CN107105732B - 乙醛前体 - Google Patents
乙醛前体 Download PDFInfo
- Publication number
- CN107105732B CN107105732B CN201580069690.9A CN201580069690A CN107105732B CN 107105732 B CN107105732 B CN 107105732B CN 201580069690 A CN201580069690 A CN 201580069690A CN 107105732 B CN107105732 B CN 107105732B
- Authority
- CN
- China
- Prior art keywords
- flavor
- acetaldehyde
- ethoxyethoxy
- propan
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title claims description 58
- 239000002243 precursor Substances 0.000 title description 9
- 239000000796 flavoring agent Substances 0.000 claims abstract description 42
- 235000019634 flavors Nutrition 0.000 claims abstract description 41
- 235000013305 food Nutrition 0.000 claims abstract description 18
- FPCMWGHDJNIKNV-UHFFFAOYSA-N 2-ethenyl-5-[2-(1-ethoxyethoxy)propan-2-yl]-2-methyloxolane Chemical compound C(C)OC(C)OC(C)(C)C1CCC(O1)(C=C)C FPCMWGHDJNIKNV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 31
- 239000004615 ingredient Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002671 adjuvant Substances 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 235000013361 beverage Nutrition 0.000 abstract description 20
- 239000003607 modifier Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 239000007921 spray Substances 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000001694 spray drying Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000005054 agglomeration Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- 229920000881 Modified starch Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000013365 dairy product Nutrition 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- 235000015203 fruit juice Nutrition 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 235000019426 modified starch Nutrition 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 235000014101 wine Nutrition 0.000 description 3
- FAIARWOGQAQTPS-UHFFFAOYSA-N (+/-)-1-Acetoxy-1-ethoxyethane Chemical compound CCOC(C)OC(C)=O FAIARWOGQAQTPS-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005913 Maltodextrin Substances 0.000 description 2
- 229920002774 Maltodextrin Polymers 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 235000019219 chocolate Nutrition 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- CEYULKASIQJZGP-UHFFFAOYSA-L disodium;2-(carboxymethyl)-2-hydroxybutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O CEYULKASIQJZGP-UHFFFAOYSA-L 0.000 description 2
- PYLIXCKOHOHGKQ-UHFFFAOYSA-L disodium;hydrogen phosphate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O PYLIXCKOHOHGKQ-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 239000001087 glyceryl triacetate Substances 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000000416 hydrocolloid Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 229940035034 maltodextrin Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229930182490 saponin Natural products 0.000 description 2
- 150000007949 saponins Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000013616 tea Nutrition 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229960002622 triacetin Drugs 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 150000004043 trisaccharides Chemical class 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- PPJVXZVTPWQOQS-UHFFFAOYSA-N 1-ethoxy-1-(1-ethoxyethoxy)ethane Chemical compound CCOC(C)OC(C)OCC PPJVXZVTPWQOQS-UHFFFAOYSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- 239000001278 2-(5-ethenyl-5-methyloxolan-2-yl)propan-2-ol Substances 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000276331 Citrus maxima Species 0.000 description 1
- 235000001759 Citrus maxima Nutrition 0.000 description 1
- 235000016795 Cola Nutrition 0.000 description 1
- 235000011824 Cola pachycarpa Nutrition 0.000 description 1
- 235000003363 Cornus mas Nutrition 0.000 description 1
- 240000006766 Cornus mas Species 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
- 229920000084 Gum arabic Polymers 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- BRHDDEIRQPDPMG-UHFFFAOYSA-N Linalyl oxide Chemical compound CC(C)(O)C1CCC(C)(C=C)O1 BRHDDEIRQPDPMG-UHFFFAOYSA-N 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000012098 RTD tea Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000015496 breakfast cereal Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000012174 carbonated soft drink Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000012182 cereal bars Nutrition 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000019987 cider Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 235000019262 disodium citrate Nutrition 0.000 description 1
- 239000002526 disodium citrate Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000007938 effervescent tablet Substances 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021554 flavoured beverage Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000015038 fortified wine Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 235000014109 instant soup Nutrition 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000019223 lemon-lime Nutrition 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 235000021577 malt beverage Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000008486 nectar Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- 238000009928 pasteurization Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 235000021572 root beer Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 235000013618 yogurt Nutrition 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
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
- A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
- A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
-
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/385—Concentrates of non-alcoholic beverages
- A23L2/39—Dry compositions
-
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- 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
- A23L27/29—Fruit flavours
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C5/00—Other raw materials for the preparation of beer
- C12C5/02—Additives for beer
- C12C5/026—Beer flavouring preparations
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
- C12G1/00—Preparation of wine or sparkling wine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
- C12G3/00—Preparation of other alcoholic beverages
- C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
- C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Inorganic Chemistry (AREA)
- Microbiology (AREA)
- Seasonings (AREA)
- Fats And Perfumes (AREA)
- Non-Alcoholic Beverages (AREA)
- Manufacture Of Tobacco Products (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Confectionery (AREA)
Abstract
本文提供5‑(2‑(1‑乙氧基乙氧基)丙‑2‑基)‑2‑甲基‑2‑乙烯基‑四氢呋喃及其在食品和饮料中作为风味和香气改性剂的用途。
Description
技术领域
本文提供了乙醛的前体及其用于将乙醛递送到食品和饮料中以典型地提供增加风味的用途。
背景技术
乙醛是一种重要但难以包封的调味料(风味)成分。它用于各种各样的调味料,但在水果调味料中特别受赞赏,其中它赋予调味料以新鲜度和多汁性的重要方面。乙醛的挥发性也提供了香气的提升,该香气极大地有助于调味料的嗅觉冲击。因此,使用乙醛对于产生例如在饮料中需要这些效果的调味料是不可或缺的。然而,由于沸点为20~21℃,这是一种在处理过程中由于蒸发而难以使用的材料,由于对于人员的过度暴露和发生火灾的危险,这可能会导致不安全的情况。一旦掺入到液体调味料中,由于蒸发而导致的乙醛损失仍然是一个问题,这也使得处理这样的调味料变得困难。除了挥发性高,乙醛还是一种非常活泼的化学物质。它可以与调味料配方中的醇反应形成缩醛;它可以进行醛醇缩合反应;它易于氧化;并且可三聚形成三聚乙醛。除了通过这些化学反应失去乙醛之外,所形成的产物会改变调味料的特性,在最坏的情况下会引起不希望的异味。
发明内容
本文提供了由下式表示的5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃:
本文还提供了将乙醛释放到水溶液中的方法,包括递送5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃。
本文进一步提供的是用于改变风味或香气的组合物,包含:
i)5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃;
ii)至少一种从由调味料载体和调味料基料构成的群组中选出的成分;和
iii)可选地,至少一种调味佐剂。
具体实施方式
通过“调味料载体”,我们指的是从调味料的角度来看基本上是中性的材料,只要它不会显著地改变调味成分的感官特性。载体可以是液体或固体。
合适的液体载体包括例如乳化体系,即溶剂和表面活性剂体系,或通常用于调味料的溶剂。通常用于调味料的溶剂的性质和类型的详细描述是无法穷尽的。合适的溶剂包括例如丙二醇、三醋精、柠檬酸三乙酯、苄醇、乙醇、植物油或萜烯。
合适的固体载体包括例如吸收树胶或聚合物,或甚至包封材料。这些材料的例子可包括成壁材料和增塑材料,例如单糖、二糖或三糖、天然或改性淀粉、水胶体、纤维素衍生物、聚乙酸乙烯酯、聚乙烯醇、蛋白质或果胶,或参考文献例如H.Scherz,Hydrokolloids:Stabilisatoren,Dickungs-und Gehermittel in Lebensmittel,Band 2derSchriftenreihe Lebensmittelchemie,Behr's Verlag GmbH&Co.,Hamburg,1996中列举的材料。封装是本领域技术人员众所周知的工艺,可以使用例如喷雾干燥、附聚、挤出、凝聚等技术来进行。
在一个实施方案中,本文提供的化合物以“调味料基料”的形式提供,即包含至少一种另外的调味成分的组合物。所述另外的调味成分不是5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃。此外,通过“调味成分”,是指这样的化合物,其用于调味制剂或组合物以赋予享乐效果。换句话说,要被认为是调味成分,这种成分必须被本领域技术人员公认为能够以主动或愉快的方式赋予或改变组合物的风味或香气,而不仅仅是具有风味或香气。
基料中存在的调味助成分的性质和类型在此不保证更详细的描述,本领域技术人员能够根据他/她的一般知识并根据预期用途或应用以及期望的感官效果对其进行选择。一般而言,这些调味助剂属于不同的化学类别,如醇、醛、酮、酯、醚、乙酸酯、腈、萜类化合物、含氮或含硫杂环化合物以及精油,并且所述加香助成分可以是天然或合成来源。无论如何,许多这些助成分在参考文献中列出,例如S.Arctander,Perfume and FlavorChemicals,1969,Montclair,New Jersey,USA或其更新版本,或其他类似性质的作品,以及调味料领域中丰富的专利文献。还应当理解,所述助成分也可以是已知以受控方式释放各种类型的调味化合物的化合物。
通过“调味料载体”,我们指的是从调味料的角度来看基本上是中性的材料,只要它不会显著地改变调味成分的感官特性。载体可以是液体或固体。
合适的液体载体包括例如乳化体系,即溶剂和表面活性剂体系,或通常用于调味料的溶剂。通常用于调味料的溶剂的性质和类型的详细描述是无法穷尽的。合适的溶剂包括例如丙二醇、三醋精、柠檬酸三乙酯、苄醇、乙醇、植物油或萜烯。
合适的固体载体包括例如吸收树胶或聚合物,或甚至包封材料。这些材料的例子可包括成壁材料和增塑材料,例如单糖、二糖或三糖、天然或改性淀粉、水胶体、纤维素衍生物、聚乙酸乙烯酯、聚乙烯醇、蛋白质或果胶,或参考文献例如H.Scherz,Hydrokolloids:Stabilisatoren,Dickungs-und Gehermittel in Lebensmittel,Band 2derSchriftenreihe Lebensmittelchemie,Behr's Verlag GmbH&Co.,Hamburg,1996中列举的材料。封装是本领域技术人员众所周知的工艺,可以使用例如喷雾干燥、附聚、挤出、凝聚等技术来进行。
除了包含至少一种化合物5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃、至少一种调味料载体、至少一种调味料基料和任选的至少一种调味佐剂的调味组合物外,由至少一种化合物5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃和至少一种调味料载体组成的组合物也代表本发明的一个具体实施方案。
此外,5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃可以有利地掺入到已调味制品中以主动地赋予或改变所述制品的风味、新鲜度、果味、多汁性或香气。因此,另一方面,本发明提供了包含5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃和食品基料的已调味制品。
为了清楚起见,必须提及的是,通过“食品”,我们指的是可食用的产品,例如食物或饮料。因此,根据本发明的已调味制品包含一种或多种根据5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃的化合物以及可选的对应于所需可食用产品的风味或香气以及风味或香气概况的有益剂。本文提供的组合物和方法可用于食物或饮料产品中。当食物产品是颗粒状或粉末状的食品时,干燥粉末可通过干式混合容易地加入到其中。典型的食物产品选自速溶汤或酱汁,早餐谷物,奶粉,婴儿食品,粉状饮料,粉状巧克力饮料,敷料,粉状谷物饮料,口香糖,泡腾片,谷物棒和巧克力棒。粉状食品或饮料可在用水、牛奶和/或果汁或其他含水液体重新复原产品后被服用。
合适的食品基料,例如食物或饮料,包括需要新鲜或水果味调的乳制品和糖果产品。本文提供的另一个实施方案是乳制品,包括但不限于非冷冻、部分冷冻和冷冻的流体乳制品,例如奶、冰淇淋、冰糕和酸奶。
在一个实施方案中,本文提供的组合物和化合物为食品提供了“新鲜”、“多汁”和“水果”风味和/或香气。
饮料产品包括但不限于碳酸软饮料,包括可乐、柠檬-酸橙、根啤酒、烈性柑橘(“清凉型”)、水果味和奶油苏打水;粉状软饮料,以及液体浓缩物诸如汽水用糖浆和果味浓缩汁(cordials);咖啡和咖啡基饮料,咖啡代用品和谷类饮料;茶,包括干混产品以及即饮茶(草药和茶叶基);水果和蔬菜汁和果汁调味饮料以及果汁饮料、蜜汁饮料(nectars)、浓缩物、潘趣酒和各种果饮(“ades”);碳酸型和不起泡的甜味和调味的水;运动/能量/健康饮料;酒精饮料加上无酒精和其他低酒精产品,包括啤酒和麦芽饮料、苹果酒和葡萄酒(不起泡型、发泡型、加烈葡萄酒和葡萄酒类果汁饮料(wine cooler));热加工的(浸泡、巴氏杀菌、超高温、通电加热或商业无菌灭菌)和热灌装包装的其他饮料;和通过过滤或其他保鲜技术制成的冷灌装产品。食品或饮料的成分的性质和类型在这里不保证更详细的描述,技术人员能够根据他的一般知识和所述产品的性质来选择它们。
在调味组合物的情况下,5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃的典型浓度在组合物总重量的约0.01%至15%,特别是约1%至约15%,更特别约1%至约5%,更特别约1%至约2%的范围内。在一个实施方案中,已调味制品中5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃的浓度基于已调味制品的总重量以重量计在约3ppm至约60ppm,特别是约3ppm至约45ppm,更特别是约3ppm至约30ppm,更特别是约12ppm至约45ppm,12ppm至约30ppm,甚至更特别是约12ppm至约15ppm,甚至更特别是约17ppm至33ppm的范围内。
在另一个实施方案中,本文提供的化合物在已调味制品中所提供的量,使得该化合物乙醛以重量计的量为制品总重量的约1ppm至约20ppm,更特别是约1ppm至约10ppm,更特别是4ppm至约10ppm,甚至更特别是约4ppm至约6ppm。
通过“调味佐剂”,我们在这里指的是能够赋予额外附加益处,例如颜色、特定的耐光性、化学稳定性等的成分。通常在调味基料中使用的佐剂的性质和类型的详细描述是无法穷尽的。然而,这些佐剂是本领域技术人员熟知的,但是必须提及的是所述成分是本领域技术人员熟知的。
为了清楚起见,必须提及的是,通过“食品”,我们指的是可食用的产品,例如食物或饮料。因此,根据本发明的已调味制品包含一种或多种根据5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃的化合物以及可选的对应于所需可食用产品的风味或香气概况的有益剂,例如咸味块。
本文还提供了包含5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃的喷雾干燥颗粒。
本文还提供喷雾干燥颗粒的制备方法,包括:a)制备喷雾干燥的进料乳液,其包含乳化剂、麦芽糖糊精和5-(2-(1-(乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃或其药理学可接受的盐之一,其中乳液具有调节为6至9之间的缓冲液。乳化剂可以选自阿拉伯树胶、皂角苷和改性淀粉。乳液也可以含有可选成分。其特别还可包含有效量的防火剂或抑爆剂。这种试剂在喷雾干燥乳液中的类型和浓度是本领域技术人员已知的。作为这种防火剂或抑爆剂的非限制性例子,可以列举无机盐、C1-C12羧酸、C1-C12羧酸的盐以及它们的混合物。特别的抑爆剂为水杨酸、乙酸、丙酸、丁酸、异丁酸、戊酸、己酸、柠檬酸、琥珀酸、羟基琥珀酸、马来酸、富马酸、草酸(oxylic acid)、乙醛酸、己二酸、乳酸、酒石酸、抗坏血酸,任何上述酸的钾盐、钙盐和/或钠盐,以及任何这些物质的混合物。其他可选成分包括抗氧化剂、着色剂和染料。
乳液可通过使用任何已知的乳化方法,例如高剪切混合、超声处理或均化而形成。这样的乳化方法是本领域技术人员熟知的。
乳液的液滴尺寸d(v,0.9)特别在1至20/μm之间,更特别地在1至15/μm之间,甚至更特别地在1至10/μm之间。更具体地,液滴尺寸可以在环境温度(25℃)下保持在该范围内存储至少一天。
在进行如下定义的雾化步骤的温度下,乳液的粘度特别是在20至300mPas之间,更特别地在70至200mPas之间,甚至更特别地在100至150mPas之间。
制备乳液后,将其喷雾干燥,从而得到干燥颗粒。喷雾干燥过程包括两个步骤,第一步是分散,第二步是干燥。首先对乳液进行雾化步骤,在此期间,乳液以液滴的形式分散到喷雾塔中。可以使用能够以液滴形式分散乳液的任何装置来进行这种分散。例如,乳液可以通过喷嘴或通过离心轮盘引导到喷雾塔中。也可以使用振动孔。胶囊的尺寸由分散在塔中的液滴的尺寸决定。如果使用喷嘴来分散液滴,则可以通过例如通过喷嘴的雾化气体的流量来控制尺寸。在使用离心轮盘进行分散的情况下,用于调节液滴大小的主要因素是液滴从盘分散到塔中的离心力。离心力又取决于旋转速度和盘的直径。乳液的进料流速、其表面张力及其粘度也是控制最终液滴尺寸和尺寸分布的参数。通过调整这些参数,本领域技术人员可以控制要分散在塔中的乳液的液滴的尺寸。
一旦喷洒在室中,则使用本领域已知的任何技术来干燥液滴。这些方法完全记载在喷雾干燥领域的专利和非专利文献中。例如,Spray-Drying Handbook,3rd ed.,K.Masters;John Wiley(1979)描述了各种各样的喷雾干燥方法。
本文提供的方法可以在任何常规喷雾塔中进行。例如,常规的多级干燥装置适合于进行该方法的步骤。它可以包括喷雾塔,以及在塔的底部处的流化床,其拦截通过塔而落下后的部分干燥的颗粒。
以下实施例仅是说明性的,并不意味着以任何方式进行限制。
实施例
实施例1
5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃的合成
将氧化芳樟醇(CAS#1365-19-1)(59mmol)、乙醚(50mL)和对甲苯磺酸(0.06mmol)的混合物冷却至5℃。用30分钟滴加溶解在乙醚(50mL)中的乙基乙烯基醚(88mmol),将混合物在室温下搅拌12小时。加入5克碳酸钠并过滤混合物。使用旋转蒸发器浓缩产物并通过Kugelrohr蒸馏(70~80℃,40mTorr)纯化,得到5.19g(37%收率)无色油状产物(四种非对映异构体的等摩尔混合物)。
1H NMR(CDCl3,400MHz):δ1.15-1.31(m,15H),1.63-1.76(m,1H),1.79-1.97(m,3H),3.43-3.61(m,2H),3.82-3.94(m,1H),4.94-5.07(m,2H),5.14-5.22(m,1H),5.81-6.00(overlapping dd,1H).
MS(EI):242(M+,0),169(2),153(38),111(46),93(27),85(18),81(24),73(100),71(31),45(39),43(47).
实施例2
对比样品1:乙酸1-乙氧基乙酯的合成
将二乙醚(50mL)、冰醋酸(10g,167mmol)和pTSA(0.01g)组合,将混合物在冰浴中冷却。用15分钟滴加50mL乙醚中的乙基乙烯基醚(18g,250mmol)。将混合物从冷浴中取出并在室温下搅拌2小时。加入碳酸钠(5g),过滤混合物。通过在大气压下分馏除去乙醚。残余物通过分馏得到17.7g(34~35℃,19mbar)乙酸1-乙氧基乙酯(134mmol,80%收率)。
1H NMR(CDCl3,400MHz):δ1.21(t,J=7.1Hz,3H),1.40(d,J=5.2Hz,3H),2.07(s,3H),3.49-3.77(m,2H),5.93(q,J=5.2Hz,1H).
MS(EI):132(M+,0),131(<1),117(3),89(5),87(12),73(55),45(61),43(100).
实施例3
评估pH 3.0时的水解速率
速溶饮料应用需要前体分子的快速水解以便快速释放乙醛。因为这样的饮料在制备时可能立即服用,所以期望释放尽可能快。
通过向1L去离子水中加入16.43g柠檬酸(CAS 77-92-9)和4.26g柠檬酸二钠(CAS144-33-2)来制备pH 3.0缓冲溶液。将实施例1~2的制剂的等分试样加入到处于Distek2100B USP 2溶解体系中的缓冲溶液中,以200rpm搅拌。使用UV/Vis光谱仪探针监测溶液中乙醛的浓度相对于时间的变化,其中每1秒测量276nm处的吸光度。释放遵循一级动力学,半反应期报告在表1中。比较样品的结果取自Gassenmeier等人的工作[1]。还直接测量了乙醛缩二乙醇样品,结果与Gassenmeier等报道的相似。实施例1比对比样品2~5更快速地释放乙醛。
表1:pH 3时乙醛前体的半反应期
[1]Gassenmeier,K.,Daniher,A.,Furrer,S.,1-Ethoxy-1-(1-ethoxy-ethoxy)-ethane:a new acetaldehyde precursor,in:Wender,L.P.B.(Ed.),Developments inFood Science Flavour Science Recent Advances and Trends,Elsevier,2006,pp.305-308
实施例4
喷雾干燥进料条件下水解速率的评估
适于制成干粉的乙醛前体必须避免在工艺的不同阶段释放显著水平的乙醛。特别地,它们在制备喷雾干燥进料乳液期间应该抗水解,其可以是中性至碱性pH,并且可以含有显著体积分数的油相。
通过向1L去离子水中加入49.92g磷酸氢二钠七水合物(CAS 7782-85-6)和1.93g磷酸二氢钠(CAS 7558-80-7)来制备pH 8.0的缓冲溶液。将0.20g实施例1~2的制剂的等分试样溶解于加入到含搅拌棒的30mL锥形瓶中的10g缓冲溶液中的0.8g柠檬烯(CAS 5989-25-7)中。使用测量276nm处吸光度的UV/Vis光谱仪探针来监测溶液中乙醛的浓度相对于时间的变化。定期停止搅拌以使油滴上升到表面,并收集水溶液的清澈的吸光度读数。释放遵循混合零级和一级动力学。t50(达到最大吸光度的50%的时间)值报告在表2中。实施例1在1小时内没有观察到吸光度的增加,这表明没有发生乙醛的释放。对比样品1的t50为2.1分钟,其如此之短,使得本领域技术人员将认为该化合物在加工过程中遇到有问题程度水解的风险。实施例1具有比对比样品1长得多的t50值,乙醛释放更缓慢。
表2:乳液中pH8时的乙醛前体的t50
实施例5
喷雾干粉的制备
根据表3制备喷雾干燥进料乳液。选择前体分子的量以产生基于化学计量为0.25g的乙醛。将实施例1的液体溶解在橙味调味料中。将该混合物加入到盐、麦芽糖糊精、水和皂苷溶液中,并使用均化器(T25UltraTurrax,IKA Works,USA)混合2分钟。然后将制剂喷雾干燥(型号190Mini-Spray Drier,Buchi Corporation,New Castle DE,USA),入口空气温度设定为138℃,出口空气温度为95℃。
表3:喷雾干燥进料配方
实施例6
速溶饮料的制备和评估
喷雾干燥制剂A和B通过将0.1g制剂与0.07g柠檬酸、7g蔗糖组合并将该混合物溶解在100mL蒸馏水中来复原。快速准备饮料,并由5人的小组品尝。发现喷雾干燥A样品比由喷雾干燥B制备的饮料更新鲜。
1)乙醛收率分析
将粉末溶解在水中,用2,4-二硝基苯肼进行衍生之后,使用反相HPLC测定来自喷雾干燥A和B的乙醛的浓度。表4中的结果表明,从喷雾干燥粉末A释放出高水平的乙醛。
表4:喷雾干燥粉末中的乙醛浓度
Claims (5)
1.一种化合物,其化学式为5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃。
2.一种将乙醛释放到水溶液中的方法,包括将5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃递送到水溶液中。
3.一种用于改变风味的组合物,包含:
i)5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃;和
ii)至少一种从由调味料载体和调味料基料构成的群组中选出的成分。
4.根据权利要求3所述的用于改变风味的组合物,还包含:
iii)至少一种调味佐剂。
5.一种已调味制品,包含:
i)5-(2-(1-乙氧基乙氧基)丙-2-基)-2-甲基-2-乙烯基四氢呋喃;和
ii)食品基料。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462096835P | 2014-12-24 | 2014-12-24 | |
US62/096,835 | 2014-12-24 | ||
PCT/EP2015/080718 WO2016102425A1 (en) | 2014-12-24 | 2015-12-21 | Acetaldehyde precursors |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107105732A CN107105732A (zh) | 2017-08-29 |
CN107105732B true CN107105732B (zh) | 2021-04-13 |
Family
ID=54979687
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201580069690.9A Expired - Fee Related CN107105732B (zh) | 2014-12-24 | 2015-12-21 | 乙醛前体 |
Country Status (8)
Country | Link |
---|---|
US (1) | US10575543B2 (zh) |
EP (1) | EP3237392A1 (zh) |
JP (1) | JP6534740B2 (zh) |
CN (1) | CN107105732B (zh) |
BR (1) | BR112017011282B1 (zh) |
MX (1) | MX2017006061A (zh) |
RU (1) | RU2017126083A (zh) |
WO (1) | WO2016102425A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3236774A1 (en) * | 2014-12-24 | 2017-11-01 | Firmenich SA | Proflavor delivery powders |
MX2017005855A (es) * | 2014-12-24 | 2017-09-26 | Firmenich & Cie | Particulas de liberacion de prosabor. |
JP6697429B2 (ja) | 2017-11-06 | 2020-05-20 | 長谷川香料株式会社 | 新規アルカンチオ酸誘導体および該化合物を含有する香料組成物 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4419280A (en) * | 1980-08-07 | 1983-12-06 | International Flavors & Fragrances Inc. | 1-Ethoxy-1-ethanol acetate and uses thereof for augmenting or enhancing aroma or taste of consumable materials |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA947310A (en) | 1970-08-29 | 1974-05-14 | Seiji Wakayama | 2-(1'-hydroxymethyl-ethyl)-5-methyl-5-vinyl-tetrahydrofuran |
CH589426A5 (zh) | 1973-11-02 | 1977-07-15 | Firmenich & Cie | |
US5079023A (en) | 1977-01-21 | 1992-01-07 | Hercules Incorporated | Foodstuffs containing aldehyde generators |
JPS59130879A (ja) | 1983-01-18 | 1984-07-27 | T Hasegawa Co Ltd | テトラヒドロフランエステル類 |
GB2332671B (en) * | 1997-12-22 | 2002-08-14 | Inst Francais Du Petrole | Acetals, their preparation and their use |
PL371375A1 (en) | 2002-03-28 | 2005-06-13 | Firmenich Sa | Compounds for the controlled release of active aldehydes |
EP3236774A1 (en) * | 2014-12-24 | 2017-11-01 | Firmenich SA | Proflavor delivery powders |
MX2017005855A (es) * | 2014-12-24 | 2017-09-26 | Firmenich & Cie | Particulas de liberacion de prosabor. |
-
2015
- 2015-12-21 CN CN201580069690.9A patent/CN107105732B/zh not_active Expired - Fee Related
- 2015-12-21 JP JP2017528580A patent/JP6534740B2/ja not_active Expired - Fee Related
- 2015-12-21 RU RU2017126083A patent/RU2017126083A/ru not_active Application Discontinuation
- 2015-12-21 EP EP15813851.1A patent/EP3237392A1/en active Pending
- 2015-12-21 BR BR112017011282-5A patent/BR112017011282B1/pt not_active IP Right Cessation
- 2015-12-21 US US15/538,116 patent/US10575543B2/en not_active Expired - Fee Related
- 2015-12-21 WO PCT/EP2015/080718 patent/WO2016102425A1/en active Application Filing
- 2015-12-21 MX MX2017006061A patent/MX2017006061A/es unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4419280A (en) * | 1980-08-07 | 1983-12-06 | International Flavors & Fragrances Inc. | 1-Ethoxy-1-ethanol acetate and uses thereof for augmenting or enhancing aroma or taste of consumable materials |
Non-Patent Citations (1)
Title |
---|
Hydroxylated Linalool Derivatives as Precursors of Volatile Monoterpenes of Muscat Grapes;Patrick J.Williams;《J.Agric.Food Chem》;19801231(第28期);第766-771页 * |
Also Published As
Publication number | Publication date |
---|---|
EP3237392A1 (en) | 2017-11-01 |
BR112017011282B1 (pt) | 2021-09-14 |
WO2016102425A1 (en) | 2016-06-30 |
US20170339993A1 (en) | 2017-11-30 |
RU2017126083A (ru) | 2019-01-24 |
US10575543B2 (en) | 2020-03-03 |
BR112017011282A2 (pt) | 2018-04-03 |
JP2018502830A (ja) | 2018-02-01 |
MX2017006061A (es) | 2017-07-27 |
CN107105732A (zh) | 2017-08-29 |
RU2017126083A3 (zh) | 2019-06-07 |
JP6534740B2 (ja) | 2019-06-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US10638782B2 (en) | Proflavor delivery particles | |
KR101816177B1 (ko) | 구형 코어-쉘-입자 | |
US20140056836A1 (en) | Spray-Dried Compositions and Their Uses | |
WO2017102955A1 (en) | Proflavour delivery particles | |
CN107105732B (zh) | 乙醛前体 | |
JP2021514608A (ja) | 貯蔵安定性のある粉末組成物 | |
JP6898707B2 (ja) | 風味付けした食品粒子の製造方法 | |
JP2020504194A (ja) | フレグランスおよびフレーバー材料 | |
EP2918175B1 (en) | Propylene glycol-free spray-dried flavour compositions and methods of producing the same | |
JP2016165268A5 (zh) | ||
CN107108452B (zh) | 半缩醛前体调味料 | |
US20140127361A1 (en) | Extruded delivery system | |
JP6985332B2 (ja) | ドデセン酸を有効成分とする飲食品の不快味のマスキング剤 | |
TWI712424B (zh) | 乳化組合物及粉末組合物 | |
CN107105722B (zh) | 前体调味料递送粉末 | |
CN111526728A (zh) | 香草组合物 | |
JP2020514424A (ja) | フレグランスおよびフレーバー材料 | |
WO2023020951A1 (en) | Flavored particles delivery system | |
JP2005204617A (ja) | 香料組成物 | |
US20230105389A1 (en) | Flavored particles delivery system | |
US20230329301A1 (en) | Proflavor delivery particles | |
CN117715534A (zh) | 风味化颗粒递送系统 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20210413 Termination date: 20211221 |
|
CF01 | Termination of patent right due to non-payment of annual fee |