Method for making tetrahydrocurcumin and a substance containing the antioxidative substance tetrahydrocurcumin

• US 5,266,344 A
• Filed: 11/20/1990
• Issued: 11/30/1993
• Est. Priority Date: 08/12/1988
• Status: Expired due to Term

• Current Assignee: Biomarker Science Company Limited
• Original Assignee: Klaus Schmidt
• Inventors: Osawa, Toshihiko, Mimura, Akio, Takahara, Yoshimasa
• Primary Examiner(s): PADEN, CAROLYN A
• Application Number:
  US07/616,093
• Time in Patent Office: 1,106 Days
• Field of Search: 426/546, 260/398.5
• US Class Current: 426/546
• CPC Class Codes: A23L 3/3481 Organic compounds containing oxygen
• CPC Class Codes: A23L 3/3499 with doubly-bound oxygen
• CPC Class Codes: A61K 2800/522 Antioxidants; Radical scavengers
• CPC Class Codes: A61K 8/35 Ketones, e.g. benzophenone
• CPC Class Codes: A61K 8/9794 Liliopsida [monocotyledons]
• CPC Class Codes: A61Q 17/00 Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
• CPC Class Codes: C07C 45/62 by hydrogenation of carbon-to-carbon double or triple bonds
• CPC Class Codes: C07C 49/255 containing ether groups, groups, groups, or groups
• CPC Class Codes: C09K 15/06 containing oxygen
• CPC Class Codes: C11B 5/0035 Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
• CPC Class Codes: C11C 3/12 by hydrogenation

Abstract

The present invention relates to a novel compound tetrahydrocurcumin and a substance containing the same, which are produced from curcumin or a substance containing it as a material. This substance has characteristic properties such as strong antioxidative activity and yellowish color generated from reducing the original color of curcumin. The curcumin is being produced from a Zingiberaceae plant classified into Curcuma longa as a tropical product and is used for a spice and a yellow pigment for curry powder and pickles. The present invention further relates to the production method.

Claims

1. Method for producing tetrahydrocurcumin, comprising reducing curcumin by a metallic catalyst in the presence of hydrogen in an organic solvent.

2. The method of claim 1, wherein said metallic catalyst is selected from the group consisting of Raney nickel, manganese catalysts, copper catalysts and zinc catalysts.

3. The method of claim 2, wherein said metallic catalyst is Raney nickel.

4. The method of claim 2, wherein said hydrogen is hydrogen gas.

5. The method of claim 1, wherein said solvent is selected from the group consisting of acetone, methanol and ethanol.

6. Hardened oil containing tetrahydrocurcumin.

7. The hardened oil of claim 6, further containing beef fat, margarine or shortening.

8. Method for producing a hardened oil containing tetrahydrocurcumin, comprising the steps of adding curcumin to fat or oil and reducing the fat or oil by hydrogen, thereby the curcumin being simultaneously changed into tetrahydrocurcumin by hydrogenation.

9. The method of claim 8, wherein said reducing step is conducted with hydrogen gas and a catalyst selected from the group consisting of Raney nickel, manganese catalysts, copper catalysts and zinc catalysts.

10. The method of claim 9, wherein said metallic catalyst is Raney nickel.

11. Method for producing reduced-form curcuminoids, comprising the steps of extracting the root of Curcuma longa into a first organic solvent, and reducing the obtained extract by a metallic catalyst in the presence of hydrogen in a second organic solvent.

12. The method of claim 11, wherein said metallic catalyst is selected from the group consisting of Raney nickel, manganese catalysts, copper catalysts and zinc catalysts.

13. The method of claim 12, wherein said metallic catalyst is Raney nickel.

14. The method of claim 12, wherein said hydrogen is hydrogen gas.

15. The method of claim 11, wherein said first organic solvent is benzene, and said second organic solvent is selected from the group consisting of acetone, methanol and ethanol.

16. The method of claim 11, wherein said reducing step is conducted with hydrogen gas and a catalyst selected from the group consisting of Raney nickel, manganese catalysts, copper catalysts and zinc catalysts.

17. Method for producing reduced-form curcuminoids, comprising reducing curcuminoids by a metallic catalyst in the presence of hydrogen in an organic solvent.