IP Library Granted Patent US 8,445,037
Granted Patent B2
US 8,445,037 · App. 12/607,617 · Granted May 21, 2013

Volatile distillate by-product of mint oil that promotes absorption and/or bioavailability of compounds of bio-medical and nutritional interest

Inventors: John Westcott Finley (Baton Rouge, LA); John Weldon Finley (Chalfont, PA); Igor Mezine (Malvern, PA); James M. Kehrer, II (Coloma, MI); Robert J. Justice, II (Portage, MI)
Assignee: A. M. Todd Company
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Quick Facts
Patent No.
US 8,445,037
App. No.
12/607,617
Granted
May 21, 2013
Kind
B2
Abstract

Disclosed is an adjuvant for improving the bioavailability of bioactive compositions. The adjuvant is prepared from a byproduct of mint flavor production. In vitro and in vivo testing confirms effectiveness. The adjuvant contains a mixture of compounds which is effective to improve the oral bioavailability of a bioactive composition normally having limited absorptivity, and it comprises a mixture of nonpolar compounds and compounds with some polar characteristics. In preferred form the nonpolar compounds comprise compounds selected from a group that includes terpene hydrocarbons and terpene derivatives and the compounds with some polar characteristics comprise compounds selected from a group that includes aldehydes, alcohols and ketones. The preferred compositions will have a ratio of nonpolar compounds and compounds with some polar characteristics is within the range of from 5:1 to 20:1. The adjuvants can enhance delivery of CoQ10 and other bioactive compositions, such as carotenoids (e.g., β-carotene), curcuminoids, lycopene, resveratrol, flavonoids and other phenolic compounds, organosulfur compounds, saponins, sterols, stanols, and mixtures of at least two of these, to the interior cellular environment, including organelles, such as the mitochondria.

Claims (14)

1. A process for preparing an adjuvant composition capable of increasing the bioavailability of a bioactive composition, comprising:

a. subjecting dried mint leaves to direct steam heat to obtain a crude mint oil;

b. heating said crude mint oil while applying and increasing a vacuum to volatilize and condense discreet fractions of said crude mint oil;

c. collecting said discreet fractions of said crude mint oil and separating low-boiling fractions as byproduct fractions from higher boiling flavor fractions;

d. analyzing the discreet byproduct fractions obtained in step c; and

e. selecting and combining suitable byproduct fractions so as to obtain an adjuvant composition comprising less than 10% limonene and less than 5% of any of menthol, menthone, menthofuran, menthyl acetate and germacrene D.

2. A process according to claim 1 wherein, the mint leaves are obtained from mint that was mowed just prior to flowering and allowed to wilt in the sun.

3. A process according to claim 1 , wherein the mint leaves are fraction is obtained from one or more mint species including Mentha piperita (peppermint), Mentha spicata (spearmint), Mentha arvensis (cornmint) and Mentha pulegium (pennyroyal).

4. A process according to claim 1 , wherein the discrete fractions are collected in increments of 1-4% of the starting volume of the crude mint oil.

5. A process according to claim 1 , wherein the adjuvant composition contains less than 1% of any of pulegone, menthyl acetate, and germacrene-d.

6. A process according to claim 1 , wherein the adjuvant comprises a mixture of nonpolar compounds and compounds with polar characteristics.

7. A process according to claim 6 , wherein the nonpolar compounds comprise compounds selected from the group consisting of terpene hydrocarbons and terpene derivatives and the compounds with polar characteristics comprise compounds selected from the group consisting of aldehydes, alcohols and ketones.

8. A process according to claim 6 , wherein the weight ratio of nonpolar compounds and compounds with polar characteristics is within the range of from 5:1 to 20:1.

9. A process according to claim 6 , wherein the adjuvant comprises at least 0.5% by weight of at least two of myrcene, farnesene and para-cymene as nonpolar compounds, and between 1 and 30% of at least two of α-pinene, β-pinene, sabinene and 1,8-cineole, and measurable amounts of at least two of myrcene, para-cymene, farnesene, neo-menthol, 1-octen-3-ol, 3-octanol, and viridiflorol.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Jun 13, 2012
From: JP MORGAN CHASE BANK, N.A., AS AGENT
To: A. M. TODD GROUP, INC.; A. M. TODD CITRUS PRODUCTS, INC.; A. M. TODD COMPANY; A. M. TODD COMPANY-WEST; GREAT SPIRIT VENTURES, LLC; TODD INTERNATIONAL COMPANY; ZINK & TREIST COMPANY, INC.; ROYAL ORGANIC PRODUCTS, LLC; A. M. TODD BOTANICAL THERAPEUTICS LLC
Reel/Frame 028367/0891 →
SECURITY AGREEMENT Recorded Dec 14, 2010
From: A.M. TODD GROUP, INC.; A.M. TODD CITRUS PRODUCTS, INC.; A.M. TODD COMPANY; A.M. TODD COMPANY-WEST; TODD INTERNATIONAL COMPANY; ZINK & TRIEST COMPANY, INC.; ROYAL ORGANIC PRODUCTS, LLC; A.M. TODD BOTANICAL THERAPEUTICS LLC
To: JPMORGAN CHASE BANK, N.A., AS AGENT
Reel/Frame 025497/0226 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2010
From: FINLEY, JOHN WESTCOTT; FINLEY, JOHN WELDON; MEZINE, IGOR; KEHRER, JAMES M., II; JUSTICE, ROBERT J.
To: A. M. TODD COMPANY
Reel/Frame 024287/0400 →
Continuity (3)
Provisional Application 61108953 · Oct 28, 2008
Provisional Application 61170763 · Apr 20, 2009
Related Publication 20100197801A1 · Aug 5, 2010