Fragrance and flavor compositions comprising aromatic derivatives

A compound of Formula I:

• wherein:
• R1 is CHO, COOH, or COORa;
• R2 is H, C1-3 alkyl (e.g., CH3), OH, CHO, or OC1-3 alkyl (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—, —CH2CH2CH2CH2O—, —CH2CH2CH2CH2CH2CH2—, —OCH2CH2CH2CH2CH2—, —CH2OCH2CH2CH2CH2—, —CH2CH2OCH2CH2CH2—, —CH2CH2CH2OCH2CH2—, —CH2CH2CH2CH2OCH2—, —CH2CH2CH2CH2CH2O—, —CH2CH2CH2CH2CH2CH2CH2—, —OCH2CH2CH2CH2CH2CH2—, —CH2OCH2CH2CH2CH2CH2—, —CH2CH2OCH2CH2CH2CH2—, —CH2CH2CH2OCH2CH2CH2—, —CH2CH2CH2CH2OCH2CH2—, —CH2CH2CH2CH2CH2OCH2—, and —CH2CH2CH2CH2CH2CH2O—,
• wherein said group Y is optionally substituted by one or more groups selected from C1-3 alkyl (e.g., CH3), OH, CHO, and OC1-3 alkyl (e.g., OCH3);
• or X—Y is absent;
• R3 is selected from H, Rb, OH, ORb, OC(O)Rb, CN, COOH, COORb, C(O)Rb, and CHO;
• R4, R5, and R6 are each independently selected from H, C1-3 alkyl (e.g., CH3), OH, CHO, or OC1-3 alkyl (e.g., OCH3);
• and
• each Ra and Rb is independently optionally substituted C1-6alkyl (e.g., CH3 or CH2CH3), C2-6alkenyl (e.g., allyl or 2-methylprop-1-enyl), CH2C3-6cycloalkyl (e.g., cyclopropylmethyl), C3-6cycloalkyl (e.g., cyclopropyl), C4-6cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl;
• provided that the compound is not ethyl 3-phenylpropiolate, methyl 3-phenylpropiolate, or 3-phenylpropiolic acid, and wherein the compound is not a compound wherein:
• (a) R1 and R2 are H, and X—Y—R3 is n-butyl, n-pentyl, n-hexyl, or n-nonyl;
• (b) R1 and R2 are H, X is —C(O)—, and Y—R3 is n-butyl, n-octyl, or n-undecyl;
• (c) R1 and R2 are H, X is —CH(OH)—, and Y—R3 is n-butyl, n-octyl, or n-undecyl;
• (d) R1 and R2 are H, X is —O—, and Y—R3 is n-butyl, n-pentyl, or n-hexyl;
• or a compound of Formula II:
• wherein:
• n is 0 or 1;
• R1 is CHO, COOH, or COORa;
• R2 is H, C1-3 alkyl (e.g., CH3), OH, CHO, or OC1-3 alkyl (e.g., OCH3);
• R3 is selected from H, Rb, OH, ORb, OC(O)Rb, CN, COOH, COORb, C(O)Rb, and CHO;
• R4, R5, and R6 are each independently selected from H, C1-3 alkyl (e.g., CH3), OH, CHO, or OC1-3 alkyl (e.g., OCH3);
• and
• each Ra and Rb is independently optionally substituted C1-6alkyl (e.g., CH3 or CH2CH3), C2-6alkenyl (e.g., allyl or 2-methylprop-1-enyl), CH2C3-6cycloalkyl (e.g., cyclopropylmethyl), C3-6cycloalkyl (e.g., cyclopropyl), C4-6cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl;
• or a compound of Formula III:
• wherein:
• n is 0 or 1;
• R1 is CHO, COOH, or COORa;
• R2 is H, C1-3 alkyl (e.g., CH3), OH, CHO, or OC1-3 alkyl (e.g., OCH3);
• R3 is selected from H, Rb, OH, ORb, OC(O)Rb, CN, COOH, COORb, C(O)Rb, and CHO;
• R4, R5, and R6 are each independently selected from H, C1-3 alkyl (e.g., CH3), OH, CHO, or OC1-3 alkyl (e.g., OCH3);
• and
• each Ra and Rb is independently optionally substituted C1-6alkyl (e.g., CH3 or CH2CH3), C2-6alkenyl (e.g., allyl or 2-methylprop-1-enyl), CH2C3-6cycloalkyl (e.g., cyclopropylmethyl), C3-6cycloalkyl (e.g., cyclopropyl), C4-6cycloalkenyl (e.g., cyclopentenyl), optionally substituted phenyl, or optionally substituted benzyl.