Octadecanoic acid derivatives for sweetness and sweet mouthfeel modulation

Abstract

The use of an octadecanoic acid derivative to modulate the sweet perception and mouthfeel of a flavor modifier and to decrease the amount of a flavor modifier used in a consumable is provided.

Description

[0001] IFF-10178-WO-PCT[2]

[0002] OCTADECANOIC ACID DERIVATIVES FOR SWEETNESS AND SWEET MOUTHFEEL MODULATION

[0003] Status of Related Application

[0004] This application claims priority to PCT Application No. PCT / CN2025 / 072626, filed January 16, 2025, the contents hereby incorporated by reference as if set forth in its entirety.

[0005] Background of Invention

[0006] Reducing sugar content in food and beverages has become a necessity in the food industry. Food and beverage manufacturers generally use non-caloric, high-intensity sweeteners, such as rebaudioside A (Reb A), aspartame, saccharin, glycosylated steviol glycosides, etc., to partially or completely replace sugar. However, these sweeteners may exhibit undesirable taste attributes such as delayed onset of sweetness, bitter and astringent aftertaste, and lack of body and mouthfeel. Consequently, sweetness modulators have become valuable tools, which reduce the use of sugar and / or sweeteners, in achieving the desired sweetness intensity and mouthfeel with reduced off-taste.

[0007] Sweetness modulators have been described in the prior art. For example, WO 2013 / 143822 teaches the use of adenosine as sweetness modulator for certain sugars; EP 2606747 describes the use of deoxycholic acid or a derivative thereof for increasing the perception of sweetness of consumables; WO 2013 / 077668 describes the sweetness modulating effect of a glycan or glycopeptide derived from soy sauce; WO 2012 / 107203 teaches the use of nobiletin or a derivative or a hydrate thereof as a sweetener or sweetness modulator; WO 2009 / 023975 describes the use of iso-mogroside V as a sweetener and sweetness modulator; US 2008 / 0242740 teaches aroma compositions of alkamides with hesperetin and / or 4-hydroxydihydrochalcones for increasing sweet sensory impressions; and WO 2007 / 014879 and WO 2007 / 107596 respectively teach the use of hesperetin and 4-hydroxydihydrochalcones for increasing the perception of sweetness of a sweettasting substance or sweet olfactory impression of a flavoring.IFF-10178-WO-PCT[2] Specification Summary of the Invention

[0008] This invention provides a method of modulating the perception of sweetness and / or sweet mouthfeel of a flavor modifier by adding an olfactory effective amount of an octadecanoic acid derivative to the flavor modifier. The present invention further relates to a flavor composition comprising the octadecanoic acid derivative.

[0009] Specifically, the present invention relates to an octadecanoic acid derivative having two or more substituents independently selected from the group consisting of a hydroxy group and a ketone group; wherein the octadecanoic acid derivative contains one or more carbon-carbon double bonds. More specifically, the octadecanoic acid derivative of the present invention has two or three substituents independently selected from the group consisting of a hydroxy group and a ketone group, and the octadecanoic acid derivative contains one to three carbon-carbon double bonds. Even more specifically, the octadecanoic acid derivative of the present invention are selected from the group consisting of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid; 9,16-dioxo-10,12,14-octadecatrienoic acid; pinellic acid; 9,10,13-trihydroxy-(E)-11-octadecenoic acid; (10E,15Z)-9, 12, 13 -trihydroxy- 10, 15 -octadecadienoic acid; (15Z)-9,12,13-trihydroxy-15-octadecenoic acid; and a mixture thereof.

[0010] In one embodiment, the present invention is directed to a method of modulating the perception of sweetness and / or the sweet mouthfeel of a flavor modifier comprising the step of adding an olfactory effective amount of the octadecanoic acid derivative to the flavor modifier.

[0011] In another embodiment, the present invention is directed to a composition comprising a flavor modifier and an olfactory effective amount of the octadecanoic acid derivative.

[0012] In another embodiment, the present invention is directed to a consumable comprising a flavor modifier and an olfactory effective amount of the octadecanoic acid derivative.

[0013] These and other embodiments of the present invention will be apparent by reading the following specification.IFF-10178-WO-PCT[2] Specification Detailed Description of the Invention

[0014] The octadecanoic acid derivatives of the present invention contain chiral centers, thereby providing a number of isomers. It is intended herein that the octadecanoic acid derivatives of the present invention include individual isomers as well isomeric mixtures.

[0015] The octadecanoic acid derivatives of the present invention include, for example, but not limited to, (10E,12E,14E,16S)-16-hydroxy-9-oxo-10,12,14-octadecatrienoic acid (CAS No.

[0016] 147383-02-6), (10E,12Z,14E)-9, 16-dioxo-10, 12, 14-octadecatrienoic acid (CAS No. 217810-46-3), (10E,12Z,14E)-(+)-16-hydroxy-9-oxo-10,12,14-octadecatrienoic acid (CAS No. 212515-33-8), (6E,8Z,1 lZ,13E,155)-15-hydroxy-5-oxo-6,8,l 1,13 -eicosatetraenoic acid (CAS No. 142828-12-4), 9,16-dioxo-10,12,14-octadecatrienoic acid (CAS No. 94450-40-5), (10E,12E,14S)-14-hydroxy-9-oxo-10,12-octadecadienoic acid (CAS No. 1012326-76-9), (95,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid (CAS No. 212515-31-6), (E,E,Z,Z)-15-hydroxy-5-oxo-6,8,11,13-eicosatetraenoic acid (CAS No. 143003-83-2), 16-hydroxy-9-oxo-10,12,14-octadecatrienoic acid (CAS No. 2934918-54-2), (10E,12E,14E)-9,16-dioxo-10,12,14-octadecatrienoic acid (CAS No.

[0017] 1423810-55-2), (6E,8Z)-18-hydroxy-5-oxo-6,8-octadecadienoic acid (CAS No. 1021188-26-0), (10E,12Z,14E)-(+)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid (CAS No. 212515-32-7), [5-(E, E, Z, Z)]-5-hydroxy-15-oxo-6,8,ll,13-eicosatetraenoic acid (CAS No. 148942-85-2), (55,6Z,8E,10E)-5-hydroxy-12-oxo-6,8,10-eicosatrienoic acid (CAS No. 131721-27-2), 16-hydroxy-9-oxo-12,14-octadecadienoic acid (CAS No. 3053438-18-6), (9E,1 lE)-8-hydroxy-13-oxo-9, 11 -octadecadienoic acid (CAS No. 3034868-58-8), 9-hydroxy- 16-oxo-l 0,12,14-octadecatrienoic acid (CAS No. 2734663-29-5), (9Z,llE)-15,16-dihydroxy-13-oxo-9,ll-octadecadienoic acid (CAS No. 2413696-13-4), (8E,10E,125)-12-hydroxy-7-oxo-8,10-octadecadienoic acid (CAS No. 2263934-95-6), (10Z,14Z)-9,16-dioxo-10,12,14-octadecatrienoic acid (CAS No. 1051970-55-8), (8E,10E)-12-hydroxy-7-oxo-8,10-octadecadienoic acid (CAS No.

[0018] 915024-55-4), (10E,12E)-14-hydroxy-9-oxo-10,12-octadecadienoic acid (CAS No. 915024-54-3), (6E,8E,10Z,12R)-12-hydroxy-5-oxo-6,8,10-eicosatrienoic acid (CAS No. 815579-37-4), [5-(all-E)]-15-hydroxy-5-oxo-6,8,ll,13-eicosatetraenoic acid (CAS No. 168749-67-5), (E, E, Z, Z)-5-hydroxy-15-oxo-6,8,l 1,13 -eicosatetraenoic acid (CAS No. 160962-37-8), (10E,12Z,14E)-16-hydroxy-9-oxo-10,12,14-octadecatrienoic acid (CAS No. 147293-07-0), (E,E,Z)-9-hydroperoxy-16-oxo-10,12,14-octadecatrienoic acid (CAS No. 132796-49-7), (E, E, Z)-16-hydroperoxy-9-oxo-10,12,14-octadecatrienoic acid (CAS No. 132796-48-6), pinellic acid (CAS No. 97134-11-7), 9,12,13-trihydroxy-10E-octadecenoic acid (CAS No. 29907-56-0), 9,10,13-trihydroxy-(£)-ll-octadecenoic acid (CAS No. 29907-57-1), (95, 10E, 125, 135,15Z)-9, 12,13-trihydroxy- 10,15-octadecadienoic acid (CAS No. 95341-44-9), 9, 12, 13 -trihydroxy- 10, 15 -octadecadienoic acidIFF-10178-WO-PCT[2] Specification (CAS No. 51146-90-8), 9, 10, 13 -trihydroxy- 11 -octadecenoic acid (CAS No. 2254062-63-8), tianshic acid (CAS No. 292039-79-3), 6,9,10-trihydroxy-7-octadecenoic acid (CAS No. 163860-24-0), 9,10,11 -trihydroxy- 12-octadecenoic acid (CAS No. 61911-67-9), (15Z)-9,12,13-trihydroxy-15 -octadecenoic acid (CAS No. 2894104-80-2), (9S, 10E,12A,13S, 15Z)-9, 12,13-trihydroxy- 10,15-octadecadienoic acid (CAS No. 74923-93-6), (10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid (CAS No. 185147-97-1), (9S, 10S, 1 IE, 13S)-9, 10, 13 -trihydroxy-11-octadecenoic acid (CAS No. 135214-44-7), (9Z)-12,13,17-trihydroxy-9-octadecenoic acid (CAS No. 183867-06-3), 11,12,13 -trihydroxy-9-octadecenoic acid (CAS No. 82617-22-9), (10E,15Z)-(-)-9,12,13-trihydroxy-10,15-octadecadienoic acid (CAS No. 912550-33-5), (12Z)-(+)-9,10,l 1-trihydroxy- 12-octadecenoic acid (CAS No. 406460-90-0), (9S,10R,11E,13S)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 135214-40-3), rel-(9R, 10E, 12 / ?, 13 / ?, 15Z)-9, 12, 13 -trihydroxy-10, 15 -octadecadienoic acid (CAS No. 95783-97-4), 9,10,18-trihydroxy-12-octadecenoic acid (CAS No. 50632-65-0), (8E)-7,10,12-trihydroxy-8-octadecenoic acid (CAS No. 212268-41-2), (9S,10E,12 / ?,13S)-9,12,13-trihydroxy-10-octadecenoic acid (CAS No. 102735-58-0), (9E,10E,12E,13S)-9,12,13-trihydroxy-10-octadecenoic acid (CAS No. 102735-59-1), (9E)-5,8,12-trihydroxy-9-octadecenoic acid (CAS No. 33418-94-9), 9, 12, 13 -trihydroxy- 15 -octadecenoic acid (CAS No. 1246095-53-3), 5,8,1 l-trihydroxy-9-octadecenoic acid (CAS No. 1217866-47-1), (9E,10E,12E,13 / ?)-9, 12, 13 -trihydroxy- 10-octadecenoic acid (CAS No. 135214-48-1), (9Z)-11,12,13 -trihydroxy-9-octadecenoic acid (CAS No. 1313411-66-3), 12,13,15-trihydroxy-9-octadecenoic acid (CAS No. 1252024-08-0), (6Z,8 / ?,9 / ?,10S)-8,9,10-trihydroxy-6-octadecenoic acid (CAS No. 1134486-98-8), (9 / ?,10E,12S,13S)-9,12,13-trihydroxy-10-octadecenoic acid (CAS No. 102735-57-9), (9 / ?,10E,12S,13 / ?)-9,12,13-trihydroxy-10-octadecenoic acid (CAS No. 135214-43-6), (9S,10E,12E,13E)-9,12,13-trihydroxy-10-octadecenoic acid (CAS No. 135214-42-5), (9Z,llE,12S,13S,15Z)-ll,12,13-trihydroxy-9,15-octadecadienoic acid (CAS No. 102735-55-7), (6S,7E,9 / ?,10S)-6,9,10-trihydroxy-7-octadecenoic acid (CAS No. 1312784-18-1), 6,7,10-trihydroxy-8-octadecenoic acid (CAS No. 1082237-30-6), (9Z,11 / ?,12S,13S)-11,12,13-trihydroxy-9-octadecenoic acid (CAS No. 874393-58-5), (9S, 10S, 11 / ?, 12Z)-9,10,11 -trihydroxy- 12-octadecenoic acid (CAS No. 339186-36-6), (9S,10E,12S,13 / ?)-9,12,13-trihydroxy-10-octadecenoic acid (CAS No. 135214-49-2), (9S,10 / ?,llE,13 / ?)-9,10,13-trihydroxy-ll-octadecenoic acid (CAS No. 135214-46-9), re / -(9 / ?, 10E, 12 / ?, 13 / ?)-9, 12, 13 -trihydroxy- 10-octadecenoic acid (CAS No. 95783-98-5), govanic acid (CAS No. 2839679-42-2), 9,12,13-trihydroxyoctadec- 10-enoic acid (CAS No. 2762197-85-1), (12Z)-9,10,l 1 -trihydroxy- 12-octadecenoic acid (CAS No. 2260920-51-0), (6 / ?,7E,9 / ?,10S)-6,9,10-trihydroxy-7-octadecenoic acid (CAS No. 1422643-49-9), (9Z)-8,ll,12-trihydroxy-9-octadecenoic acid (CAS No. 1235223-65-0), re / -(-)-(7E,9 / ?,10 / ?)-6,9,10-trihydroxy-7-octadecenoic acid (CAS No. 1134486-96-6), (9Z)-IFF-10178-WO-PCT[2] Specification 12,13,16-trihydroxy-9-octadecenoic acid (CAS No. 400072-30-2), 9, 10, 13 -trihydroxy- 10-octadecenoic acid (CAS No. 377077-32-2), (9R,10S,11E,13S)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 135214-47-0), (9Z,llS,12S,13S,15Z)-ll,12,13-trihydroxy-9,15-octadecadienoic acid (CAS No. 102693-71-0), 6,9,10-trihydroxy-7-octadecenoic acid (CAS No.

[0019] 1217884-08-6), 5,6,9-trihydroxy-7-octadecenoic acid (CAS No. 1121833-68-8), (12E)-9,10,13-trihydroxy-12-octadecenoic acid (CAS No. 1021439-89-3), (9R,10R,11E,13R)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 135214-45-8), (9R,10S,11E,13R)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 135214-41-4), (9R,10R,11E,13S)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 135214-39-0), (9S,10S,11E,13R)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 135214-38-9), (Z)-threo-(+)-9,10,18-trihydroxy-12-octadecenoicacid (CAS No. 17705-69-0), (9S,10Z,12S,13S)-9,12,13-trihydroxy-10-octadecenoic acid (CAS No.

[0020] 2100285-35-4), (9Z,15Z)-11,12, 13 -trihydroxy-9, 15 -octadecadienoic acid (CAS No. 2086276-35-7), 9,12,13-trihydroxy-7-octadecenoic acid (CAS No. 1456890-87-1), (6R,7E,9R,10R)-6,9,10-trihydroxy-7-octadecenoic acid (CAS No. 1385017-59-3), 11,12, 15 -trihydroxy- 13 -octadecenoic acid (CAS No. 1137524-54-9), (6A,7E,9S,10A)-6,9,10-trihydroxy-7-octadecenoic acid (CAS No.

[0021] 1134486-95-5), (11E)-9,12,13-trihydroxy-11-octadecenoic acid (CAS No. 864072-98-0), rel-(9R,10R,11E,13S)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 157543-40-3), rel-(9R,10S,11E,13R)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 157543-39-0), rel-(9R,10R,11E,13R)-9,10,13-trihydroxy-11-octadecenoic acid (CAS No. 157543-38-9), (9Z,12S,13S,14E,16S)-12,13,16-trihydroxy-9,14-octadecadienoic acid (CAS No. 95341-43-8), (9Z,12S,13R,14E,16S)-12,13,16-trihydroxy-9,14-octadecadienoic acid (CAS No. 95341-39-2), [9R-(9R*,10E,12R*,13S*,15Z)]-9,12,13-trihydroxy-10,15-octadecadienoic acid (CAS No. 95341-35-8), 12,13,16-trihydroxy-9,14-octadecadienoic acid (CAS No. 85514-06-3), (6S,7E,9R,10R)-6,9,10-trihydroxy-7-octadecenoic acid (CAS No. 3051497-78-7), 11,12,13 -trihydroxyoctadeca-9,15-dienoic acid (CAS No. 2914886-09-0), (9Z,11R,12R,13S)-11,12,13-trihydroxy-9-octadecenoic acid (CAS No. 2914886-08-9), 9, 12, 13 -trihydroxy- 11 -octadecenoic acid (CAS No.

[0022] 2540664-47-7), 9, 10, 13 -trihydroxyoctadec- 12-enoic acid (CAS No. 2468202-30-2), (6Z,12Z)-9,10,11 -trihydroxy-6, 12-octadecadienoic acid (CAS No. 2363711-66-2), 9,12,13-trihydroxyoctadec- 10-enoic acid (CAS No. 2304500-55-6), (6E)-5,8,9-trihydroxy-6-octadecenoic acid (CAS No. 2260920-93-0), (5Z)-7,8,9-trihydroxy-5-octadecenoic acid (CAS No. 2260920-90-7), 5,6,9-trihydroxyoctadec-7-enoic acid (CAS No. 2260920-77-0), 5,6,7-trihydroxyoctadec-8-enoic acid (CAS No.2260920-76-9), 9, 10, 13 -trihydroxyoctadec- 11-enoic acid (CAS No.2260913-90-2, 2260913-89-9), (12Z)-9,10,18-trihydroxy-12-octadecenoic acid (CAS No. 2226939-50-8), (6Z,8S,9S,10A)-8,9,10-trihydroxy-6-octadecenoic acid (CAS No. 2094503-37-2), rel-(+)-(7A,9A,10A,12E)-7,9,10-trihydroxy-12-octadecenoic acid (CAS No. 1964495-82-6),IFF-10178-WO-PCT[2] Specification (6A,7E,9S,10S)-6,9,10-trihydroxy-7-octadecenoic acid (CAS No. 1613374-63-2), (6S,7E,9S,10S)-6,9,10-trihydroxy-7-octadecenoic acid (CAS No. 1613374-62-1), (9S, 10E,13S)-9, 12,13-trihydroxy-10-octadecenoic acid (CAS No. 1186614-43-6), rel-(9R, IOS, 1 IE, 13S)-9, 10,13-trihydroxy- 11 -octadecenoic acid (CAS No. 157543-41-4), 9, 10, 13 -trihydroxy- 15 -octadecenoic acid (CAS No. 53279-39-3), 12,13,15-trihydroxy-9-octadecenoic acid (CAS No. 2990992-38-4), (9Z)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 263399-35-5), (12Z)-9,10-dihydroxy-12-octadecenoic acid (CAS No. 263399-34-4), 12,13-dihydroxy-9-octadecenoic acid (CAS No.

[0023] 53734-71-7), 9,10-dihydroxy-12-octadecenoic acid (CAS No. 53734-70-6), 7,10-dihydroxy-8(E)-octadecenoic acid (CAS No. 131021-99-3), re / -(9Z,12A,13A)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 73889-55-1), leukotoxin diol (CAS No. 189191-41-1), 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid (CAS No. 252255-87-1), (9Z,12S,13S)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 7293-40-5), 7,10-dihydroxy-8-octadecenoic acid (CAS No. 95318-29-9), re / -(9A,10S,12Z)-9,10-dihydroxy-12-octadecenoic acid (CAS No. 59959-49-8), (9Z,12A,13A)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 23201-88-9), (6Z)-10,13-dihydroxy-6-octadecenoic acid (CAS No. 1583297-79-3), [A-[A*, A*-(Z)]]-9,10-dihydroxy-12-octadecenoic acid (CAS No.

[0024] 125356-86-7), (15Z)-10,13-dihydroxy-15-octadecenoic acid (CAS No. 1583295-92-4), (10 )-9,12-dihydroxy-10-octadecenoic acid (CAS No. 872453-89-9), (8E)-10,12-dihydroxy-8-octadecenoic acid (CAS No. 276867-66-4), (9Z)-5,8-dihydroxy-9-octadecenoic acid (CAS No.

[0025] 1695564-73-8), (9Z)-1 l,12-dihydroxy-9-octadecenoic acid (CAS No. 1158829-22-1), 11,13-dihydroxy-14-octadecenoic acid (CAS No. 131785-80-3), 9,12-dihydroxy-10-octadecenoic acid (CAS No. 75922-02-0), re / -(9Z,12A,13S)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 59981-84-9), 8,ll-dihydroxy-9-octadecenoic acid (CAS No. 928-07-4), re / -(5Z,12A,13S)-12,13-dihydroxy-5 -octadecenoic acid (CAS No. 877605-38-4), (7. S',8. S'.9Z)-7.8-dihydroxy-9-octadecenoic acid (CAS No. 215878-54-9), 7,8-dihydroxy-9-octadecenoic acid (CAS No. 143288-73-7), 12, 13 -dihydroxy-5 -octadecenoic acid (CAS No. 94376-63-3), rel-(9R,10R,12E)-9,10-dihydroxy-12-octadecenoic acid (CAS No. 59959-43-2), 9, 13 -dihydroxy- 11 -octadecenoic acid (CAS No. 58401-06-2), (9E)-11,12-dihydroxy-9-octadecenoic acid (CAS No. 18417-02-2), (Z)-9,12-dihydroxy-10-octadecenoic acid (CAS No. 928-08-5), (Z)-7,10-dihydroxy-8-octadecenoic acid (CAS No. 928-06-3), (9Z)-7,8-dihydroxy-9-octadecenoic acid (CAS No. 2043320-32-5), (8E,10S)-7,10-dihydroxy-8-octadecenoic acid (CAS No. 796055-35-1), [R*, R*-(E)]-10, 13-dihydroxy- 11 -octadecenoic acid (CAS No. 160057-62-5), [R*,R*-(E)]-8,11-dihydroxy-9-octadecenoic acid (CAS No. 148409-58-9), [R*,S*-(E)]-8,11-dihydroxy-9-octadecenoic acid (CAS No. 148409-57-8), 9, 10-dihydroxy- 11 -octadecenoic acid (CAS No. 144751-25-7), 8,12-dihydroxy-9-octadecenoic acid (CAS No. 143288-75-9), [R-[R*,S*-(Z)]]-5,8-dihydroxy-9-octadecenoic acid (CAS No. 138078-50-9), 10, 13 -dihydroxy- 11 -octadecenoic acid (CAS No.IFF-10178-WO-PCT[2] Specification 107903-45-7), [R*,R*-(Z)]-6,7-dihydroxy-9-octadecenoic acid (CAS No. 106927-63-3), rel-(87?,97?,12Z)-8,9-dihydroxy-12-octadecenoic acid (CAS No. 59959-41-0), (11E)-9,10-dihydroxy-11-octadecenoic acid (CAS No. 18421-37-9), (9Z)-6,8-dihydroxy-9-octadecenoic acid (CAS No.

[0026] 3034066-02-6), (1 lZ)-9,10-dihydroxy-l 1 -octadecenoic acid (CAS No. 2768863-95-0), re / -(77?,8E,107?)-7,10-dihydroxy-8-octadecenoic acid (CAS No. 2561417-53-4), 9,12-dihydroxyoctadec- 10-enoic acid (CAS No. 2561417-07-8, 2292114-75-9), re / -(107?,l 1Z,137?)-10, 13 -dihydroxy- 11 -octadecenoic acid (CAS No. 2561416-33-7), (67?,87?,9Z)-6,8-dihydroxy-9-octadecenoic acid (CAS No. 2509076-22-4), ( 9Z, 15Z)- 12,13, 14-trihydroxy-9, 15 -octadecadienoic acid (CAS No. 2363711-64-0), 8,9-dihydroxyoctadec- 10-enoic acid (CAS No. 2247640-99-7), (9Z,125,137?)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 2135834-88-5), (9E)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 2100282-82-2), (12Z)-9,11 -dihydroxy- 12-octadecenoic acid (CAS No. 1449743-05-8), (45,115,12E)-4,ll-dihydroxy-12-octadecenoic acid (CAS No.

[0027] 1384110-19-3), 11,12, 13 -trihydroxy-9, 14-octadecadienoic acid (CAS No. 1356156-29-0), (87?,9Z)-6,8-dihydroxy-9-octadecenoic acid (CAS No. 1299384-00-1), re / -(57?,87?,9Z)-5,8-dihydroxy-9-octadecenoic acid (CAS No. 1299383-64-4), (10Z)-7,8,9-trihydroxy-10-hexadecenoic acid (CAS No. 1297566-08-5), (12E)-10,ll-dihydroxy-12-octadecenoic acid (CAS No. 1204593-67-8), (10E)-12,13-dihydroxy-10-octadecenoic acid (CAS No. 1204593-66-7), rel-(10E,127?,135)-12,13-dihydroxy-10-octadecenoic acid (CAS No. 1161732-91-7), rel-(10R,11S,12E)-10,11-dihydroxy-12-octadecenoic acid (CAS No. 1161732-89-3), rel-(9R,11R,12S)-11,12-dihydroxy-9-octadecenoic acid (CAS No. 1161732-87-1), rel-(9R,10S,11E)-9,10-dihydroxy-11-octadecenoic acid (CAS No. 1161732-86-0), (11E)-10,13-dihydroxy-11-octadecenoic acid (CAS No. 1000991-39-8), (6Z)-5,12-dihydroxy-6-octadecenoic acid (CAS No.

[0028] 877672-27-0), (10E)-9,13-dihydroxy-10-octadecenoic acid (CAS No. 872453-82-2), (95,1 lE,135)-9,12,13-trihydroxy-l 1 -octadecenoic acid (CAS No. 871469-70-4), (12Z)-8,9-dihydroxy- 12-octadecenoic acid (CAS No. 817194-09-5), (9S,12Z,17R)-9,17-dihydroxy-12-octadecenoic acid (CAS No. 710354-44-2), (9S,12Z,16R)-9,16-dihydroxy-12-octadecenoic acid (CAS No. 710354-43-1), 11,12, 13 -trihydroxy- 10-octadecenoic acid (CAS No. 377077-33-3), ll,12-dihydroxy-9-octadecenoic acid (CAS No. 256933-13-8), (95, 10E, 125,137?,15Z)-9, 12,13-trihydroxy-10,15 -octadecadienoic acid (CAS No. 211236-19-0), (95,10E,127?,137?,15Z)-9,12,13-trihydroxy-10,15 -octadecadienoic acid (CAS No. 211236-17-8), (9Z,12R,13S,14E,16S)-12,13,16-trihydroxy-9,14-octadecadienoic acid (CAS No. 211236-16-7), (9Z,127?,137?,14E,165)-12,13,16-trihydroxy-9, 14-octadecadienoic acid (CAS No. 211236-15-6), (9Z,11E,12E,13E,15Z)-11,12,13-trihydroxy-9, 15 -octadecadienoic acid (CAS No. 205380-40-1), (9Z,115, 127?, 137?, 15Z)-11,12,13-trihydroxy-9, 15 -octadecadienoic acid (CAS No. 205380-39-8), (9Z,14E)-12,13,16-trihydroxy-9, 14-octadecadienoic acid (CAS No. 185149-07-9), [97?-(97?*,10E,125*,135*,15Z)]-9,12,13-IFF-10178-WO-PCT[2] Specification trihydroxy- 10, 15 -octadecadienoic acid (CAS No. 95341-38-1), (9Z,12S,13S,14E,16E)-12,13,16-trihydroxy-9,14-octadecadienoic acid (CAS No. 95341-36-9), (9Z,12S,13E,14E,16E)-12,13,16-trihydroxy-9,14-octadecadienoic acid (CAS No. 95341-32-5), (9S,10S,l 1E,12Z,15Z)-9,1O,11-trihydroxy- 12, 15 -octadecadienoic acid (CAS No. 339186-37-7), 9, 10, 13 -trihydroxy- 11,15-octadecadienoic acid (CAS No. 53279-40-6), rel-(-)-(9R, 10S, 1 IS, 12Z,15Z)-9,10,11 -trihydroxy-12, 15 -octadecadienoic acid (CAS No. 1134486-94-4), (9S,10E,llE,13S,15Z)-9,10,13-trihydroxy-11, 15 -octadecadienoic acid (CAS No. 95341-40-5), (11E,15Z)-9,10,13-trihydroxy-11,15-octadecadienoic acid (CAS No. 185148-53-2), (9S, 10S, HE, 13S,15Z)-9, 10,13-trihydroxy- 11,15-octadecadienoic acid (CAS No. 95341-42-7), (9S,10E,llE,13E,15Z)-9,10,13-trihydroxy-ll,15-octadecadienoic acid (CAS No. 95341-33-6), 12,15, 16-trihydroxy-9, 13 -octadecadienoic acid (CAS No. 69910-30-1), (6Z,9Z)-12,13,17-trihydroxy-6,9-octadecadienoic acid (CAS No. 710338- 15-1), (4E,7E,13E)-7,13-dihydroxy-4-octadecenoic acid (CAS No. 115482-48-9), (9Z,12S,13E,15E,16S)-12,15,16-trihydroxy-9,13-octadecadienoic acid (CAS No. 95588-22-0), (9Z,12E,13E,15S,16S)-12,15,16-trihydroxy-9,13-octadecadienoic acid (CAS No. 95588-21-9), ( 9Z, 12S, 13E, 15S,16S)- 12,15, 16-trihydroxy-9, 13 -octadecadienoic acid (CAS No. 95341-41-6), (9Z,12E,13E,15E,16S)-12,15,16-trihydroxy-9,13-octadecadienoic acid (CAS No. 95341-34-7), (6Z,9Z,llE,12E,13S)-ll,12,13-trihydroxy-6,9-octadecadienoic acid (CAS No. 2914886-10-3), 9, 12, 13 -trihydroxy-4, 15 -octadecadienoic acid (CAS No. 2716987-40-3), 9,10,13-trihydroxyoctadeca-11,15 -dienoic acid (CAS No. 2242618-28-4), (9S,10E,l 1E,13S,14Z)-9,1O,13-trihydroxy-ll,14-octadecadienoic acid (CAS No. 1860028-79-0), (8Z)-1 l,12,20-trihydroxy-8-eicosenoic acid (CAS No. 1426241-90-8), 12, 13 -dihydroxy- 1 l-methoxy-9-octadecenoic acid (CAS No. 1036767-87-9), (9S, 1 OS, 1 IE, 13 R, 15Z)-9,10,13 -trihydroxy- 11,15 -octadecadienoic acid (CAS No. 211236-20-3), 9-Hydroperoxy- 13 -hydroxy- 10-octadecenoic acid (CAS No. 209616-73-9), [R*, S* -(E) | -10, 13 -dihydroxy- 11 -octadecenoic acid (CAS No. 160057-61-4), 7,12-dihydroxy-9-octadecenoic acid (CAS No. 143288-77-1), 10-hydroperoxy-9-hydroxy-12-octadecenoic acid (CAS No. 142521-58-2), [E-[E*, S*-(Z)]]-9,10-dihydroxy-12-octadecenoicacid(CASNo. 125356-88-9), [S-[E*, S*-(Z)]]-9,10-dihydroxy-12-octadecenoic acid (CAS No. 125356-87-8), [S-[E*, E*- (Z)]]-9,10-dihydroxy-12-octadecenoic acid (CAS No. 125356-85-6), [9R-(9R*,10S*,11E,13R*,15Z)]-9,10,13-trihydroxy-11,15-octadecadienoic acid (CAS No. 95341-37-0), (Z)-9,10,14,15-tetrahydroxy-5-octadecenoic acid (CAS No. 85056-43-5), 14,15-dihydroxy-9-octadecenoic acid (CAS No. 85056-42-4), 9, 13 -dihydroxy- 10-methoxy- 11 -octadecenoic acid (CAS No. 79926-04-8), 9, 13 -dihydroxy- 12-methoxy- 10-octadecenoic acid (CAS No. 79926-02-6), re / -(9E,12E,13S)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 59981-85-0), rel-(9E,12R,13R)-12,13-dihydroxy-9-octadecenoic acid (CAS No. 59981-83-8), re / -(8Z,12E,13E)-12,13-dihydroxy-8 -octadecenoic acid (CAS No. 59959-56-7), re / -(5Z,12E,13E)-12,13-dihydroxy-5-octadecenoicIFF-10178-WO-PCT[2] Specification acid (CAS No. 59959-55-6), re / -(7Z,12A,13A)-12,13-dihydroxy-7-octadecenoic acid (CAS No.

[0029] 59959-54-5), re / -(6Z,12A,13A)-12,13-dihydroxy-6-octadecenoic acid (CAS No. 59959-53-4), re / -(6Z,llA,12A)-ll,12-dihydroxy-6-octadecenoic acid (CAS No. 59959-52-3), re / -(6Z,10A, HA)-10,1 l-dihydroxy-6-octadecenoic acid (CAS No. 59959-51-2), re / -(9A,10S,12E)-9,10-dihydroxy-12-octadecenoic acid (CAS No. 59959-50-1), re / -(6Z,9A,10A)-9,10-dihydroxy-6-octadecenoic acid (CAS No. 59959-48-7), rc / -(7 / ?.8 / ?. l2Z)-7.8-dihydroxy-l2-octadcccnoic acid (CAS No.

[0030] 59959-40-9), re / -(6A,7 R, WZ)-6,7 -dihydroxy- 10-octadecenoic acid (CAS No. 59959-38-5), re / -(6 / ?.7 / ?. I IZ)-6.7-dihydroxy- 11 -octadecenoic acid (CAS No. 59959-37-4), rel-(6R,7R,12Z)-6,7-dihydroxy-12-octadecenoic acid (CAS No. 59959-36-3), re / -(5A,6A,12Z)-5,6-dihydroxy-12-octadecenoic acid (CAS No. 59959-28-3), 9, 13 -dihydroxy- 10-octadecenoic acid (CAS No. 58401-05-1), 7,8,16-trihydroxy-9,12-octadecadienoic acid (CAS No. 2749168-96-3), 7,8,17-trihydroxy-9,12-octadecadienoic acid (CAS No. 2748975-63-3), 7,9,10-trihydroxy-12,15-octadecadienoic acid (CAS No. 2111873-96-0), (9Z)-14,15-dihydroxy-9-octadecenoic acid (CAS No. 740041-10- 5). It is intended herein that the octadecanoic acid derivatives of the present invention also include heptadecanoic or nonadecanoic acid derivatives such as, for example, (7Z, 14Z)-10, 11,12-trihydroxy-7,14-heptadecadienoic acid (CAS No. 1187942-80-8), (9S,12S,13S)-9,12,13-trihydroxy-10,15 -heptadecadienoic acid (CAS No. 2222638-03-9), 8,1 l,12-trihydroxy-9-heptadecenoic acid (CAS No. 83156-44-9), 10,ll,12-trihydroxy-8-heptadecenoic acid (CAS No.

[0031] 83156-43-8), (9S,10E,12A,13S)-9,12,13-trihydroxy-10-nonadecenoic acid (CAS No. 1027175-53- 6), 9, 12-dihydroxy- 15 -nonadecenoic acid (CAS No. 105798-59-2), [R*,S*-(Z)]-9,12-dihydroxy-10-nonadecenoic acid (CAS No. 167115-68-6), [R*,R*-(Z)]-9,12-dihydroxy-10-nonadecenoic acid (CAS No. 167115-67-5), [R*,R*-(Z)]-6,9-dihydroxy-7-nonadecenoic acid (CAS No. 167115-63-1) and (13Z)-9,ll-dihydroxy-13-nonadecenoic acid (CAS No. 1348592-84-6).

[0032] It is further intended herein that the octadecanoic acid derivatives of the present invention include a derivative such as a glycosylated derivative thereof and a combination thereof.

[0033] The octadecanoic acid derivatives of the present invention may be obtained commercially, synthesized chemically (Sunazuka et al., Tetrahedron Letters (2002), 43(7): 1265-1268; Sabitha et al., Helvetica Chimica Acta (2009), 92(10): 2052-2057) or extracted from plants such as, for example, but not limited to, Corchorus olitorius L. (Tiliaceae) (Yoshikawa et al., Chemical & Pharmaceutical Bulletin (1998), 46(6): 1008-1014), Diospyros kaki leaves (Liu et al., Food Chemistry (2024), 455: 139814), Mikania congesta (Herz et al., Phytochemistry (1985), 24(8): 1761-1768), Chenopodium quinoa (Qian, Guangtao et al., Food Chemistry (2024), 448: 138575), Tricholoma mesoamericanum (Gamboa-Becerra et al., International Journal of Food Science andIFF-10178-WO-PCT[2] Specification Technology (2024), 59(6): 4348-4358), Pinellia ternate (Nagai et al., International Immunopharmacology (2002), 2(8): 1183-1193), Elephantopus tomentosus (Wang et al., Redai Yaredai Zhiwu Xuebao (2012), 20(4): 413-417), Ailanthus altissima (Wang et al., Zhongcaoyao (2012), 43(4): 649-652), the genus Salsola (Oueslati etal., Journal of Natural Products, 2006, 69(9): 1366-1369), Rudbeckia fulgida (Herz et al., Phytochemistry (1985), 24(1): 89-91), Sterculia monosperma (Berry et al., Journal of the American Oil Chemists' Society (1982), 59(1): 57-58), Arabidopsis thaliana (Andersson et al., Journal of Biological Chemistry (2006), 281: 31528-31537), Triticum aestivum (Simsek et al., International Journal of Food Sciences and Nutrition (2014), 65(7): 803-808) and Ajuga decumbens (Sun et al., Shenyang Yaoke Daxue Xuebao (2012), 29(10): 758-764).

[0034] For the first time, (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid, 9,16-dioxo-10,12,14-octadecatrienoic acid, pinellic acid, 9,10,13-trihydroxy-(E)-ll-octadecenoic acid, (10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid and (15Z)-9,12,13-trihydroxy-15-octadecenoic acid were also identified in Sterculia monosperma by the present applicants.

[0035] Additional glycosylated derivatives can be prepared via transglycosylation reactions with, for example, but not limited to, glucose, fructose, galactose, rhamnose, ribose, mannose, arabinose, fucose, maltose, lactose, sucrose, rutinose, sorbose, xylulose, ribulose, rhammulose and xylose.

[0036] As used herein, the term “a” or “an” is understood to mean one or more. The term “an octadecanoic acid derivative” is understood to mean one or more of the octadecanoic acid derivatives.

[0037] Accordingly, the present invention provides a method of using an octadecanoic acid derivative of the present invention to modulate the sweet perception and sweet mouthfeel of a flavor modifier and / or decrease the amount of a flavor modifier used in a consumable.

[0038] If provided as a botanical extract, preferably the extract is enriched for an octadecanoic acid derivative of the present invention to achieve a content of about 0.001% and greater, respectively. For example, the botanical extract contains an octadecanoic acid derivative from about 0.001% to about 95%, from about 0.002% to about 50% or from about 0.002% to about 10%. Unless otherwise specified, percentages (% s) are by weight.IFF-10178-WO-PCT[2] Specification A natural sweetener includes, for example, but not limited to, sucrose, fructose, glucose, high fructose com syrup, Stevia rebaudiana compositions including pure components of Reb A, stevioside, and rebaudioside D (Reb D), rebaudioside M (Reb M), xylose, arabinose, or rhamnose, as well as sugar alcohols such as erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof. An artificial sweetener includes, for example, but not limited to, aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.

[0039] A flavoring is a preparation that provides a consumable with a particular taste and / or smell. A flavor modulator is a subset of the flavoring. It is added to the consumable to improve taste profile such as, for example, by enhancing sweetness perception, masking off-notes of the sweeteners and improving mouthfeel without adding their own strong taste. The flavor modulators of the present invention include, for example, but not limited to, a stevia composition including stevioside, steviolbioside Reb A, rebaudioside B (Reb B), rebaudioside C (Reb C), Reb D, rebaudioside E (Reb E), rebaudioside F (Reb F), Reb M, dulcoside A, dulcoside B, rubusoside, alpha-glucosyl stevia, fructosyl stevia, galactosyl stevia, beta-glucosyl stevia, siamenoside, mogrosidc IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, a salt thereof, a glycosylated derivative thereof and a combination thereof. The glycosylated derivatives can be prepared via transglycosylation reactions with, for example, but not limited to, glucose, fructose, galactose, rhamnose, ribose, mannose, arabinose, fucose, maltose, lactose, sucrose, rutinose, sorbose, xylulose, ribulose, rhammulose and xylose. In one embodiment, the flavor modulators of the present invention include Reb A, Reb C, rubusoside, Reb D, mogroside V, Luo Han Guo, monatin acid, a salt thereof, a glycosylated derivative thereof and a combination thereof. The flavor modulators of the present invention exhibit weak intrinsic sweetness. Some other flavorings of the present invention include, for example, but not limited to, curculin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, cyclocarioside I and a combination thereof.

[0040] Accordingly, the term “a flavor modifier” of the present invention refers to a sweetener including a natural sweetener and an artificial sweetener or a flavor modulator set forth in the above.IFF-10178-WO-PCT[2] Specification The term “sweetness” or “sweetness intensity” is understood to mean the relative strength of sweet sensation as observed or experienced by an individual, e.g., a human, or a degree or amount of sweetness detected by a taster, for example on the scale from 0 (none) to 8 (very strong) used in sensory evaluations according to the procedure described in American Society for Testing Materials, Special Technical Publication-434: “Manual on Sensory Testing Methods,” ASTM International, West Conshohocken, PA. (1996). In certain embodiments, modification of sweet perception may also affect the perception of other basic tastes. For example, increasing sweetness perception may decrease the perception of sourness, bitterness and salty (Mojet et al., Chemical Senses (2004), 29: 671-681). Thus, sweet modulation may reduce, mask and balance other flavors. A balanced flavor profile can be achieved through modulating basic tastes.

[0041] The term “sweet mouthfeel” is understood to mean syrupy and / or sugar-like mouthfeel. Sweet mouthfeel provides perception of syrupiness that is viscous or thick, which resembles mouthfeel provided by high concentrations of sugar.

[0042] The term “olfactory effective amount” is understood to mean the amount of an octadecanoic acid derivative used in a combination with a flavor modifier, wherein the octadecanoic acid derivative increases the perception of sweetness of the flavor modifier. Its olfactory effective amount may vary depending on many factors including other ingredients, their relative amounts and the olfactory effect that is desired. Any amount of an octadecanoic acid derivative that provides the desired degree of sweetness modulation without exhibiting off-taste can be used. In certain embodiments, the olfactory effective amount ranges from about 0.1 ppb to about 5000 ppm by weight, preferably from about 1 ppb to about 1000 ppm by weight and more preferably from about 10 ppb to about 100 ppm by weight. When used in the form of a botanical extract such as a Sterculia monosperma leaf extract, the olfactory effective amount ranges from about 100 ppb to about 5000 ppm by weight, preferably from about 1 to about 1000 ppm by weight and more preferably from about 5 to about 500 ppm.

[0043] A consumable includes, for example, a food product (e.g., a beverage), a sweetener such as a natural sweetener or an artificial sweetener, a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition and a cosmetic product. The consumable may further contain a flavoring.IFF-10178-WO-PCT[2] Specification In some embodiments, a consumable is a food product including, for example, but not limited to, fruits, vegetables, juices, meat products such as ham, bacon and sausage, egg products, fruit concentrates, gelatins and gelatin-like products such as jams, jellies, preserves and the like, milk products such as yogurt, ice cream, sour cream and sherbet, icings, syrups including molasses, com, wheat, rye, soybean, oat, rice and barley products, nut meats and nut products, cakes, cookies, confectionaries such as candies, gums, fruit flavored drops, and chocolates, chewing gums, mints, creams, pies and breads. In a certain embodiment, the food product is a beverage including, for example, but not limited to, coffee, tea, carbonated soft drinks, such as Coke and Pepsi, noncarbonated soft drinks and other fruit drinks, sports drinks such as Gatorade and alcoholic beverages such as beers, wines and liquors. A consumable also includes prepared packaged products, such as granulated flavor mixes, which upon reconstitution with water provide noncarbonated drinks, instant pudding mixes, instant coffee and tea, coffee whiteners, malted milk mixes, pet foods, livestock feed, tobacco, and materials for baking applications, such as powdered baking mixes for the preparation of breads, cookies, cakes, pancakes, donuts and the like. A consumable also includes diet or low-calorie food and beverages containing little or no sucrose. A preferred consumable includes carbonated beverages. Consumables further include condiments such as herbs, spices and seasonings, flavor enhancers (e.g., monosodium glutamate), dietetic sweeteners and liquid sweeteners.

[0044] In other embodiments, a consumable is a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition or a cosmetic product. Preferred compositions are pharmaceutical compositions containing an octadecanoic acid derivative, one or more pharmaceutically acceptable excipients, and one or more active agents that exert a biological effect other than sweetness modulation. Such active agents include pharmaceutical and biological agents that have an activity other than taste modulation. Such active agents are well known in the art (See, e.g., The Physician's Desk Reference). Such compositions can be prepared according to procedures known in the art, for example, as described in Remington's Pharmaceutical Sciences, Mack Publishing Co., Easton, PA. In one embodiment, such an active agent includes a bronchodilator, an anorexiant, an antihistamine, a nutritional supplement, a laxative, an analgesic, an anesthetic, an antacid, a H2 -receptor antagonist, an anticholinergic, an antidiarrheal, a demulcent, an antitussive, an antinauseant, an antimicrobial, an antibacterial, an antifungal, an antiviral, an expectorant, an anti-inflammatory agent, an antipyretic and a mixture thereof. In another embodiment, the active agent is selected from the group consisting of an antipyretic and analgesic, e.g., ibuprofen, acetaminophen or aspirin, a laxative, e.g., phenolphthalein dioctyl sodium sulfosuccinate, an appetite depressant, e.g., an amphetamine, phenylpropanolamine,IFF-10178-WO-PCT[2] Specification phenylpropanolamine hydrochloride, or caffeine, an antacid, e.g., calcium carbonate, an antiasthmatic, e.g., theophylline, an antidiarrheal, e.g., diphenoxylate hydrochloride, an agent against flatulence, e.g., simethecon, a migraine agent, e.g., ergotamine tartrate, a psychopharmacological agent, e.g., haloperidol, a spasmolytic or sedative, e.g., phenobarbital, an antihyperkinetic, e.g., methyldopa or methylphenidate, a tranquilizer, e.g., a benzodiazepine, hydroxyzine, meprobramate or phenothiazine, an antihistaminic, e.g., astemizol, chlorpheniramine maleate, pyridamine maleate, doxylamine succinate, brompheniramine maleate, phenyltoloxamine citrate, chlorcyclizine hydrochloride, pheniramine maleate, or phenindamine tartrate, a decongestant, e.g., phenylpropanolamine hydrochloride, phenylephrine hydrochloride, pseudoephedrine hydrochloride, pseudoephedrine sulfate, phenylpropanolamine bitartrate, or ephedrine, a beta-receptor blocker, e.g., propranolol, an agent for alcohol withdrawal, e.g., disulfuram, an antitussive, e.g., benzocaine, dextromethorphan, dextromethorphan hydrobromide, noscapine, carbetapentane citrate, and chlophedianol hydrochloride, a fluorine supplement, e.g., sodium fluoride, a local antibiotic, e.g., tetracycline or clindamycin, a corticosteroid supplement, e.g., prednisone or prednisolone; an agent against gout, e.g., colchicine or allopurinol, an antiepileptic, e.g., phenytoin sodium, an agent against dehydration, e.g., electrolyte supplements, an antiseptic, e.g., cetylpyridinium chloride, a NSAID, e.g., acetaminophen, ibuprofen, naproxen, or a salt thereof, a gastrointestinal active agent, e.g., loperamide and famotidine, an alkaloid, e.g., codeine phosphate, codeine sulfate, or morphine, a supplement for trace elements, e.g., sodium chloride, zinc chloride, calcium carbonate, magnesium oxide, and other alkali metal salts and alkali earth metal salts; a vitamin, an ion-exchange resin, e.g., cholestyramine, a cholesterol-depressant and lipid-lowering substance, an antiarrhythmic, e.g., N-acetylprocainamide and an expectorant, e.g., guaifenesin. Examples of dietary supplements or nutraceuticals include, for example, but are not limited to, an enteral nutrition product for treatment of nutritional deficit, trauma, surgery, Crohn's disease, renal disease, hypertension, obesity and the like, to promote athletic performance, muscle enhancement or general well-being or inborn errors of metabolism such as phenylketonuria. In particular, such compositions can contain one or more amino acids which have a bitter or metallic taste or aftertaste. Such amino acids include, for example, but are not limited to, an essential amino acid such as L isomers of leucine, isoleucine, histidine, lysine, methionine, phenylalanine, threonine, tryptophan, tyrosine and valine. Dental hygienic compositions are known in the art and include, for example, but not limited to, a toothpaste, a mouthwash, a plaque rinse, a dental floss, a dental pain reliever (such as Anbesol) and the like. In one embodiment, the dental hygienic composition includes one natural sweetener. In another embodiment, the dental hygienic composition includes more than one natural sweetener. In yet another embodiment, the dental hygienic composition includes sucrose and com syrup, or sucrose and aspartame. AIFF-10178-WO-PCT[2] Specification cosmetic product includes, for example, but not limited to, a face cream, a lipstick, a lip gloss and the like. Other suitable cosmetic products of use in this invention include a lip balm, such as Chapstick or Burt’s Beeswax Lip Balm.

[0045] In addition, the present invention also provides methods for modulating the perception of sweetness of a flavor modulator and decreasing its use level in a consumable by incorporating an octadecanoic acid derivative. In one embodiment, the invention provides a consumable containing an olfactory effective amount of an octadecanoic acid derivative and a flavor modulator in a reduced amount in order to achieve the same level of sweetness when the flavor modulator is used alone in a traditional amount. In this respect, the amount of flavor modulator used in a consumable can be reduced by at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95%, from about 60% to about 99% or from about 20% to about 50%.

[0046] As indicated, an octadecanoic acid derivative can be used in a consumable as a sweetness modulator, which retains a desired sweetness but contains lower amounts of a natural sweetener or an artificial sweetener. For example, an improved carbonated soft drink can be produced with the same sweetness as the known carbonated soft drink but with lower sugar content by adding an octadecanoic acid derivative.

[0047] Additional materials can also be used in conjunction with an octadecanoic acid derivative of the present invention to encapsulate and / or deliver the lingering aftertaste masking effect. Some well-known materials are, for example, but not limited to, polymers, oligomers, other nonpolymers such as surfactants, emulsifiers, lipids including fats, waxes and phospholipids, organic oils, mineral oils, petrolatum, natural oils, perfume fixatives, fibers, starches, sugars and solid surface materials such as zeolite and silica. Some preferred polymers include polyacrylate, polyurea, polyurethane, polyacrylamide, polyester, polyether, polyamide, poly (acrylate -co -acrylamide), starch, silica, gelatin and gum Arabic, alginate, chitosan, polylactide, poly (melamine -formaldehyde), poly(urea-formaldehyde), or a combination thereof.IFF-10178-WO-PCT[2] Specification The following are provided as specific embodiments of the present invention. Other modifications of this invention will be readily apparent to those skilled in the art. Such modifications are understood to be within the scope of this invention. Materials were purchased from Aldrich Chemical Company unless noted otherwise. As used herein all percentages are weight percent unless otherwise noted, ppm is understood to stand for parts per million, L is understood to be liter, mL is understood to be milliliter, g is understood to be gram, Kg is understood to be kilogram, mol is understood to be mole, mmol is understood to be millimole, psig is understood to be pound-force per square inch gauge, and mmHg be millimeters (mm) of mercury (Hg). IFF as used in the examples is understood to mean International Flavors & Fragrances Inc., New York, NY, USA.IFF-10178-WO-PCT[2] Specification Example I: Sample Preparation and Sensory Evaluation

[0048] An extract of Sterculia monosperma leaves was prepared according to a known method (WO 2020 / 118002) but using an alcohol as the solvent such as ethanol at a specified level of 30-60% and at a specified temperature of 40-60 °C. Subsequent filtration provided a filtrate, which was a water-soluble extract. The leaf residue was further treated with an alcohol as the solvent such as ethanol at a specified level of 50-80% and at a specified temperature of 30-70 °C. The treated leaf residue was then combined with a solvent commonly used in flavors such as Neobee®, dried and filtered to afford an oil-soluble extract.

[0049] Both water-soluble and oil-soluble extracts were enriched with (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid (0.01-1.5%), 9,16-dioxo-10,12,14-octadecatrienoic acid (0.01-1.0%), pinellic acid (0.008-0.8%), 9,10,13-trihydroxy-(E)-ll-octadecenoic acid (0.002-0.2%), (10E,15Z)-9, 12, 13 -trihydroxy- 10, 15 -octadecadienoic acid (0.05-1.5%) and (15Z)-9,12,13-trihydroxy-15-octadecenoic acid (0.05-1.5%).

[0050] (9S,10E,12E,14E)-9-Hydroxy-16-oxo-10,12,14-octadecatrienoic acid (CAS No. 212515-31-6), 9, 16-dioxo-10, 12, 14-octadecatrienoic acid (CAS No. 217810-46-3), pinellic acid (CAS No.

[0051] 97134-11-7), 9,10,13-trihydroxy-(E)-11-octadecenoic acid (CAS No. 29907-57-1), (10E,15Z)-9, 12, 13 -trihydroxy- 10, 15 -octadecadienoic acid (CAS No. 185147-97-1) and (15Z)-9,12,13-trihydroxy- 15 -octadecenoic acid (CAS No. 2894104-80-2) were also each isolated, and respective structures were elucidated by analyzing high resolution LCMS, UV absorbance and proton and carbon NMR spectra.

[0052] The flavor profiles of the samples were characterized through sensory evaluation. Perception of sweetness and sweet mouthfeel were also expressed using a sweetness intensity scale of 0 to 8, where 0 = no perception of sweetness, 4 = moderate perception of sweetness, 6.5 = strong perception of sweetness and 8 = extreme strong perception of sweetness.IFF-10178-WO-PCT[2] Specification Example II: Sucrose Sweetness Modulation

[0053] (95, 10E, 12E, 14E)-9-Hydroxy- 16-oxo- 10,12, 14-octadecatrienoic acid, 9, 16-dioxo-10, 12,14-octadecatrienoic acid, pinellic acid, 9.10. l3-trihydroxy-(A)-l l-octadcccnoic acid, (10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid and (15Z)-9,12,13-trihydroxy-15-octadecenoic acid displayed no innate taste or odor at concentrations of 0.01 and 1 ppm in water.

[0054] A sucrose solution (6%) was prepared in water and used as the base control. (9S,10E,12E,14E)-9-Hydroxy-16-oxo-10,12,14-octadecatrienoic acid, 9, 16-dioxo-10, 12,14-octadecatrienoic acid, pinellic acid and 9, 10, 13-trihydroxy-(E)-l 1 -octadecenoic acid mixture (with a weight ratio of 4:1), (10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid and (15Z)-9, 12, 13 -trihydroxy- 15 -octadecenoic acid were each evaluated in the base control at respective concentrations. The flavor profile of the sucrose solution with added octadecanoic acid derivatives is reported in the following:

[0055] Concentration

[0056] Compound Flavor Profile

[0057] (PPm)

[0058] None (Base Control) N / A Slightly sweet

[0059] (95,10E,12E,14E)-9- 0.1 Slightly increased sweet mouthfeel

[0060] Hydroxy- 16-oxo- 10, 12,14- octadecatrienoic acid Increased perception of sweetness with slight 0.3

[0061] caramel note, increased sweet mouthfeel Increased perception of sweetness with caramel 0.02

[0062] 9,16-Dioxo-10,12,14- note, increased sweet mouthfeel octadecatrienoic acid Clear perception of increased sweetness, clear 0.1

[0063] perception of increased and clean sweet mouthfeel Increased perception of sweetness, increased sweet Pinellic acid and 9,10,13- 0.2

[0064] mouthfeel

[0065] trihydroxy-( E)- 11- octadecenoic acid Increased perception of sweetness, slightly

[0066] 0.5

[0067] increased and clean sweet mouthfeel (10E,15Z)-9, 12,13- Increased perception of sweetness, upfront and T rihydroxy- 10,15- 1

[0068] lingering, clearly increased sweet mouthfeel ( 15Z)-9, 12, 13 -Trihydroxy- Increased perception of sweetness, upfront and

[0069] 1

[0070]

[0071] 15 -octadecenoic acid lingering, increased sweet mouthfeel

[0072] (9S,10E,12E,14E)-9-Hydroxy-16-oxo-10,12,14-octadecatrienoic acid, 9, 16-dioxo-10,12,14-octadecatrienoic acid, pinellic acid, 9, 10, 13-trihydroxy-(E)-l 1 -octadecenoic acid, (10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid and (15Z)-9,12,13-trihydroxy-15-octadecenoic acid each provided increased sweetness perception and sweet mouthfeel. 9,16-Dioxo-10,12,14-octadecatrienoic acid exhibited superior effect at low levels of 0.02 and 0.1 ppm.IFF-10178-WO-PCT[2] Specification Example III: Additional Sucrose Sweetness Modulation

[0073] Additional sucrose sweetness modulation with (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid is reported in the following:

[0074] Concentration Sweetness Compound Flavor Profile

[0075] (PPm) Intensity None

[0076] N / A Slightly sweet 0 (Base Control)

[0077] 0.005 Slightly sweeter 1 0.01 Some sweeter 3 (9S,10E,12E,14E)

[0078] -9-Hydroxy-16- 0.05 Sharp sweet, sugary mouthfeel 4 oxo-10, 12,14- 0.1 Sharp sweet, honey-like, sugary mouthfeel 5 octadecatrienoic

[0079] Acid 1 Sharp sweet, honey-like, sugary mouthfeel 6 Sharp sweet, some aroma, slightly

[0080] 5 7 astringency

[0081] 0.05 Slightly sweeter 2 0.1 Sweeter 4 Pinellic Acid 0.5 Upfront sweet, sugary mouthfeel 5

[0082] 1 Upfront sweet, more body, sugary mouthfeel 6 5 Upfront sweet, more body, some astringency 7

[0083]

[0084] The addition of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid resulted in enhanced sweetness perception and sweet mouthfeel when used with sucrose.IFF-10178-WO-PCT[2] Specification Example IV: Reb A Sweetness Modulation

[0085] A Reb A base solution (200 ppm) was prepared in water. The flavor profile of the Reb A solution with added (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid is reported in the following:

[0086] Concentration Sweetness Compound Flavor Profile

[0087] (PPm) Intensity None

[0088] N / A Slightly sweet 0 (Base Control)

[0089] 0.005 Slightly sweeter 1 0.01 Some sweeter 3 Some sweeter, sugary mouthfeel, slightly (9S,10E,12E,14E) 0.05 4 less lingering off-note

[0090] -9-Hydroxy-16- oxo-10, 12,14- Sharp sweet, honey-like, sugary mouthfeel,

[0091] 0.1 5 octadecatrienoic less lingering off-note

[0092] Acid

[0093] Sharp sweet, honey-like, sugary mouthfeel,

[0094] 1 6 less lingering off-note

[0095] Sharp sweet, honey-like, sugary mouthfeel,

[0096] 5 7 less lingering off-note, some astringency

[0097] 0.05 Slightly sweeter 2 0.1 Some sweeter, slightly less lingering off- 4 note

[0098] Upfront sweet, sugary mouthfeel, less

[0099] 0.5 5 Pinellic Acid lingering, less off-note

[0100] Upfront sweet, more body, sugary

[0101] 1 6 mouthfeel, less lingering off-note

[0102] Upfront sweet, more body, sugary

[0103] 5 mouthfeel, less lingering off-note, some 7

[0104]

[0105] The addition of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid resulted in enhanced sweetness perception and sweet mouthfeel when used with Reb A.IFF-10178-WO-PCT[2] Specification Example V: Luo Han Guo Sweetness Modulation

[0106] A Luo Han Guo base solution (60 ppm) was prepared in water. The flavor profile of the Luo Han Guo solution with added (9S,10E,12E,14E)-9-hydroxy- 16-oxo- 10,12, 14-octadecatrienoic acid and pinellic acid is reported in the following:

[0107] Concentration Sweetness Compound Flavor Profile

[0108] (PPm) Intensity None

[0109] N / A Slightly sweet 0 (Base Control)

[0110] 0.01 Some sweeter 2 (95,10E,12E,14E) 0.05 Sweeter, sugary mouthfeel 4 -9-Hydroxy-16- oxo-10, 12,14- Sharp sweet, sugary mouthfeel, less

[0111] 0.1 6 octadecatrienoic lingering off-note

[0112] Acid

[0113] Sharp sweet, honey mouthfeel, less lingering

[0114] 1 7 off-note

[0115] 0.05 Slightly sweeter 2 0.1

[0116] Pinellic Ac Some sweeter, less off-taste 4 id

[0117] Upfront sweeter and sugary mouthfeel,

[0118] 1 6 lingering off-note

[0119]

[0120] The addition of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid resulted in enhanced sweetness perception and sweet mouthfeel when used with Luo Han Guo.IFF-10178-WO-PCT[2] Specification Example VI: Sucralose Sweetness Modulation

[0121] A sucralose base solution (100 ppm) was prepared in water. The flavor profile of the sucralose solution with added (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid is reported in the following:

[0122] Concentration Sweetness Compound Flavor Profile

[0123] (PPm) Intensity None

[0124] N / A Slightly sweet 0 (Base Control)

[0125] 0.01 Some sweeter 2 (9S,10E,12E,14E) 0.05 Some sweeter, sugary mouthfeel 4 -9-Hydroxy-16- oxo-10, 12,14- Sharp sweet, enhanced mouthfeel, less

[0126] 0.1 6 octadecatrienoic lingering off-notes

[0127] Acid

[0128] Sharp sweet, honey-like mouthfeel, less

[0129] 1 7 lingering off-notes

[0130] 0.05 Slightly sweeter 2 Pinellic Acid 0.1 Some sweeter, less lingering off-notes 4 Upfront sweet, sugary mouthfeel, less

[0131] 1 6 lingering off-notes

[0132]

[0133] The addition of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid resulted in enhanced sweetness perception and sweet mouthfeel when used with sucralose.IFF-10178-WO-PCT[2] Specification Example VII: Aspartame Sweetness Modulation

[0134] An aspartame base solution (500 ppm) was prepared in water. The flavor profile of the aspartame solution with added (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid is reported in the following:

[0135] Concentration Sweetness Compound Flavor Profile

[0136] (PPm) Intensity None

[0137] N / A Slightly sweet 0 (Base Control)

[0138] 0.01 Slightly sweeter 2 (9S,10E,12E,14E) 0.05 Some sweeter 4 -9-Hydroxy-16- oxo-10, 12,14- Sharp sweet, enhanced mouthfeel, ess

[0139] 0.1 6 octadecatrienoic lingering off-notes

[0140] Acid

[0141] Sharp sweet, honey-like mouthfeel, ess

[0142] 1 7 lingering off-notes

[0143] 0.05 Slightly sweeter 2 Pinellic Acid 0.1 Some sweeter, less lingering off-notes 4 Upfront sweet, sugary mouthfeel, less

[0144] 1 6 lingering off-notes

[0145]

[0146] The addition of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid resulted in enhanced sweetness perception and sweet mouthfeel when used with aspartame.IFF-10178-WO-PCT[2] Specification Example VIII: Octadecanoic Acid Derivative Mixtures for Sweetness Modulation

[0147] The sweetness modulation effect of (9. S'. I0L. I2L. l4A')-9-hydroxy-l6-oxo-IO.12,14-octadecatrienoic acid and pinellic acid mixtures, provided as a Sterculia monosperma leaf extract, was also examined. Water solutions of the Sterculia monosperma leaf extract were prepared, comprising a mixture of (95, I0A'.12E, 14 / ’.')-9-hydroxy- 16-oxo- 10.12, 14-octadecatrienoic acid (0.005%) and pinellic acid (0.01%) having a weight ratio of 1:2 (“Mixture”). Sweetener base solutions were prepared as described in Examples II and IV. The respective flavor profile of the sucrose and Reb A solutions with added mixture is reported in the following:

[0148] Sweetener Mixture (ppm) Flavor Profile

[0149] 10 Not sweet

[0150] 100 Not sweet, slight fruity aroma

[0151] None

[0152] (Water Solutions) 500 Not sweet, slight fruity aroma, faint leafy off-not Not sweet, fruity aroma, slight mouthfeel with vegetal 1000

[0153] off-notes

[0154] Sucrose N / A Slightly sweet

[0155] (Base Control)

[0156] 1 Very slightly sweeter

[0157] Slightly sweeter, natural fruit juice-like, slight sugary 10

[0158] mouthfeel

[0159] 50 Sweeter, honey -like mouthfeel

[0160] Sucrose

[0161] 100 Lasting and enhanced sweetness, sugary mouthfeel Upfront sweet, fruity sweetness, pleasant sugary, 200

[0162] honey mouthfeel

[0163] 1000 Upfront sweet, fruity, slightly astringent

[0164] Reb A N / A Slightly sweet

[0165] (Base Control)

[0166] 1 Very slightly sweeter

[0167] 10 Slightly sweeter, slight sugary mouthfeel

[0168] 50 Sweeter, honey-like mouthfeel, less lingering off-notes Reb A Upfront sweet, sugary mouthfeel, less lingering off- 100

[0169] notes

[0170] Upfront sweet, sugary mouthfeel, less lingering off- 200

[0171] notes

[0172] 1000 Upfront sweeter, fruity, slightly astringent

[0173]

[0174] IFF-10178-WO-PCT[2] Specification The addition of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid and pinellic acid mixtures, provided as a Sterculia monosperma leaf extract, resulted in a synergistic enhancement of sweetness perception and sweet mouthfeel when the extract was applied at concentrations of 10 ppm or greater in sucrose and Reb A, respectively.

Claims

IFF-10178-WO-PCT[2] Specification WHAT IS CLAIMED IS:

1. A method of modulating the perception of sweetness of a flavor modifier comprising the step of adding to the flavor modifier an olfactory effective amount of an octadecanoic acid derivative, wherein the octadecanoic acid derivative has two or more substituents independently selected from the group consisting of a hydroxy group and a ketone group; and wherein the octadecanoic acid derivative contains one or more carbon-carbon double bonds.

2. The method of claim 1, wherein the flavor modifier is a sweetener.

3. The method of claim 2, wherein the sweetener is a natural sweetener selected from the group consisting of sucrose, fructose, glucose, high fructose com syrup, rebaudioside A, stevioside, rebaudioside D, rebaudioside M, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof.

4. The method of claim 2, wherein the sweetener is an artificial sweetener selected from the group consisting of aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.

5. The method of claim 1, wherein the flavor modifier is a flavor modulator selected from the group consisting of stevioside, steviolbioside rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, dulcoside A, dulcoside B, rubusoside, alpha-glucosyl stevia, fructosyl stevia, galactosyl stevia, beta-glucosyl stevia, siamenoside, mogrosidc IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, a salt thereof, a glycosylated derivative thereof and a combination thereof.

6. The method of claim 1, wherein the olfactory effective amount is from about 1 ppb to about 1000 ppm by weight.

7. The method of claim 1, wherein the octadecanoic acid derivative has two or three substituents independently selected from the group consisting of a hydroxy group and a ketone group, and wherein the octadecanoic acid derivative contains one to three carboncarbon double bonds.IFF-10178-WO-PCT[2] Specification 8. The method of claim 1, wherein the octadecanoic acid derivative is selected from the group consisting of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid; 9,16- dioxo-10,12,14-octadecatrienoic acid; pinellic acid; 9,10,13-trihydroxy-(E)-ll- octadecenoic acid; (10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid; (15Z)- 9, 12, 13 -trihydroxy- 15 -octadecenoic acid; and a mixture thereof.

9. The method of claim 8, wherein the octadecanoic acid derivative is provided as a Sterculia monospermci leaf extract.

10. A composition comprising a flavor modifier and an olfactory effective amount of an octadecanoic acid derivative, wherein the octadecanoic acid derivative has two or more substituents independently selected from the group consisting of a hydroxy group and a ketone group; and wherein the octadecanoic acid derivative contains one or more carboncarbon double bonds.

11. The composition of claim 10, wherein the flavor modifier is a sweetener.

12. The composition of claim 11, wherein the sweetener is a natural sweetener selected from the group consisting of sucrose, fructose, glucose, high fructose com syrup, rebaudioside A, stevioside, rebaudioside D, rebaudioside M, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof.

13. The composition of claim 11, wherein the sweetener is an artificial sweetener selected from the group consisting of aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.IFF-10178-WO-PCT[2] Specification 14. The composition of claim 10, wherein the flavor modifier is a flavor modulator selected from the group consisting of stevioside, steviolbioside rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, dulcoside A, dulcoside B, rubusoside, alpha-glucosyl stevia, fructosyl stevia, galactosyl stevia, beta-glucosyl stevia, siamenoside, mogrosidc IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, a salt thereof, a glycosylated derivative thereof and a combination thereof..

15. The composition of claim 10, wherein the olfactory effective amount is from about 10 ppb to about 100 ppm by weight.

16. The composition of claim 10, wherein the octadecanoic acid derivative has two or three substituents independently selected from the group consisting of a hydroxy group and a ketone group, and wherein the octadecanoic acid derivative contains one to three carboncarbon double bonds.

17. The composition of claim 10, wherein the octadecanoic acid derivative is selected from the group consisting of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid; 9,16-dioxo-10,12,14-octadecatrienoic acid; pinellic acid; 9,10,13-trihydroxy-(E)-11-octadecenoic acid; (10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid; (15Z)-9,12,13-trihydroxy-15-octadecenoic acid; and a mixture thereof.

18. The composition of claim 10, wherein the octadecanoic acid derivative is provided as a Sterculia monospermci leaf extract.

19. A consumable comprising a flavor modifier and an olfactory effective amount of an octadecanoic acid derivative, wherein the octadecanoic acid derivative is selected from the group consisting of (9S,10E,12E,14E)-9-hydroxy-16-oxo-10,12,14-octadecatrienoic acid; 9,16-dioxo-10,12,14-octadecatrienoic acid; pinellic acid; 9,10,13-trihydroxy-(E)-ll- octadecenoic acid; (10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid; (15Z)- 9, 12, 13 -trihydroxy- 15 -octadecenoic acid; and a mixture thereof.

20. The consumable of claim 19, wherein the octadecanoic acid derivative is provided as a Sterculia monosperma leaf extract.

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