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US 2026/0078079 A1Published application
Fragrance and flavor compositions comprising norbornane and norbornene derivatives
AssigneeOsmo Labs, PBC
InventorsBradley B. GILBERT, Benjamin AMORELLI, Gregory L. WARREN, Alex J. BERKOWITZ, Andrew P. PATRON
Life of this patent
Estimating the term…
Abstract
The present application relates to bicyclo[2.2.1]heptane and bicyclo[2.2.1]heptene derivatives, methods of making them, and methods of using them as flavor and fragrance ingredients in food, cosmetic, pharmaceutical, consumer, and other compositions and products.
Claims13
A compound of Formula I or Formula II:
- R1 is H, C1-5alkyl, C3-5cycloalkyl, OC1-5alkyl, or OC3-5cycloalkyl;
- X is selected from O, C(RX1)(RX2), C(O), C(O)O, C(RX1)(RX2)C(RX1)(RX2), C(RX)═C(RX), C(RX1)(RX2)O, OC(RX1)(RX2), C(RX1)(RX2)C(O), and C(O)C(RX1)(RX2);
- Y is selected from a bond, C(RX1)(RX2), C(O), C(RX1)(RX2)C(RX1)(RX2), C(RX)═C(RX), C(RX1)(RX2)O, OC(RX1)(RX2), C(RX1)(RX2)C(O), and C(O)C(RX1)(RX2);
- Z is selected from a bond, O, CN, CHO, C(O)O, C(O), C(RX1)(RX2)O, C(RX1)(RX2)CN, C(RX1)(RX2)CHO, C(RX1)(RX2)C(O), C(RX1)(RX2)OC(O), and C(RX1)(RX2)C(O)O, provided that when Z is CN, CHO, C(RX1)(RX2)CN, or C(RX1)(RX2)CHO, then R2 is absent;
- or wherein X—Y—Z—R2 is:
- R2 is H, OH, C1-6alkyl, C2-6alkenyl, C3-6cycloalkyl, C3-6cycloalkenyl, C6-12bicycloalkyl, C6-12bicycloalkenyl, aryl, or heteroaryl, or when Z is CN, CHO, C(RX1)(RX2)CN, or C(RX1)(RX2)CHO, then R2 is absent;
- RX is selected from H, C1-6alkyl, C2-6alkenyl, and C3-6cycloalkyl;
- RX1 and RX2 are each independently selected from H, OH, C1-6alkyl, C2-6alkenyl, and C3-6cycloalkyl;
- provided that the group X—Y—Z— does not form a peroxide (—O—O—) or acid anhydride ((C(O)—O—C(O)) structure;
- and
- optionally provided that Y is not C(O), C(RX1)(RX2)O, or C(RX1)(RX2)C(O), when Z is O, CN, CHO, C(O)O, or C(O);
- and all enantiomers, diastereomers, endo/exo, and E/Z isomers thereof;
- in free or salt form;
- provided that the compound is not any of the Selected Compounds.
11 more elements
A compound of Formula I or Formula II:
- R1 is H, C1-5alkyl, C3-5cycloalkyl, OC1-5alkyl, or OC3-5cycloalkyl;
- X is selected from O, C(RX1)(RX2), C(O), C(O)O, C(RX1)(RX2)C(RX1)(RX2), C(RX)═C(RX), C(RX1)(RX2)O, OC(RX1)(RX2), C(RX1)(RX2)C(O), and C(O)C(RX1)(RX2);
- Y is selected from a bond, C(RX1)(RX2), C(O), C(RX1)(RX2)C(RX1)(RX2), C(RX)═C(RX), C(RX1)(RX2)O, OC(RX1)(RX2), C(RX1)(RX2)C(O), and C(O)C(RX1)(RX2);
- Z is selected from a bond, O, CN, CHO, C(O)O, C(O), C(RX1)(RX2)O, C(RX1)(RX2)CN, C(RX1)(RX2)CHO, C(RX1)(RX2)C(O), C(RX1)(RX2)OC(O), and C(RX1)(RX2)C(O)O, provided that when Z is CN, CHO, C(RX1)(RX2)CN, or C(RX1)(RX2)CHO, then R2 is absent;
- or wherein X—Y—Z—R2 is:
- R2 is H, OH, C1-6alkyl, C2-6alkenyl, C3-6cycloalkyl, C3-6cycloalkenyl, C6-12bicycloalkyl, C6-12bicycloalkenyl, aryl, or heteroaryl, or when Z is CN, CHO, C(RX1)(RX2)CN, or C(RX1)(RX2)CHO, then R2 is absent;
- RX is selected from H, C1-6alkyl, C2-6alkenyl, and C3-6cycloalkyl;
- RX1 and RXa are each independently selected from H, OH, C1-6alkyl, C2-6alkenyl, and C3-6cycloalkyl;
- provided that the group X—Y—Z— does not form a peroxide (—O—O—) or acid anhydride ((C(O)—O—C(O)) structure;
- and
- optionally provided that Y is not C(O), C(RX1)(RX2)O, or C(RX1)(RX2)C(O), when Z is O, CN, CHO, C(O)O, or C(O);
- and all enantiomers, diastereomers, endo/exo, and E/Z isomers thereof;
- in free or salt form;
- optionally provided that the compound is not one or more of the Selected Compounds;
- for use as a flavor or fragrance ingredient.
12 more elements
A flavor composition and/or fragrance composition comprising a compound of Formula I or Formula II:
- R1 is H, C1-5alkyl, C3-5cycloalkyl, OC1-5alkyl, or OC3-5cycloalkyl;
- X is selected from O, C(RX1)(RX2), C(O), C(O)O, C(RX1)(RX2)C(RX1)(RX2), C(RX)═C(RX), C(RX1)(RX2)O, OC(RX1)(RX2), C(RX1)(RX2)C(O), and C(O)C(RX1)(RX2);
- Y is selected from a bond, C(RX1)(RX2), C(O), C(RX1)(RX2)C(RX1)(RX2), C(RX)═C(RX), C(RX1)(RX2)O, OC(RX1)(RX2), C(RX1)(RX2)C(O), and C(O)C(RX1)(RX2);
- Z is selected from a bond, O, CN, CHO, C(O)O, C(O), C(RX1)(RX2)O, C(RX1)(RX2)CN, C(RX1)(RX2)CHO, C(RX1)(RX2)C(O), C(RX1)(RX2)OC(O), and C(RX1)(RX2)C(O)O, provided that when Z is CN, CHO, C(RX1)(RX2)CN, or C(RX1)(RX2)CHO, then R2 is absent;
- or wherein X—Y—Z—R2 is:
- R2 is H, OH, C1-6alkyl, C2-6alkenyl, C3-6cycloalkyl, C3-6cycloalkenyl, C6-12bicycloalkyl, C6-12bicycloalkenyl, aryl, or heteroaryl, or when Z is CN, CHO, C(RX1)(RX2)CN, or C(RX1)(RX2)CHO, then R2 is absent;
- RX is selected from H, C1-6alkyl, C2-6alkenyl, and C3-6cycloalkyl;
- RX1 and RX2 are each independently selected from H, OH, C1-6alkyl, C2-6alkenyl, and C3-6cycloalkyl;
- provided that the group X—Y—Z— does not form a peroxide (—O—O—) or acid anhydride ((C(O)—O—C(O)) structure;
- and
- optionally provided that Y is not C(O), C(RX1)(RX2)O, or C(RX1)(RX2)C(O), when Z is O, CN, CHO, C(O)O, or C(O);
- and all enantiomers, diastereomers, endo/exo, and E/Z isomers thereof;
- in free or salt form;
- optionally provided that the compound is not one or more of the Selected Compounds;
- in admixture with one or more non-toxic, orally acceptable, pharmaceutically acceptable, cosmetically acceptable, or acceptable for a household product, carriers or excipients.
12 more elements
Dependencies are inferred from the claim text.