CA1284337C - Huiles de cuisson synthetiques renfermant des esters d'acides dicarboxyliques - Google Patents

Huiles de cuisson synthetiques renfermant des esters d'acides dicarboxyliques

Info

Publication number: CA1284337C
Authority: CA; Canada
Prior art keywords: diester; edible oil; radical; synthetic edible; carbon atoms
Prior art date: 1986-02-06
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 - Lifetime

Application number

CA000501295A

Other languages

English (en)

Inventor

John G. Fulcher

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Frito Lay Inc

Original Assignee

Frito Lay Inc

Priority date (The priority date 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 date listed.)

1986-02-06

Filing date

1986-02-06

Publication date

1991-05-21

1986-02-06 Application filed by Frito Lay Inc filed Critical Frito Lay Inc

1986-02-06 Priority to CA000501295A priority Critical patent/CA1284337C/fr

1991-05-21 Application granted granted Critical

1991-05-21 Publication of CA1284337C publication Critical patent/CA1284337C/fr

2008-05-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000008162 cooking oil Substances 0.000 title description 2
150000001990 dicarboxylic acid derivatives Chemical class 0.000 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
150000005690 diesters Chemical class 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
241000124008 Mammalia Species 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
-1 alkyl radical Chemical class 0.000 claims description 27
239000008157 edible vegetable oil Substances 0.000 claims description 22
235000013305 food Nutrition 0.000 claims description 17
YNKNRQTXVROGIX-ZHTVLWRQSA-N bis[(z)-octadec-9-enyl] 2,2-dihexadecylpropanedioate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)C(CCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCC)C(=O)OCCCCCCCC\C=C/CCCCCCCC YNKNRQTXVROGIX-ZHTVLWRQSA-N 0.000 claims description 9
MVDKKZZVTWHVMC-UHFFFAOYSA-N 2-hexadecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)=O MVDKKZZVTWHVMC-UHFFFAOYSA-N 0.000 claims description 7
235000015112 vegetable and seed oil Nutrition 0.000 claims description 7
238000002844 melting Methods 0.000 claims description 6
230000008018 melting Effects 0.000 claims description 6
210000000813 small intestine Anatomy 0.000 claims description 6
239000008158 vegetable oil Substances 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 4
239000002285 corn oil Substances 0.000 claims description 4
235000005687 corn oil Nutrition 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
230000002503 metabolic effect Effects 0.000 claims description 3
235000019737 Animal fat Nutrition 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
150000003254 radicals Chemical class 0.000 claims 2
238000010438 heat treatment Methods 0.000 claims 1
239000003921 oil Substances 0.000 abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
235000019198 oils Nutrition 0.000 description 17
150000001875 compounds Chemical class 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000003925 fat Substances 0.000 description 7
235000019197 fats Nutrition 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
150000002632 lipids Chemical class 0.000 description 4
150000003626 triacylglycerols Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
102000019280 Pancreatic lipases Human genes 0.000 description 3
108050006759 Pancreatic lipases Proteins 0.000 description 3
235000013367 dietary fats Nutrition 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
229940055577 oleyl alcohol Drugs 0.000 description 3
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
229940116369 pancreatic lipase Drugs 0.000 description 3
108091016642 steapsin Proteins 0.000 description 3
239000000126 substance Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
235000019577 caloric intake Nutrition 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001793 charged compounds Chemical class 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
150000000185 1,3-diols Chemical class 0.000 description 1
HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
CMMJFNRRYIRABI-UHFFFAOYSA-N 2,2-dihexadecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)(C(O)=O)CCCCCCCCCCCCCCCC CMMJFNRRYIRABI-UHFFFAOYSA-N 0.000 description 1
235000021411 American diet Nutrition 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
240000008415 Lactuca sativa Species 0.000 description 1
239000004367 Lipase Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
230000029087 digestion Effects 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003778 fat substitute Substances 0.000 description 1
235000013341 fat substitute Nutrition 0.000 description 1
235000021588 free fatty acids Nutrition 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
125000005645 linoleyl group Chemical group 0.000 description 1
229940040461 lipase Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000346 malonyl group Chemical group C(CC(=O)*)(=O)* 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
235000013310 margarine Nutrition 0.000 description 1
239000003264 margarine Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
235000012045 salad Nutrition 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1

Landscapes

Edible Oils And Fats (AREA)
Coloring Foods And Improving Nutritive Qualities (AREA)

CA000501295A 1986-02-06 1986-02-06 Huiles de cuisson synthetiques renfermant des esters d'acides dicarboxyliques Expired - Lifetime CA1284337C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000501295A CA1284337C (fr)	1986-02-06	1986-02-06	Huiles de cuisson synthetiques renfermant des esters d'acides dicarboxyliques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000501295A CA1284337C (fr)	1986-02-06	1986-02-06	Huiles de cuisson synthetiques renfermant des esters d'acides dicarboxyliques

Publications (1)

Publication Number	Publication Date
CA1284337C true CA1284337C (fr)	1991-05-21

Family

ID=4132426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000501295A Expired - Lifetime CA1284337C (fr)	1986-02-06	1986-02-06	Huiles de cuisson synthetiques renfermant des esters d'acides dicarboxyliques

Country Status (1)

Country	Link
CA (1)	CA1284337C (fr)

1986
- 1986-02-06 CA CA000501295A patent/CA1284337C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1993-11-23	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 19931123

Publication	Publication Date	Title
US4582927A (en)	1986-04-15	Synthetic cooking oils containing dicarboxylic acid esters
US4673581A (en)	1987-06-16	Fried food product fried in synthetic cooking oils containing dicarboxylic acid esters
US5603978A (en)	1997-02-18	Esterified propylene oxide-extended glycerols useful as fat substitutes
US4582715A (en)	1986-04-15	Acylated glycerides useful in low calorie fat-containing food compositions
EP0757031B1 (fr)	2000-03-15	Succédané de graisse pauvre en calories
US3579548A (en)	1971-05-18	Triglyceride esters of alpha-branched carboxylic acids
US4959466A (en)	1990-09-25	Partially esterified polysaccharide (PEP) fat substitutes
US5858439A (en)	1999-01-12	Reduced calorie fat mimetics comprising esterified propoxylated monoglycerides and diglycerides
EP0325010B1 (fr)	1993-03-24	Substituts non-digestibles de valeur basse calorique pour les matières grasses
US6617141B1 (en)	2003-09-09	Enzymatic process for preparing reduced-calorie fats containing behenic acid
CA1284337C (fr)	1991-05-21	Huiles de cuisson synthetiques renfermant des esters d'acides dicarboxyliques
AU594040B2 (en)	1990-03-01	Synthetic cooking oils containing dicarboxylic acid esters
US5043179A (en)	1991-08-27	Triol triester derivatives as low calorie fat mimetics
US5068119A (en)	1991-11-26	Acid-hydrolyzable ester derivatives as low calorie fat mimetics
WO2001060172A1 (fr)	2001-08-23	Compositions grasses hypocaloriques
RU2008771C1 (ru)	1994-03-15	Низкокалорийный пищевой продукт
US20010048964A1 (en)	2001-12-06	Low calorie fat compositions
JP2003253293A (ja)	2003-09-10	低カロリー脂肪代替組成物及びその組成物を含有する食品