IP Library Granted Patent US 10,898,423
Granted Patent B2
US 10,898,423 · App. 16/796,632 · Granted Jan 26, 2021

Synergistic antioxidant compositions

Inventors: Olga Dueva-Koganov (Emeryville, CA); Taylor Oswald (Oakland, CA); Christine Crane (Walnut Creek, CA); Robert Bianchini (Dana Point, CA)
Assignee: RODAN & FIELDS, LLC
A61K8/602A61K8/375A61K8/58A61Q19/00A61Q19/08
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Quick Facts
Patent No.
US 10,898,423
App. No.
16/796,632
Granted
Jan 26, 2021
Kind
B2
Abstract

The antioxidant compositions of various embodiments comprise methyl carboxymethylphenylaminocarboxy propylphosphonate, also known as MCAP, (2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid, also known as rosmarinic acid, and 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-4H-chromen-4-one, also known as rutin wherein the antioxidant composition demonstrate a synergistic effect compared with the MCAP, the rosmarinic acid, or the rutin alone. The methods include treating skin or hair damaged by reactive oxygen species, preventing skin or hair damage, and treating aged skin.

Claims (35)

1. An antioxidant composition comprising: methyl carboxymethylphenylaminocarboxy propylphosphonate (MCAP),

(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid (rosmarinic acid), and

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-4H-chromen-4-one (rutin),

wherein the ratio of the MCAP: the rosmarinic acid: the rutin in the antioxidant composition is about 1:100:100.

2. The antioxidant composition of claim 1 , wherein the antioxidant composition demonstrates a synergistic effect compared with the MCAP, the rosmarinic acid, or the rutin, alone.

3. The antioxidant composition of claim 1 , wherein the MCAP is present in the antioxidant composition in an amount of about 0.0001 wt. % to about 1.0 wt. %.

4. The antioxidant composition of claim 1 , wherein the rosmarinic acid is present in the antioxidant composition in an amount of about 0.0001 wt. % to about 1.0 wt. %.

5. The antioxidant composition of claim 1 , wherein the rutin is present in the antioxidant composition in an amount of about 0.0001 wt. % to about 1.0 wt. %.

6. The antioxidant composition of claim 2 , wherein the synergistic effect is an increase in absorbance of light at 250-400 nm.

7. The antioxidant composition of claim 6 , wherein the total amount of the increased absorbance is significantly more than the absorbance of any of the MCAP, the rosmarinic acid, or the rutin alone.

8. A topical formulation comprising the antioxidant composition of claim 1 .

9. The topical formulation of claim 8 , wherein the topical formulation further comprising a solvent.

10. The topical formulation of claim 9 , wherein the solvent is selected from the group consisting of pentylene glycol, butylene glycol, water, ethanol, and combinations thereof.

11. The topical formulation of claim 8 , wherein the total amount of the antioxidant composition in the topical formulation is about 0.000001 wt. % to about 5.0 wt. %.

12. The topical formulation of claim 8 , wherein the topical formulation further comprises a pharmaceutical additive, a cosmetic additive, water, or combinations thereof.

13. The topical formulation of claim 12 , wherein the pharmaceutical additive is selected from the group consisting of diluents, fillers, disintegrants, binders, lubricants, surfactants, hydrophobic vehicles, water soluble vehicles, emulsifiers, buffers, humectants, moisturizers, solubilizers, preservatives, colorants, plastizers, carriers, excipients, and combinations thereof.

14. The topical formulation of claim 12 , wherein the cosmetic additive is selected from the group consisting of vitamins, cosmetic peptides, oil control agents, sensation modifying agents, skin lightening agents, hydrating formulations, a sunblock agent, a compound that absorbs or reflects UV photons, other skin care agent and combinations thereof.

15. The topical formulation of claim 8 , wherein the topical formulation is formulated in a form selected from the group consisting of a solution, fluid, emulsion, suspension, solid, semi-solid, jelly, paste, gel, hydrogel, ointment, lotion, emulsion, cream, foam, mousse, liquid, spray, suspension, dispersion, powder, aerosol, color cosmetic, hair treatment, scalp care product, or transdermal patch.

16. A method of treating skin damage by reactive oxygen species in a subject in need thereof comprising topically administering to the skin of the subject an antioxidant composition comprising:

methyl carboxymethylphenylaminocarboxy propylphosphonate (MCAP),

(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl) prop-2-enoyl]oxy}propanoic acid (rosmarinic acid), and

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-4H-chromen-4-one (rutin),

wherein the ratio of the MCAP: the rosmarinic acid: the rutin in the antioxidant composition is about 1:100:100.

17. The method of claim 16 , wherein the antioxidant composition demonstrates a synergistic effect compared with the MCAP, the rosmarinic acid, or the rutin alone.

18. The method of claim 16 , wherein the subject is an infant, a child, an adolescent, or an adult.

19. The method of claim 16 , wherein the skin damage is damage to lipids, proteins, DNA, or combinations thereof.

20. The method of claim 16 , wherein the reactive oxygen species is generated by UV radiation, pollution, heating, or combinations thereof.

21. A method of improving the appearance of aged skin in a subject in need thereof comprising topically administering to the skin of the subject an antioxidant composition comprising: methyl carboxymethylphenylaminocarboxy propylphosphonate (MCAP),

(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl) prop-2-enoyl]oxy}propanoic acid (rosmarinic acid), and

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-4H-chromen-4-one (rutin),

wherein the ratio of the MCAP: the rosmarinic acid: the rutin in the antioxidant composition is about 1:100:100.

22. The method of claim 21 , wherein the antioxidant composition demonstrates a synergistic effect compared with the MCAP, the rosmarinic acid, or the rutin alone.

23. The method of claim 21 , wherein the characteristic of the skin is selected from the group consisting of firmness, elasticity, fine lines, wrinkles, skin texture, skin tone, appearance, and any combination thereof.

24. The method of claim 21 , wherein improving the appearance of the skin results in smoother skin, firmer skin, brighter complexion, improved texture of the skin, even-looking skin, or younger-looking skin.

25. The method of claim 21 , wherein improving the appearance of the skin results in an increase in elasticity of the skin, a decrease in the fine lines of the skin, a decrease in the wrinkles of the skin, a more consistent skin tone, and any combination thereof.

Assignments (13)
ASSIGNMENT OF SECURITY INTERESTS IN PATENT COLLATERAL Recorded Feb 2, 2026
From: CITIBANK, N.A., IN ITS CAPACITY AS THE WITHDRAWING AGENT
To: ANKURA TRUST COMPANY, LLC, IN ITS CAPACITY AS SUCCESSOR AGENT
Reel/Frame 074643/0097 →
MERGER Recorded Oct 9, 2024
From: RODAN & FIELDS, LLC
To: RODAN & FIELDS BEAUTY, LLC
Reel/Frame 068844/0351 →
PATENT SECURITY AGREEMENT Recorded Sep 27, 2024
From: RODAN & FIELDS BEAUTY, LLC
To: ANKURA TRUST COMPANY, LLC, AS COLLATERAL AGENT
Reel/Frame 069066/0818 →
RELEASE OF SECURITY INTEREST IN PATENT COLLATERAL RECORDED ON APRIL 28, 2023, AT REEL/FRAME 063480/0786 Recorded Sep 27, 2024
From: ANKURA TRUST COMPANY, LLC, AS COLLATERAL AGENT
To: RODAN & FIELDS, LLC
Reel/Frame 069066/0803 →
PATENT SECURITY AGREEMENT Recorded Sep 27, 2024
From: RODAN & FIELDS BEAUTY, LLC
To: ANKURA TRUST COMPANY, LLC, AS COLLATERAL AGENT
Reel/Frame 069066/0810 →
SECURITY INTEREST Recorded May 2, 2023
From: RODAN & FIELDS, LLC
To: ANKURA TRUST COMPANY, LLC
Reel/Frame 063501/0804 →
SECURITY INTEREST Recorded May 2, 2023
From: RODAN & FIELDS, LLC
To: CITIBANK, N.A.
Reel/Frame 063501/0785 →
SECURITY INTEREST Recorded Apr 28, 2023
From: RODAN & FIELDS, LLC
To: ANKURA TRUST COMPANY, LLC
Reel/Frame 063480/0786 →
SECURITY INTEREST Recorded Apr 28, 2023
From: RODAN & FIELDS, LLC
To: ANKURA TRUST COMPANY, LLC
Reel/Frame 063480/0179 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2020
From: DUEVA-KOGANOV, OLGA
To: RODAN & FIELDS, LLC
Reel/Frame 053076/0224 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2020
From: BIANCHINI, ROBERT
To: RODAN & FIELDS, LLC
Reel/Frame 052953/0746 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2020
From: CRANE, CHRISTINE
To: RODAN & FIELDS, LLC
Reel/Frame 051908/0500 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2020
From: OSWALD, TAYLOR
To: RODAN & FIELDS, LLC
Reel/Frame 051908/0590 →
Continuity (2)
Provisional Application 62808052 · Feb 20, 2019
Related Publication 20200261344A1 · Aug 20, 2020