USRE23329E - Antioxidant - Google Patents
Antioxidant Download PDFInfo
- Publication number
- USRE23329E USRE23329E US23329DE USRE23329E US RE23329 E USRE23329 E US RE23329E US 23329D E US23329D E US 23329DE US RE23329 E USRE23329 E US RE23329E
- Authority
- US
- United States
- Prior art keywords
- antioxidant
- composition
- propylene glycol
- water
- fatty
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 230000003078 antioxidant Effects 0.000 title description 25
- 239000003963 antioxidant agent Substances 0.000 title description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 26
- 235000006708 antioxidants Nutrition 0.000 description 24
- 239000000843 powder Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 235000013601 eggs Nutrition 0.000 description 12
- LNTHITQWFMADLM-UHFFFAOYSA-N Gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 10
- 235000013305 food Nutrition 0.000 description 10
- 229940075579 Propyl Gallate Drugs 0.000 description 9
- 239000003925 fat Substances 0.000 description 9
- 235000019197 fats Nutrition 0.000 description 9
- ZTHYODDOHIVTJV-UHFFFAOYSA-N propyl 3,4,5-trihydroxybenzoate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 9
- 235000010388 propyl gallate Nutrition 0.000 description 9
- 239000000473 propyl gallate Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 229940074391 Gallic acid Drugs 0.000 description 5
- 235000010323 ascorbic acid Nutrition 0.000 description 5
- 229960005070 ascorbic acid Drugs 0.000 description 5
- 235000004515 gallic acid Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 235000008939 whole milk Nutrition 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Vitamin C Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 235000014438 salad dressings Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 235000014121 butter Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000003000 nontoxic Effects 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 2
- -1 gallic acid ester Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- 229940039717 Lanolin Drugs 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 231100000229 OECD 452 Chronic Toxicity Study Toxicity 0.000 description 1
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012495 crackers Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000015071 dressings Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000021149 fatty food Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M palmitate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000087 stabilizing Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C15/00—Butter; Butter preparations; Making thereof
- A23C15/18—Preservation
- A23C15/20—Preservation by addition of preservatives or antioxidants
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C3/00—Preservation of milk or milk preparations
- A23C3/08—Preservation of milk or milk preparations by addition of preservatives
Definitions
- This invention relates to an antioxidant and A more particularly to anantioxidant composition with non-toxic qualities. It is an object of the invention to provide an antioxidant material for stabilizing and preserving such food substancesas butter, salad dressings, mayonnaise, cheese spreads, whole milk powder, egg powder, margarine, lanolin, and other fatty food products. or food products containing amounts of fatty matter sufliciently large to make them subject to rancidity development and which contain a considerable amount of moisture or water in the form of an emulsion.
- propyl gallate is an excellent antioxidant but it is not readily soluble in oil mixtures. Further, it is practically insoluble in fatty emulsions or those products which contain water as a part of their composition. Propyl gallate is, however, very freely soluble in propylene glycol, and propylene glycol is readily miscible with emulsions or with fatty mixtures which contain water.
- Other gallic acid esters may likewise be incorporated in similar solvents.
- ascorbic acid and its esters such as isoascorbyl palmitate, may be dissolved in propylene glycol and then incorporated in the fats and fatty emulsions.
- My antioxidant composition is particularly desirable and efiicient for such products as salad dressings, and in the manufacture of egg powder and whole milk powder.
- a good salad dressing contains, among other ingredients, approximately 42% water and 42% vegetable oil (corn or cottonseed oil). Rancidity development (which is a frequent occurrence in these products), is due largely to this high percentage of oil.
- the stability of these dressings can be materially increased by the addition of 0.25% to 0.50% of my antioxidant composition either to the fat or oil before emulsiiication or incorporation with the other ingredients.
- the egg powder is many times more stable against rancidity and consequent unpalatability.
- the liquid whole. eggs contain an average of 73.7% water and 10.5% fat, and that any antioxidant, used must either be emulsiflable or be incorporated in an edible solvent which is water miscible. Propylene glycol is water miscible and chronic toxicity studies have proved it is non-toxic.
- Egg powder contains an average of from 2% to 5% water and 45% to 50% fat. The use of my antioxidant composition in this product eliminates the need of gas-packing as frequently done at present to extend the keeping time of egg powders.
- Whole milk powder has not found a ready market because of unpalatability due to rapid rancidity development of butter i'at it contains. This is also true of cream powder.
- Whole milk powder averages 25% to 35% fat and 1.5%.to 5% water.
- My antioxidant in amounts of 0.125% to 0.25% can be added to protect the stability of the butter fat, preferably after vacuum pan concentration, although it can be added at any time during the manufacture of the powder before ying.
- the ratio of propyl gallate to propylene glycol is not critical, since the latter is essentially a carrier for the former.
- the important element is the proportion of gallic acid ester in the final product. It is there normally from .0005% to .005% of the fat to be protected.
- the proportion of the ascorbyl palmitate and ascorbic acid esters is normally about the same as that of propyl gallate.
- An antioxidant composition comprising a solution of an antioxidant acid ester selected from the group consisting of esters of ascorbic and gallic acid, which ester is soluble in propylene glycol in propylene glycol] [2.
- antioxidant ester is a gallic acid ester-J [3.
- a composition as set forth tateJ [5. A composition as set forth tateJ [6. An antioxidant composition consisting of a'small proportion of propyl gallate and a large.
- a 'food mmposition comprising a fatty substance containing an important percentage of water having distributed substantially uniformly therethrough an antioxidant composition comprising a solution of an antioxidant acid ester m claim 1. m which the antioxidant ester is ascorbyl palmi- 4 group consisting of ascorbic and gallic acid. which ester is soluble in the propylene glycol.
- a food composition comprising a fatty substance containing an important percentage of water having distributed substantially unifoflnly therethrough an antioxidant composition comprising propylene glycol and a small proportion of propyl gallate.
- a food composition comprising a fatty substance containing an important percentage of water having'distributed substantially uniformly therethrough an antioxidant composition comselected from the group consistin of esters of ascorbic and gallic acid, which ester is soluble in propylene glycol, in propylene glycol.
- the fatty material is egg powder.
- a food composition comprising a fatty substance containing an important percentage of water having distributed substantially uniformly therethrough an antioxidant composition comprising propylene glycol, and a small proportion of a nontoxic ester of an acid selected from the prising propylene glycol and a small proportion of propyl gallate, the proportion of propyl gailate in the food composition being approximately .0005 to 905% of the fatty constituent thereof.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Seasonings (AREA)
Description
Reiseued Jen. is, 1951 ANTIOXIDANT Lloyd A. Hall, Chicago, Ill., assignor to The Gritiith Laboratories, Inc., a corporation of Delaware No Drawing. Original No. 2,500,543, dated March 14, 1950, Serial No. 806,282, July 20, 1945. Application for reissue April 20, 1950, Serial No.
7 Claims. (Cl. 99-103) Matter enclosed in heavy brackets appears in the original patent but forms no part oftliis reissue specification; matter printed in italics indicates the additions made by reissue This invention relates to an antioxidant and A more particularly to anantioxidant composition with non-toxic qualities. It is an object of the invention to provide an antioxidant material for stabilizing and preserving such food substancesas butter, salad dressings, mayonnaise, cheese spreads, whole milk powder, egg powder, margarine, lanolin, and other fatty food products. or food products containing amounts of fatty matter sufliciently large to make them subject to rancidity development and which contain a considerable amount of moisture or water in the form of an emulsion.
It has been found diflicult properly to incorporate a good many antioxidant materials in emulsiiied fats. This is due to the water phase which permits improper protection of the fatty matter because of separation. For example, propyl gallate is an excellent antioxidant but it is not readily soluble in oil mixtures. Further, it is practically insoluble in fatty emulsions or those products which contain water as a part of their composition. Propyl gallate is, however, very freely soluble in propylene glycol, and propylene glycol is readily miscible with emulsions or with fatty mixtures which contain water. Other gallic acid esters may likewise be incorporated in similar solvents. Likewise ascorbic acid and its esters, such as isoascorbyl palmitate, may be dissolved in propylene glycol and then incorporated in the fats and fatty emulsions.
As an example of the invention, 4 lbs. of propyl gallate is dissolved in 96 lbs. of propylene glycol. This solution is effected with agitation at a temperature of 120 F. The resulting solution is clear and transparent. The resulting solution may be employed in very small proportion, preferably at the ratio of about 4 oz. to 100 lbs. of fat or oil to be protected. The amounts may be increased beyond this without undesirable effects and may be reduced below it if the amount of protection required is not as great as normal.
My antioxidant composition is particularly desirable and efiicient for such products as salad dressings, and in the manufacture of egg powder and whole milk powder. A good salad dressing contains, among other ingredients, approximately 42% water and 42% vegetable oil (corn or cottonseed oil). Rancidity development (which is a frequent occurrence in these products), is due largely to this high percentage of oil. The stability of these dressings can be materially increased by the addition of 0.25% to 0.50% of my antioxidant composition either to the fat or oil before emulsiiication or incorporation with the other ingredients.
One of the reasons for the unpalatability of egg .powder is the rancidity developed by the e lat. In the processing of whole eggs for the I manufacture of whole egg powder, the liquid fore atomizing into the spray dryer.
whole eggs are whipped together, forming an emulsion before pumping to the spray nozzle be- When my antioxidant composition is added to the egg emulsion in an amount 2 oz. to 4 oz. per 100.1bs. of emulsion and the product dried, the egg powder is many times more stable against rancidity and consequent unpalatability. In this example, it should be understood the liquid whole. eggs contain an average of 73.7% water and 10.5% fat, and that any antioxidant, used must either be emulsiflable or be incorporated in an edible solvent which is water miscible. Propylene glycol is water miscible and chronic toxicity studies have proved it is non-toxic. Egg powder contains an average of from 2% to 5% water and 45% to 50% fat. The use of my antioxidant composition in this product eliminates the need of gas-packing as frequently done at present to extend the keeping time of egg powders.
Whole milk powder has not found a ready market because of unpalatability due to rapid rancidity development of butter i'at it contains. This is also true of cream powder. Whole milk powder averages 25% to 35% fat and 1.5%.to 5% water. My antioxidant in amounts of 0.125% to 0.25% can be added to protect the stability of the butter fat, preferably after vacuum pan concentration, although it can be added at any time during the manufacture of the powder before ying.
The ratio of propyl gallate to propylene glycol is not critical, since the latter is essentially a carrier for the former. The important element is the proportion of gallic acid ester in the final product. It is there normally from .0005% to .005% of the fat to be protected.
The proportion of the ascorbyl palmitate and ascorbic acid esters is normally about the same as that of propyl gallate.
The foregoing detailed description has been given for clearness of understanding only, and no unnecessary limitations should be understood therefrom.
What I claim as new, and desire to secure by Letters Patent, is:
[1. An antioxidant composition comprising a solution of an antioxidant acid ester selected from the group consisting of esters of ascorbic and gallic acid, which ester is soluble in propylene glycol in propylene glycol] [2. A composition as set forth in claim 1. in
a v which the antioxidant ester is a gallic acid ester-J [3. A composition as set forth 'in claim 1. in which the antioxidant ester ispropyl gallateJ [4. A composition as set forth in claim 1, in which the antioxidant ester is ascorbic acid ester.] i
[5. A composition as set forth tateJ [6. An antioxidant composition consisting of a'small proportion of propyl gallate and a large.
proportion of propylene glycol] v ['1. An antioxidant composition consisting of less than 10% propyl gallate and more than 90% r of propylene glycol] 9. A 'food mmposition comprising a fatty substance containing an important percentage of water having distributed substantially uniformly therethrough an antioxidant composition comprising a solution of an antioxidant acid ester m claim 1. m which the antioxidant ester is ascorbyl palmi- 4 group consisting of ascorbic and gallic acid. which ester is soluble in the propylene glycol.
13. A food composition comprising a fatty substance containing an important percentage of water having distributed substantially unifoflnly therethrough an antioxidant composition comprising propylene glycol and a small proportion of propyl gallate. I
14. A food composition comprising a fatty substance containing an important percentage of water having'distributed substantially uniformly therethrough an antioxidant composition comselected from the group consistin of esters of ascorbic and gallic acid, which ester is soluble in propylene glycol, in propylene glycol.
'9. A food composition as set forth in claim 8.
, in which the fatty material is egg powder.
10. A food composition as set forth in claim 8,- 1 in which the fatty material is whole milk powder.
11. A food composition as set forth in claim 8, in which the fatty material is salad dressing.
12. A food composition comprising a fatty substance containing an important percentage of water having distributed substantially uniformly therethrough an antioxidant composition comprising propylene glycol, and a small proportion of a nontoxic ester of an acid selected from the prising propylene glycol and a small proportion of propyl gallate, the proportion of propyl gailate in the food composition being approximately .0005 to 905% of the fatty constituent thereof.
I LLOYD A. HALL.
. 'amaancas crran The following references are of record in the file of this patent or the original patent:
UNITED STATES PATENTS Number Name Date 1,784,360 Kaegebehn' 'Dec. 9, 1930 2,199,200 Musher Apr. 23, 1940 r 2,205,820 Cracker June 25, 1940 2,255,191 Sabalitschka Sept. 9, 1941 2,393,816 Riemenschneider Aug. 28, 1945 OTHER REFERENCES Quarterly Journal of Pharmacy and Pharmacology," vol. XVI, No. 3. July-September 1943, 9988s 232-243.
Publications (1)
Publication Number | Publication Date |
---|---|
USRE23329E true USRE23329E (en) | 1951-01-16 |
Family
ID=2090558
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US23329D Expired USRE23329E (en) | Antioxidant |
Country Status (1)
Country | Link |
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US (1) | USRE23329E (en) |
-
0
- US US23329D patent/USRE23329E/en not_active Expired
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