Tyrosinase activity controlling agent, process for producing the same and external preparation containing the same
Disclosed is a tyrosinase activity controlling agent comprising, as an active ingredient, a compound that has tyrosinase inhibiting or promoting activity, an external preparation comprising the controlling agent, and a process for producing the compound.
1. An arbutin ester compound represented by formula (1):
wherein Ra is selected from the group consisting of:
R 1 —CH═CH 2 , wherein R 1 is a single bond, an unsubstituted alkyl group or an arylene group;
wherein R 1 is a single bond, an alkyl group or an arylene group;
R 1 —COOCH═CH 2 , wherein R 1 is a single bond, an alkyl group or an arylene group;
R 1 —COOH, wherein R 1 is a single bond, an alkyl group or an arylene group;
R 1 —COO—R 2 , wherein R 1 is a single bond, an alkyl group or an arylene group; and R 2 is an alkyl group or an aryl group; and
R 1 —C(CH 3 ) 3 , wherein R 1 is a single bond, an alkyl group or an arylene group.
2. A process for producing an arbutin ester compound, comprising the step of carrying out an esterification reaction of arbutin with a carboxylic acid compound represented by one of formulae (11) to (15) or (17):
A-OCO—R 1 —CH═CH 2 Formula (11)
wherein A is hydrogen or a substituted or unsubstituted alkyl or vinyl group; and R 1 is a single bond, an unsubstituted alkyl group or an arylene group;
A-OCO—R 1 —C(CH 3 )═CH 2 Formula (12)
wherein A is hydrogen or a substituted or unsubstituted alkyl or vinyl group; and R 1 is a single bond, an alkyl group or an arylene group;
A-OCO—R 1 —COOCH═CH 2 Formula (13)
wherein A is hydrogen or a substituted or unsubstituted alkyl or vinyl group; and R 1 is a single bond, an alkyl group or an arylene group;
A-OCO—R 1 —COOH Formula (14)
wherein A is hydrogen or a substituted or unsubstituted alkyl or vinyl group; and R 1 is a single bond, an alkyl group or an arylene group;
A-OCO—R 1 —COO—R 2 Formula (15)
wherein A is hydrogen or a substituted or unsubstituted alkyl or vinyl group; R 1 is a single bond, an alkyl group or an arylene group; and R 2 is an alkyl group or an aryl group;
A-OCO—R 1 —C(CH 3 ) 3 Formula (17)
wherein A is hydrogen or a substituted or unsubstituted alkyl or vinyl group; and R 1 is a single bond, an alkyl group or an arylene group.
3. The process according to claim 2 , wherein the esterification is carried out in the presence of an enzyme catalyst.
4. The process according to claim 2 , wherein the esterification is carried out in the presence of a chemical catalyst.
5. The process according to claim 2 , wherein the esterification is carried out while performing a dehydration treatment.
6. The process according to claim 2 , wherein the esterification reaction step is followed by the steps of:
extracting and isolating unreacted carboxylic acid derivative(s) from the esterification reaction mixture with a nonpolar organic solvent; and subsequently,
adding excess water to extract and isolate unreacted arbutin and to precipitate the arbutin ester compound.
7. A composition comprising an arbutin ester compound according to claim 1 and a suitable carrier.
8. An external preparation for the skin comprising the composition according to claim 7 .
9. The arbutin ester compound of claim 1 , wherein —Ra is selected from the group consisting of:
—R 1 —CH═CH 2 , wherein R 1 is a single bond, an unsubstituted alkyl group or an arylene group;
—R 1 —C(CH 3 )═CH 2 , wherein R 1 is a single bond, an alkyl group or an arylene group;
—R 1 —COOCH═CH 2 , wherein R 1 is a single bond, an alkyl group or an arylene group; and
—R 1 —C(CH 3 ) 3 , wherein R 1 is a single bond, an alkyl group or an arylene group.
10. The arbutin ester compound of claim 1 , wherein —Ra is selected from the group consisting of:
—R 1 —CH═CH 2 , wherein R 1 is a single bond or an unsubstituted alkyl group having 1 to 16 carbon atoms;
—R 1 —C(CH 3 )═CH 2 , wherein R 1 is a single bond;
—R 1 —COOCH═CH 2 , wherein R 1 is an alkyl group having 1 to 16 carbon atoms; and
—R 1 —C(CH 3 ) 3 , wherein R 1 is a single bond.
11. An arbutin ester compound selected from the group consisting of 6-O-acryloyl arbutin, 6-O-methacryloyl arbutin, 6-O-vinyladipoyl arbutin, 6-O-adipoyl arbutin, 6-O-methyladipoyl arbutin, 6-O-decenoyl arbutin, 6-O-oleoyl arbutin, 6-O-pivaloyl arbutin, 6-O-butanoyl arbutin, 6-O-laruoyl arbutin, 6-O-stearoyl arbutin, and 6-O-(10-undecylenoyl) arbutin.
12. The arbutin ester compound of claim 11 , wherein the compound is 6-O-(10-undecylenoyl)arbutin.
13. A composition comprising an arbutin ester compound of claim 11 and a suitable carrier.
14. An external preparation for the skin comprising the composition of claim 13 .