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US 2026/0234091 A1Published application
Fragrance and flavor compositions comprising adamantane derivatives
OwnerAlexander WILTSCHKO, Brendan LEHNERT +5inventors
InventorsAlexander WILTSCHKO, Brendan LEHNERT, Chase BUCHHOLZ, Jacob YASONIK, Wei QIAN, Bradley B. GILBERT, Andrew P. PATRON
Life of this patent
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Abstract
The present application relates to 2-ethyl-2-adamantanol and related compounds, methods of making them, and methods of using them as flavor and fragrance ingredients in food, cosmetic, pharmaceutical, consumer, and other compositions and products.
Claims17
A compound of Formula I:
- wherein:
- R1 is selected from OH, OR3, O(CO)R3, CN, COOH, COOR3, CH2OH, CH2OR3, C(O)R3, CH(R4)OR3, CH(R4)OH, CHO, CH2COOH, and CH2COOR3;
- R2 is H or optionally substituted C1-6alkyl, C2-6alkenyl, C2-6alkynyl, or C3-6 cycloalkyl;
- R3 and R4 are each independently selected from C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-7cycloalkyl, C3-7cycloalkenyl, heterocycloalkyl, aryl, and heteroaryl, each of which is optionally substituted by one or more groups as defined herein;
- wherein the adamantane core is optionally substituted by one or more groups as defined herein;
- provided that the compound is not 2-methyl-2-adamantanol or 2-ethyl-2-admantanol;
- and
- wherein the compound is not a compound wherein:
- (a) R1 is OH and R2 is H, methyl, ethyl, propyl, isopropyl, cyclopropyl, n-butyl, tert-butyl, cyclobutyl, sec-butyl, isobutyl, cyclopropylmethyl, cyclopentyl, 1-ethylpropyl, n-pentyl, n-hexyl, cyclohexyl, vinyl, allyl, 1-propenyl, isopropenyl,1-propynyl, 2-propynyl, hydroxymethyl, aminomethyl, iodomethyl, cyanomethyl, 2-hydroxyethyl, methoxymethyl, aminoethyl, 3-hydroxypropyl, or 2-oxoethyl;
- (b) R1 is OCH3 and R2 is H, methyl, ethynyl, bromomethyl, aminomethyl, benzyl, allyl, 3-hydroxypropyl, isopropenyl, acetyl, carboxyl, CH2COOH, CH2CH2COOH, 1-oxopropyl, or 3-oxobutyl;
- (c) R1 is O(CO)R3 and R3 is C1-2alkyl, and R2 is methyl, ethyl, ethynyl, vinyl, carboxy, acetyl, cyanomethyl, bromomethyl, CH2COOH, 3-oxobutyl, or 3-(dimethylamino)propyl;
- (d) R1 is CH2OH, and R2 is methyl, aminomethyl, hydroxymethyl, allyl, 2-hydroxyethyl, vinyloxymethyl, (dimethylamino)methyl, 2-methoxyethyl, or CH2O(CO)C(CH3)═CH2;
- (e) R1 is CH2OR3, R2 is methyl, and R3 is CH2Cl, CH2OCH═CH3, CH2O(CO)C(CH3)═CH2;
- (f) R1 is CH2OCH═CH3, and R2 is CH2OCH═CH3 or CH2OH;
- (g) R1 is COOH, and R2 is methyl, 2-propenyl, aminomethyl, CH2COOMe, CH2CONHMe, CH2CH2COOH, CH2CH2CONHMe;
- (h) R1 is COOMe, and R2 is methyl, 2-propenyl, aminomethyl, dicyanomethyl, 2-methoxyethyl, CH2COOMe, CH2CONHMe, CH2CH2COOH, CH2CH2CONHMe, or 2-phenylethyl;
- or
- (i) R1 is CN, and R2 is methyl, hydroxymethyl, cyanomethyl, benzyl, 2-propenyl, n-butyl, aminohydroxymethyl, CH2COOH, CH2COOMe, CH2COOEt, CH2CH2CH2CO2Et, 3-cyanopropyl, 2-methyl-2-buten-4-yl, 4-hydroxybutyl, 4-cyanobutyl, 4-chlorobutyl, 4-bromobutyl, or tetrazolylmethyl.
15 more elements
A compound of Formula I:
- wherein:
- R1 is selected from OH, OR3, O(CO)R3, CN, COOH, COOR3, CH2OH, CH2OR3, C(O)R3, CH(R4)OR3, CH(R4)OH, CHO, CH2COOH, and CH2COOR3;
- R2 is H or optionally substituted C1-6alkyl, C2-6alkenyl, C2-6alkynyl, or C3-6cycloalkyl;
- R3 and R4 are each independently selected from C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-7cycloalkyl, C3-7cycloalkenyl, heterocycloalkyl, aryl, and heteroaryl, each of which is optionally substituted by one or more groups as defined herein;
- wherein the adamantane core is optionally substituted by one or more groups as defined herein,
- for use as a flavor or fragrance ingredient.
3 more elements
A flavor composition and/or fragrance composition comprising a compound of Formula I:
- wherein:
- R1 is selected from OH, OR3, O(CO)R3, CN, COOH, COOR3, CH2OH, CH2OR3, C(O)R3, CH(R4)OR3, CH(R4)OH, CHO, CH2COOH, and CH2COOR3;
- R2 is H or optionally substituted C1-6alkyl, C2-6alkenyl, C2-6alkynyl, or C3-6cycloalkyl;
- R3 and R4 are each independently selected from C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-7cycloalkyl, C3-7cycloalkenyl, heterocycloalkyl, aryl, and heteroaryl, each of which is optionally substituted by one or more groups as defined herein;
- wherein the adamantane core is optionally substituted by one or more groups as defined herein, in admixture with one or more non-toxic, orally acceptable, pharmaceutically acceptable, cosmetically acceptable, or acceptable for a household product, carriers or excipients.
2 more elements
Dependencies are inferred from the claim text.