Hydroxytyrosol derivatives, their method of preparation and use in personal care

Patent metadata

Field	Value
Publication number	US-9334229-B2
Application number	US-201314070746-A
Country	US
Kind code	B2
Filing date	Nov 4, 2013
Priority date	Nov 4, 2013
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

Hydroxytyrosol derivative compositions, methods for their manufacture, and their use in personal care products are disclosed. Lipophilic hydroxytyrosol carbonate ester compound can be made by oxidizing a substituted hydroxybenzaldehyde compound with an oxidizing agent such as hydrogen peroxide under mild conditions. The process involves enzymatic esterification of 4-(2-hydroxyethyl)phenol to form the corresponding ester, the introduction of a formyl group ortho to the phenolic hydroxyl group of the ester to form a lipophilic formyltyrosol ester; oxidation of the lipophilic formyltyrosol ester with a peroxide compound to form a lipophilic hydroxytyrosol ester compound; and reaction of lipophilic hydroxytyrosol ester compound with carbonic acid ester derivatives to form a lipophilic hydroxytyrosol carbonic ester compound. These compounds are useful is a wide variety of personal care compositions as anti-aging compounds that are stable against oxidation.

First claim

What we claim is:

1. A lipophilic hydroxytyrosol carbonate ester compound having a structure represented by the general Formula 2:

wherein R 1 is a saturated or unsaturated, branched or straight chain, substituted or unsubstituted, aliphatic, alicyclic, or alkaryl C 1 -C 22 aliphatic, alicyclic, or alkaryl group; and wherein R 2 is a saturated or unsaturated, branched or straight chain, substituted or unsubstituted C 2 -C 24 aliphatic, alicyclic, or alkaryl group.

2. The compound of claim 1 , wherein R 2 is a C 8 -C 24 group.

3. The compound of claim 2 , wherein R 2 is a C 10 -C 24 group.

4. The compound of claim 3 , wherein R 2 is a C 12 -C 24 group.

5. The compound of claim 4 , wherein R 2 has at least 6 more carbon atoms than the R 1 group.

6. The compound of claim 4 , wherein R 2 has at least 10 more carbon atoms than the R 1 group.

7. The compound of claim 1 , wherein R 1 is substituted with one to three groups selected from C 1 -C 6 -alkoxy, carboxyl, C 1 -C 15 aminocarbonyl, C 1 -C 15 amido, cyano, C 2 -C 15 -alkoxycarbonyl, C 2 -C 15 -alkoxycarbonyloxy, C 2 -C 15 alkanoyloxy, hydroxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, thiol, thioether, and halogen.

8. The compound of any one of claims 1 - 7 , wherein R 2 is an aliphatic group.

9. The compound of any one of claims 1 - 7 , wherein R 2 is un-substituted.

10. The compound of any one of claims 1 - 7 , wherein R 2 ═C 12 -C 24 and R 1 ═C 1 -C 6 .

11. A composition for topical application to a keratinous surface, said composition comprising a lipophilic hydroxytyrosol carbonate ester compound of the general Formula 2:

wherein R 1 is a saturated or unsaturated, branched or straight chain, substituted or unsubstituted, aliphatic, alicyclic, or alkaryl C 1 -C 22 aliphatic, alicyclic, or alkaryl group; and
wherein R 2 is a saturated or unsaturated, branched or straight chain, substituted or un-substituted C 2 -C 24 aliphatic, alicyclic, or alkaryl group.

12. The composition of claim 11 , wherein said composition comprises a cosmetic composition.

13. The composition of claim 12 , wherein said composition comprises an eyeliner, eyeshadow, lipstick, mascara, foundation, blush, or nail polish.

14. The composition of claim 11 , wherein said composition comprises a skin care composition.

15. The composition of claim 14 , wherein said composition comprises a skin moisturizer, anti-aging lotion, infant care product, body oil, after-bath and shower product, soap, shampoo, or sun screen or sun tan lotion.

Assignees

• Eastman Chem Co

Inventors

• Boaz Neil Warren
• Maleski Robert Joseph

Classifications

• C07C69/30

  esterified with trihydroxylic compounds (fats, oils C11B, C11C) · CPC title

• C07C67/293

  by isomerisation; by change of size of the carbon skeleton · CPC title

• C07C69/28

  esterified with dihydroxylic compounds · CPC title

• C07C69/96 Primary

  Esters of carbonic or haloformic acids · CPC title

• C07C69/738

  Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} · CPC title