A Process for Preparation of Bioavailable White Curcumin - A Unique Blend of Hydrogenated Curcuminoids

• US 20170258743A1
• Filed: 12/04/2015
• Published: 09/14/2017
• Est. Priority Date: 12/15/2014
• Status: Active Grant

• Current Assignee: Aurea Biolabs Private Limited
• Original Assignee: Aurea Biolabs Private Limited
• Inventors: Gopi, Sreeraj, Jacob, Joby, George, Robin
• Granted Patent: US 10,639,285 B2
• Time in Patent Office: Days
• CPC Class Codes: A23L 33/105 Plant extracts, their artificial duplicates or their derivatives
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: A61K 31/121 acyclic
• CPC Class Codes: A61K 47/6951 using cyclodextrin cyclodextrins used as simple excipients A61K47/40
• CPC Class Codes: C07C 37/00 Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 39/12 polycyclic with no unsaturation outside the aromatic rings
• CPC Class Codes: C07C 41/20 by hydrogenation of carbon-to-carbon double or triple bonds
• CPC Class Codes: C07C 41/26 by introduction of hydroxy or O-metal groups
• CPC Class Codes: C07C 43/23 containing hydroxy or O-metal groups
• CPC Class Codes: C07C 45/62 by hydrogenation of carbon-to-carbon double or triple bonds
• CPC Class Codes: C07C 49/225 containing six-membered aromatic rings and other rings
• CPC Class Codes: C07C 49/245 containing six-membered aromatic rings
• CPC Class Codes: C07C 49/255 containing ether groups, groups, groups, or groups
• CPC Class Codes: C08B 37/0015 Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes

Abstract

The present invention discloses a process for preparation of white curcumin from purified curcuminoids. The curcuminoids are obtained by solvent extraction and crystallization of dried turmeric powder. The autoclave is charged with ethyl acetate and the 95% purity curcuminoids mixture is added to and stirred for uniformity at room temperature. 5% (w/w) of 10% palladium carbon is added to the reaction mixture and allowed for hydrogenation in the presence of hydrogen gas at 2 lbps pressure and stirred continuously for 15 hours. Once the reaction is completed, the reaction mixture is filtered and washed with ethyl acetate. The ethyl acetate is distilled off and crude mass is stirred with water to obtain a solid precipitate. Finally, the solid obtained is filtered and dried to pale brown crystals of white curcumin. White curcumin is encapsulated with beta-cyclodextrin, which exhibited increased bioavailability. White curcumin also exhibited anti-oxidant and chemopreventive activities.

Claims

1. A process for preparation of white curcumin, the process comprising the steps of:

a. charging an autoclave with ¾

th volume of an organic solvent;

b. adding 40-60 g of 95% total curcuminoids to the organic solvent to form a reaction mixture and stirring the reaction mixture for uniformity at room temperature;

c. adding 2-3 g of 10% palladium carbon as catalyst to the reaction mixture;

d. subjecting the reaction mixture to hydrogenation at pressure of 2 lbps and stirring the reaction mixture for 15 hours in the presence of hydrogen gas;

e. monitoring the completion of the reaction using the Thin Layer Chromatography (TLC);

f. filtering the reaction mixture through a cotton canvas filter cloth to remove the traces of palladium carbon and washing the filtrate with 50 ml of ethyl acetate;

g. distilling the ethyl acetate to obtain a crude mass of white curcumin;

h. stirring the crude mass with 2 liters of purified water to obtain a solid precipitate of white curcumin; and

i. filtering the solid precipitate and drying the solid precipitate to obtain pale brown crystals of white curcumin.

2. The process as claimed in claim 1, wherein the organic solvent used is selected from a group consisting of ethyl acetate, methanol and ethanol.

3. The process as claimed in claim 1, wherein white curcumin obtained is a mixture of tetrahydrocurcuminoids, hexahydrocurcuminoids and octahydrocurcuminoids at the concentration of 75-80%, 15-20% and 3-5% respectively.

4. The process as claimed in claim 1, wherein white curcumin is encapsulated with beta-cyclodextrin to improve the bioavailability of white curcumin.

5. The process as claimed in claim 1, wherein the yield of white curcumin 36 g-54 g.

6. A white curcumin encapsulated with beta-cyclodextrin, wherein white curcumin comprises mixture of tetrahydrocurcuminoids, hexahydrocurcuminoids and octahydrocurcuminoids at the concentration of 75-80%, 15-20% and 3-5% respectively.

7. The white curcumin as claimed in claim 6, wherein white curcumin exhibited high rate of absorption with high residence time.

8. The white curcumin as claimed in claim 6, wherein white curcumin exhibited anti-oxidant and chemotherapeutic activity.

9. The white curcumin as claimed in claim 6, wherein white curcumin is added as food supplement and exhibited heat stability at a normal cooking temperature of 120°

C.-200°

C.