WO2011073035A1 - Maillard flavor compositions with polar solvents different from water and methods for making such compositions - Google Patents
Maillard flavor compositions with polar solvents different from water and methods for making such compositions Download PDFInfo
- Publication number
- WO2011073035A1 WO2011073035A1 PCT/EP2010/068688 EP2010068688W WO2011073035A1 WO 2011073035 A1 WO2011073035 A1 WO 2011073035A1 EP 2010068688 W EP2010068688 W EP 2010068688W WO 2011073035 A1 WO2011073035 A1 WO 2011073035A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polar solvent
- phase
- maillard
- lipid
- oil
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 233
- 239000002798 polar solvent Substances 0.000 title claims abstract description 125
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 92
- 235000019634 flavors Nutrition 0.000 title claims abstract description 92
- 238000000034 method Methods 0.000 title claims abstract description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 150000002632 lipids Chemical class 0.000 claims abstract description 183
- 235000013305 food Nutrition 0.000 claims abstract description 132
- 108010005094 Advanced Glycation End Products Proteins 0.000 claims abstract description 59
- 230000002708 enhancing effect Effects 0.000 claims abstract description 23
- 239000000376 reactant Substances 0.000 claims description 119
- 238000006243 chemical reaction Methods 0.000 claims description 99
- 239000003921 oil Substances 0.000 claims description 80
- 241001465754 Metazoa Species 0.000 claims description 64
- 239000003995 emulsifying agent Substances 0.000 claims description 61
- 239000000839 emulsion Substances 0.000 claims description 48
- 239000004530 micro-emulsion Substances 0.000 claims description 46
- 235000019198 oils Nutrition 0.000 claims description 39
- 239000000047 product Substances 0.000 claims description 32
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 23
- 235000019197 fats Nutrition 0.000 claims description 23
- 125000003277 amino group Chemical group 0.000 claims description 21
- 238000002156 mixing Methods 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 244000144977 poultry Species 0.000 claims description 8
- 235000013594 poultry meat Nutrition 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 230000007071 enzymatic hydrolysis Effects 0.000 claims description 7
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 7
- 235000015278 beef Nutrition 0.000 claims description 6
- 230000001804 emulsifying effect Effects 0.000 claims description 6
- 239000000787 lecithin Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 235000010445 lecithin Nutrition 0.000 claims description 5
- 229920000223 polyglycerol Polymers 0.000 claims description 5
- 239000003760 tallow Substances 0.000 claims description 5
- 241000287828 Gallus gallus Species 0.000 claims description 4
- 150000003904 phospholipids Chemical class 0.000 claims description 4
- 238000001338 self-assembly Methods 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 3
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 235000019687 Lamb Nutrition 0.000 claims description 3
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 239000002285 corn oil Substances 0.000 claims description 3
- 238000001125 extrusion Methods 0.000 claims description 3
- 239000004006 olive oil Substances 0.000 claims description 3
- 235000008390 olive oil Nutrition 0.000 claims description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- 239000000828 canola oil Substances 0.000 claims description 2
- 235000019519 canola oil Nutrition 0.000 claims description 2
- 239000003240 coconut oil Substances 0.000 claims description 2
- 235000019864 coconut oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 238000009928 pasteurization Methods 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims 1
- 235000019629 palatability Nutrition 0.000 abstract description 70
- 235000015872 dietary supplement Nutrition 0.000 abstract description 27
- 239000003814 drug Substances 0.000 abstract description 23
- 239000012071 phase Substances 0.000 description 130
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 112
- 235000011187 glycerol Nutrition 0.000 description 39
- 239000004615 ingredient Substances 0.000 description 27
- 235000000346 sugar Nutrition 0.000 description 25
- 238000010438 heat treatment Methods 0.000 description 22
- 235000008429 bread Nutrition 0.000 description 21
- 239000000463 material Substances 0.000 description 21
- 239000003925 fat Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 150000008163 sugars Chemical class 0.000 description 17
- 239000003623 enhancer Substances 0.000 description 16
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 15
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 15
- 235000001727 glucose Nutrition 0.000 description 15
- 239000008103 glucose Substances 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
- -1 alkane glycols Chemical class 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 235000001014 amino acid Nutrition 0.000 description 13
- 150000001413 amino acids Chemical class 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 239000000693 micelle Substances 0.000 description 12
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 11
- 235000018417 cysteine Nutrition 0.000 description 11
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 9
- 238000011534 incubation Methods 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 7
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 235000019157 thiamine Nutrition 0.000 description 7
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 7
- 229960003495 thiamine Drugs 0.000 description 7
- 239000011721 thiamine Substances 0.000 description 7
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 6
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 6
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 235000016709 nutrition Nutrition 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 235000018102 proteins Nutrition 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 5
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 5
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 5
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000035611 feeding Effects 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- 229930091371 Fructose Natural products 0.000 description 4
- 239000005715 Fructose Substances 0.000 description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 4
- 235000019789 appetite Nutrition 0.000 description 4
- 230000036528 appetite Effects 0.000 description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
- 235000019568 aromas Nutrition 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 230000007073 chemical hydrolysis Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 238000010411 cooking Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 230000035764 nutrition Effects 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 235000010958 polyglycerol polyricinoleate Nutrition 0.000 description 4
- 235000015277 pork Nutrition 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000013589 supplement Substances 0.000 description 4
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 150000002314 glycerols Chemical class 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- 235000011888 snacks Nutrition 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 210000001835 viscera Anatomy 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- 239000007762 w/o emulsion Substances 0.000 description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 2
- MQFYRUGXOJAUQK-UHFFFAOYSA-N 2-[2-[2-(2-octadecanoyloxyethoxy)ethoxy]ethoxy]ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCOCCOCCOC(=O)CCCCCCCCCCCCCCCCC MQFYRUGXOJAUQK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000007976 Ketosis Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NKSOSPOXQKNIKJ-CLFAGFIQSA-N Polyoxyethylene dioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCOC(=O)CCCCCCC\C=C/CCCCCCCC NKSOSPOXQKNIKJ-CLFAGFIQSA-N 0.000 description 2
- 229930182558 Sterol Chemical class 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000004596 appetite loss Effects 0.000 description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 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
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000008277 ketosamines Chemical class 0.000 description 2
- 150000002584 ketoses Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000021266 loss of appetite Nutrition 0.000 description 2
- 208000019017 loss of appetite Diseases 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- 235000006286 nutrient intake Nutrition 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical class CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
- PAFJZWHXMSQJKV-UQZRNVAESA-N (3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol;octadecanoic acid Chemical compound OC[C@@H](O)C1OC[C@H](O)[C@H]1O.OC[C@@H](O)C1OC[C@H](O)[C@H]1O.OC[C@@H](O)C1OC[C@H](O)[C@H]1O.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O PAFJZWHXMSQJKV-UQZRNVAESA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- NMSBTWLFBGNKON-UHFFFAOYSA-N 2-(2-hexadecoxyethoxy)ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCO NMSBTWLFBGNKON-UHFFFAOYSA-N 0.000 description 1
- ILCOCZBHMDEIAI-UHFFFAOYSA-N 2-(2-octadecoxyethoxy)ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCO ILCOCZBHMDEIAI-UHFFFAOYSA-N 0.000 description 1
- IQUCNXSZNHPPML-UHFFFAOYSA-N 2-chloro-n-[(4-chlorophenyl)-phenylmethyl]acetamide Chemical compound C=1C=C(Cl)C=CC=1C(NC(=O)CCl)C1=CC=CC=C1 IQUCNXSZNHPPML-UHFFFAOYSA-N 0.000 description 1
- ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 2-dodecanoyloxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCC ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 238000003691 Amadori rearrangement reaction Methods 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- YTBSYETUWUMLBZ-UHFFFAOYSA-N D-Erythrose Natural products OCC(O)C(O)C=O YTBSYETUWUMLBZ-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- YTBSYETUWUMLBZ-IUYQGCFVSA-N D-erythrose Chemical compound OC[C@@H](O)[C@@H](O)C=O YTBSYETUWUMLBZ-IUYQGCFVSA-N 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- YTBSYETUWUMLBZ-QWWZWVQMSA-N D-threose Chemical compound OC[C@@H](O)[C@H](O)C=O YTBSYETUWUMLBZ-QWWZWVQMSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 206010056474 Erythrosis Diseases 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 241000699694 Gerbillinae Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 241000219745 Lupinus Species 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000282339 Mustela Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000010399 Wasting Syndrome Diseases 0.000 description 1
- NCHJGQKLPRTMAO-XWVZOOPGSA-N [(2R)-2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NCHJGQKLPRTMAO-XWVZOOPGSA-N 0.000 description 1
- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 1
- FOLJTMYCYXSPFQ-CJKAUBRRSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@H](O)[C@@H](CO)O1 FOLJTMYCYXSPFQ-CJKAUBRRSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 239000006053 animal diet Substances 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229930183167 cerebroside Natural products 0.000 description 1
- 150000001784 cerebrosides Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 1
- 229940031016 ethyl linoleate Drugs 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 150000002270 gangliosides Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000011194 good manufacturing practice Methods 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 150000002386 heptoses Chemical class 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 210000000003 hoof Anatomy 0.000 description 1
- 210000003284 horn Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000019866 hydrogenated palm kernel oil Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 229940074928 isopropyl myristate Drugs 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940075495 isopropyl palmitate Drugs 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 231100000647 material safety data sheet Toxicity 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940032066 peg-4 dilaurate Drugs 0.000 description 1
- 229940032052 peg-8 dioleate Drugs 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000003996 polyglycerol polyricinoleate Substances 0.000 description 1
- 229940104257 polyglyceryl-6-dioleate Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XEIOPEQGDSYOIH-MURFETPASA-N propan-2-yl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(C)C XEIOPEQGDSYOIH-MURFETPASA-N 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229940120731 pyruvaldehyde Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003538 tetroses Chemical class 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 210000000515 tooth Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 150000003641 trioses Chemical class 0.000 description 1
- 235000000112 undernutrition Nutrition 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
- A23L27/215—Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning
Definitions
- the invention relates generally to flavor compositions and methods for making flavor compositions and particularly to Maillard flavor compositions, methods for making Maillard compositions, and their use for enhancing palatability of comestible compositions.
- nonenzymic browning comprises pyrolysis, carmelization, and Maillard reactions.
- Maillard reaction may be the most significant.
- the Maillard reaction is actually a group of complex chemical reactions between available carbonyl groups and available amino groups.
- reducing groups can be found on reducing sugars and amino groups can be found on free amino acids, peptides, and proteins.
- a reactive carbonyl group of a reducing sugar condenses with a free amino group, with a concomitant loss of a water molecule.
- the resultant N-substituted glycoaldosylamine is not stable.
- the aldosylamine compound rearranges, through an Amadori rearrangement, to form a ketosamine.
- Ketosamines that are so-formed may further react through any of the following three pathways: (a) further dehydration to form reductones and dehydroreductones; (b) hydrolytic fission to form short chain products, such as diacetyl, acetol, pyruvaldehyde, and the like, which can, in turn, undergo Strecker degradation with additional amino groups to form aldehydes, and condensation, to form aldols; and (c) loss of water molecules, followed by reaction with additional amino groups and water, followed by condensation and/or polymerization into melanoids.
- Factors that affect the rate and/or extent of Maillard reactions include among others the temperature, water activity (A w ), and pH.
- the Maillard reaction is enhanced by high temperature, low moisture levels (e.g., Aw from about 0.6 to about 0.7), and alkaline pH.
- the skilled artisan will appreciate that Maillard reactions are thus very complex and a great variety of reaction products can be generated.
- the reaction may generate compounds that contribute to the palatability of a food or to a unique flavor profile associated with that food cooked in a particular way.
- WO/03/051139 Al discloses the method for producing a composition for chicken flavors which includes making the Maillard reaction in a water phase and adding oil after start of the chemical reactions. This is very different from the present invention where the complete reaction occurs in the presence of oil, of an emulsifier and of at least one polar solvent, which is different from water.
- Emulsions in food systems are also well known. Both oil- in- water (e.g., salad dressings, milk) and water-in-oil (e.g., butter, margarine) emulsions are common.
- W09962357 discloses emulsions used for various purposes in the food industry, including delivery of flavor compositions.
- US20080038428 proposes using emulsions with an aqueous continuous phase as a means of conducting Maillard reactions.
- WO2007060177 discloses an oil-in-water emulsion wherein the oil droplets are structured using emulsifiers that can be useful for performing a Maillard reaction.
- WO00033671 discloses processes for producing Maillard reaction aroma products in an emulsifier and water mixture. However, no oil and no polar solvent different from water is used. With these 2 parameters, the man skilled in the art cannot predict the efficiency of the Maillard reaction in the particular system of the present invention which is clearly demonstrated in example 1. These systems are useful but inefficient for conducting Maillard reactions and delivering Maillard compositions useful for enhancing palatability. There is, therefore, a need for new and efficient methods for producing Maillard reaction products and Maillard compositions that are useful for enhancing palatability.
- compositions comprise a structured lipid phase comprising a continuous lipid phase comprising a lipid and a dispersed polar solvent.
- a polar solvent is a polar solvent different from water or a mixture of polar solvents where at least one of the polar solvents is different form water.
- the composition comprises at least a first reactant having a free carbonyl group and a second reactant having an amino group available for reaction with the free carbonyl on the first reactant.
- Maillard reaction occurs between the first reactant and the second reactant. This reaction produces at least one Maillard reaction product.
- Maillard flavor compositions are useful for enhancing the palatability of products to an animal, e.g., food compositions.
- FIG. 1 illustrates a polar solvent-in-oil microemulsion.
- Polar solvent may comprize water or not.
- the continuous phase is an oil wherein the typical size of the polar solvent domain is between 0.5 and 100 nm and an emulsifier is used to obtain this structure.
- emulsifiers There might be one type of emulsifiers or several types of emulsifiers.
- FIG. 2 illustrates a polar solvent -in-oil emulsion.
- Polar solvent may comprize water or not.
- the continuous phase is an oil wherein the typical size of the polar solvent domain is between 50 nm and 1 mm and an emulsifier might be used to obtain this structure.
- FIG. 3 illustrates a mixture between a polar solvent-in-oil emulsion and a polar solvent-in-oil microemulsion. It is composed of polar solvent-in-oil emulsion droplets and polar solvent-in-oil microemulsion droplets. The two types of droplets define polar solvent domains which are surrounded by emulsifiers. There might be one type of emulsifiers or several types of emulsifiers. The size of the polar solvent domains are typically the sizes of a polar solvent-in-oil emulsion droplet or of polar solvent microemulsion droplet. [ ⁇ Laurent, Send drawing ⁇ ]
- structured lipid or “structured lipid phase” means a polar solvent-in-lipid dispersion comprising a continuous lipid phase made of oil, lipid or emulsifiers (also called lipohilic additives), and a dispersed polar solvent featuring polar solvent domains that are dispersed, emulsified, or microemulsified within the lipidic phase.
- the polar solvent may be a mixture of various solvents including at least one polar solvent different from water.
- polar solvent includes low molecular weight glycols, alkane glycols and mixtures thereof , as well as mixtures of these polar solvents with water.
- low molecular weight glycols include glycerol (glycerine), propylene glycol and di propylene glycol. Any low molecular weight glycol can be used.
- alkane polyols correspond to the formula R-CH2-(CHOH)n-CH20H, wherein n is a whole number from 0 to 4 and R corresponds to H or OH.
- the polar solvent can also be methanol, propanol, iso-propanol, n-butanol and ethanol.
- a preferred polar solvent is glycerol or a mixture glycerol/water.
- a polar solvent is a polar solvent different from water or a mixture of polar solvents where at least one of the polar solvents is different form water.
- Preferred embodiments of the structured lipid further comprise one or more lipophilic additives (also called emulsifiers) that emulsify or stabilize the structured lipid phase by reducing the surface tension between the continuous and dispersed phases.
- Structured lipids may be present on their own or coexist with a product or with an excess water or with an excess of polar solvent or with an excess of any other food constituant.
- Structured lipids encompass lipids with or without art-recognized structures such as polar solvent-in-oil emulsions, polar solvent-in-oil microemulsions, reversed microemulsions, liquid crystalline structures (e.g., reversed micellar cubic, reversed bicontinuous cubic, or reversed hexagonal structures), lamellar liquid crystalline structures, sponge phases (L3) or the like, or any combinations thereof.
- polar solvent-in-oil emulsions polar solvent-in-oil microemulsions, reversed microemulsions, liquid crystalline structures (e.g., reversed micellar cubic, reversed bicontinuous cubic, or reversed hexagonal structures), lamellar liquid crystalline structures, sponge phases (L3) or the like, or any combinations thereof.
- a reversed structure is defined as a structure in which the stabilizing film is curved towards the polar solvent.
- Preferred structured lipids include reversed polar solvent-in-oil microemulsions, polar solvent-in-oil structures or emulsions, or combinations thereof.
- Reversed microemulsions are preferably of the L2 or bicontinuous type.
- Preferred polar solvent-in-oil reversed microemulsions show a phase separation when diluted with polar solvent, and dilution with polar solvent or with an aqueous phase results in a two phase or in a multiphase system: reversed microemulsion plus polar solvent or aqueous phase or other phases.
- the structured lipid includes any structure that has the characteristic of a polar solvent-in-oil emulsion, polar solvent-in-oil microemulsion, reversed microemulsion, liquid crystalline structure (e.g., reversed micellar cubic, reversed bicontinuous cubic, or reversed hexagonal structures), lamellar liquid crystalline structure, sponge phase (L3) or the like, or any combinations thereof at storage temperatures or at temperatures at which the Maillard reaction occurs or at any temperatures between storage temperatures and temperatures at which the Maillard reaction occurs.
- liquid crystalline structure e.g., reversed micellar cubic, reversed bicontinuous cubic, or reversed hexagonal structures
- lamellar liquid crystalline structure e.g., sponge phase (L3) or the like, or any combinations thereof at storage temperatures or at temperatures at which the Maillard reaction occurs or at any temperatures between storage temperatures and temperatures at which the Maillard reaction occurs.
- lipophilic additive or "emulsifier” means a compound or composition that comprises one or more molecules, compounds, or ingredients for emulsifying or stabilizing a water-in- oil emulsion or a water-in-oil microemulsion.
- the lipophilic additive or emulsifier can also be defined using its hydrophilic-hydrophobic balance (HLB).
- HLB hydrophilic-hydrophobic balance
- Suitable emulsifiers or emulsifier mixtures have a HLB preferably lower than 8, preferably lower than 7.
- Emulsifiers include monoglycerides, including saturated and unsaturated monoglycerides, diglycerides, phospholipids, lecithins, polyglycerol esters of fatty acids, propylene glycerol esters of fatty acids, polyglycerol polyricinoleates, stearoyl lactylates, sorbitan esters of fatty acids, derivatives of the foregoing, salts of the foregoing, particularly sodium and/or calcium salts, or any combinations the foregoing.
- emulsifiers are mono- or di- glyceride esters of fatty acids, for example, esters of tartaric acid, acetic acid, citric acid, lactic acid, sorbic acid, or other edible, food-grade, or food-compatible acids, monoglyceride phosphates, and other derivatives or salts of mono- or diglycerides.
- lipophilic additives are long- chain alcohols, fatty acids, pegylated fatty acids, glycerol fatty acid esters, derivatives of mono- diglycerides, pegylated vegetable oils, sorbitan esters, polyoxyethylene sorbitan esters, propylene glycol mono- or diesters, phosphatides, cerebrosides, gangliosides, cephalins, lipids, glycolipids, sulfatides, sugar esters, sugar ethers, sucrose esters, sterols, polyglycerol esters, myristic acid, oleic acid, lauric acid, stearic acid, palmitic acid, PEG 1-4 stearate, PEG 2-4 oleate, PEG-4 dilaurate, PEG-4 dioleate, PEG-4 distearate, PEG-6 dioleate, PEG-6 distearate, PEG-8-dioleate, PEG-3-16 castor
- Examples of commercial products that may be useful as emulsifiers herein include Dimodan® Distilled Monoglycerides, Panodan® DATEM (Diacetyl Tartaric Acid Esters), GrindstedTM ACETEM (Acetic Acid Esters of Monoglycerides), GrindstedTM CITREM (Citric Acid Esters of Monoglycerides), GrindstedTM LACTEM (Lactic Acid Esters of Monoglycerides), GrindstedTM Mono-Di (Mono and Diglycerides), GrindstedTM PGE or PGPR (Polyglycerol Esters of Fatty Acids, Polyglycerol Polyricinoleate), GrindstedTM PGMS (Propylene Glycerol Esters of Fatty Acids), and GrindstedTM SMS or STS (Sorbitan Monostearate, Sorbitan Tristearate) (all, Danisco, Denmark).
- Dimodan® Distilled Monoglycerides Panodan® DATEM (Diacetyl
- one or more proteins with emulsifying properties may also be useful as emulsifiers, alone, or more preferably, in combination with any other emulsifier or combination thereof.
- Presently preferred emulsifiers comprise saturated or unsaturated monoglycerides, lecithins, phospholipids, or any combination thereof.
- microemulsion means an immiscible lipid-polar solvent system in which a dispersed phase is dispersed within a continuous phase and wherein the droplets, domains, or channels of the dispersed phase are of an average nominal size on the order of less than about 300 nm in diameter. More preferably they average 100 nm, 80 nm, 50 nm, or less.
- the microemulsion contains micelles, droplets, domains, or channels that range in size from about 0.5 to about 300 nm.
- the polar solvent domains ranges in size from 2 to about 200 nm, or 10 to 100 nm.
- Microemulsions are generally thermodynamically stable and can be clear or nearly clear.
- microemulsified When an immiscible lipid-polar solvent system has been prepared so as to form a microemulsion, it is sometimes referred to herein as "microemulsified.”
- Presently preferred structure lipids encompass microemulsions having an L2 structure.
- the polar solventsolvent droplet size is about 100 times smaller than in a normal water-in-oil emulsion or polar solventsolvent- in-oil- emulsion.
- the dispersed phase droplets are known as "micelles.”
- a normal or standard "emulsion” refers to an immiscible lipid-polar solvent system where a dispersed phase is dispersed within a continuous phase, and wherein the dispersed phase includes droplets, domains, or channels of nominal size larger than about 250 nm in diameter, or in some embodiments, larger than 300 nm to about 1 ⁇ .
- These emulsions are generally thermodynamically unstable and at least slightly turbid.
- the immiscible phases will generally separate given time, depending on temperature and other factors. The skilled artisan will appreciate that many emulsions contain at least some droplets, domains, or channels of less than 200, 100, 50, or even 10 nm.
- Emulsions are nonetheless generally differentiated from microemulsions, which exclude such large droplets, domains and channels.
- an immiscible lipid-polar solvent system When an immiscible lipid-polar solvent system has been prepared so as to form an emulsion, it is sometimes referred to herein as "emulsified.”
- emulsified When an immiscible lipid-polar solvent system has been prepared so as to form an emulsion, it is sometimes referred to herein as "emulsified.”
- emulsion also means emulsions like oil-in-polar solvent-in-oil double emulsion.
- polar solvent-in-oil emulsion or microemulsion means that the continuous phase is lipid and the dispersed phase contains the polar solvent.
- a polar solvent is a polar solvent different from water or a mixture of polar solvents where at least one of the polar solvents is different form water.
- emulsions and microemulsions may be solid, semi-solid or liquid.
- a polar solvent dispersed phase can comprise any manner, variety, or combination of micelles, droplets, domains, or channels.
- the polar solvent can contain any polar solvent with at least one polar solvent different from water, and any solutes or combination of solutes may be dissolved therein to the limit of their solubility, including reducing reactants, amino reactants, catalysts, salts, buffers, acids, and the like.
- the polar solvent phase predominantly contains one or more reducing sugars and amino acids or proteins dissolved therein.
- the polar solvent phase contains phosphate- containing or carboxylate-containing compounds, such as salts, acids, or buffers. Such compounds are useful for adjusting the pH, buffering against pH changes, and catalyzing Maillard reactions.
- reducing reactant means a reactant that comprises a reactive aldehyde (-CHO) or keto (-CO-) group, e.g., a reactant with a free or available carbonyl group, such that the carbonyl group is available to react with an amino group on a reactant in a Maillard reaction.
- the reducing reactant is a reducing sugar, e.g., a sugar that can reduce a test reagent, e.g., can reduce Cu 2+ to Cu , or can be oxidized by such reagents.
- Monosaccharides, disaccharides, oligosaccharides, polysaccharides (e.g., dextrins, starches, and edible gums) and their hydrolysis products are suitable reducing reactants if they have at least one reducing group that can participate in a Maillard reaction.
- Reducing sugars include aldoses or ketoses such as glucose, fructose, maltose, lactose, glyceraldehyde, dihydoxyacetone, arabinose, xylose, ribose, mannose, erythrose, threose, and galactose.
- reducing reactants include uronic acids (e.g., glucuronic acid and galacturonic acid) or Maillard reaction intermediates bearing at least one carbonyl group such as aldehydes, ketones, alpha-hydroxycarbonyl or dicarbonyl compounds.
- uronic acids e.g., glucuronic acid and galacturonic acid
- Maillard reaction intermediates bearing at least one carbonyl group such as aldehydes, ketones, alpha-hydroxycarbonyl or dicarbonyl compounds.
- amino reactant means a reactant having a free amino group that is available to react with a reducing reactant in a Maillard reaction.
- Amino reactants include amino acids, peptides (including dipeptides, tripeptides, and oligopeptides), proteins, proteolytic or nonenzymatic digests thereof, and other compounds that react with reducing sugars and similar compounds in a Maillard reaction.
- the amino reactant also provides one or more sulfur-containing groups.
- the term "Maillard reaction product” means any compound produced by a Maillard reaction.
- the Maillard reaction product is a compound that provides flavor ("Maillard flavor”), color (“Maillard color”), or a combination thereof.
- flavor includes “odor” and "taste.”
- Maillard flavor composition means a composition comprising a structured lipid, a first reducing reactant, a second amino reactant, and optionally Maillard reaction products produced by a Maillard reaction between the first and second reactants.
- animal means any animal that could benefit from enhanced palatability resulting from Maillard compositions, including human, avian, bovine, canine, equine, feline, hicrine, lupine, murine, ovine, or porcine animals.
- the term "companion animal” means domesticated animals such as cats, dogs, rabbits, guinea pigs, ferrets, hamsters, mice, gerbils, horses, cows, goats, sheep, donkeys, pigs, and the like.
- palatability refer to a quality of a food, food supplement, food additive, dietary supplement, medicament, or the like, that makes it appealing or pleasing to one or more of an animal's senses, particularly the senses of taste and smell. Accordingly, palatability is determined subjectively. As used herein, whenever an animal shows a preference for one of two or more foods, the preferred food has greater or enhanced palatability. For companion animals and other non-human species, the relative palatability of one food compared to one or more other foods can be determined, for example, in side-by-side, free-choice comparisons, e.g., by relative consumption of the foods, or other appropriate measures of preference indicative of palatability.
- palatability can be considered both independently and inter dependently.
- initial appeal is an aspect of palatability that induces an animal to initially taste or try a food, dietary supplement, or medicament.
- Continuous consumption palatability' is an aspect of palatability that induces an animal to continue consuming a product that has been initially only tasted or tried.
- Repeated presentation palatability or “repeated feeding palatability” is an aspect of palatability evident when a food composition, dietary supplement, or medicament, which has previously been both tasted and consumed, is presented repeatedly to the animal for consumption over time. For example, a complete and nutritionally-balanced food composition that is fed daily to an animal will hopefully provide palatability for each repeated presentation of feeding, such that the animal continues to consume adequate quantities of the food.
- palatability enhancer means any compound, composition, formulation, or other material useful for enhancing the palatability of a comestible composition such as a food composition, supplement, medicament, or the like. Palatability enhancers enhance palatability at any one or more of the aspects of palatability. Thus, such palatability enhancers may contribute to initial appeal, continued consumption, or repeated presentation aspects of palatability, or any combination thereof. Examples of palatability enhancers include fats (e.g., tallow), flavors, aromas, extracts, digests, and the like.
- animal digest means a material that results from chemical and/or enzymatic hydrolysis of clean, undecomposed animal tissue.
- animal digest as used herein, is fully consistent with the definition of animal digest promulgated by the Association of American Feed Control Officials, Inc. (AAFCO).
- Animal digest is preferably derived from animal tissues, including cold-blooded marine animals, excluding hair, horns, teeth, hooves, and feathers. The skilled artisan will appreciate that while such tissues are not preferred, trace amounts might be found unavoidably even under good manufacturing practices. Also not included are visceral contents or foreign or fecal matter, although trace contaminant amounts are sometimes present.
- Animal digests in accordance herewith are suitable for use in food or feed compositions. Specifically included are (1 ) Digest of Beef (or Poultry, Pork, Lamb, Fish, etc): material from beef (poultry, pork, etc.) which results from chemical and/or enzymatic hydrolysis of clean and undecomposed tissue; (2) Digest of Beef (or Pork, Lamb, etc) By- Products: material from beef (poultry, pork, etc.) which results from chemical and/or enzymatic hydrolysis of clean and undecomposed tissue from non-rendered clean parts from cattle (pigs, lambs, fish, etc), other than meat, for example lungs, spleen, kidneys, brain, livers, blood, bone, partially- defatted low-temperature fatty tissue, and stomachs and intestines, freed of their contents; and (3) Digest of Poultry By-Products: material which results from chemical and/or enzymatic hydro
- the term "effective amount” means an amount of a compound, material, composition, medicament, or other material that is effective to achieve a particular desired result. Such results include, but are not limited to, one or more of the following: (a) enhancing palatability; (b) inducing an animal to consume more of a particular food or other material than the animal otherwise would, in either a single feeding or over the course of multiple feedings; or (c) inducing an animal to consume a medicament or a food or dietary supplement that the animal might not otherwise voluntarily consume. [0030]
- the term "food” or “food composition” means a product or composition that is intended for ingestion by an animal, including a human, and provides at least one nutrient or comestible ingredient to the animal.
- food includes any food, feed, snack, food supplement, treat, meal substitute, or meal replacement, whether intended for a human or another animal.
- Food encompasses such products in any form, solids, liquids, gels, or mixtures or combinations thereof. Thus, beverages of any type are clearly encompassed within the term “food.”
- the skilled artisan will appreciate that the ingredients or components of a food composition are comestible or edible by an animal in the normal course, and such ingredients or components do not include compounds that are toxic or otherwise deleterious to health in the amounts used in the food composition.
- pet food or "pet food composition” or the like, means a composition intended for consumption by a non-human animal, preferably by a companion animal.
- Nutritionally-balanced pet food compositions are widely known and used in the art.
- a "nutritionally-complete,” “nutritionally-balanced,” or “complete and nutritionally- balanced” food is one that contains all known required nutrients for the intended recipient or consumer of the food, in appropriate amounts and proportions, based, for example, on recommendations of recognized or competent authorities in the field of companion animal nutrition. Such foods are therefore capable of serving as a sole source of dietary intake to maintain life or promote production, without the addition of supplemental nutritional sources.
- the terms include any food, feed, snack, food supplement, treat, meal substitute, or meal replacement, whether intended for a human or another animal, in any form, including solids, liquids, gels and the like.
- Such foods, when intended for companion animals are frequently in the form of extruded pet foods, such as kibble-type foods for dogs and/or cats.
- dietary supplement means a product that is intended to be ingested in addition to the normal animal diet.
- Dietary supplements may be in any form, e.g., solid, liquid, gel, tablets, capsules, powder, and the like. Preferably they are provided in convenient dosage forms.
- dietary supplements are provided in bulk consumer packages such as bulk powders, liquids, gels, or oils.
- supplements are provided in bulk quantities to be included in other food items such as snacks, treats, supplement bars, beverages, and the like.
- a Maillard flavor composition e.g., for enhancing palatability of a food composition or the like, and that food composition or the like whose palatability is to be enhanced, are administered to an animal (1) together in a food composition, or the like (e.g., dietary supplement, or medicament), or (2) separately, at the same or different frequency, using the same or different administration routes, at about the same time, or periodically.
- a food composition, or the like e.g., dietary supplement, or medicament
- Periodically means that the Maillard flavor composition is administered on a dosage schedule acceptable for that specific palatability enhancer and that the food, dietary supplement, or medicament, is provided to an animal routinely as appropriate for the particular animal.
- “About the same time” generally means that the food, dietary supplement, or medicament, and the Maillard flavor composition are administered at the same time or within about 72 hours of each other.
- “In conjunction” specifically includes administration schemes wherein a palatability enhancer is administered for a predetermined, prescribed, or desired period, and the compositions disclosed herein are administered within a defined window of time before, during, or after providing the food, dietary supplement, or medicament whose palatability is to be enhanced, the window being between from about 0 to about 240 minutes before the start of, and after the completion of, e.g., the animal's normal feeding time, supplement time, or medicament administration time.
- single package means that the components of a kit are physically associated, in or with one or more containers, and considered a unit for manufacture, distribution, sale, or use.
- Containers include, but are not limited to, bags, boxes or cartons, bottles, packages of any type or design or material, over- wrap, shrink-wrap, affixed components (e.g., stapled, adhered, or the like), or combinations thereof.
- a single package may be containers of individual Maillard flavor compositions and comestible compositions, e.g., food ingredients or food compositions, physically associated such that they are considered a unit for manufacture, distribution, sale, or use.
- kits are associated by directions on one or more physical or virtual kit components instructing the user how to obtain the other components, e.g., in a bag or other container containing one component and directions instructing the user to go to a website, contact a recorded message or a fax-back service, view a visual message, or contact a caregiver or instructor to obtain instructions on how to use the kit, or safety or technical information about one or more components of a kit.
- Examples of information that can be provided as part of a virtual kit include instructions for use; safety information such as material safety data sheets; poison control information; information on potential adverse reactions; clinical study results; dietary information such as food composition or caloric composition; general information on improving palatability in the diet, or Maillard reaction products for such us, or increasing appetite in an animal in need thereof; health consequences stemming from a decrease in nutrient intake, or from inadequate nutrient intake; or general information on nutrition or providing optimal nutrition; self-help relating to nutrition and appetite; caregiver information for those caring for animals with nutritional challenges, and diseases that result in decreased body weight, wasting, or the like, or other loss of appetite challenges; improving acceptance of orally-administered dietary supplements or medicaments, and use, benefits, and potential side-effects or counter-indications, if any, for the compositions described herein, e.g., palatability enhancers.
- safety information such as material safety data sheets; poison control information; information on potential adverse reactions; clinical study results
- dietary information such as
- ranges herein are stated in shorthand, so as to avoid having to set out at length and describe each and every value within the range. Any appropriate value within the range can be selected, where appropriate, as the upper value, lower value, or the terminus of the range.
- a range of 0.1 to 1.0 represents the terminal values of 0.1 and 1.0 and the intermediate values of 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, and all intermediate ranges encompassed within 0.1 to 1.0, such as 0.2 to 0.5, 0.2 to 0.8, 0.7 to 1.0, and so on.
- the invention provides methods for making Maillard flavor compositions suitable for enhancing the palatability of foods, dietary supplements, medicaments, or other comestible materials.
- the methods comprise (a) making a structured lipid phase comprising a continuous lipid phase comprising a lipid and a dispersed polar solvent, different from water, or a mixture of polar solvents, with at least one polar solvent different from water and which contains at least a first reactant having a free carbonyl group, and a second reactant having an amino group available for reaction with the free carbonyl on the first reactant; and optionally (b) incubating the structured lipid phase under conditions of time and temperature sufficient for a Maillard reaction to occur between the first and second reactants, such that at least one Maillard reaction product is formed.
- the Maillard flavor compositions comprise one or more Maillard reaction products, including Maillard flavors, Maillard colors, and Maillard aromas.
- the Maillard reaction products are generally present or produced in structured lipids, e.g., polar solvent-in-oil emulsions, a polar solvent-in-oil microemulsions, a liquid crystalline phase where the lipid is the continuous phase or a self-assembly structure where the lipid is the continuous phase.
- the emulsions, microemulsions, the liquid crystalline phase where the lipid is the continuous phase and the self-assembly structure where the lipid is the continuous phase comprise a structured lipid phase having a continuous lipid phase and a dispersed polar solvent phase.
- the structure can be bicontinuous; the lipid forms a continuous phase and the polar solvent form also a continuous phase.
- the structure lipids or the emulsion or the microemulsion contains at least a first reactant having a free carbonyl group, and a second reactant having an amino group available for reaction with the free carbonyl on the first reactant, such that, upon incubating the structured lipid phase at a suitable temperature for a suitable time, a Maillard reaction occurs between the first and second reactants, and at least one Maillard reaction product is formed.
- the invention also provides the Maillard flavor compositions produced using these methods.
- the Maillard reaction that occurs within the structured lipid occurs within the micelles, dispersed droplets, domains, and/or channels of the polar solvent phase.
- the polar solvent soluble reactants are concentrated in the polar solvent phase, and perhaps with the interfacial areas between the continuous and dispersed phases of the structured lipid phase, e.g., polar solvent-in-oil emulsions and microemulsions.
- the first, or reducing reactant, the second, or amino reactant, and other Maillard reactants are polar solvent-soluble and cannot migrate out of the micelles, polar solvent domains, droplets, and/or channels of the dispersed polar solvent phase.
- the hydrophilic reactants e.g., sugars and amino acids
- the hydrophilic reactants do not migrate out of polar solvent domains into the oil; they remain concentrated in the hydrophilic micelles, droplets, and/or channels. This keeps their concentration relatively high and therefore increases the Maillard reaction rate.
- many reaction products resulting from the Maillard reaction are hydrophobic. In prior systems, the reaction products accumulate and gradually shift the equilibrium away from product formation. This decreases the reaction rate or decreases the extent of conversion of reactant to product.
- the hydrophobic Maillard reaction products migrate out of the micelle into the continuous lipid phase (e.g., oil).
- This migration removes the Maillard reaction products from the micelles, droplets, and/or channels and shifts the equilibrium of the Maillard reaction to product formation. This results in an increase in the reaction rate and ultimately the extent of the conversion from reactants to products, i. e. , the production of Maillard reaction products and Maillard compositions.
- the reactants remain concentrated within the hydrophilic micelles, droplets, domains, and/or channels while the hydrophobic reaction products migrate out into the lipophilic environment of the continuous lipid phase.
- the oil was not present which makes this migration less efficient and leads to a lower Maillard reaction yield.
- the Maillard reaction products produced by the methods of the invention have a different flavor profile and different concentrations as compared to control reactions conducted in water, normal oil-in- water emulsions, structured oil-in-water emulsions, other bulk aqueous phase systems, or other reported Maillard reaction environments.
- the Maillard reactions products and compositions obtained herein are easier to make, more economical to make, easier to store, easier to maintain, easier to use, and easier to introduce in products, particularly foods and related compositions.
- the structured lipid phase comprises from about 0.1 % to about 99.7%) lipid and from about 0.3% to about 95% polar solvent phase.
- the structured lipid phase can comprise any relative proportions of lipid to polar solvent phase provided that the structured lipid phase can be prepared, e.g., as a polar solvent- in-oil emulsion or microemulsion.
- the lipid is an oil, afat, an emulsifier (also called lipophilic additive) or mixture of thereof.
- the structured lipid phase comprises from about 0.5% to about 99.5% lipid, preferably from about 1% to about 99.5% lipid, more preferably from about 5% to about 95% lipid, and from about 0.5% to about 90% polar solvent phase, preferably from about 1% to about 85% polar solvent phase, more preferably from about 1%) to about 80%) polar solvent phase.
- Oil is used in the broad sense.
- An oil can be liquid, solid (fat), crystallized, or amorphous at room temperature.
- Possible oils for making the structured lipid are mineral oils, hydrocarbons, vegetable oils, animal oils, waxes, alcohols, fatty acids, mono-, di-, tri-acylglycerols, essential oils, flavoring oils, lipophilic vitamins, esters, nutraceuticals, terpins, terpenes and mixtures thereof.
- Possible oils for making the structured lipids also comprise oils, such as those described above, which have been partially hydrolyzed. These oils may be hydrolyzed by any suitable hydrolysis procedure, such as alkaline hydrolysis, steam stripping or enzymatic hydrolysis.
- the first reactant is a reducing reactant such as an aldose, ketose, uronic acid, or Maillard reaction intermediates bearing at least one carbonyl group, particularly a monosaccharide, a disaccharide, an oligosaccharide, a polysaccharide, or their hydrolysis products, provided that it has at least one reducing group.
- the saccharide can have any number of carbon atoms, and thus may be a triose, a tetrose, a pentose, a hexose, a heptose, and so on, or any combination thereof.
- the first reactant is a reducing sugar.
- Preferred reducing sugars for use herein are glucose, fructose, mannose, maltose, lactose, xylose, arabinose, or any combination thereof.
- Preferred reducing sugars are readily-available reducing sugars that are food-derived, or generally regarded as safe (GRAS) ingredients.
- the second reactant is any amino reactant with an available amino group that can participate in a Maillard reaction.
- the second reactant is an amino acid, peptide, hydrolyzed protein, polypeptide, or any combination thereof.
- the step of making the structured lipid phase comprises mixing the lipid and the polar solvent, to generate a structured lipid phase wherein the mixing step is sufficient to form a polar solvent-in-oil emulsion, a polar solvent-in-oil microemulsion, or other structured lipid phase.
- Mixing as used herein is a very broad term intended to encompass any act of combining the lipid and polar solvent into the form of an emulsion or microemulsion.
- the skilled artisan has available a large number of methods, and devices for forming structured lipid phases. Any such methods or devices known in the art for forming an emulsion or microemulsion are useful herein.
- the microemulsion may be a fully- or partially-self-assembling microemulsion.
- the Maillard reactants tend to be polar solvent-soluble. Therefore, the polar solvent soluble reactants are dissolved or dispersed within the polar solvent phase before the mixing step. In one embodiment, at least the first and second reactants are dissolved in the polar solvent before the mixing. In other embodiments, additional polar solvent-soluble compounds are dissolved in the polar solvent. Such compounds may include additional Maillard reactants, catalysts, buffers, compounds for adjusting pH such as acids, buffers, or salts, emulsifiers, and stabilizers. In various embodiments, the polar solvent comprises from about 0.001% to about 50% reducing reactants, about 0.001%) to about 50% amino reactants, and from about 0.001%) to about 50%> other solutes or additives.
- the step of making the structured lipid phase generally comprises adding one or more emulsifiers before or during the mixing step.
- the emulsifiers are useful for emulsifying or stabilizing, or both, the structured lipid phase.
- the emulsifiers have a hydrophilic lipophilic balance (HLB) of less than about 8, preferably less than 7.
- HLB hydrophilic lipophilic balance
- the structured lipid phase comprises from about 0.1% to about 99.6% emulsifier.
- the emulsifier can comprise any one or more emulsifying compounds, and preferably, the emulsifier is suitable for use in a food system, or as a food additive, or is GRAS.
- the emulsifier is a monoglyceride, a diglyceride, a polyglycerol ester, or a phospholipid, a lecithin, or any combination thereof.
- the emulsifier can encompass a saturated or unsaturated molecule, such as mono- or di-glycerides.
- the lipid phase preferably comprises a lipid derived from a plant or animal that is an edible or comestible lipid.
- the lipid comprises beef tallow, lamb tallow, lard, poultry fat, chicken fat, soy oil, sunflower oil, palm oil, cotton seed oil, rapeseed oil, coconut oil, corn oil, canola oil, olive oil, or any combination thereof in various embodiments.
- the lipid phase comprises lipids such as those described above that have been partially hydrolyzed. These lipids may be hydrolyzed by any suitable hydrolysis procedure, such as alkaline hydrolysis, steam stripping, or enzymatic hydrolysis.
- hydrolyzed lipid phase produced by these processes is unlikely to be completely hydrolyzed in that amounts of mono-, di- and/or triglycerides will be present in the hydrolyzed lipid phase. If desired, these glycerides may be removed by conventional separation techniques, but this is not necessary.
- the method comprises a further step of adding at least a portion of the structured lipid to at least one comestible ingredient, food composition, dietary supplement, medicament, or other material.
- the adding step is conducted before, during, or after the incubating step, or a combination thereof.
- the adding step is conducted before the incubation step, or before the conclusion of the incubation.
- the incubation step is conducted at least in part, in conjunction with a further step of processing the comestible ingredient, food composition, dietary supplement, or medicament.
- the incubation step is conducted, and thus further Maillard reaction products form, at least in part, during storage, or during shipment of the comestible ingredient, food composition, dietary supplement, or medicament.
- the adding step is conducted prior to the incubating step, and preferably the incubating step is conducted, at least in part, in conjunction with a thermal process applied to the food composition, dietary supplement, or medicament.
- a thermal process applied to the food composition, dietary supplement, or medicament.
- Any type or kind of thermal process used the arts of food processing or pharmaceutical processing may be useful for the methods herein.
- Preferred thermal process comprises extrusion, retorting, baking, or pasteurization.
- the adding step comprises adding at least one additional composition that provides or enhances palatability of the comestible ingredient, food composition, dietary supplement, medicament, or other material.
- additional composition that provides or enhances palatability of the comestible ingredient, food composition, dietary supplement, medicament, or other material.
- the additional palatability enhancer is an animal digest.
- the method can be conducted in a variety of manners to produce the structure lipid phase.
- the making step comprises dissolving at least the first and second reactants in the polar solvent; mixing the polar solvent with one or more lipids and one or more emulsifiers; and forming a polar solvent-in-oil emulsion or microemulsion.
- Energy input in the form of mixing, agitating, emulsifying, blending, micronizing, and the like is preferably used in the making step.
- the incubating step comprises allowing the reactants to interact at any temperature conductive for conducting a Maillard reaction, e.g., room temperature or lower depending on the reactants.
- incubating step comprises heating to a temperature of from about 60°C to about 180°C.
- the temperatures for incubating or heating are from about 80°C to 150°C, or preferably, the temperatures are from about 90°C to 120°C.
- the time for the incubating step is from about 1 minute to about 12 hours.
- the incubation time is from about 1 minute to about 640 minutes.
- Other preferred times for incubation are from about 5 minutes to about 300 minutes, preferably from about 10 minutes to about 180 minutes.
- the time and temperature combination are sufficient for a Maillard reaction to occur within the polar solvent-in-oil system.
- the Maillard reaction occurs during a retorting process.
- the required times and temperature may differ substantially from those required in bulk aqueous Maillard reactions, or even other complex food systems. Accordingly, the time and temperature for the nonenzymic reactions can be readily determined by observing or measuring an increase in reaction product(s) or a decrease in reactants. Incubation temperatures can be obtained using any suitable heating method such as microwave heating or can be obtained in any suitable process such as baking or retorting.
- the polar solvent further comprises one or more of a catalyst suitable for enhancing the rate of Maillard reactions, or a compound for adjusting the pH of the polar solvent.
- the catalyst preferably comprises a compound having a phosphate or a carboxylate group, or other known Maillard reaction catalyst or enhancer.
- the structured lipid phase comprises more than 0.3% polar solvent, more than 0.1%> lipid.
- the structured lipid phase comprises from about 0.5% to about 90% polar solvent and from about 10% to about 99.5% lipid. More preferably, the structured lipid phase comprises from about 0.5% to about 69% polar solvent, and from about 31% to about 99.5% lipid. Even more preferably, the structured lipid phase comprises from about 0.5% to about 25% polar solvent, and from about 25% to about 99.5% lipid.
- the HLB of the emulsifier is preferably less than about 8, preferably less than about 7.
- the methods for making the Maillard flavor compositions have proven to provide enhanced conversions of Maillard reactants into Maillard reaction products, including Maillard flavors and Maillard colors.
- the methods provide a conversion of Maillard reactants into Maillard reaction products in the structured lipid phase that exceeds the conversion of Maillard reactants into Maillard reaction products in a control Maillard reaction conducted under the same conditions with the same reactants in an aqueous system, or in a structured lipid phase containing only water as a polar solvent or in pure polar solvent phase.
- the conversion of Maillard reactants is at least 10% greater than the conversion in the control reaction resulting in an enhanced formation of Maillard reaction products, particularly in some key compounds like furfuryl thiol (FFT) or methyl furyl thiol (MFT).
- the conversion of Maillard reactants is at least 50% higher than in the control reaction.
- the reaction is nearly complete, providing a conversion of reactants of at least 80, 85, 90, 95%, or more.
- the invention provides products made using the methods of the invention.
- the invention provides a Maillard flavor composition
- a Maillard flavor composition comprising a structured lipid phase, a polar solvent, different from water, and at least one Maillard reaction product.
- the structure lipid phase comprises any amounts or proportions of lipid, emulsifier, and polar solvent that can form a polar solvent-in-oil emulsion or microemulsion.
- the structured lipid phase comprises from about 0.3% to about 95% polar solvent and from about 5% to about 99.7% lipid plus emulsifier. More preferably, the structured lipid phase comprises from about 0.5% to about 75%) polar solvent, most preferably from about 0.5 to about 25%.
- the emulsifier has a HLB less than 8 and the lipid comprises a comestible oil or fat.
- the Maillard reaction product is produced within and is within the structured lipid phase.
- the Maillard flavor compositions are produced by the methods of the invention.
- the Maillard flavor composition is produced by a method comprising (a) making a structured lipid phase comprising a continuous lipid phase comprising a lipid, and a dispersed phase comprising a polar solvent, wherein the polar solvent phase contains at least a first reactant the reactant having a free carbonyl group, and a second reactant having an amino group available for reaction with the free carbonyl on the first reactant; and (b) incubating the structured lipid phase under conditions of time and temperature sufficient for a Maillard reaction to occur between the first and second reactants, such that at least one Maillard reaction product is formed.
- the Maillard flavor composition is produced by a method comprising making a structured lipid phase comprising a continuous lipid phase comprising a lipid, and a dispersed phase comprising a polar solvent, wherein the polar solvent phase contains at least a first reactant the reactant having a free carbonyl group, and a second reactant having an amino group available for reaction with the free carbonyl on the first reactant.
- the Maillard reaction may be added to a product.
- the Maillard reaction may occur at a further stage. This further stage may include thermal processing, extrusion, retorting, home preparation such as cooking, frying, heating, pan heating, oven heating, oven baking, microwave heating, steam heating of the product.
- the structured lipid phase is a microemulsion.
- the microemulsion can exist at suitable temperature.
- microemulsion has a temperature lower than 50°C, more preferably lower than 40°C.
- the emulsifier comprises a saturated or unsaturated monoglyceride in certain embodiments.
- the composition can further comprise at least one catalyst of a Maillard reaction, at least one additional palatability enhancer, or both.
- the invention provides comestible compositions comprising at least one comestible ingredient and at least one Maillard flavor composition.
- the comestible composition comprises from about 0.001 % to about 50% Maillard flavor composition.
- the comestible composition is a food, dietary supplement, medicament, or other comestible material, most preferably a food composition.
- the comestible composition further comprises at least one additional palatability enhancer such as an animal digest.
- the comestible composition with the added Maillard flavor composition has measurably enhanced palatability compared to a control comestible composition that does not contain the Maillard flavor composition.
- the comestible composition is preferred by at least a factor of 10%> more than the control comestible composition. It other embodiments, an improvement of 20, 30, 40, or 50% is observed.
- the comestible composition is preferred up to 2 : 1 , 3 : 1 or more over the control comestible composition.
- the comestible composition is a food composition.
- the food composition is formulated as an animal food such as a pet food or companion animal food.
- the invention provides methods for enhancing palatability of a comestible composition.
- the methods comprise adding to a comestible composition at least one Maillard flavor composition in an amount effective for enhancing palatability of the comestible composition compared to a control that does not have the Maillard flavor composition added.
- the amount of Maillard flavor composition added is preferably from about 0.001%) to about 50% of the comestible composition.
- the invention also provides the comestible compositions produced using these methods.
- the invention provides food compositions comprising at least one comestible ingredient and a polar solvent-in-oil emulsion, microemulsion, or another reversed structured phase comprising a continuous lipid phase comprising a comestible fat or oil and a dispersed polar solvent phase.
- the polar solvent has dissolved therein at least a comestible reducing reactant having a free carbonyl, and a comestible second reactant containing an amino group, and an emulsifier having an HLB less than 8.
- the reducing reactant and the second reactant can undergo a Maillard reaction to form at least one Maillard reaction product under suitable conditions.
- the emulsion or microemulsion comprises from about 0.3% to about 95% polar solvent and from about 5% to about 99.7% lipid plus emulsifier. More preferably, the structured lipid phase comprises from about 0.5% to about 75%) polar solvent, most preferably from about 0.5 to about 25%.
- Preferred emulsifier include saturated and unsaturated monoglycerides.
- the food composition has been subjected to a thermal processing step or storage conditions under which at least one Maillard reaction product is formed from the reducing reactant and the second reactant. Any thermal processing step above ambient temperature at which a Maillard reaction product can form is useful herein.
- the food composition is a pet food composition in one embodiment.
- the composition comprises at least one additional palatability enhancer.
- the invention provides comestible compositions comprising (1) one or more comestible ingredients and (2) one or more structured lipids comprising a continuous lipid phase comprising a lipid and a dispersed polar solvent which at least a first reactant having a free carbonyl group, and a second reactant having an amino group available for reaction with the free carbonyl on the first reactant.
- the comestible ingredients are any comestible ingredients compatible with the structured lipids.
- the comestible ingredients are ones that require or are made more palatable by heating, e.g., by warming or by cooking.
- the comestible compositions are made by combining one or more comestible ingredients with one or more structured lipids.
- the compositions can be stored or otherwise retained until needed, e.g., for consumption or for further preparation and subsequent consumption.
- compositions can be consumed as made but are preferably heated before consumption.
- the first and second reactants react to produce Maillard reaction products that increase the palatability of the comestible compositions. Although the reaction occurs, it is generally slower than optimal.
- the compositions are heated to temperatures useful to prepare the comestible ingredients for consumption, generally by cooking or otherwise heating the compositions.
- the first and second reactants react to produce one or more Maillard reaction products. Heating facilitates the reaction process and produces more Maillard reaction products than would not have been produced without heating.
- Such Maillard reaction products increase the palatability of the comestible compositions, particularly when produced in amounts made by heating.
- any temperature suitable for preparing the comestible compositions and for causing a Maillard reaction is suitable.
- the compositions are heated to temperatures of from about 60°C to about 400°C, or from about 60°C to 350°C, or from about 60°C to 300°C or from about 60°C to 250°C, or from about 60°C to 233°C, or from about 60°C to 220°C, or from about 70°C to 180°C, or from about 80°C to 120°C, or from about 80°C to 100°C.
- Heating the compositions containing the structured lipids causes the first and second reactants react and form Maillard reaction products that increase the palatability of the compositions.
- the comestible compositions can be heated by any suitable means.
- the compositions are baked or cooked in an oven; heated on a stove or by a fire, e.g., in a pan, pot, or other suitable container; steam heated; or heated using a microwave oven.
- the first and second reactants can be any such reactant compatible with the comestible ingredients in the composition.
- the first and second reactants are (1) one or more reducing sugars and one or more amino acids or (2) one or more reducing sugars and one or more proteins.
- the structured lipids are mixed with the comestible ingredients, topically applied to the comestible ingredients, added onto or into preferred locations or sections in or on the ingredients, or otherwise distributed evenly or unevenly in or on the ingredients.
- food compositions that will be heated for serving comprise the product ingredients and one or more one or more structured lipids.
- the product is placed in an oven and heated to a temperature suitable for baking the product.
- the heat induces a reaction involving the first and second reactants.
- the reaction produces Maillard reaction products that enhance the palatability of the comestible composition.
- the comestible compositions are food compositions suitable for consumption by an animal, more preferably food compositions suitable for consumption by a companion animal, most preferably food compositions suitable for consumption by pets .
- the comestible composition is a pet food suitable for warming in a microwave oven. The pet food is heated sufficiently to produce Maillard reaction products in the food and served to the pet.
- the invention provides compositions made by heating comestible compositions comprising (1) one or more comestible ingredients and (2) one or more structured lipids comprising a continuous lipid phase comprising a lipid and a dispersed polar solvent which contains at least a first reactant having a free carbonyl group, and a second reactant having an amino group available for reaction with the free carbonyl on the first reactant.
- the compositions have an enhanced palatability due to the presence of Maillard reaction products resulting from heating the compositions as described herein.
- kits suitable for enhancing palatability of a comestible composition comprise in separate containers in a single package or in separate containers in a virtual package, as appropriate for the kit component, one or more Maillard flavor composition and one or more of (1) one or more ingredients suitable for consumption by an animal, (2) one or more palatability enhancers, (3) instructions for combining kit components to produce a composition useful for enhancing palatability of a food composition, (4) instructions for using Maillard reaction products, Maillard flavor compositions, or other components of the kit for the benefit of the animal, (5) a vessel for preparing or combining the kit components to produce a composition for administration to an animal, such as bowl, container, bag, or the like, (6) a means for admixing one or more kit components, such as a spoon, a spatula, or other suitable utensil, or (7) a means for administering combined or prepared kit components to an animal, such as a bowl, a spoon, a bottle, a cup, or
- the Maillard flavor composition comprises at least one Maillard reaction product and a structured lipid phase comprising, for example, at least 0.1% polar solvent, and at least 50% lipid plus emulsifier.
- the emulsifier has a HLB less than 8, and the lipid is a comestible oil or fat.
- the Maillard reaction product is produced within the structured lipid phase.
- kits suitable for enhancing palatability of a food composition comprising, in separate containers in a single package, or in separate containers in a virtual package, a polar solvent-in-oil emulsion or microemulsion comprising a continuous lipid phase comprising a comestible fat or oil and a dispersed polar solvent which contains at least a comestible reducing reactant having a free carbonyl, and a comestible second reactant containing an amino group, and an emulsifier.
- the emulsifier has an HLB less than 8.
- the reducing reactant and the second reactant can preferably undergo a Maillard reaction to form at least one Maillard reaction product under suitable conditions.
- kits further comprise one or more of ( 1 ) one or more ingredients suitable for consumption by an animal, (2) one or more palatability enhancers, (3) instructions for combining kit components to produce a composition useful for enhancing palatability of a food composition, (4) instructions on applying a thermal processing step to combined or uncombined kit components to produce one or more Maillard reaction products (5) instructions for using Maillard reaction products, Maillard flavor compositions, and other components of the kit for the benefit of the animal, (6) a vessel for preparing or combining the kit components to produce a composition for administration to an animal, such as a bowl, container, bag, box or the like, (7) a means for admixing one or more kit components, such as a spoon, spatula, or other utensil, or (8) a means for administering combined or prepared kit components to an animal,
- the invention provides means for communicating information about, or instruction for use of, a Maillard flavor composition
- a Maillard flavor composition comprising at least one Maillard reaction product and a structured lipid phase comprising at least 0.1% polar solvent, and at least 50% lipid plus emulsifier; wherein the emulsifier has a HLB less than 8, the lipid comprising a comestible oil or fat, wherein the Maillard reaction product is produced within the structured lipid phase, wherein the information is about, or the instructions are for, one or more of: (1) instructions for administering the composition to an animal in conjunction with at least one comestible ingredient; (2) instructions for one or more methods of using the composition for enhancing palatability of a food composition; (3) information on providing proper nutrition, including the use of the composition, to an animal in need of foods having enhanced palatability, or an animal having a diminished appetite due to a disease or other health condition; (4) information about palatability, and appetite; (5) information regarding physical, cellular and biochemical results of under-nutrition, conditions causing
- the means of communicating comprises a physical or electronic document, digital storage media, optical storage media, audio presentation, audiovisual display, or visual display containing the information or instructions.
- the means can be a displayed web site, visual display kiosk, brochure, product label, package insert, advertisement, handout, public announcement, audiotape, videotape, DVD, CD-ROM, computer readable chip, computer readable card, computer readable disk, USB device, Fire Wire device, computer memory, or any combination thereof.
- the invention provides packages comprising a Maillard flavor composition generally comprising at least one Maillard reaction product and a structured lipid phase comprising at least 0.1% polar solvent, and at least 50% lipid plus emulsifier; wherein the emulsifier has a HLB less than 8, the lipid comprising a comestible oil or fat, wherein the Maillard reaction product is produced within the structured lipid phase.
- the package contains a word or words, picture, design, logo, graphic, symbol, acronym, slogan, phrase, or other device, or combination thereof, either directly on the package or on a label affixed thereto, indicating that the composition is useful for enhancing palatability of a food composition.
- the Maillard flavor composition in the package is a component of a comestible composition.
- the Maillard flavor composition in the package is a component of a food composition.
- Method 1 The following method (“Method 1") was used to prepare the compositions used in some of the Examples. Reducing sugars, amino acids, catalysts (where used), and acids or bases (where used) were added to glycerol and agitated until dissolved, resulting in a glycerol solution. The glycerol solution was mixed with fat or oil and lipophilic additives (emulsifiers).
- glycerol-in-oil emulsion comprising a continuous structured lipid phase, having dispersed glycerol phase featuring glycerol domains that are emulsified or microemulsified within the lipidic phase.
- structured lipid phase Such glycerol-in-oil emulsions are referred to herein as "structured lipid phase.”
- Method 1 produces a flavor composition (a "Maillard flavor composition") containing Maillard reaction products, e.g., Maillard flavors.
- the Maillard flavor composition is stored at 10°C to 60°C until use.
- the Maillard flavor composition can be conveniently added to a fat or oil that is sprayed onto, or added to the food composition in amounts of from about 0.001% to about 9%, by weight, based on total food composition.
- the other flavors including flavors prepared by using hydrolytic enzymes to clean animal tissue, including liver and/or viscera, e.g., animal digests, can be added to or applied to the food composition.
- Method 2 The following method (“Method 2") was used to prepare the compositions used in some of the Examples. The steps of Method 1 were repeated except that a mixture of glycerol and water was used. Maillard flavor compositions prepared according to Method 2 can be conveniently added to a fat or oil that is sprayed onto, or added to the food composition in amounts of from about 0.001% to about 9% by weight based on total food composition. When used with other flavors, the other flavors, including flavors prepared by using hydrolytic enzymes to clean animal tissue, including liver and/or viscera, e.g., animal digests, can be added to or applied onto the food composition.
- Method 2 Maillard flavor compositions prepared according to Method 2 can be conveniently added to a fat or oil that is sprayed onto, or added to the food composition in amounts of from about 0.001% to about 9% by weight based on total food composition.
- the other flavors including flavors prepared by using hydrolytic enzymes to clean animal tissue, including liver and/or viscera, e.g., animal digests, can
- a first Maillard flavor composition was made according to the invention using Method 1. Glucose, cysteine and thiamine (Vitamin Bl) were used as reactants for the Maillard reaction. A second Maillard flavor composition was made by mixing glucose, cysteine and thiamine in glycerol to produce a glycerol solution. A third Maillard flavor composition was made by mixing glucose, cysteine and thiamine in glycerol and mixing this glycerol solution to fat or oil without lipophilic additives to produce a biphasic glycerol / fat or oil solution. A fourth Maillard flavor composition was made using the steps of Method 1 except that water was used instead of glycerol.
- Glucose, cysteine and thiamine were also used as reactants.
- a fifth Maillard flavor composition was made by mixing glucose, cysteine and thiamine in water to produce an aqueous solution. Each compositions contained 1.5% glucose, 0.9% cysteine and 0.7% thiamine by weight. The detailed composition of these five Maillard flavor compositions are given in Table 1.
- a structured lipid phase was prepared using Method 2 and using the components shown in Table 3. Reducing sugars and amino acids were added to glycerol and agitated until dissolved, resulting in a glycerol solution. The glycerol solution was mixed with fat or oil and lipophilic additives. The resulting mixture was agitated at 500 to 3000 rpm, for 1 to 5 minutes, to generate a glycerol-in-oil emulsion according to the invention, referred to herein as "structured lipid phase.”
- the structured lipid phase was coated externally on a chilled bread dough (at 1.0% based on the weight of the food product).
- the coated bread dough (test food product) was then stored overnight at +4°C.
- a control sample was prepared as follows: glucose (6.0%), rhamnose (0.2%), fructose (7.2%)), cysteine (3.6%) and proline (24.0%) were added to glycerol (59.0%) and agitated until dissolved, resulting in a glycerol solution.
- This glycerol solution was then coated externally on a chilled bread dough (at 0.1% based on the weight of the food product, to ensure similar reducing sugars and amino acids levels between the control and test food products). The coated bread dough (control food product) was then stored overnight at +4°C.
- test food product and the control food product were heated in a microwave oven (1 min 30 s, 750 W).
- the aroma perceived in the room during microwave heating and the flavor of the microwave heated food products were evaluated by a selected panel.
- the panel found the aroma and flavor from the control food product to be almost indistinguishable from those of a non- coated chilled bread dough (yeast-leavened bread aroma/flavor), whereas the test food product gave a rich, freshly baked bread aroma/flavor impression.
- a structured lipid phase was prepared using Method 2 and using the components shown in Table 4. Reducing sugars and amino acids were added to glycerol and water and agitated until dissolved, resulting in a wet glycerol solution. The wet glycerol solution was mixed with fat or oil and lipophilic additives. The resulting mixture was agitated at 500 to 3000 rpm, for 1 to 5 minutes, to generate a wet glycerol-in-oil emulsion according to the invention, referred to herein as "structured lipid phase.”
- the structured lipid phase was coated externally on a chilled bread dough (at 1.5% based on the weight of the food product).
- the coated bread dough (test food product) was then stored overnight at +4°C.
- a control sample was prepared as follows: glucose (4.75%), rhamnose (1.25%) and proline (19.0%)) were added to water (30.0%) and glycerol (45.0%) and agitated until dissolved, resulting in a glycerol solution. This glycerol solution was then coated externally on a chilled bread dough (at 0.3% based on the weight of the food product, to ensure similar reducing sugars and amino acids levels between the control and test food products). The coated bread dough (control food product) was then stored overnight at +4°C.
- test food product and the control food product were heated in a microwave oven (1 min 30 s, 750 W).
- the aroma perceived in the room during microwave heating and the flavor of the microwave heated food products were evaluated by a selected panel.
- the panel found the aroma and flavor from the control food product to be almost indistinguishable from those of a non- coated chilled bread dough (yeast- leavened bread aroma/flavor), whereas the test food product gave a rich, freshly baked bread aroma/flavor impression.
- a structured lipid phase was prepared using Method 2 and using the components shown in Table 5. Reducing sugars and amino acids were added to glycerol and water and agitated until dissolved, resulting in a wet glycerol solution. The wet glycerol solution was mixed with fat or oil and lipophilic additives. The resulting mixture was agitated at 500 to 3000 rpm, for 1 to 5 minutes, to generate a wet glycerol-in-oil emulsion according to the invention, referred to herein as "structured lipid phase.”
- the structured lipid phase was coated externally on a chilled bread dough (at 1.0% based on the weight of the food product).
- the coated bread dough (test food product) was then stored overnight at +4°C.
- a control sample was prepared as follows: glucose (3.2%), rhamnose (2.9%), cysteine (3.0%)) and proline (20.1%) were added to water (17.5%) and glycerol (53.3%) and agitated until dissolved, resulting in a wet glycerol solution.
- This wet glycerol solution was then coated externally on a chilled bread dough (at 0.7% based on the weight of the food product, to ensure similar reducing sugars and amino acids levels between the control and test food products). The coated bread dough (control food product) was then stored overnight at +4°C.
- test food product and the control food product were heated in a microwave oven (1 min 30 s, 750 W).
- the aroma perceived in the room during microwave heating and the flavor of the microwave heated food products were evaluated by a selected panel.
- the panel found the aroma and flavor from the control food product to be almost indistinguishable from those of a non- coated chilled bread dough (yeast-leavened bread aroma/flavor), whereas the test food product gave a rich, freshly baked bread aroma/flavor impression.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Polymers & Plastics (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Fodder In General (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2010333115A AU2010333115B2 (en) | 2009-12-18 | 2010-12-02 | Maillard flavor compositions with polar solvents different from water and methods for making such compositions |
MX2012006918A MX2012006918A (en) | 2009-12-18 | 2010-12-02 | Maillard flavor compositions with polar solvents different from water and methods for making such compositions. |
CN201080064147.7A CN102762110B (en) | 2009-12-18 | 2010-12-02 | Maillard flavor compositions with polar solvents different from water and methods for making such compositions |
BRBR112012014938-5A BR112012014938A2 (en) | 2009-12-18 | 2010-12-02 | Maillard flavor compositions with polar solvents other than water and methods for producing such compositions |
CA2784520A CA2784520A1 (en) | 2009-12-18 | 2010-12-02 | Maillard flavor compositions with polar solvents different from water and methods for making such compositions |
NZ600751A NZ600751A (en) | 2009-12-18 | 2010-12-02 | Maillard flavor compositions with polar solvents different from water and methods for making such compositions |
RU2012130440/13A RU2012130440A (en) | 2009-12-18 | 2010-12-02 | TASTE-AROMATIC COMPOSITIONS OF MAYAR WITH POLAR SOLVENTS DIFFERENT FROM WATER, AND METHODS FOR PRODUCING SUCH COMPOSITIONS |
EP10784552A EP2512263A1 (en) | 2009-12-18 | 2010-12-02 | Maillard flavor compositions with polar solvents different from water and methods for making such compositions |
IL220435A IL220435A0 (en) | 2009-12-18 | 2012-06-14 | Maillard flavor compositions with polar solvents different from water and methods for making such compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09179975 | 2009-12-18 | ||
EP09179975.9 | 2009-12-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011073035A1 true WO2011073035A1 (en) | 2011-06-23 |
Family
ID=42272265
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2010/068688 WO2011073035A1 (en) | 2009-12-18 | 2010-12-02 | Maillard flavor compositions with polar solvents different from water and methods for making such compositions |
Country Status (11)
Country | Link |
---|---|
EP (1) | EP2512263A1 (en) |
CN (1) | CN102762110B (en) |
AU (1) | AU2010333115B2 (en) |
BR (1) | BR112012014938A2 (en) |
CA (1) | CA2784520A1 (en) |
CL (1) | CL2012001648A1 (en) |
IL (1) | IL220435A0 (en) |
MX (1) | MX2012006918A (en) |
NZ (1) | NZ600751A (en) |
RU (1) | RU2012130440A (en) |
WO (1) | WO2011073035A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2644602A1 (en) | 2012-03-26 | 2013-10-02 | Nestec S.A. | Use of oxazolines as aroma/flavour precursors |
CN103987277A (en) * | 2011-12-12 | 2014-08-13 | 雀巢产品技术援助有限公司 | Enzymatically hydrolysed lipids as flavour ingredients |
CN104921053A (en) * | 2015-07-06 | 2015-09-23 | 天宁香料(江苏)有限公司 | Preparation method of chicken flavor essence seasoning |
CN107981156A (en) * | 2017-11-27 | 2018-05-04 | 江南大学 | A kind of method and its dispensing for promoting brown stain in food microwave heating process |
US10076126B2 (en) * | 2013-09-24 | 2018-09-18 | Nestec S.A. | Process for preparing a flavour composition |
US10136666B2 (en) * | 2013-09-24 | 2018-11-27 | Nestec S.A. | Deep eutectic solvents and flavour generation |
US11576397B2 (en) | 2016-02-05 | 2023-02-14 | Conopco, Inc. | Frozen confection |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019214567A1 (en) * | 2018-05-08 | 2019-11-14 | Epc Natural Products Co., Ltd. | Sweetener and flavor compositions, methods of making and methods of use thereof |
CN113543651A (en) * | 2019-12-16 | 2021-10-22 | 弗门尼舍有限公司 | Flavor compositions for beverage and personal care applications |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0030327A2 (en) * | 1979-12-07 | 1981-06-17 | Societe Des Produits Nestle S.A. | Process for preparing an aromatizing agent |
WO1999062357A1 (en) | 1998-06-01 | 1999-12-09 | Kerry Ingredients (Uk) Limited | Flavour delivering systems comprising a microemulsion or hydrated reversed micelles |
EP1008305A1 (en) * | 1998-12-10 | 2000-06-14 | Societe Des Produits Nestle S.A. | An aroma product comprising saturated C16 and C18 monoglycerides |
WO2003051139A1 (en) | 2001-12-19 | 2003-06-26 | Dsm Ip Assets B.V. | Compositions with a chicken flavour, use and production thereof |
WO2007060177A1 (en) | 2005-11-22 | 2007-05-31 | Nestec S.A. | Oil-in-water emulsion and its use for the delivery of functionality |
US20080038428A1 (en) | 2004-04-06 | 2008-02-14 | Quest International Services B.V. | Process for Preparing Maillard Flavour Preparations |
WO2010008452A1 (en) * | 2008-06-24 | 2010-01-21 | Nestec S.A. | Maillard flavor compositions and methods for making such compositions |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1528813A (en) * | 2003-09-29 | 2004-09-15 | 华南理工大学 | Glucoprotein production method |
CN101518324B (en) * | 2009-04-09 | 2013-02-20 | 天津春发生物科技集团有限公司 | Meat flavor and preparation method thereof |
-
2010
- 2010-12-02 BR BRBR112012014938-5A patent/BR112012014938A2/en not_active IP Right Cessation
- 2010-12-02 AU AU2010333115A patent/AU2010333115B2/en not_active Ceased
- 2010-12-02 CA CA2784520A patent/CA2784520A1/en not_active Abandoned
- 2010-12-02 WO PCT/EP2010/068688 patent/WO2011073035A1/en active Application Filing
- 2010-12-02 NZ NZ600751A patent/NZ600751A/en not_active IP Right Cessation
- 2010-12-02 EP EP10784552A patent/EP2512263A1/en not_active Withdrawn
- 2010-12-02 CN CN201080064147.7A patent/CN102762110B/en not_active Expired - Fee Related
- 2010-12-02 MX MX2012006918A patent/MX2012006918A/en not_active Application Discontinuation
- 2010-12-02 RU RU2012130440/13A patent/RU2012130440A/en not_active Application Discontinuation
-
2012
- 2012-06-14 IL IL220435A patent/IL220435A0/en unknown
- 2012-06-18 CL CL2012001648A patent/CL2012001648A1/en unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0030327A2 (en) * | 1979-12-07 | 1981-06-17 | Societe Des Produits Nestle S.A. | Process for preparing an aromatizing agent |
WO1999062357A1 (en) | 1998-06-01 | 1999-12-09 | Kerry Ingredients (Uk) Limited | Flavour delivering systems comprising a microemulsion or hydrated reversed micelles |
EP1008305A1 (en) * | 1998-12-10 | 2000-06-14 | Societe Des Produits Nestle S.A. | An aroma product comprising saturated C16 and C18 monoglycerides |
WO2000033671A2 (en) | 1998-12-10 | 2000-06-15 | Societe Des Produits Nestle S.A. | An aroma product comprising monoglyceride or phospholipid |
WO2003051139A1 (en) | 2001-12-19 | 2003-06-26 | Dsm Ip Assets B.V. | Compositions with a chicken flavour, use and production thereof |
US20080038428A1 (en) | 2004-04-06 | 2008-02-14 | Quest International Services B.V. | Process for Preparing Maillard Flavour Preparations |
WO2007060177A1 (en) | 2005-11-22 | 2007-05-31 | Nestec S.A. | Oil-in-water emulsion and its use for the delivery of functionality |
WO2010008452A1 (en) * | 2008-06-24 | 2010-01-21 | Nestec S.A. | Maillard flavor compositions and methods for making such compositions |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103987277A (en) * | 2011-12-12 | 2014-08-13 | 雀巢产品技术援助有限公司 | Enzymatically hydrolysed lipids as flavour ingredients |
EP2644602A1 (en) | 2012-03-26 | 2013-10-02 | Nestec S.A. | Use of oxazolines as aroma/flavour precursors |
WO2013143904A1 (en) | 2012-03-26 | 2013-10-03 | Nestec S.A. | Use of oxazolines as aroma/flavour precursors |
US10076126B2 (en) * | 2013-09-24 | 2018-09-18 | Nestec S.A. | Process for preparing a flavour composition |
US10136666B2 (en) * | 2013-09-24 | 2018-11-27 | Nestec S.A. | Deep eutectic solvents and flavour generation |
CN104921053A (en) * | 2015-07-06 | 2015-09-23 | 天宁香料(江苏)有限公司 | Preparation method of chicken flavor essence seasoning |
US11576397B2 (en) | 2016-02-05 | 2023-02-14 | Conopco, Inc. | Frozen confection |
CN107981156A (en) * | 2017-11-27 | 2018-05-04 | 江南大学 | A kind of method and its dispensing for promoting brown stain in food microwave heating process |
Also Published As
Publication number | Publication date |
---|---|
RU2012130440A (en) | 2014-01-27 |
AU2010333115A1 (en) | 2012-07-19 |
EP2512263A1 (en) | 2012-10-24 |
AU2010333115B2 (en) | 2014-10-30 |
CN102762110B (en) | 2014-11-05 |
CL2012001648A1 (en) | 2012-10-19 |
NZ600751A (en) | 2015-01-30 |
IL220435A0 (en) | 2012-08-30 |
CN102762110A (en) | 2012-10-31 |
MX2012006918A (en) | 2012-07-10 |
BR112012014938A2 (en) | 2015-08-25 |
CA2784520A1 (en) | 2011-06-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2009271740B2 (en) | Maillard flavor compositions and methods for making such compositions | |
AU2010333115B2 (en) | Maillard flavor compositions with polar solvents different from water and methods for making such compositions | |
EP1483973B1 (en) | Fat or oil composition | |
JP4116844B2 (en) | Oil composition | |
US20110124743A1 (en) | Palatability enhancers and methods for enhancing palatability | |
JPWO2003084556A1 (en) | Process for producing oil and fat composition containing licorice hydrophobic component | |
WO2007122801A1 (en) | Gip secretion inhibitor | |
WO2018008715A1 (en) | Gel-form food composition and food using same | |
JPH0860180A (en) | Oil and fat composition and food containing the same | |
JP4149445B2 (en) | Water-in-oil emulsified fat composition | |
JP4119537B2 (en) | Low salt food emulsion | |
Ponnampalam | Nutritional modification of muscle long-chain omega-3 fatty acids in lambs: effects on growth, and composition and quality of meat |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201080064147.7 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10784552 Country of ref document: EP Kind code of ref document: A1 |
|
REEP | Request for entry into the european phase |
Ref document number: 2010784552 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010784552 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2784520 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 220435 Country of ref document: IL Ref document number: MX/A/2012/006918 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 5346/DELNP/2012 Country of ref document: IN |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012001648 Country of ref document: CL |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010333115 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: A201208901 Country of ref document: UA Ref document number: 2012130440 Country of ref document: RU |
|
ENP | Entry into the national phase |
Ref document number: 2010333115 Country of ref document: AU Date of ref document: 20101202 Kind code of ref document: A |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112012014938 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112012014938 Country of ref document: BR Kind code of ref document: A2 Effective date: 20120618 |