New Cooling Compounds. John C. Leffingwell Society of Flavor Chemist s November 20, 2008

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1 ew Cooling Compounds John C. Leffingwell Society of Flavor Chemist s ovember 20, 2008

2 World Production of Menthol Leffingwell, andbook of Cosmetic Science and Technology, 3d edition (2009), In Press

3 World Uses of Menthol Leffingwell, andbook of Cosmetic Science and Technology, 3d edition (2009), In Press

4 Thermo TRP Receptors & Agonists Table 4 Thermoreceptor Agonists Chemical agonist (botanical source) Capsaicin (hot chilli peppers, e.g., Tabasco) Piperine (black pepper corns) Allicin (fresh garlic) Camphor (Cinnamomum camphora) D-9-Tetrahydrocannabinol (Cannabis sativa) 2-Aminoethoxydiphenyl borate (synthetic) 4-a-phorbol 12,13-didecanoate (synthetic) (-)-Menthol (peppermint) 1,8-Cineole, eucalyptol (eucalyptus) WS-3 (synthetic) Icilin (synthetic) Cinnamaldehyde (cinnamon, cassia) Allyl isothiocyanate (mustard, horseradish) Benzyl isothiocyanate (mustard, horseradish) Phenethyl isothiocyanate (mustard, horseradish) ThermoTRP TRPV1 TRPV1 TRPV1, TRPA1 TRPV3, TRPV1 TRPV2, TRPA1 TRPV1, TRPV2, TRPV3 TRPV4 TRMP8, TRPV3 TRPM8 TRPM8 TRPM8, TRPA1 TRPA1, TRPV3 TRPA1 TRPA1 TRPA1 Leffingwell, andbook of Cosmetic Science and Technology, 3d edition (2009), In Press

5 Menthoxy Cooling Agents Thru GRAS 23 (-)- Isopulegol FEMA X Menthol Coolact-10 FEMA X Menthol Frescolat ML FEMA X Menthol Frescolat MGA FEMA X Menthol + Coolact 38D FEMA X Menthol MB FEMA 4308 ~0.45 X Menthol MMPD FEMA 3849 Coolact 5 FEMA 4154 Menthone lactic acid ketal FEMA 4285 Menthyl methyl ether FEMA 4054

6 More Menthoxy Cooling Agents Thru GRAS 23 Monomenthyl succinate FEMA 3810 ~ X Menthol Monomenthyl glutarate FEMA 4006 ~ Menthol Questice FEMA 4155 R 1 R 2 Menthol propylene glycol carbonate FEMA 3806 Isomer 1 R 1 =, R 2 =C 3 Isomer 1 R 1 =C 3, R 2 = Menthol ethylene glycol carbonate Frescolat MGC FEMA 3805

7 Amide GRAS Cooling Agents Thru GRAS 23 WS-3 FEMA X Menthol WS-23 FEMA X Menthol WS-5 FEMA X Menthol C 2 Et Menthyl,-dimethylsuccinamide FEMA 4230

8 Givaudan s ew Powerful GRAS Cooling Agents Furrer et al., Chem. Percept. (June 2008) 1: ; Galopin et al., US Patent 7,414,152 (August 19, 2008); Bell et al., W (Feb. 22, 2007) 2j = FEMA X Menthol C 2k = FEMA X Menthol

9 ew GRAS 24 Cooling Agents or Menthyl cyclopropanecarboxamide FEMA Ethyl-2,2-diisopropylbutanamide FEMA 4557 C -(2-(Pyridin-2-yl)ethyl)-3-pmenthanecarboxamide FEMA X Menthol -p-benzeneacetonitrilementhanecarboxamide FEMA X Menthol Cubebol FEMA 4497

10 Leffingwell, andbook of Cosmetic Science and Technology, 3d edition (2009), In Press

11 Leffingwell, andbook of Cosmetic Science and Technology, 3d edition (2009), In Press

12 Relative Cooling & Bitterness in 5% sucrose Johnson SS, Stawski BZ, Sheldon GT. Confections Containing a Blend of Physiological Cooling Agents. U.S. Patent Application , 2007, ct. 25. (Wrigley)

13 Adapted from Johnson SS, Stawski BZ, Sheldon GT. Confections Containing a Blend of Physiological Cooling Agents. U.S. Patent Application , 2007, ct. 25. (Wrigley)

14 ther Potential Cooling Agents Leffingwell, andbook of Cosmetic Science and Technology, 3d edition (2009), In Press; From W (2006) & US (2007)

15 ther Potential Cooling Agents WS X Menthol WS X Menthol WS X Menthol C C 2 5 ~2.2 X Menthol W 2006/ (2006) ~10 X Menthol W 2006/ (2006) ~0.75 X Menthol US Patent (2007)

16 ther Potential Cooling Agents ase-1 Cooling, o bitterness JP (2004) -benzo[1,3]dioxol-5-yl- 3-p-menthanecarboxamide ~100 X Menthol W 2006/ (2006)

Most people use cosmetics every day. For instance,

Most people use cosmetics every day. For instance, DERMATOLOGY FUMITAKA FUJITA Central Research Laboratories, Mandom Corp Osaka, Osaka 540-8530, Japan Transient receptor potential channels in sensory irritation TRP channels as tools for the predictive