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US4146651A
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Acetals and ketals of ascorbic acid and anti-nitrosamine compositions and methods using same
Assignee: Maple Leaf Foods Inc
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Filing: 1977-05-20
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Granted: 1979-03-27
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Expires: 1997-05-20
Abstract
Abstract Novel acetal and ketal derivatives of ascorbic acid having utility in controlling the formation of undesirable nitrosamines in cooked, nitrite cured meat products are disclosed. Meat treating compositions containing these compounds, methods of treating meats with same and meat products containing same are also disclosed.
Inventors
- 👤 Kekhusroo R. Bharucha
- 👤 Charles K. Cross
- 👤 Leon J. Rubin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 20:39
CPC Classifications
A; A23; A23B; A23B4/00; A23B4/14; A23B4/18; A23B4/20; A23B4/02; A23B4/023; A23B4/0235
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
154 words
The process for nitrosamine control in nitrite cured meats comprising treating the meat with a composition containing a derivative of ascorbic acid of the formula: ##STR2## wherein R' is hydrogen or a hydrocarbon group having from 1 to 7 carbon atoms and R" is alkyl or alkenyl of 6 to 20 carbon atoms, either straight or branched chain, with the proviso that the total number of carbon atoms in R' and R" is at least 10, or R" is a hydrocarbon chain of one to fourteen carbon atoms substituted by a mono or bicyclic hydrocarbon radical wherein the ring or rings are 5 or 6 membered and wherein the ring or rings may each contain up to 3 alkyl or alkenyl substituents or from one to seven carbon atoms, or an edible salt thereof, in an amount effective to reduce the quantity of nitrosamines formed when the cured meat is cooked at frying temperatures.
Claim 2
Dependent Claim
154 words
The process for nitrosamine control in nitrite cured meats comprising treating the meat with a composition containing a derivative of ascorbic acid of the formula: ##STR2## wherein R' is hydrogen or a hydrocarbon group having from 1 to 7 carbon atoms and R" is alkyl or alkenyl of 6 to 20 carbon atoms, either straight or branched chain, with the proviso that the total number of carbon atoms in R' and R" is at least 10, or R" is a hydrocarbon chain of one to fourteen carbon atoms substituted by a mono or bicyclic hydrocarbon radical wherein the ring or rings are 5 or 6 membered and wherein the ring or rings may each contain up to 3 alkyl or alkenyl substituents or from one to seven carbon atoms, or an edible salt thereof, in an amount effective to reduce the quantity of nitrosamines formed when the cured meat is cooked at frying temperatures.
Claim 3
Dependent Claim
28 words
The process as defined by claim 1, wherein the treatment comprises incorporating said derivative or salt in a nitrite curing solution and injecting said solution into the meat.
Claim 4
Dependent Claim
31 words
The process as defined by claim 1, wherein the treatment comprises dissolving said derivative or salt in a liquid solvent medium and applying the solution to surfaces of sliced cured meat.
Claim 5
Dependent Claim
13 words
The process as defined by claim 3, wherein the meat is sliced bacon.
Claim 6
Dependent Claim
26 words
The process as defined by claim 4, wherein the treatment comprises applying to slices of cured bacon an edible oil solution containing said derivative or salt.
Claim 7
Dependent Claim
18 words
The process as defined by claim 1, wherein the meat is a pork cut for production of bacon.
Claim 8
Dependent Claim
25 words
The process as defined by claim 6, wherein the treatment comprises curing said pork cut with a nitrite curing solution containing said derivative or salt.
Claim 9
Dependent Claim
45 words
The process as defined by claim 1, wherein the derivative is applied to the meat in an amount such that the cured meat contains from about 500 to 1000 parts by weight of the derivative or salt per million parts by weight of the meat.
Claim 10
Dependent Claim
21 words
The process as defined by claim 1, wherein R' is hydrogen and R" is alkyl having 12 to 20 carbon atoms.
Claim 11
Dependent Claim
21 words
The process as defined in claim 1, wherein R' is hydrogen and R" is alkenyl of 12 to 20 carbon atoms.
Claim 12
Dependent Claim
32 words
The process of claim 1, wherein the said derivative is selected from the group consisting of the acetals of tetradecanal, hexadecanal, octadecanal and octadec-9-en-1-al with ascorbic acid and the sodium salts thereof.
Claim 13
Dependent Claim
26 words
The process of claim 1, wherein the meat is treated with a derivative of erythorbic acid of the recited formula or with an edible salt thereof.
Claim 14
Dependent Claim
15 words
The process of claim 12, wherein said derivative is the hexadecanal acetal of erythorbic acid.
Claim 15
Dependent Claim
138 words
A nitrite cured meat product containing from about 100 to 1000 parts by weight of an ascorbic acid derivative of the formula: ##STR3## wherein R' is hydrogen or a hydrocarbon group having from 1 to 7 carbon atoms and R" is alkyl or alkenyl of 6 to 20 carbon atoms, either straight or branched chain, with the proviso that the total number of carbon atoms in R' and R" is at least 10, or R" is a hydrocarbon chain of one to fourteen carbon atoms substituted by a mono or bicyclic hydrocarbon radical wherein the ring or rings are 5 or 6 membered and wherein the ring or rings may each contain up to 3 alkyl or alkenyl substituents of from one to seven carbon atoms, or edible salt thereof, per million parts by weight of the meat.
Claim 16
Dependent Claim
138 words
A nitrite cured meat product containing from about 100 to 1000 parts by weight of an ascorbic acid derivative of the formula: ##STR3## wherein R' is hydrogen or a hydrocarbon group having from 1 to 7 carbon atoms and R" is alkyl or alkenyl of 6 to 20 carbon atoms, either straight or branched chain, with the proviso that the total number of carbon atoms in R' and R" is at least 10, or R" is a hydrocarbon chain of one to fourteen carbon atoms substituted by a mono or bicyclic hydrocarbon radical wherein the ring or rings are 5 or 6 membered and wherein the ring or rings may each contain up to 3 alkyl or alkenyl substituents of from one to seven carbon atoms, or edible salt thereof, per million parts by weight of the meat.
Claim 17
Dependent Claim
14 words
The product as defined by claim 14 wherein the nitrite cured meat is bacon.
Claim 18
Dependent Claim
26 words
The product as defined by claim 14 wherein in said ascorbic acid derivative R' is hydrogen and R" is alkyl of 12 to 20 carbon atoms.
Claim 19
Dependent Claim
26 words
The product as defined by claim 14, wherein in said ascorbic acid derivative R' is hydrogen and R" is alkenyl of 12 to 20 carbon atoms.
Claim 20
Dependent Claim
27 words
The product of claim 14, wherein the ascorbic acid derivative is selected from the group consisting of acetals of tetradecanal, hexadecanal, octadecanal and octadec-9-en-1-al with ascorbic acid.
Claim 21
Dependent Claim
32 words
A nitrite cured meat product as defined in claim 14, wherein the meat contains a derivative of erythorbic acid of the recited formula or an edible salt thereof in the amount specified.
Claim 22
Dependent Claim
20 words
A nitrite cured meat product as defined in claim 19, wherein said derivative is the hexadecanal acetal of erythorbic acid.
Claim 23
Dependent Claim
131 words
A meat curing composition containing a nitrite meat curing salt and, as an anti-nitrosamine agent, an ascorbic acid derivative of the formula: ##STR4## wherein R' is hydrogen or a hydrocarbon group having from 1 to 7 carbon atoms and R" is alkyl or alkenyl of 6 to 20 carbon atoms, either straight or branched chain, with the proviso that the total number of carbon atoms in R' and R" is at least 10, or R" is a hydrocarbon chain of one to fourteen carbon atoms substituted by a mono or bicyclic hydrocarbon radical wherein the ring or rings are 5 or 6 membered and wherein the ring or rings may each contain up to 3 alkyl or alkenyl substituents of from one to seven carbon atoms, or an edible salt thereof.
Claim 24
Dependent Claim
131 words
A meat curing composition containing a nitrite meat curing salt and, as an anti-nitrosamine agent, an ascorbic acid derivative of the formula: ##STR4## wherein R' is hydrogen or a hydrocarbon group having from 1 to 7 carbon atoms and R" is alkyl or alkenyl of 6 to 20 carbon atoms, either straight or branched chain, with the proviso that the total number of carbon atoms in R' and R" is at least 10, or R" is a hydrocarbon chain of one to fourteen carbon atoms substituted by a mono or bicyclic hydrocarbon radical wherein the ring or rings are 5 or 6 membered and wherein the ring or rings may each contain up to 3 alkyl or alkenyl substituents of from one to seven carbon atoms, or an edible salt thereof.
Claim 25
Dependent Claim
24 words
The composition of claim 21, wherein in said ascorbic acid derivative R' is hydrogen and R" is alkyl of 12 to 20 carbon atoms.
Claim 26
Dependent Claim
24 words
The composition of claim 21, wherein in said ascorbic acid derivative R' is hydrogen and R" is alkenyl of 12 to 20 carbon atoms.
Claim 27
Dependent Claim
33 words
The composition of claim 21, wherein the ascorbic acid derivative is selected from the group consisting of the acetals of tetradecanal, hexadecanal, octadecanal and octadec-9-en-1-al with ascorbic acid and the sodium salts thereof.
Claim 28
Dependent Claim
20 words
The composition of claim 21, wherein said ascorbic acid derivative is a derivative of erythorbic acid of the recited formula.
Claim 29
Dependent Claim
15 words
The composition of claim 25, wherein said derivative is the hexadecanal acetal of erythorbic acid.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-03-26 | 1982-09-25 | 1983-03-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-26 | 1986-09-25 | 1987-03-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-26 | 1990-09-25 | 1991-03-27 | $7700.00 | Window Closed / Lapsed |