Sterol esters as food additives

Details Sterol esters as food additives Sterol esters as food additives

1998-05-21

2002-05-28

Qazi, Sabiha (Department: 1616)

Fire escape, ladder, or scaffold

Torso harness

Attached to strand wound on reel, and means for retarding...

C514S182000, C426S601000, C426S605000

Reexamination Certificate

active

06394230

ABSTRACT:

STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
Not Applicable.
BACKGROUND OF THE INVENTION
Phytosterols have been found to be effective in reducing serum cholesterol in humans. Phytosterols are steroids that bear a close structural relationship to cholesterol but differ in the configuration of the side chains at the 17-position. It is well known that &bgr;-sitosterol and the fatty acid esters of &bgr;-sitosterol are effective in reducing serum cholesterol. Recent studies have found that &bgr;-sitostanol and the fatty acid esters of &bgr;-sitostanol are particularly effective in reducing serum cholesterol and LDL levels. It has been recently reported that the fatty acid esters of &bgr;-sitostanol are particularly effective cholesterol-reducing agents presumably because they are in solution. Such esters can be introduced into the body as additives in food products such as margarine. Margarines containing &bgr;-sitosterol and those containing &bgr;-sitosterol fatty acid esters as well as margarines containing &bgr;-sitostanol and &bgr;-sitostanol fatty acid esters have been shown to reduce serum cholesterol levels in humans.
BRIEF SUMMARY OF THE INVENTION
The present invention pertains to a food additive containing a sterol or stanol ester of a fatty acid or a dicarboxylic acid ester of a sterol or stanol made by the process described herein below. The food additive can be incorporated into food for the purpose of lowering serum cholesterol in humans and/or for reducing the absorption of cholesterol from foods and/or beverages. The food additive is prepared by combining a sterol and/or stanol fatty acid ester thereof and/or a dicarboxylic acid ester of a sterol or stanol made by the process described herein and an edible solubilizing agent, an effective amount of a suitable antioxidant and an effective amount of a suitable dispersant. The sterol and/or stanol esters made by the process described herein can be used without removing the catalyst because the catalyst is non-toxic and used at low levels. Another advantage is that when the fatty acid esters of sterols or stanols are prepared by transesterification, the ester that is transesterified can be either a lower alkyl ester such as a methyl or an ethyl ester or a triglyceride which is a triglyceryl ester of a C
6-22
fatty acid such as a conventional fat or oil.
Another aspect of the invention pertains to a method of reducing the absorption of cholesterol into the bloodstream which comprises orally introducing into the body an effective amount of a substance containing a &bgr;-sitostanol ester made by reacting a stanol and a carboxylic acid in the presence of an effective amount of a catalyst selected from the group consisting of calcium oxide, calcium hydroxide, a calcium salt of a carboxylic acid, magnesium hydroxide and combinations thereof.
BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING
Not Applicable.
DETAILED DESCRIPTION OF THE INVENTION
The term sterol is well known to those skilled in the art and generally refers to those compounds having a perhydrocyclopentanophenanthrene ring system (the ring system depicted in Formula III herein) and having one or more OH substituents, examples of which include, but are not limited to, cholesterol, campesterol, ergosterol, sitosterol, and the like. It is common to obtain sterols as mixtures of compounds such as, for example, GENEROL® 122N sterols, a trademark product of Henkel Corporation, Gulph Mills, Pa. GENEROL® 122N sterol contains 25-30% campesterol, 17-22% stigmasterol and 45-50% sitosterol.
The term stanol is well known to those skilled in the art and generally refers to those compounds having a saturated perhydrocyclopentanophenanthrene ring system (the ring system depicted in Formula II herein) and having one or more OH substituents, examples of which include, but are not limited to, campestanol, sitostanol which also known as &bgr;-sitostanol and stigmastanol, coprostanol, cholestanol and the like.
The food additive according to the invention is comprised of a sterol and/or stanol ester of a fatty acid wherein the ester is made by reacting a sterol and/or stanol with a fatty acid having from 6 to 22 carbon atoms in the presence of an effective amount of a catalyst selected from the group consisting of calcium oxide, calcium hydroxide, a calcium salt of a carboxylic acid, magnesium hydroxide and combinations thereof or a dicarboxylic acid ester of a sterol or stanol of the formula I. Since the catalyst is non-toxic and used at low levels, the sterol and/or stanol ester of the fatty acid can be added directly to foods without further processing such as removal of the catalyst. The sterol can be any sterol. Examples of suitable sterols include, but are not limited to, campesterol, ergosterol, stigmasterol, sitosterol or a combination thereof. A preferred sterol is &bgr;-sitosterol. A commercially available combination of sterols is GENEROL® 122N sterols as set forth herein. The stanol can be any stanol. Examples of suitable stanols include, but are not limited to, campestanol, sitostanol which is also known as &bgr;-sitostanol and stigmastanol, coprostanol, cholestanol and the like. A preferred stanol is &bgr;-sitostanol.
The amount of sterol and/or stanol fatty acid ester that can be used in the food additive is an effective amount which is any amount necessary to either reduce serum cholesterol in humans after ingestion of a food containing the food additive or an amount necessary to reduce the absorption of cholesterol from foods and/or beverages. A preferred food additive composition of the instant invention comprises from about 70% to about 80% vegetable oil, from about 1% to about 2% tocopherols, and from about 10% to about 25% sterol and/or stanol fatty acid ester prepared by the method according to the invention.
The food additive is prepared by combining a sterol and/or stanol ester of a fatty acid made by the process described herein and an edible solubilizing agent, an effective amount of a suitable antioxidant and an effective amount of a suitable dispersant. The solubilizing agent can be vegetable oil such as, for example, sunflower oil, palm kernel oil, coconut oil, rape seed oil, tallow, corn oil, canola oil, linseed oil, palm oil, olive oil, sesame oil, safflower oil, and the like, monoglycerides, diglycerides, triglycercides, tocopherols, and the like, and mixtures thereof. The antioxidant can be ascorbic acid (Vitamin C), tocopherols such as &agr;-tocopherol (vitamin E), &bgr;-carotene, an extract of the bark of the maritime pine, Pinus maritima and combinations thereof. The extract of the bark of the maritime pine, also known as PYCNOGENOL™, contains procyanidines consisting of catechin and epicatechin units linked by C—C bonds to form dimers, trimers and other oligomers up to a chain length of 6-7 molecules and phenolic acids and its glucose derivatives. PYCNOGENOL™ is produced according to U.S. Pat. No. 4,698,360, which is incorporated herein for reference. The extract used according to the invention may be prepared essentially by extracting maritime pine bark in comminuted form with boiling water, saturating the filtered extract with sodium chloride or, alternatively, adding ammonium sulfate to 20% w/v, separating the precipitate formed, repeatedly extracting the supernatant with {fraction (1/10)} volume of ethyl acetate, drying the collected ethyl acetate extracts, concentrating the dried extract, pouring it into 3 volumes of chloroform with stirring and collecting the precipitate which may be purified by repeating the dissolution in ethyl acetate and precipitation with chloroform. Mixtures of the above antioxidants can also be used.
A suitable dispersant is any biologically acceptable surface active agent, examples of which include, but are not limited to, an alkyl polyglycoside, lecithin, polysorbate 80, sodium lauryl sulfate, and the like. The alkyl polyglycosides which can be used in the invention have the formula V
R
1
O(R
2
O)
b
(Z)
a
  V
wherein R
1
is a monovalent organic radical having from about 6 to about 3

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