Uses of kombic acid as an antioxidant

Details Uses of kombic acid as an antioxidant Uses of kombic acid as an antioxidant

2001-07-19

2002-12-03

Carr, Deborah D. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C514S547000, C514S559000

Reexamination Certificate

active

06489494

ABSTRACT:

STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
Not applicable
REFERENCE TO A “MICROFICHE APPENDIX”
Not applicable
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to the polyisoprenoic natural terpenoid with the common name kombic acid and the chemical name 16(2′, 5′-dihydroxy-3′-methylphenyl)-2,6,10,14-tetramethyl-2,6,10,14-hexadecatetraenoic acid. More particularly, the present invention relates to the use of kombic acid and its derivatives as an antioxidant in the stabilization of human and animal foods against the development of rancidity and color and odor development; as an antioxidant in dietary supplements and other human and animal health formulations; as a stabilizer in cosmetic and other personal care applications; and as a stabilizer against oxidative degradation in plastics. The present invention also encompasses improved methods of isolating kombic acid and its derivatives.
2. General Background of the Invention
Fats and oils are water-insoluble, hydrophobic substances of vegetable, land animal or marine animal origin that consist mostly of glyceryl esters of fatty acids, called triglycerides. Their structure is shown below, where R
1
, R
2
, and R
3
can be the same or different —(CH
2
)
x
CH
3
chains, with x being an odd number of 5 or greater.
The chains (the Rs) may be completely saturated with respect to hydrogen or have one or more double bonds. When R
1
is seventeen carbons with no double bonds, the chain is called stearic; in this case there are thirty-five hydrogen atoms attached to the seventeen carbons. With one double bond the same carbon-length chain is called oleic and there are thirty-three attached hydrogen atoms. When there is more than one double bond, the fatty acids are polyunsaturated. Linoleic acid, for example, has eighteen carbons atoms and two double bonds, and linolenic acid has three double bonds and eighteen carbon atoms.
There are roughly 100 million metric tons of fats and oils consumed globally with about 80% used for human food. The balance is used as industrial oils, in animal feed, to make soap, and to produce oleochemicals, which have many industrial applications, most notably as plastics additives and food processing ingredients.
The principal fats and oils used in food are canola, soybean, palm, sunflower seed, coconut, palm kernel, sesame, olive, corn, cottonseed, edible tallow and lard. The most frequently occurring fatty acids found in these fats and oils are stearic, oleic, linoleic, linolenic, palmitic (C
16:0
), palmitoleic (C
61:1
), myristic(C
14:0
) and lauric(C
12:0
). The first two digits in the carbon subscript refer to carbon chain length, and the number after the colon refers to the number of double bonds in the chain.
Myristoleic acid, which has fourteen carbon atoms and one double bond in the chain has an ester derivative, cetyl myristoleate, with claimed efficacy in relieving the pain of rheumatoid arthritis and osteoarthritis
1, 2
. The myristoleic acid used to make this product up to now has been derived from beef tallow.
There are two commonly accepted reference sources with respect to published treatises on fats and oils: “Bailey's Industrial Oil and Fat Products,” Fourth Edition, John Wiley & Sons, and Gunstone and Padley's, “Lipid Technologies and Applications,” Marcel Dekker, Inc. In “Bailey's” there is the following discussion of sources of myristoleic acid, all based on land animal or marine animal origin.
9-Tetradecenoic (myristoleic) acid is the most common of the tetradecenoic acids, being first detected in whale oil in 1925 at about 1.4%, later in whale blubber oil, in shark liver oil, Antarctic whale oil, eel oil, and turtle oil. In 1924 it was suggested to occur in butterfat; it was found to constitute 1% of the total acids. It also occurs in goat milk fat, human milk fat, and various animal depot fats, (particularly beef tallow).
It is noteworthy that there is not the slightest reference in Bailey's to any vegetable oil sources.
Gunstone and Padley, in their well-recognized reference work mention hundreds of fatty acids but make no reference of any sort to myristoleic acid. Useful products can be obtained from myristoleic acid, most notably cetyl myristoleate, a possible remedy for alleviating the pain and inflammation of arthritis and related maladies
1, 2
. However, cetyl myristoleate based on myristoleic acid sourced from animal origins, up to now the only ostensible source, has several disadvantages:
1) Fatty acids derived from beef tallow run the risk, albeit slight, of inducing bovine spongiform encephalitis (mad-cow disease).
2) Any fatty acid sourced from land animal or marine animal origins cannot be Kosher or the Islamic equivalent, Halal.
3) Any fatty acids sourced from land animal or marine animal origins cannot be “vegetarian” or “vegetable-oil food-grade.”
Myristoleic acid, however, is not exclusively sourced from non-vegetable oil origins. There is a tree that produces a nut containing a vegetable butter that is a relatively good source of myristoleic acid
3, 4, 5, 6, 7
. The fat is known as kombo butter. It comes from the seeds of Pycnanthus Kombo (Myristicaceae family) found in West Central Africa. Other compounds isolated from P. Kombo (P. Angolensis) include 2′-hydroxy-4′-7-dimethoxy isoflavone and 2′-hydroxy formonometin
8
. In addition, U.S. Pat. No. 5,674,900 00 describes the isolation and use of terpenoid quinones from the stems and leaves (not the seedfat) of P. kombo for use in treating diabetes
9
.
The seedfat of P. kombo is reddish-brown and has a distinct aromatic odor. The fat also contains 20-30% of kombic acid. Kombic acid is not a fatty acid per se, rather it is a substituted fatty acid, and must be separated and removed from kombo butter in manufacturing downstream oleochemical products such as myristoleic acid. From kombo butter, the unit operations to obtain relatively pure distilled fatty acid mixtures containing appreciable levels of myristoleic acid include: 1) fat (kombo butter) saponification to split the fat and form the sodium soaps of the fatty acids, thereby separating and removing the glycerine, 2) acidulation of the sodium soaps of the fatty acids to reform the free fatty acids, and 3) molecular distillation of the crude fatty acids for purposes of purification. The cetyl esters can then be formed by conventional esterification reactions. The present invention describes the unexpected isolation, and manufacture of substituted fatty acids and substituted fatty acid derivatives from the seed fat of Pycnanthus Kombo via alcohol extraction and supercritical CO
2
methods and their use as antioxidants. This substituted fatty acid is kombic acid and the substituted fatty acid derivatives are derivatives of kombic acid.
BRIEF SUMMARY OF THE INVENTION
The method of the present invention provides an antioxidant and stabilizer in human and animal pharmaceuticals and dietary supplements. The method of the present invention also solves the problems of stabilization of human and animal foods against the development of rancidity, color and odor; stabilization of cosmetic and other personal care products; and the stabilization of plastics against oxidative degradation by using kombic acid, or a kombic acid derivative, as an antioxidant. In addition, the invention method solves the problem of isolating kombic acid in a highly purified form on a large scale for such use.


REFERENCES:
patent: 5674900 (1997-10-01), Ubillas et al.
Lok, C.M., Groenewegen, A., Stroink, B.A., and Ward, J.P.,Phytochemistry, vol. 22, No. 9, pp. 1973-1976, 1983.

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