New Cooling Related Compounds




       John C. Leffingwell




    Society of Flavor Chemist’s
          November 20, 20...
World Production of Menthol




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




Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press
Thermo TRP Receptors & Agonists

Table 4 Thermoreceptor Agonists
Chemical agonist (botanical source)                      ...
Menthoxy Cooling Agents Thru GRAS 23
                                                               O
                    ...
More Menthoxy Cooling Agents Thru GRAS 23
               O                                                     O        O
...
Amide GRAS Cooling Agents Thru GRAS 23



              H
              N

          O                           O       N...
Givaudan’s New Powerful GRAS Cooling Agents




Furrer et al., Chem. Percept. (June 2008) 1:119–126; Galopin et al., US Pa...
New GRAS 24 Related Cooling Agents

                              O

                          N
                         ...
Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press
Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press
Relative Cooling & Bitterness in 5% sucrose




 Johnson SS, Stawski BZ, Sheldon GT. Confections Containing a Blend of
 Ph...
Adapted from Johnson SS, Stawski BZ, Sheldon GT. Confections
Containing a Blend of Physiological Cooling Agents. U.S. Pate...
Other Potential Cooling Agents




Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press;
...
Other Potential Cooling Agents

                       OH
                                                 H
             ...
Other Potential Cooling Agents


                  O
              H                        H
              N             ...
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New Cooling Compounds

  1. 1. New Cooling Related Compounds John C. Leffingwell Society of Flavor Chemist’s November 20, 2008 Revised Jan. 20, 2009
  2. 2. World Production of Menthol Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press
  3. 3. World Uses of Menthol Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press
  4. 4. Thermo TRP Receptors & Agonists Table 4 Thermoreceptor Agonists Chemical agonist (botanical source) ThermoTRP Capsaicin (hot chilli peppers, e.g., Tabasco) TRPV1 Piperine (black pepper corns) TRPV1 Allicin (fresh garlic) TRPV1, TRPA1 Camphor (Cinnamomum camphora) TRPV3, TRPV1 D-9-Tetrahydrocannabinol (Cannabis sativa) TRPV2, TRPA1 2-Aminoethoxydiphenyl borate (synthetic) TRPV1, TRPV2, TRPV3 4-a-phorbol 12,13-didecanoate (synthetic) TRPV4 (-)-Menthol (peppermint) TRMP8, TRPV3 1,8-Cineole, eucalyptol (eucalyptus) TRPM8 WS-3 (synthetic) TRPM8 Icilin (synthetic) TRPM8, TRPA1 Cinnamaldehyde (cinnamon, cassia) TRPA1, TRPV3 Allyl isothiocyanate (mustard, horseradish) TRPA1 Benzyl isothiocyanate (mustard, horseradish) TRPA1 Phenethyl isothiocyanate (mustard, horseradish) TRPA1 Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press
  5. 5. Menthoxy Cooling Agents Thru GRAS 23 O O OH O OH O O OH OH OH (-)- Isopulegol Coolact-10 Frescolat ML Frescolat MGA FEMA 2962 FEMA 3784 FEMA 3748 FEMA 3807 0.25 X Menthol 0.2-0.4 X Menthol 0.43 X Menthol 0.41 X Menthol O OH + OH OH O O OH HO HO HO Coolact 38D MHB MMPD FEMA 4053 FEMA 4308 FEMA 3849 0.11 X Menthol ~0.45 X Menthol OH O O O O O Coolact 5 Menthone lactic acid ketal Menthyl methyl ether FEMA 4154 FEMA 4285 FEMA 4054
  6. 6. More Menthoxy Cooling Agents Thru GRAS 23 O O O OH O O OH O Monomenthyl succinate Monomenthyl glutarate FEMA 3810 FEMA 4006 ~0.2-0.3 X Menthol ~0.1-0.15 Menthol O H N O O Questice FEMA 4155 O R1 O R2 OH O O O O Menthol propylene glycol carbonate Menthol ethylene glycol carbonate FEMA 3806 Frescolat MGC Isomer 1 – R1=OH, R2=CH3 FEMA 3805 Isomer 1 – R1=CH3, R2=OH
  7. 7. Amide GRAS Cooling Agents Thru GRAS 23 H N O O N H WS-3 WS-23 FEMA 3455 FEMA 3804 1.5 X Menthol 0.75 X Menthol O H N CO2Et N O O O WS-5 FEMA 4309 Menthyl N,N-dimethylsuccinamide 4 X Menthol FEMA 4230
  8. 8. Givaudan’s New Powerful GRAS Cooling Agents Furrer et al., Chem. Percept. (June 2008) 1:119–126; Galopin et al., US Patent 7,414,152 (August 19, 2008); Bell et al., WO2007019719 (Feb. 22, 2007) H H N N O CN O N 2j = FEMA 4496 2k = FEMA 4549 10 X Menthol 40-100 X Menthol
  9. 9. New GRAS 24 Related Cooling Agents O N H O N H Menthyl N-Ethyl-2,2-diisopropyl- cyclopropanecarboxamide butanamide FEMA 4558 FEMA 4557 Not Cooling – Umami-like U.S. Patent Application 20080292763 H H N N OH O N O CN N-(2-(Pyridin-2-yl)ethyl)-3-p- N-p-Benzeneacetonitrile- Cubebol menthanecarboxamide menthanecarboxamide FEMA 4497 FEMA 4549 FEMA 4496 40-100 X Menthol 10 X Menthol
  10. 10. Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press
  11. 11. Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press
  12. 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 20070248717, 2007, Oct. 25. (Wrigley)
  13. 13. Adapted from Johnson SS, Stawski BZ, Sheldon GT. Confections Containing a Blend of Physiological Cooling Agents. U.S. Patent Application 20070248717, 2007, Oct. 25. (Wrigley)
  14. 14. Other Potential Cooling Agents Leffingwell, Handbook of Cosmetic Science and Technology, 3d edition (2009), In Press; From WO 2006103401 (2006) & US20070155755 (2007)
  15. 15. Other Potential Cooling Agents OH H O OH N O OH O O O WS-30 WS-14 WS-4 0.2-0.25 X Menthol 0.75 X Menthol 0.16-0.33 X Menthol O O O NH HN HN C2H5O O NC O ~2.2 X Menthol ~10 X Menthol ~0.75 X Menthol WO 2006/099762 (2006) WO 2006/099762 (2006) US Patent 7030273 (2007)
  16. 16. Other Potential Cooling Agents O H H N N O O O O Hase-1 N-benzo[1,3]dioxol-5-yl- Cooling, No bitterness 3-p-menthanecarboxamide JP2004059474 (2004) ~100 X Menthol WO 2006/092074 (2006)

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