FRAGRANCES FROM THE ESTERS OF FATTY ACIDS
The invention relates to the generation of compounds, e.g., fragrance molecules with desirable olfactory properties that can be derived from readily available fatty acids.
1 . A compound of the Formula I:
wherein:
R 1 is H, C 1-6 alkyl, or —C(O)C1-6 alkyl;
R 2 is O, CH 2 , or CHC 1-6 alkyl; and
n is an integer from 0 to 6.
2 . The compound of claim 1 , wherein R 1 is H, CH 3 , or CH 2 CH 3 .
3 . The compound of claim 1 , wherein R 1 is —C(O)CH 3 .
4 . The compound of claim 1 , wherein R 2 is CH 2 or CHCH 3 .
5 . The compound of claim 1 , wherein R 2 is O.
6 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
7 . A method of producing a compound of claim 1 :
or a salt thereof, wherein R 1 is H, C 1-6 alkyl, or —C(O)C 1-6 alkyl; R 2 is O, CH 2 , or CHC 1-6 alkyl; and n is an integer from 0 to 6; the method comprising:
providing a compound of Formula III
wherein R is C 1-6 alkyl or —CH 2 CH(ORG)CH 2 ORG, wherein RG is independently selected from the group consisting of hydrogen, —C(O)C 2-20 alkyl, and —C(O)C 2-20 alkenyl, R 2 is —CH 2 or —CHC 1-10 alkyl, and n is an integer from 0 to 6; and
reacting the compound of Formula III with at least two equivalents of a methylating agent under conditions appropriate to obtain the compound of Formula I.
8 . The method of claim 7 , wherein the methylating agent is methyllithium, methylmagnesium chloride, or methylmagnesium bromide.
9 . The method of claim 7 , further comprising the step of performing reductive ozonolysis on the compound of Formula I wherein R 2 is CH 2 or CHC 1-10 alkyl to produce a corresponding compound of Formula I wherein R 2 is O.
10 . The method of claim 7 , further comprising the step of alkylating the compound of Formula I wherein R 1 is H with an alkylating agent to form a corresponding compound of Formula I wherein R 1 is C1-6 alkyl.
11 . The method of claim 10 , further comprising the step of performing reductive ozonolysis on the compound of Formula I wherein R 1 is C 1-6 alkyl and R 2 is CH 2 or CHC 1-10 alkyl to produce a corresponding compound of Formula I wherein R 2 is O.
12 . A method of producing a compound of claim 1 :
wherein R 1 is H, C 1-6 alkyl, or —C(O)C 1-6 alkyl; R 2 is O, CH 2 , or CHC 1-6 alkyl; and n is an integer from 0 to 6; the method comprising:
providing a compound of Formula IV
wherein R is H, C 1-6 alkyl or —CH 2 CH(ORG)CH 2 ORG, wherein RG is independently selected from the group consisting of hydrogen, —C(O)C 2-20 alkyl, and —C(O)C 2-20 alkenyl, R 2 is —CH 2 or —CHC 1-10 alkyl, and n is an integer from 0 to 6; and
reacting the compound of Formula IV with an acid followed by (i) etherifying the compound with a C 1-6 alcohol to produce compounds wherein R is C 1-6 alkyl or (ii) hydroxylating the compound with water to produce compounds wherein R is H; and
converting the ester to the corresponding aldehyde.
13 . The method of claim 12 , wherein the acid is H 2 SO 4 or HCl.
14 . The method of claim 12 , wherein the alcohol is methanol or ethanol.
15 . The method of claim 12 , further comprising the step of converting the C(O)OR group of the compound of Formula IV to CH 2 OH, and optionally converting the CH 2 OH group to a C(O)H group.
16 . The method of claim 15 , further comprising the step of converting the compound of Formula IV wherein RO is H to a compound of Formula IV wherein CH 2 C(O)H is CH═CH 2 .
17 . The compound of claim 1 , wherein R 1 is H.
18 . The compound of claim 1 , wherein R 1 is CH3.
19 . The compound of claim 1 , wherein R 2 is CH2.
20 . The compound of claim 1 , wherein n is 4 or 5.