USE OF EVODONE OR A DERIVATIVE THEREOF AS A COOLING AGENT

Abstract

Use as a cooling agent of a compound of general formula (I)

##STR00001##

in which: R.sup.1 and R.sup.2 are chosen independently of each other as a hydrogen atom or a C.sub.1-C.sub.6-alkyl group; and X represents ═O, —OAc, —O—C.sub.1-C.sub.6-alkyl, —N—OH or —OH.

Claims

1. A method comprising applying a cooling agent, of a compound of general formula (I) ##STR00003## in which: R.sup.1 and R.sup.2 are chosen independently of each other as a hydrogen atom or a C.sub.1-C.sub.6-alkyl group; and X represents ═O, —OAc, —O—C.sub.1-C.sub.6-alkyl, —N—OH or —OH.

2. The method comprising applying a cooling agent of a compound of general formula (I) according to claim 1, wherein R.sup.1 and R.sup.2 are chosen independently of each other as being a hydrogen atom or a —CH.sub.3, —C.sub.2H.sub.5 or —(CH.sub.2).sub.2CH.sub.3 group.

3. The method comprising applying a cooling agent of a compound of general formula (I) according to claim 1, wherein R.sup.1 and R.sup.2 are identical and are chosen as being a hydrogen atom.

4. The method comprising applying a cooling agent of a compound of general formula (I) according to claim 1, wherein X represents ═O, —OAc or —OH.

5. The method comprising applying a cooling agent of a compound of general formula (I) according to claim 4, wherein X represents ═O.

6. The method comprising applying a cooling agent of a compound of general formula (I) according to claim 1, wherein the compound of general formula (I) is evodone.

Description

EXAMPLE 1

Cream Containing Evodone

[0041] Creams (water-in-oil emulsion) containing respectively: [0042] 1% of evodone—cream 1; [0043] 1% of Frescolat ML (i.e. menthyl lactate)—cream 2; [0044] 1% of Eucalydiol (i.e. citriodiol)—cream 3; [0045] 1% of CO.sub.2 extract of cucebe (30% cubelol)—cream 4;
are prepared.

[0046] To measure the cooling effect, 100 mg of one of the creams 1 to 4 or of a placebo are applied onto the inner side of both forearms of persons who have agreed to test the product. After one minute, each participant is asked to rate the cooling effect on a scale of 0 to 3 (i.e. score), with 3 being the maximum effect.

[0047] Each cream (including the placebo) is applied randomly and blindly to the forearms of 17 people.

[0048] The obtained results are reported in Table 1 below.

TABLE-US-00001 TABLE 1 Cooling power of the creams 1 to 4 Tested Cooling power (obtained cream by adding the scores) Cream 1 30 Cream 2 25 Cream 3 15 (p < 0.05) Cream 4 30

[0049] It should be noted that evodone has a cooling effect similar to that which can be provided by molecules such as citriodiol or cubebol found in the CO2 extract of cubebe pepper. In addition, the cooling effect is significantly greater than that obtained with menthyl lactate (i.e. Frescolat ML—commercial reference).

EXAMPLE 2

Cream Containinci Evodone

2.1—Experimental Protocol

[0050] For this study, the cooling effect of 5 compositions containing different cooling agents is evaluated in vivo according to the following protocol.

[0051] 22 female subjects aged from 18 to 63 were selected. On the back of each subject, between the two scapulas, six areas of 3 cm×2.5 cm are delimited. On 5 areas chosen each time randomly, 15 mg of the compositions to be tested are applied. Nothing is applied onto the sixth area (i.e. control).

[0052] From the time of application of the creams (T0), the skin temperature of the different zones is measured on each subject using a thermal camera (Thermovision SC6000HS (Flirsystems)—resolution 640×512—frequency 125 Hz) at the following times: T0, T0+15 s, T0+30 s, T0+45 s, T0+1 min, T0+1 min30 s, T0+2 min, T0+3 min, T0+4 min, T0+5 min, T0+6 min, T0+8 min and T0+10 min. The measurements are performed at 21° C.±1.5° C., the subject lying on his stomach and motionless. The temperatures are measured with an accuracy of around 0.10° C.

[0053] A variance test (ANOVA) is used to compile and validate the results. The normality of the ANOVA residues is verified by the Shapiro-Wilk test with a significance level set at 1%, and the homogeneity of the variances on the residues is verified by a Levene test at 5%.

[0054] If these two conditions are met, the statistical analysis allowing comparing the parameters measured at the different times is conducted by a one-factor variance analysis (ANOVA) test on repeated measurements. The significance level is set at 5%.

[0055] If one of the two conditions is not met, the statistical analysis is performed by an ANOVA on the data transformed into ranks, at a threshold of 5%.

[0056] If there is a significant difference in ANOVA, a 5% Dunnett test is performed to compare all kinetic times to T0.

2.2—Used Compositions

[0057] The creams 1 to 4 described in example 1 were tested. In addition, cream 5 containing 33.3% of evodone/33.3% of eucalydiol/33.3% of cubeb extract (30% cubebol) has also been tested.

2.3—Experimental Results

[0058] The obtained experimental results are reported in Table 2 below.

TABLE-US-00002 TABLE 2 Cooling power of the creams 1 to 5 Applied cream Cream Cream Cream Cream Cream — 1 2 3 4 5 Time T Temperature deviation (in ° C.) T0 −0.1 −1.0 −1.1 −1.2 −0.9 −1.2 T0 + 15 s −0.1 −1.1 −1.3 −1.2 −1.0 −1.2 T0 + 30 s −0.2 −1.3 −1.4 −1.4 −1.2 −1.4 T0 + 45 s −0.1 −1.5 −1.6 −1.5 −1.3 −1.5 T0 + 1 min −0.2 −1.6 −1.7 −1.6 −1.4 −1.6 T0 + 1 min30 s −0.2 −1.7 −1.8 −1.7 −1.5 −1.7 T0 + 2 min −0.2 −1.7 −1.8 −1.7 −1.5 −1.7 T0 + 3 min −0.2 −1.4 −1.6 −1.5 −1.3 −1.5 T0 + 4 min −0.3 −1.2 −1.3 −1.3 −1.1 −1.2 T0 + 5 min −0.3 −1.0 −1.1 −1.1 −0.9 −1.0 T0 + 6 min −0.3 −0.9 −1.0 −1.0 −0.8 −0.9 T0 + 8 min −0.4 −0.7 −0.8 −0.8 −0.6 −0.8 T0 + 10 min −0.4 −0.7 −0.8 −0.8 −0.6 −0.7

2.4—Conclusion

[0059] It should be noted that evodone has a cooling effect similar to that which can be provided by molecules such as menthyl lactate (i.e. Frescolat ML—commercial reference), citriodiol or cubebol found in the CO.sub.2 extract of cubebe pepper.