanoal; 9-decen-1-ol; phenoxyethyl isobutyrate; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; geraniol; citronellol; cedaraldehyde acetal; 3-isoborneolcyclohexanol; cedaryl methyl ether; isolongayl ketone; octoponitrile; octoponitrile; heliotropin; eugenol; vanillin; diphenyl ether; hydroxycitronellol ionone; methyl ionone; isomethyl ionone; irisone; cis-3-hexenol and its esters; indaminom musk fragrance; naphthalenem musk fragrance; isochroman musk fragrance; macrocyclic ketones; macrocyclic lactone musk fragrances; and ethylene glycol diterpenoid.

[0048] The flavoring and flavoring ingredients in a particular product's fragrance or flavor composition are selected based on the product's intended use and the desired aroma. For example, flavoring ingredients used in toothpaste, mouthwash, and oral hygiene products may be selected to impart a "fresh" sensation, including but not limited to spearmint oil, peppermint oil, star anise oil, lemon oil, and menthol.

[0049] Flavor compositions can be used to mask unpleasant tastes in oral medications. For example, if a medication is salty, a composition with flavors of cinnamon, raspberry, orange, maple syrup, caramel, or licorice can be used to mask the taste. If a medication is too sweet, a composition with flavors of berries, vanilla, or gum arabic can make the medication more palatable. For bitter medications, compositions with flavors of cocoa, chocolate mint, wild cherry, walnut, licorice, and sage can be used, while sour medications can be improved with compositions with fruity, citrus, or cherry flavors. These flavors can be provided by the natural or synthetic flavoring ingredients discussed herein.

[0050] Examples of flavoring ingredients used in food flavor compositions include, but are not limited to: glucosylstevioside, isomenthyl alcohol, thiocarbonate, cathinane, 1,5-octadien-3-ol, 2-mercaptohept-4-ol, 4-3-(methylthio)decaldehyde, (4Z,7Z)-tetadecan-4,7-dienal, Polygonum hydropiper oil, Camellia sinensis extract, glutamyl-2-aminobutyric acid, glutamyl-2-aminobutyric acid, glutamyl-n-valine-glycine. Glutamine-valine, N1-(2,3-dimethoxybenzyl)-N2-(2-(pyridin-2-yl)ethyl)oxalamide, 1-(2-hydroxy-4-methylcyclohexyl) ethyl ketone, Mexican lemon oil, Persian lemon oil, 6-methoxy-2,6-dimethylheptanal, 3,5-undecadien-2-one, 2,5-undecadien-1-ol, triethylthiazol, 4-methylpentyl-4-methylvalerate, ( R)-N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide, 2-N-acetylglutamate, 1,3-propanediol, Sichuan pepper extract, Tasmanian pepper extract, peppermint oil, mangosteen distillate, ethyl 3-(2-hydroxyphenyl)propionate, 1-cyclopropanemethyl-4-methoxybenzene, isopentenyl thiobutyrate, isopentenyl thiobutyrate, podophyllin, stevioside, 1-(2 4-Dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-1-one, ethyl 5-formyloxydecanoate, ethyl 3-[3-(2-isopropyl-5-methyl-cyclohexyl)ureo]butyrate, 2-isopropyl-4-methyl-3-thiazoline, 2,6,10-trimethyl-9-undecenal, 5-mercapto-5-methyl-3-hexanone, Mayer's lemon oil, stevia glycoside extract, stevia, rebaudioside A 60%, berberine, 4-amino-5-(3-(isopropylamino)-2,2-dimethyl-3-oxopropoxy)-2-methylquinoline-3-carboxylic acid, 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol, (1-methyl-2-(1,2,2-trimethylbicyclo[3.1.0]hex-3-ylmethyl)cyclopropyl)methanol, eucalyptus oil and peppermint oil. See LJ Marnett et al., GRAS Flavorings 26, Food Technology, pp. 44-45 (2013).

[0051] Preferred solvents and excipients used in the compositions and products disclosed herein include, but are not limited to, triethyl citrate, glyceryl triacetate, glycerol, propylene glycol, dipropylene glycol, isopropyl myristate, ethanol, water, triglycerides, liquid waxes, propylene glycol derivatives (e.g., polymers), and ethylene glycol derivatives (e.g., polymers).

[0052] The amount of a specific spice or flavor ingredient in a spice or flavor composition cannot be precisely described because it depends on the type of product to be flavored or seasoned, the intended use of the product, and the desired aroma and / or flavor. The amount of a spice or flavor ingredient in a spice or flavor composition is typically from about 1% to about 99% of the spice composition's mass. If the amount of an ingredient is too small, sufficient aroma or flavor intensity may not be achieved. Furthermore, if the amount of an ingredient is too large, a larger dose of reagent may be required to dissolve the ingredient, which may reduce the desired aromatic or flavor characteristics of the final product by inhibiting the volatilization or other mechanisms of flavor or spice dispersion during product use or consumption. Therefore, the amount of each spice and flavor ingredient in a given spice or flavor composition must be selected based on the aromatic and / or flavor characteristics of the selected ingredient, the overall composition of the product, and the expected aromatic and / or flavor effect.

[0053] Additives may be used in the flavor and fragrance compositions disclosed herein. These additives include, but are not limited to, solvents, surfactants, pH adjusters, buffers, thickeners, drying agents, emulsifiers, foaming agents, stabilizers, antioxidants, and disintegrants. Other flavor and fragrance composition additives will be selected according to the intended use of the composition.

[0054] Solvents that can be used in the fragrance and flavor compositions disclosed herein, such as water-soluble organic solvents, include, but are not limited to, ethanol, propanol, isopropanol, butanol, 3-methoxy-3-methyl-1-butanol, benzyl alcohol, ethyl carbitol (diethylene glycol monoethyl ether), ethylene glycol, propylene glycol, dipropylene glycol, butanediol, hexanediol, glycerol, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, and dipropylene glycol monomethyl ether. These water-soluble solvents can be used alone or in combination. The content of water-soluble organic solvents in the compositions of this application can be determined according to the desired composition properties, and is typically from about 1% to about 99% by mass.

[0055] Oil-soluble organic solvents that can be used with the flavor and fragrance compositions of this application include, but are not limited to, isoparaffins, paraffin, limonene, pinene, triethyl citrate, benzyl benzoate, isopropyl myristate, glyceryl triacetate, and silicone oil.

[0056] Preferred solvents include, but are not limited to, triethyl citrate, triacetin, glycerol, ethanol, water, triglycerides, liquid waxes, propylene glycol derivatives, and ethylene glycol derivatives.

[0057] In some embodiments, the flavor and fragrance compositions and products disclosed herein may further comprise other substances, including but not limited to chelating agents, preservatives, antioxidants, deodorants, bactericides, ultraviolet absorbers, pH adjusters, insecticides, insect repellents, insecticides, colorants, excipients, and buffers. The substances used in, or used with, the flavor and fragrance compositions of this application may be determined based on the product in which the composition is contained. When used in a flavor or fragrance composition, the substance may be an additive; when used with a flavor or fragrance composition, it may be considered part of a product composition containing the flavor or fragrance composition.

[0058] Excipients that may be used in the flavor and fragrance compositions and products disclosed herein may vary depending on the intended use of the product and its overall composition. In some cases, excipients may be included in the flavor or fragrance composition or may be present independently of the composition. Excipients used in or with flavor compositions for oral pharmaceutical products may include, but are not limited to, tablet coatings, such as cellulose ether hydroxypropyl methylcellulose, synthetic polymers, shellac, corn gluten, zein, or other polysaccharides, and gelatin. In contrast, cosmetic excipients may include, but are not limited to, carbomer 940 ETD, triethanolamine, purified water, glycerin, imidazolidinyl urea, EDTA, polyvinyl alcohol, methylparaben, phenoxyethanol, ethanol, peg 7 glyceryl cocoate, peg 6 triglyceride caprylic acid, acemulogar LAM V, isopropyl myristate, Tegosoft CT, xanthan gum, Sepicide CL, polyquaternium 7, and petrolatum oil. For a given product, other excipients suitable for use with or in the flavor and / or fragrance composition will be readily selected by those skilled in the art.

[0059] Buffers that can be used with the flavor and fragrance compositions of this application may vary depending on the intended use of the product and its overall composition. In some cases, buffers may be included in the flavor or fragrance composition or may exist independently of the composition. Examples of buffers that can be used in or with the flavor and fragrance compositions of this application include, but are not limited to, citrates, acetates, and phosphates. For example, trisodium citrate is known to be used as a flavoring agent or preservative, imparting a sour taste to the flavor while also acting as a buffer. Trisodium citrate is an ingredient in many sodas and other beverages, as well as beverage mixtures and German sausages. In cosmetics, disodium hydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, and citric acid can be used to buffer the pH of the product. In toothpaste, calcium carbonate and / or dicalcium phosphate can be used as pH buffers. Other buffers suitable for use with or in the flavor and / or fragrance compositions for a particular product will be readily selected by those skilled in the art.

[0060] In a third aspect, this disclosure provides a product comprising compound 1 or any one of 1.1 to 1.55 thereof, compound 2 or any one of 2.1 to 2.40 thereof, or compound 3 or any one of 3.1 to 3.40 thereof, or composition 1 or any one of 1.1 to 1.11 thereof. In some implementations, the product may be selected from the following: personal care products (e.g., soap, skin cream or lotion, lip balm, shampoo, shower gel, body wash, moisturizer, deodorant, antiperspirant, aftershave, cologne, perfume or other hair or skin care products), sunscreen, insect repellents and pesticides, detergents, household cleaners (e.g., surface cleaners, metal cleaners, wood cleaners, glass cleaners, body cleaners such as soap, dish soap or laundry detergent), air fresheners, space sprays, aromatherapy, candles, cosmetics (e.g., perfume, cologne, nail polish, eyeliner, mascara, lipstick, foundation, concealer, blush, bronzer, eyeshadow, lip liner, lip balm), cologne, talcum powder and pet bedding.

[0061] Several embodiments of this application have been described. For those skilled in the art, the above is illustrative and not restrictive, and is presented by way of example only. Therefore, embodiments of this application may be embodied in other specific forms without departing from its spirit or essential characteristics.

[0062] Those skilled in the art will recognize or be able to determine equivalent embodiments of the present application through means not exceeding conventional experimentation. Therefore, it should be understood that the embodiments described herein are presented as examples only, the scope of the present application is thus indicated by the appended claims and their equivalents, and the present application may be implemented in ways different from those specifically described above.

[0063] The term "about," when used to describe one of the compositions of this application, refers to a range of ±5%, ±4%, ±3%, ±2.5%, ±2%, ±1.5%, ±1%, ±0.75%, ±0.5%, ±0.25%, or ±0.1% of the stated percentage. In one embodiment, the term "about" refers to ±5% of the stated percentage. For example, "about 50%" refers to a range of 45% to 55%. In one embodiment, the term "about" refers to ±2.5% of the stated percentage. In one embodiment, the term "about" refers to ±1% of the stated percentage. In one embodiment, the term "about" refers to ±0.5% of the stated percentage. In one embodiment, the term "about" refers to ±0.1% of the stated percentage.

[0064] As used herein, unless the context clearly indicates otherwise, the singular forms “a,” “an,” and “the” include plural referents. Thus, for example, references to “a flavoring ingredient” include not only a single flavoring ingredient but also a combination or mixture of two or more different flavoring ingredients, and references to “an additive” include a single additive as well as two or more additives, and so on.

[0065] As used herein, the phrases “for example,” “like,” “such as,” or “including” are intended to introduce examples that further clarify a more general subject. These examples are provided only to aid in understanding this disclosure and are not intended to be limiting in any way. Furthermore, as used herein, the terms “may,” “optional,” “optionally,” or “may optionally” mean that the situation described below may or may not occur, and therefore the description includes both the situation where the situation occurs and the situation where the situation does not occur. For example, the phrase “optionally exist” means that the object may or may not exist, and therefore the description includes both the situation where the object exists and the situation where the object does not exist.

[0066] As used herein, "optionally substituted" means that the indicated core group or functional group is not substituted or is substituted by one or more groups (up to the maximum number allowed by the valence rule), wherein the groups are selected from: halogens, hydroxyl groups, cyano groups, C... 1-6 Alkyl, C 2-6 alkenyl, C 2-6 alkynyl group, C 3-6 cycloalkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, -O-Si(R) x 3. -OR x -C(O)H, -C(O)-R x -C(O)-OR x -C(O)-NH-R x -C(O)-N-(R) x (R) x -OC(O)-R x -NH(R) x )-C(O)-R x -N(R) x (R) x )-C(O)-R x ), -NH(R x ), -N(R x (R) x ), heterocyclic alkyl, aryl and heteroaryl; wherein each of the C 1-6 Alkyl, C 3-6 Cycloalkyl, heterocycloalkyl, aryl, or heteroaryl groups are further optionally converted to one or more halogens, hydroxyl groups, cyano groups, or C groups. 1-6Alkyl, C 2-6 alkenyl, C 2-6 alkynyl group, C 3-6 cycloalkyl, C 1-6 Halogenated alkyl groups, -O-Si(R) x 3, -O-Rx, -C(O)H, -C(O)-R x -C(O)-OR x -C(O)-NH-R x -C(O)-N-(R) x (R) x -OC(O)-R x -NH(R) x )-C(O)-R x -N(R) x (R) x )-C(O)-R x ), -NH(R x ), -N(R x (R) x ), substituted with heterocyclic alkyl, aryl and heteroaryl; and wherein each R x Independently selected from hydrogen and C 1-6 Alkyl, C 2-6 alkenyl, C 2-6 alkynyl group, C 3-6 Cycloalkyl, heterocycloalkyl, aryl, and heteroaryl.

[0067] As used in this article, the term "C" 1-6 "Alkyl" refers to a saturated straight-chain or branched radical consisting essentially of 1 to 6 carbon atoms and a corresponding number of hydrogen atoms. An example C 1-6 Alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and tert-hexyl. Based on this disclosure, those skilled in the art will readily understand other C... 1-6 Alkyl group. The term "C" 1-3 Alkyl", C 1-4 "Alkyl" and similar terms have a similar meaning, referring to saturated straight-chain or branched free radicals that are essentially composed of 1 to 3 (or 4) carbon atoms and a corresponding number of hydrogen atoms. A similar term is "C..." 2-6 "alkenyl", "C" 2-6 "Alkyne", "C" 3-6 cycloalkyl, C 1-6 "Halogenated alkyl", "C" 1-6"Alkoxy" and the like refer to the corresponding functional groups having the stated number of carbon atoms, wherein "alkenyl" refers to an unsaturated straight-chain or branched radical having at least one double bond, "alkynyl" refers to an unsaturated straight-chain or branched radical having at least one triple bond, "haloalkyl" refers to an alkyl radical with at least one halogen atom attached to a carbon atom, and "alkoxy" refers to an alkyl radical with at least one oxygen atom attached to it, and the connection point of the functional group is through the oxygen atom (i.e., forming an ether). Exemplary alkenyl groups include vinyl and allyl. Exemplary alkynyl groups include ethynyl and propynyl. Exemplary haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, 3,3,3-trifluoroethyl, and similar groups containing chlorine, bromine, or iodine. "Cycloalkyl" refers to a carbon ring linked by a ring of carbon atoms. Exemplary cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0068] As used herein, the term "heteroaryl" refers to an aromatic radical having 5 to 20 ring-forming atoms (i.e., ring atoms), wherein at least one ring atom (e.g., 1 to 5) is a carbon atom, and at least one of the remaining ring atoms is a nitrogen, sulfur, or oxygen atom. Heteroaryl rings include monocyclic, bicyclic, and polycyclic fused ring systems, provided that at least one ring in the ring system has at least one heteroatom (N, S, or O), and all rings are aromatic. Exemplary 5-membered heteroaryl groups include furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, pyrazolyl, isothiazolyl, isoxazolyl, imidazoleyl, triazolyl, oxadiazolyl, thiazolyl, and tetrazolyl. Exemplary 6-membered heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, and 1,2,4-triazinyl. Exemplary fused heteroaryl groups include benzoxazolyl, benzothiazolyl, benzoisothiazolyl, benzoisothiazolyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl. Based on this disclosure, those skilled in the art will readily understand other heteroaryl groups. Typically, heteroaryl groups are attached to the host structure via carbon atoms. However, those skilled in the art will recognize that certain other atoms, such as heterocyclic atoms, may also be attached to the host structure.

[0069] As used herein, the term "aryl" refers to an aromatic radical having 5 or 6 ring-forming atoms (i.e., ring atoms), all of which are carbon atoms. Exemplary aryl groups include phenyl and naphthyl.

[0070] As used herein, the term "heterocyclic alkyl" refers to a non-aromatic radical having 3 to 20 ring-forming atoms (i.e., ring atoms), wherein at least one ring atom (e.g., 1 to 5) is a carbon atom, and at least one of the remaining ring atoms is a nitrogen, sulfur, or oxygen atom, and wherein at least one ring is non-aromatic. Heterocyclic alkyl rings include monocyclic, bicyclic fused, bicyclic spiral, polycyclic bridged, and polycyclic fused ring systems, provided that at least one ring in the ring system has at least one heteroatom (N, S, or O), and at least one ring in the ring system is non-aromatic (e.g., saturated). Exemplary saturated heterocyclic alkyl groups include aziridine, aziridinyl, ethylene oxide, oxadienoyl, tetrahydrofuranyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, and thiomorpholinyl. Heterocyclic alkyl ring systems include ring systems in which an aromatic ring is fused to a non-aromatic ring, such as those obtained by partially reducing a polycyclic aromatic ring system. Exemplary ring systems of this category include indolinyl, tetrahydroquinolinyl, and tetrahydroisoquinolinyl. Other heterocyclic alkyl groups will be readily understood by those skilled in the art based on this disclosure. Heterocyclic alkyl groups can be attached to the host structure via carbon or nitrogen atoms of the ring.

[0071] As used herein, the term "compound," unless otherwise stated, means any particular compound disclosed herein and includes its tautomers, regioisomers, geometric isomers, and, where applicable, stereoisomers, including its optical isomers (enantiomers) and other stereoisomers (diastereomers), as well as pharmaceutically acceptable salts and derivatives thereof, where applicable in the context. In its usage context, the term "compound" generally refers to a single compound, but may also include other compounds, such as stereoisomers, regioisomers, and / or optical isomers (including racemic mixtures), and mixtures of specific enantiomers or enriched enantiomers of the disclosed compound. In the context, the term also refers to a prodrug form of a compound modified to facilitate administration and delivery of the compound to the site of action. The term also refers to any particular chemical compound in which one or more atoms are substituted by another isotope of the same element.

[0072] The full disclosure of each patent document and scientific article cited herein is incorporated herein in its entirety and is applicable for all purposes. The functionality and advantages of these and other embodiments will be more fully understood through the following non-limiting examples. These examples are illustrative in nature and should not be considered as limiting the scope of the embodiments discussed herein.

[0073] Example Several other known synthetic routes provide alkynylbenzenes from the corresponding halobenzenes. For example, the reaction forms are as follows: Published in Khan et al., WO 2017 / 180923; Miao et al., CN108191711 (2018); Miao et al., CN1030877211 (2013); Wang et al., Liquid Crystals 46(2):257-71(2019); Li et al., Org.&Biomolec. Chem. 21(29): 5935-38 (2023); Xu, Org. Lett. 16(3):948-51 (2014); Muller et al., Bioconjugate Chem. 28(9):2372-83 (2017).

[0074] The compounds disclosed herein can be prepared according to methods known in the art. For example, the compounds disclosed herein can be obtained using the following synthetic methods: Option 1. Acetylation.

[0075] Option 2. Ketone nucleus synthesis and acetylation Option 3. Ether nucleus synthesis and acetylation.

[0076] Further modification of the functional groups within group R in Schemes 2 and 3 can be carried out according to standard methods, such as ester hydrolysis, ketone reduction, alcohol oxidation, ester formation, and terminal alkyne carboxylation.

[0077] Ethyl 3-phenylpropynate was obtained and its olfactory properties were studied. The pure liquid compound and a 10% dilution of the compound in ethanol were examined by an experienced fragrance chemist (master perfumer). The results showed that the compound exhibited favorable odor characteristics.

[0078] Synthesis Examples The compounds of Examples 1 to 53 were prepared according to the steps described below. The compounds of Example 54 (ethyl 3-phenylpropynate) and Example 55 (methyl 3-phenylpropynate) were commercially available and purchased from the open market.

[0079] 1H-NMR spectra were recorded at 400 MHz on a Bruker Avance AV-I-400 or Bruker Avance AV-II-400 instrument. Unless otherwise specified, chemical shift values ​​are expressed in ppm relative to tetramethylsilane. The multiplicity of the NMR signal is represented by the following abbreviations or combinations thereof: br = broad peak, d = doublet, m = multiplet, q = quartet, quintet, s = singlet, t = triplet.

[0080] Purification method information: Method A: Rapid chromatography (SiO2, 0-30% EtOAc / heptane) Method B: Rapid chromatography (SiO2, 0-10% EtOAc / heptane) Method C: Instrument model: Reveleris™ preparative MPLC; Column: Dr. Maisch Reprosil C18 (150x25 mm, 10μm); Flow rate: 40 mL / min; Column temperature: room temperature; Mobile phase A: 0.1% (v / v) formic acid aqueous solution, Mobile phase B: 0.1% (v / v) formic acid acetonitrile solution; Gradient: t=0 min 5% B, t=1 min 5% B, t=2 min 30% B, t=17 min 70% B, t=18 min 100% B, t=23 min 100% B; UV detector: 220, 254, 340 nm, ELSD detector.

[0081] Method D: Rapid chromatography (SiO2, 0-15% EtOAc / heptane) Method E: Rapid chromatography (SiO2, 0-20% Et2O / heptane) Method F: Rapid chromatography (SiO2, 0-20% EtOAc / heptane) Method G: Rapid chromatography (SiO2, 0-25% MTBE / heptane) Method H: Vacuum distillation (0.1–0.2 mbar, 165 °C) Method I: Vacuum distillation (0.1-0.2 mbar, 170 °C) Method J: Vacuum distillation (0.1-0.2 mbar, 180 °C) Method K: Vacuum distillation (0.1-0.2 mbar, 160 °C) LCMS analysis method information: Method 1: UPLC: Waters I-Class, acquisition method: UPLC_AN_ACID, column: XSelect CSHC18 XP (50x2.1mm 2.5µm), flow rate: 0.6 ml / min; column temperature: 40°C, mobile phase A: 0.1% formic acid aqueous solution, mobile phase B: 0.1% formic acid acetonitrile solution, gradient: t=0 min 5% B, t=2.0 min 98% B, t=2.7 min 98% B, run time: 0.3 min, PDA detector: 210-320nm and 215nm.

[0082] Method 2: UPLC: Waters I-Class, acquisition method: UPLC_AN_BASE, column: XSelect CSHC18 XP (50x2.1mm 2.5µm), flow rate: 0.6 ml / min; column temperature: 25°C, mobile phase A: 10mM ammonium bicarbonate aqueous solution (pH 9.5), mobile phase B: acetonitrile, gradient: t=0 min 5% B, t=2 min 98% B, t=2.7 min 98% B, run time: 0.3 min, PDA detector: 210-320nm.

[0083] Method 3: Acquisition method: U_T3_ACID_00-20, System: Agilent 1290 with SQ-MSD, Column: XSelect HSS T3 XP (50x2.1mm, 2.5µm), Flow rate: 0.8 ml / min; Column temperature: 40°C, Mobile phase A: 0.1% formic acid aqueous solution, Mobile phase B: 0.1% formic acid acetonitrile solution, Linear gradient: t=0 min 0% B, t=4.5 min 20% B, t=5 min 20% B, Run time: 1 min, DAD detector: 210, 215, 210-320nm, PDA detector: 210-320nm, MSD detector: ESI positive / negative ion mode, Mass range 90-1500.

[0084] Method 4: Acquisition method: U_AN_ACID, System: Agilent 1290 with SQ-MSD, Column: XSelectCSH XP C18 (50x2.1mm, 2.5µm), Flow rate: 0.8 ml / min, Column temperature: 40°C, Mobile phase A: 0.1% formic acid aqueous solution, Mobile phase B: 0.1% formic acid acetonitrile solution, Linear gradient: t=0 min 5% B, t=0.5 min 5% B, t=4.5 min 98% B; t=5 min 98% B, Run time: 0.5 min, DAD detector: 210-320nm, 215 nm, PDA detector: 210-320nm, MSD detector: ESI positive / negative ion mode, Mass range 90-1500.

[0085] Method 5: Acquisition method: UPLC_AN_BASE, column: XSelect CSH C18 XP (50x2.1mm 2.5µm), flow rate: 0.6 ml / min; column temperature: 25°C, mobile phase A: 10mM ammonium bicarbonate aqueous solution (pH=9.5), mobile phase B: 100% acetonitrile, gradient: t=0 min 5% B, t=2 min 98% B, t=2.7 min 98% B, run time: 0.3 min, PDA detector: 210-320nm, ELSD detector: gas pressure 40 psi, drift tube temperature: 50°C.

[0086] Method 6: Acquisition method: U_AN_BASE, System: Agilent 1290 with SQ-MSD, Column: XSelectCSH XP C18 (50x2.1mm, 2.5µm), Flow rate: 0.8 ml / min, Column temperature: 25°C, Mobile phase A: 10mM ammonium bicarbonate aqueous solution (pH 9.5), Mobile phase B: Acetonitrile, Linear gradient: t=0 min 5% B, t=0.5 min 5% B, t=4.5 min 98% B; t=5 min 98% B, Run time: 0.5 min, DAD detector: 210-320nm, 215 nm, PDA detector: 210-320nm, MSD detector: ESI positive / negative ion mode, Mass range 90-1500.

[0087] Method 7: UPLC: Waters I-Class, Acquisition method: UPLC_AN_ACID, Column: XSelect CSHC18 XP (50x2.1mm 2.5µm), Flow rate: 0.6 ml / min; Column temperature: 40°C, Mobile phase A: 0.1% formic acid aqueous solution, Mobile phase B: 0.1% formic acid acetonitrile solution, Gradient: t=0 min 5% B, t=2 min 98% B, t=2.7 min 98% B, Postrun time: 0.3 min, PDA detector: 210-320nm, ELSD detector: Gas pressure 40 psi, Drift tube temperature: 50°C.

[0088] Method 8: G40-300_M350 method, instrument: Agilent 8890 gas chromatograph, G7081B 5977B MSD mass spectrometer detector (EI-positive ion mode, detector temperature: 280°C) mass range 50-350, detector: FID / detector temperature: 325°C, column: Agilent DB-5MS (20 m, inner diameter 180 µm, film thickness 0.18 µm), average linear velocity: 39 cm / s, injection volume: 1 µl, injection port temperature: 250°C, split ratio: 100:1, carrier gas: helium; initial temperature: 40°C, initial time: 0.5 min, solvent delay: 1.1 min, heating rate 120°C / min to 115°C; 110°C / min to 175°C; 80°C / min to final temperature 300°C, hold time 2.0 min.

[0089] Example 1: Ethyl 3-([1,1'-biphenyl]-4-yl)propynate 4-Iodo-1,1'-biphenyl (75.00 g, 1 Eq, 267.8 mmol) and DMF (500 mL) were added to a 2 L three-necked flask equipped with a thermometer. Copper oxide powder (38.34 g, 1.8 Eq, 482.0 mmol) was added, followed by ethyl propynate (53 mL, 1.9 Eq, 508.7 mmol). The mixture was heated at 110°C for 18 hours. The mixture was filtered through diatomaceous earth, and the filter cake was washed with DCM. The filtrate was concentrated, diluted with brine (2 L), and extracted with Et2O (2 x 1.5 L). The combined organic phases were dried over Na₂SO₄, filtered, concentrated, and purified by rapid column chromatography (SiO₂, 0-25% EtOAc / heptane) to give ethyl 3-([1,1'-biphenyl]-4-yl)propynate (44.638 g, 178.34 mmol, yield 66.61%). LCMS: Method 1, 1.96 min, M+H = 251; calculated value 251.297. 1 H NMR (400 MHz, CDCl3) δ 7.70 - 7.54(m, 6H), 7.51 - 7.42 (m, 2H), 7.42 - 7.34 (m, 1H), 4.32 (q, J = 7.1 Hz, 2H), 1.37 (t, J = 7.1 Hz, 3H).

[0090] Example 2: Ethyl 3-(4-(cyclopent-1-en-1-yl)phenyl)propynate Step 1: Ethyl 3-(4-bromophenyl)propynate: Ethyl propargylate (6.8 mL, 1.9 Eq, 67.2 mmol) and copper oxide powder (5.06 g, 802 μL, 1.8 Eq, 63.6 mmol) were added to a DMF (101 mL) solution of 1-bromo-4-iodobenzene (10.0 g, 1 Eq, 35.3 mmol). The mixture was heated at 110 °C for 72 hours. The mixture was diluted with Et2O, filtered through diatomaceous earth, and the filter cake was washed with Et2O. The filtrate was further diluted with Et2O, washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was achieved by rapid column chromatography (SiO2, gradient 0-10% EtO2 / heptane) to give ethyl 3-(4-bromophenyl)propargylate (4.52 g, 17 mmol, yield 47%, purity 94%). GCMS: Method 8, 3.25 min, 251.9; calculated value 251.9.

[0091] Step 2: Ethyl 3-(4-(cyclopent-1-en-1-yl)phenyl)propynate: Ethyl 3-(4-bromophenyl)propynate (2.47 g, 93% by weight, 1 Eq, 9.08 mmol), cyclopent-1-en-1-ylboronic acid (1.12 g, 1.1 Eq, 9.98 mmol), and potassium carbonate (3.76 g, 3 Eq, 27.2 mmol) were dissolved in a solution of 1,4-dioxane (48.4 mL) / water (12.1 mL) and purged with argon gas for 5 min. Then, 1,1'-bis(diphenylphosphine)ferrocene-palladium(II) dichloride (332 mg, 0.05 Eq, 454 μmol) was added, and the mixture was stirred at 100 °C for 1 h. The mixture was filtered through diatomaceous earth, and the filter cake was washed with EtOAc. The organic phase was washed with saturated aqueous NaHCO3 solution, HCl (1 M), and brine, dried over Na2SO4, filtered, and concentrated. Ethyl 3-(4-(cyclopent-1-en-1-yl)phenyl)propynate was purified by rapid chromatography (SiO2, 0-10% Et2O / heptane) followed by purification method C to obtain 568.9 mg, 2.19 mmol, yield 24.1%, purity 92.5%. LCMS: Method 4, 3.8 min, M+H = 241; calculated value 241.302. 1 H NMR (400MHz, CDCl3) δ 7.57 - 7.48 (m, 2H), 7.46 - 7.37 (m, 2H), 6.30 (p, J = 2.3 Hz,1H), 4.30 (q, J = 7.1 Hz, 2H), 2.70 (tq, J = 7.0, 2.3 Hz, 2H), 2.55 (tq, J =7.6, 2.5 Hz, 2H), 2.03 (p, J = 7.5 Hz, 2H), 1.36 (t, J = 7.1 Hz, 3H).

[0092] General Method 1: Examples 3-13 The compounds of Examples 3 to 13 were prepared by coupling aryl iodides with propynyl esters under copper(II) oxide catalysis according to the following general method.

[0093] To a DMF (0.4 M) solution of iodide (1 Eq), propynate (1.9 Eq, R' = Me, Et) and copper(II) oxide (1.8 Eq) were added, and the mixture was heated at 110°C for 18 hours. The reaction mixture was diluted with Et₂O, filtered through diatomaceous earth, and the filter cake was washed with Et₂O. The filtrate was further diluted with Et₂O, washed with brine, dried over Na₂SO₄, filtered, and concentrated. The target product was obtained by purification (see Method).

[0094] The following examples are prepared according to general method 1, from the corresponding iodides and propynyl esters.

[0095] General Method 2: Examples 14-35 The compounds of Examples 14 to 35 were prepared by coupling phenylacetylene with alkyl chloroformate according to the following general method.

[0096] To an anhydrous THF (0.5 M) solution of acetylene (1 Eq), n-butyllithium (1.6 M hexane solution, 1.6 Molar, 1.1 Eq) was added dropwise at -78°C, and the mixture was stirred at -78°C for 30 minutes. The cooling bath was removed, and chloroformate (1 Eq, R' = Me, Et) was added. The mixture was allowed to warm to room temperature naturally and stirred for 1 hour. The reaction mixture was concentrated and purified (see Methods) to obtain the target product.

[0097] The following examples are prepared according to General Method 2, from the corresponding acetylene and chloroformate.

[0098] General Method 3: Examples 36-53 The compounds of Examples 36 to 53 were prepared by coupling dibromostyrene with alkyl chloroformate in the presence of n-butyllithium according to the following general method.

[0099] To an anhydrous THF (0.15 M) solution of dibromostyrene (1 Eq), n-butyllithium (1.6 M hexane solution, 3 Eq) was added dropwise at 0°C, and the mixture was stirred at 0°C for 30 min. Chloroformate (1 Eq, R' = Me, Et) was added, and the mixture was stirred again at 0°C for 30 min. The reaction was quenched by adding a saturated aqueous NH4Cl solution, and the mixture was partially concentrated to remove THF. The layers were diluted with water and DCM and separated. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. The target product was obtained after purification (see Method).

[0100] The representative steps for the synthesis of dibromostyrene are provided below.

[0101] The following examples are prepared according to General Method 3, from the corresponding dibromostyrene and chloroformate.

[0102] Synthetic intermediates The following steps provide synthetic intermediates for use in the general methods 1, 2, or 3 shown above.

[0103] 1-(2,2-Dibromovinyl)-3-methylbenzene: To a solution of carbon tetrabromide (8.28 g, 1.5 Eq, 25.0 mmol) and triphenylphosphine (13.1 g, 3 Eq, 49.9 mmol) in dichloromethane (33.3 mL), m-methylbenzaldehyde (1.96 mL, 1 Eq, 16.6 mmol) was added at room temperature, and the mixture was stirred at room temperature for 30 minutes. Water was added, and the mixture was extracted with DCM (3 times). The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was performed by rapid column chromatography (SiO2, 0-10% EtOAc / heptane) to give 1-(2,2-dibromovinyl)-3-methylbenzene (4.78 g, 17.1 mmol, 100% yield, 98.5% purity). 1 H NMR (400MHz, CDCl3) δ 7.45 (s, 1H), 7.38 – 7.29 (m, 2H), 7.28 – 7.23 (m, 1H), 7.16 (s, 1H), 2.37 (s, 3H).

[0104] 6-(2,2-dibromovinyl)-1,2,3,4-tetrahydronaphthalene To a solution of carbon tetrabromide (9.31 g, 1.61 Eq, 28.1 mmol) and triphenylphosphine (14.7 g, 3.22 Eq, 56.0 mmol) in dichloromethane (174 mL), 5,6,7,8-tetrahydronaphthalene-2-carboxaldehyde (3.00 g, 93% by weight, 1 Eq, 17.4 mmol) was added at room temperature. The mixture was stirred at room temperature for 1 hour, followed by stirring at 50°C for another 1 hour. Water was added, and the mixture was extracted with DCM (3 times). The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was achieved by rapid column chromatography (SiO2, 0-10% EtOAc / heptane) to give 6-(2,2-dibromovinyl)-1,2,3,4-tetrahydronaphthalene (3.58 g, 8.5 mmol, 49% yield, 75% purity). 1 H NMR (400 MHz, CDCl3) δ 7.41 (s, 1H),7.29 (ddd, J = 8.1, 3.9, 2.1 Hz, 1H), 7.23 (dd, J = 11.4, 2.0 Hz, 1H), 7.05(d, J = 8.0 Hz, 1H), 2.82 – 2.68 (m, 4H), 1.79 (p, J = 3.2 Hz, 4H).

[0105] 5-(2,2-dibromovinyl)-2,3-dihydro-1H-indene: To a solution of carbon tetrabromide (9.26 g, 1.5 Eq, 27.9 mmol) and triphenylphosphine (14.6 g, 3 Eq, 55.8 mmol) in dichloromethane (75 mL), 2,3-dihydro-1H-indene-5-carboxaldehyde (2.72 g, 1 Eq, 18.6 mmol) dissolved in dichloromethane (5 mL) was added at 0°C, and the mixture was stirred at room temperature for 1 hour. Water was added, and the mixture was extracted with DCM. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was performed by rapid column chromatography (SiO2, 0-15% EtOAc / heptane) to give 5-(2,2-dibromovinyl)-2,3-dihydro-1H-indene (3.03 g, 10.0 mmol, 53.9% yield). GCMS: Method 8, 3.47 min, 301.9; Computed value 302.1.

[0106] 1-(tert-butoxy)-4-(2,2-dibromovinyl)benzene: To a solution of carbon tetrabromide (9.31 g, 1.67 Eq, 28.1 mmol) and triphenylphosphine (14.7 g, 3.33 Eq, 56.0 mmol) in dichloromethane (168 mL), 4-(tert-butoxy)benzaldehyde (2.93 mL, 1 Eq, 16.8 mmol) was added at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was added, and the mixture was extracted with DCM (3 times). The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was performed by rapid column chromatography (SiO2, 0-10% EtOAc / heptane) to give 1-(tert-butoxy)-4-(2,2-dibromovinyl)benzene (2.17 g, 6.50 mmol, yield 38.6%). It was used directly without further analysis.

[0107] 1-(2,2-Dibromovinyl)-4-isobutylbenzene: To a solution of carbon tetrabromide (9.2 g, 1.5 Eq, 28 mmol) and triphenylphosphine (15 g, 3 Eq, 55 mmol) in dichloromethane (180 mL), 4-isobutylbenzaldehyde (3.1 mL, 1 Eq, 18 mmol) was added at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was added, and the mixture was extracted with DCM (3 times). The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was performed by rapid column chromatography (SiO2, 0-10% EtOAc / heptane) to give 1-(2,2-dibromovinyl)-4-isobutylbenzene (3.6 g, 11 mmol, 61% yield). 1 H NMR (400 MHz, CDCl3) δ 7.53 – 7.38 (m,3H), 7.14 (dd, J = 8.0, 1.4 Hz, 2H), 2.48 (dd, J = 9.7, 7.1 Hz, 2H), 1.87(dpd, J = 13.6, 6.7, 1.4 Hz, 1H), 0.90 (d, J = 6.7 Hz, 6H).

[0108] 1-(2,2-Dibromovinyl)-4-isopropoxybenzene: To a solution of carbon tetrabromide (9.09 g, 1.5 Eq, 27.4 mmol) and triphenylphosphine (14.4 g, 3 Eq, 54.8 mmol) in dichloromethane (183 mL), 4-isopropoxybenzaldehyde (2.90 mL, 1 Eq, 18.3 mmol) was added at room temperature, and the mixture was stirred at room temperature for 16 hours. Water was added, and the mixture was extracted with DCM (3 times). The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was performed by rapid column chromatography (SiO2, 0-10% EtOAc / heptane) to give 1-(2,2-dibromovinyl)-4-isopropoxybenzene (4.99 g, 15.6 mmol, 85.3% yield). 1 H NMR (400MHz, CDCl3) δ 7.57 – 7.43 (m, 2H), 7.39 (s, 1H), 6.91 – 6.78 (m, 2H), 4.57(p, J = 6.1 Hz, 1H), 1.34 (d, J = 6.1 Hz, 6H 4-(sec-butoxy)benzaldehyde: Potassium carbonate (27.16 g, 2 Eq, 196.5 mmol) and 2-bromobutane (16.09 mL, 1.5 Eq, 147.4 mmol) were added to a DMF (50 mL) solution of 4-hydroxybenzaldehyde (12.00 g, 1 Eq, 98.26 mmol). The mixture was heated at 75 °C for 16 h. The layers were diluted with water and DCM and separated. The aqueous phase was extracted twice with DCM, and the combined organic phases were washed with brine, dried over Na₂SO₄, filtered, and concentrated. Purification was achieved by rapid column chromatography (SiO₂, 0–25% EtOAc / MTBE) to give 4-(sec-butoxy)benzaldehyde (16.62 g, 93.25 mmol, 94.90% yield). GCMS: Method 8, 2.80 min, 178.1; calculated value 178.2. 1 H NMR (400 MHz, CDCl3) δ 9.87 (s, 1H), 7.86 – 7.75 (m,2H), 7.02 – 6.92 (m, 2H), 4.43 (h, J = 6.1 Hz, 1H), 1.85 – 1.63 (m, 2H), 1.34(d, J = 6.1 Hz, 3H), 0.99 (t, J = 7.4 Hz, 3H).

[0109] 1-(sec-butoxy)-4-(2,2-dibromovinyl)benzene: To a solution of carbon tetrabromide (23.7 g, 1.5 Eq, 71.5 mmol) and triphenylphosphine (37.5 g, 3 Eq, 143 mmol) in dichloromethane (150 mL), 4-(sec-butoxy)benzaldehyde (8.50 g, 1 Eq, 47.7 mmol) dissolved in dichloromethane (25 mL) was added at 0°C, and the mixture was stirred at room temperature for 1 hour. Water was added, and the mixture was extracted with DCM. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was performed by rapid column chromatography (SiO2, 0-15% EtOAc / heptane) to give 1-(sec-butoxy)-4-(2,2-dibromovinyl)benzene (13.8 g, 41.3 mmol, 86.6% yield). GCMS: Method 8, 3.44 min, 333.9; Computed value 334.0. 1 H NMR (400 MHz, CDCl3) δ7.53 – 7.42 (m, 2H), 7.39 (s, 1H), 6.90 – 6.80 (m, 2H), 4.32 (h, J = 6.1 Hz,1H), 1.81 – 1.56 (m, 2H), 1.30 (d, J = 6.1 Hz, 3H), 0.97 (t, J = 7.5 Hz, 3H).

[0110] 5-(2,2-dibromovinyl)-1,2,3,4-tetrahydronaphthalene: To a solution of carbon tetrabromide (7.76 g, 1.5 Eq, 23.4 mmol) and triphenylphosphine (12.3 g, 3 Eq, 46.8 mmol) in dichloromethane (50 mL), 5,6,7,8-tetrahydronaphthalene-1-carboxaldehyde (2.50 g, 1 Eq, 15.6 mmol) dissolved in dichloromethane (5 mL) was added at 0°C, and the mixture was stirred at room temperature for 16 hours. Water was added, and the mixture was extracted with DCM. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification was performed by rapid column chromatography (SiO2, 0-15% EtOAc / heptane) to give 5-(2,2-dibromovinyl)-1,2,3,4-tetrahydronaphthalene (3.46 g, 10.9 mmol, 70.2% yield). GCMS: Method 8, 3.40 min, 315.9; Computed value 316.0.

[0111] Trimethyl((4-(2-methylprop-1-en-1-yl)phenyl)ethynyl)silane A solution of (2-(4-bromophenyl)ethynyl)trimethylsilane (2.0 g, 1 Eq, 7.9 mmol), 4,4,5,5-tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborane (1.8 mL, 1.1 Eq, 8.7 mmol), and potassium carbonate (3.3 g, 3 Eq, 24 mmol) in 1,4-dioxane (63 mL) / water (16 mL) was bubbled with argon for 5 min. Then, 1,1'-bis(diphenylphosphine)ferrocene-palladium(II) dichloride (0.29 g, 0.05 Eq, 0.39 mmol) was added, and the mixture was stirred at 110 °C for 5 h. The mixture was filtered through diatomaceous earth, and the filter cake was washed with EtOAc. The organic phase was washed with water and brine, dried over Na₂SO₄, filtered, and concentrated. Trimethyl((4-(2-methylprop-1-en-1-yl)phenyl)ethynyl)silane (1.8 g, 6.5 mmol, 82% yield, 82% purity) was purified by rapid chromatography (SiO2, 0-100% MTBE / heptane). GCMS: Method 8, 4.58 min, 228.2; calculated value 228.4. 1 H NMR (400 MHz, CDCl3) δ 7.46 – 7.35 (m, 2H), 7.18 – 7.11 (m, 2H), 6.23 (d, J = 2.4 Hz, 1H), 1.88 (dd, J = 19.0, 1.4 Hz, 6H), 0.24 (s, 9H).

[0112] 1-Ethynyl-4-(2-methylprop-1-en-1-yl)benzene: To a solution of trimethyl((4-(2-methylprop-1-en-1-yl)phenyl)ethynyl)silane (1.8 g, 82% by weight, 1 Eq, 6.5 mmol) in tetrahydrofuran (65 mL), TBAF (1 M THF solution, 7.8 mL, 1.2 Eq, 7.8 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated and further purified by rapid chromatography (SiO2, 0–100% MTBE / heptane, then 0–20% MTBE / heptane) to give 1-ethynyl-4-(2-methylprop-1-en-1-yl)benzene (0.63 g, 3.8 mmol, yield 58%, purity 93%). 1H NMR (400 MHz, CDCl3) δ 7.47 – 7.37 (m,2H), 7.21 – 7.14 (m, 2H), 6.24 (d, J = 1.9 Hz, 1H), 3.06 (s, 1H), 1.89 (dd, J= 18.6, 1.4 Hz, 6H).

[0113] Example 54: Odor Characteristic Determination The aroma characteristics of the compounds selected within this disclosure are determined through evaluation by a lead perfumer and four to six trained sensory evaluators. The sensory evaluators are trained using an internal classification system comprising 11 major categories and 62 subcategories, along with reference materials. Evaluators are experienced with hundreds of additional aroma descriptors but have not received specialized training. Evaluators receive training on the use of a scoring scale that also includes internal reference standards. Evaluators must pass a final examination on the classification system, designed by our perfumery team, before they can evaluate the compounds.

[0114] The overall score for a sensory evaluation group can be obtained by calculating the arithmetic mean of all group members' scores for a specific sample on a specific attribute. Alternatively, the overall score can be generated by fitting all group members' scores into a model that can correct for differences in the intercept or slope of the latent function upon which each group member's score is based under a given perception, i.e., correcting for differences in group member scores.

[0115] The chief perfumer, with their profound understanding of fragrance components, high level of technical expertise, and recognized experience in creating complex perfumes, reviews the sensory evaluation panel's scores and may supplement the panel's scores as appropriate to improve accuracy.

[0116] The test sample was dissolved in ethanol at a concentration of 10% w / v. At time zero (t=0), a new test fragrance strip (white pulp board type, 5 x 0.5 inches) was immersed in the 10% solution of the test compound. At time t=0, the odor description was recorded within 1–2 minutes after the fragrance strip was wetted to allow most of the ethanol solvent to evaporate, thus allowing for a more accurate determination of the odor of the test compound. Evaluations were conducted at room temperature in a laboratory benchtop environment. For the determination of longevity, the fragrance strip was left open on the laboratory benchtop during each evaluation interval (without using jars or other sealed containers).

[0117] The results are shown in the table below. The embodiments provided herein are merely illustrative and are not intended to limit in any way the various aspects and implementations of the invention described herein.

Claims

1. Compounds with the structure of Formula I: Formula I in: R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); X is selected from -O-, -CH2-, -C(O)-, CH(OH), and -CH(OR)-; Y Selected from -CH2CH2CH2CH2-, -CH2CH2OCH2-, -CH2OCH2CH2-, -OCH2CH2CH2-, -CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, -OCH2CH2-, -CH2CH2CH2CH2CH2-, -OCH2CH2CH2 CH2-, -CH2OCH2CH2CH2-, -CH2CH2OCH2CH2-, -CH2CH2CH2OCH2-, -CH2CH2CH2CH2O-, -CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2-, -CH2OCH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2-, -CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2OCH2-, -CH2CH2CH2CH2CH2O-, -CH2CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2CH2-, -CH2OC H2CH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2CH2-, -CH2CH2CH2OCH2CH2CH2-, -CH2CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2CH2OCH2-, and -CH2CH2CH2CH2CH2CH2O-; in, The group Y may optionally be selected from one or more C groups. 1-3 Alkyl groups (e.g., CH3), OH, CHO, and OC 1-3 Alkyl groups (e.g., OCH3) are substituted; Or XY indicates that it does not exist; R 3 Selected from H, R b OH, OR b OC(O)R b CN, COOH, COOR b C(O)R b and CHO;R 4 R 5 and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl; provided that the compound is not ethyl 3-phenylpropynate, methyl 3-phenylpropynate, or 3-phenylpropynic acid, and that the compound is not one of the following: in: (a)R 1 and R 2 Let H be the integer part of the set, and XYR be the integer part of the set. 3 It is n-butyl, n-pentyl, n-hexyl, or n-nonyl; (b)R 1 and R 2 H is H, X is -C(O)-, and YR 3 It is n-butyl, n-octyl, or n-undecyl; (c)R 1 and R 2 H is H, X is -CH(OH)-, and YR is -CH(OH)-. 3 It is n-butyl, n-octyl, or n-undecyl; (d)R 1 and R 2 H is H, X is -O-, and YR is -O-. 3 It is n-butyl, n-pentyl, or n-hexyl; Or compounds with the structure of formula II: Formula II in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b , OH, OR b OC(O)R b , CN, COOH, COOR b , C(O)R b , and CHO; R 4 R 5 and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl or optionally substituted benzyl; Or compounds with a structure of formula III: Formula III in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b , OH, OR b OC(O)R b , CN, COOH, COOR b , C(O)R b , and CHO; R 4 R 5 and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl.

2. Compounds with the structure of Formula I: Formula I in: R 1 For H, CH3, CH2CH3, CH2CH2CH3, CH(CH3)2, CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); X is selected from -O-, -CH2-, -C(O)-, -CH(OH)-, and -CH(OR)-; Y Selected from -CH2CH2CH2CH2-, -CH2CH2OCH2-, -CH2OCH2CH2-, -OCH2CH2CH2-, -CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, -OCH2CH2-, -CH2CH2CH2CH2CH2-, -OCH2CH2CH2 CH2-, -CH2OCH2CH2CH2-, -CH2CH2OCH2CH2-, -CH2CH2CH2OCH2-, -CH2CH2CH2CH2O-, -CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2-, -CH2OCH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2-, -CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2OCH2-, -CH2CH2CH2CH2CH2O-, -CH2CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2CH2-, -CH2OC H2CH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2CH2-, -CH2CH2CH2OCH2CH2CH2-, -CH2CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2CH2OCH2-, and -CH2CH2CH2CH2CH2CH2O-; Wherein, the group Y may optionally be selected from one or more C 1-3 Alkyl groups (e.g., CH3), OH, CHO, and OC 1-3 Alkyl groups (e.g., OCH3) are substituted; Or XY indicates that it does not exist; R 3 Selected from H, R b OH, OR b OC(O)R b CN, COOH, COOR b C(O)R b and CHO; and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), optionally substituted phenyl or optionally substituted benzyl; Or compounds with the structure of formula II: Formula II in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b , OH, OR b OC(O)R b , CN, COOH, COOR b , C(O)R b , and CHO; R 4 R 5 and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl or optionally substituted benzyl; Or compounds with a structure of formula III: Formula III in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b , OH, OR b OC(O)R b , CN, COOH, COOR b , C(O)R b , and CHO; R 4 R 5 and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl or optionally substituted benzyl; Used as a flavoring agent or spice ingredient.

3. A flavor composition and / or spice composition comprising a compound of formula I: Formula I in: R 1 For H, CH3, CH2CH 3, CH2CH2CH 3, CH(CH3)2, CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); X is selected from -O-, -CH2-, -C(O)-, -CH(OH)-, and -CH(OR)-; Y Selected from -CH2CH2CH2CH2-, -CH2CH2OCH2-, -CH2OCH2CH2-, -OCH2CH2CH2-, -CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, -OCH2CH2-, -CH2CH2CH2CH2CH2-, -OCH2CH2CH2 CH2-, -CH2OCH2CH2CH2-, -CH2CH2OCH2CH2-, -CH2CH2CH2OCH2-, -CH2CH2CH2CH2O-, -CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2-, -CH2OCH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2-, -CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2OCH2-, -CH2CH2CH2CH2CH2O-, -CH2CH2CH2CH2CH2CH2CH2-, -OCH2CH2CH2CH2CH2CH2-, -CH2OC H2CH2CH2CH2CH2-, -CH2CH2OCH2CH2CH2CH2-, -CH2CH2CH2OCH2CH2CH2-, -CH2CH2CH2CH2OCH2CH2-, -CH2CH2CH2CH2CH2OCH2-, and -CH2CH2CH2CH2CH2CH2O-; Wherein, the group Y may optionally be selected from one or more C 1-3 Alkyl groups (e.g., CH3), OH, CHO, and OC 1-3 Alkyl groups (e.g., OCH3) are substituted; Or XY indicates that it does not exist; R 3 Selected from H, R b OH, OR b OC(O)R b CN, COOH, COOR b C(O)R b and CHO; and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), optionally substituted phenyl or optionally substituted benzyl; Or compounds of formula II: Formula II in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b , OH, OR b OC(O)R b , CN, COOH, COOR b , C(O)R b , and CHO; R 4 R 5 and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl or optionally substituted benzyl; Or compounds of formula III: Formula III in: n is 0 or 1; R 1 For CHO, COOH, or COOR a ; R 2 For H, C 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); R 3 Selected from H, R b , OH, OR b OC(O)R b , CN, COOH, COOR b , C(O)R b , and CHO; R 4 R 5 and R 6 Each is independently selected from H and C. 1-3 Alkyl groups (e.g., CH3), OH, CHO, or OC 1-3 Alkyl groups (e.g., OCH3); and Each R a and R b Each of the Cs can be substituted independently. 1-6 Alkyl groups (e.g., CH3 or CH2CH3), C 2-6 alkenyl (e.g., allyl or 2-methylpropyl-1-enyl), CH2C 3-6 cycloalkyl (e.g., cyclopropylmethyl), C 3-6 Cycloalkyl (e.g., cyclopropyl), C 4-6 Cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl or optionally substituted benzyl; Mixed with one or more non-toxic, orally acceptable, pharmaceutically acceptable, cosmetically acceptable, or household product acceptable carriers or excipients.

4. The composition according to claim 3, wherein the compound of formula I is a compound of formula Ia: Formula Ia in, R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl, R 2 R 4 and R 6 Each independently represents H and C. 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl (e.g., OCH3), and R 3 For R b OR b And R b It is selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, allyl, 2-methylprop-1-enyl, phenyl, cyclopentyl, or cyclohexenyl.

5. The composition according to claim 3, wherein the compound of formula II is a compound of formula IId, IIe or IIf: Formula IId Formula IIe Formula IIf in, R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl, and R 4 and R 6 Each independently represents H and C. 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3).

6. The composition according to claim 3, wherein the compound of formula III is a compound of formula IIId, IIIe, or IIIf: Formula IIId Formula IIIe Formula IIIf in, R a Selected from methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl, and R 6 For H, C 1-3 Alkyl (e.g., CH3) or OC 1-3 Alkyl groups (e.g., OCH3).

7. The composition according to claim 3, wherein the compound is selected from the following compounds: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,as well as .

8. The composition according to claim 3, wherein the compound is selected from the following compounds: ， ， ， ， as well as .

9. The composition according to any one of claims 3 to 8, wherein the composition further comprises one or more solvents.

10. The composition according to any one of claims 3 to 8, wherein the composition further comprises one or more other flavoring agents or fragrances.

11. A product comprising the compound of claim 1 or the composition of any one of claims 3 to 10, for example selected from the following: personal care products (e.g., soap, skin cream or lotion, lip balm, shampoo, shower gel, body wash, moisturizer, deodorant, antiperspirant, aftershave, cologne, perfume or other hair or skin care products), sunscreen, insect repellent and insecticide, detergent, household cleaner (e.g., surface cleaner, metal cleaner, wood cleaner, glass cleaner, body cleaner such as soap, dishwashing liquid or laundry detergent), air freshener, room spray, aromatherapy, candle, cosmetics (e.g., perfume, cologne, nail polish, eyeliner, mascara, lipstick, foundation, concealer, blush, bronzer, eyeshadow, lip liner, lip balm), cologne, talcum powder and pet bedding.

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