Takasago Sensates. Products that impart a SENSATION when applied topically

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Emmeline Bell
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1 Sensates

2 Takasago Sensates Products that impart a SENSATION when applied topically Applica ons: cosme cs and personal care Sensate types: Cooling, warming, numbing

3 Mechanism of Temperature Sensa on Temperature sensa on is dependent on thermosensi ve neurons present in the epidermis and dermis. The signal transduc on is triggered by the flow of ions (mainly Ca +2 ) across temperature- ac vated transient receptor poten al (TRP) ion channels. Different TRPs have been iden fied that respond to different temperature ranges. Some TRPs are also responsive to small molecules such as menthol and capsaicin, leading to a percep on of temperature change. A. Patapou an, et. al.., Nature Reviews:Neuroscience 4, (2003) S.- E. Jordt, et. al., Current Opinion in Neurobiology, 13, (2003)

4 Mechanism of Temperature Sensa on A. Patapou an, et. al.., Nature Reviews:Neuroscience 4, (2003)

5 Mechanism of Temperature Sensa on A. Patapou an, et. al.., Nature Reviews:Neuroscience 4, (2003)

6 Cooling Agents l- Menthol Drawbacks: Strong Odor Short Dura on of Ac vity Irrita ng There is a need for be er cooling agents

7 Stereoisomers of Menthol l- menthol d- isomenthol d- neomenthol d- neoisomenthol d- menthol l- isomenthol l- neomenthol l- neoisomenthol

8 Stereoisomers of Menthol l- menthol d- isomenthol d- neomenthol d- neoisomenthol Threshold (ppm) Cooling >25 d- menthol l- isomenthol l- neomenthol l- neoisomenthol Threshold (ppm) Cooling

9 Asymmetric Catalysis (BINAP) World leader in asymmetric catalysis technology and commercial- scale produc on Series of asymmetric aroma chemicals with special quali es, including lower odor threshold, increased substan vity, and cooling and warming sensa ons

10 Receptor Ac vity of Menthol Menthol s mulates entry of Ca 2+ and increases intracellular Ca 2+ concentra on in cold- sensi ve neurons S mula on of cold receptors by menthol can be explained by sensi za on of the cold- induced inward Ca 2+ current. Reid, G. & Flonta, M.- L. Neurosci. Le. 297, (2001).

11 Takasago Cooling Materials via l- Menthol Technology l- Menthol Coolact 10 Coolact P Coolact 38D

12 Coolact P Coolact P is highly refined l- Isopulegol. It has a clean, fresh herbaceous note and a cooling profile that is similar to, but less intense than l- Menthol. Coolact P is an intermediate of the menthol process and Takasago is the only company that can manufacture it on industrial scale.

13 Coolact P Strong Intensity Menthol Coolact P Weak Time (min) Comparison of the Cooling Profiles of Coolact P and l- Menthol

14 Coolact 38D Coolact 38D (Menthanediol) is a cooling agent with a profile similar to that of menthol. It has a slight odor and is highly stable. It is also an excellent skin penetra on enhancer, and thus is useful in combina on with other sensates to increase their efficacy.

15 Coolact 10 Coolact 10 (Menthoxypropanediol), is a patented Takasago specialty. It imparts an excellent cooling sensa on with good tenacity and li le or no odor. Coolact 10 is extremely stable and suitable for use in a variety of applica ons. Its resistance to decomposi on means that it can be incorporated into a variety of formula ons without concern for loss of ac vity during processing and storage.

16 Coolact 10 Strong Intensity Menthol Coolact 10 Weak Time (min) Comparison of the Cooling Profiles of Coolact 10 and l- Menthol

17 Rela ve Sensi vity to Cooling Lips>Trigeminal Area>Other Face Areas>Armpits>Inside Forearm, Breast>Other Arm Areas, Thigh, Back>Hands, Feet>>Palm, Soles H.R.Watson, et. al., J. Soc. Cosmet. Chem., 29, (1978)

18 Coolact 10 (%) 80 % Repor ng Effect moderate strong Time, minutes, a er applica on Intensity and Dura on of Cooling Sensa on of Coolact 10

19 Cooling Profiles of Sensates 5 Cooling Intensity l-menthol Coolact 10 Coolact P Coolact 38D Time (min)

20 Compe ve Cooling Agents Menthyl PCA Menthone Glycerin Acetal Menthyl Lactate These materials are unstable and prone to hydrolysis, releasing menthol. The Coolact products are stable and do not generate menthol.

21 Warming Sensate

22 Capsaicin and Other Natural Warming Materials Capsaicin Piperine Gingerol

23 Takasago s Warming Agent Hotact VBE A vanillyl alcohol deriva ve having a warming effect similar to capsaicin or capsicum extract but generally producing less irrita on.

24 Evalua on of Vanillyl Alkyl Ethers Sensate Intensity Methyl Ethyl n-propyl Allyl n-butyl The n- butyl ether analog is the most intense of the series Amyl i-amyl cyclohexyl n-hexyl

25 Hotact VBE Hotact VBE is a vanillyl alcohol deriva ve. The Guaiacol (o- methoxyphenol) substructure is believed to be essen al to the ac vity, similar to compounds like Capsaicin (Chili) or Gingerone (Ginger) which also have a pungent effect. Hotact VBE was developed by Takasago as an alterna ve ingredient to Capsicum extract. It imparts a warming effect on skin.

26 Hotact VBE Concentra on Effec ve in Impar ng a Warming Sensa on on Skin Capsaicin 0.02% Capsicum Extract 0.4% Hotact VBE 0.2%

27 Hotact VBE Advantages of Hotact VBE over Capsicum Extract Colorless Odorless Consistent 100% Ac ve

28 Combina ons of Sensate Effects

29 Combina ons of Sensates Cooling materials with different cooling effects can be combined to produce a wide range of sensory proper es and profiles Warming materials with different hea ng effects can also be combined to produce a wide range of sensory profiles Synergis c combina ons of cooling and warming materials can also be used to produce significant enhancements of these sensory proper es, intensi es and profiles

30 Enhancement of Cooling Effects Combina on of a cooling agent: l- Menthol Coolact P Coolact 10 And Hotact VBE Enhances the cooling effect Cool Feeling Composi on US6,328,982; EP

31 Enhancement of Cooling Effects 3.00 Cooling Assessment :10 l- menthol : Hotact VBE 50:1 l- menthol : Hotact VBE only l- menthol Time (min) l- Menthol and Hotact VBE

32 Enhancement of Cooling Effects 3.00 Cooling Assessment :10 Coolact 10 : Hotact VBE 200:1 Coolact 10 : Hotact VBE only Coolact Coolact 10 and Hotact VBE Time (min)

33 Product Applica ons of Sensates Lipstick/lip gloss Skin creams/lotions Sunscreens After-sun products Body washes Shampoos Condi oners Shave creams AP/DEO

34 Commercial Products Containing Sensates

35 Commercial Products Containing Sensates

36 Formula ng Guidelines Solubility All Takasago Sensates are of moderate polarity and are soluble in the great majority of solvents Soluble in Esters Low MW alcohols Ketones Glycols Insoluble in Water Hydrocarbons

37 Formula ng Guidelines Stability Stable at ph 3-10 Stable up to ~85 C during processing Hotact VBE suscep ble to UV Light

38 Formula ng Guidelines Efficacy Best efficacy when in water phase of emulsion. Use polysorbates to disperse into water phase. Do not use carbohydrate thickeners gums, starches, etc. The intensity and dura on of effects on intact skin depend on a number of factors Subject sensi vity Site of applica on Product form Speed of skin penetra on Polarity of product Concentra on of ac ve Mixtures of ac ves

39 Sensates Takasago Sensates Available Exclusively from Lipo Chemicals Coolact 10 Coolact P Coolact 38D Hotact VBE

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

New Cooling Compounds. John C. Leffingwell Society of Flavor Chemist s November 20, 2008 ew Cooling Compounds John C. Leffingwell Society of Flavor Chemist s ovember 20, 2008 World Production of Menthol Leffingwell, andbook of Cosmetic Science and Technology, 3d edition (2009), In Press World