CN114208928B - Flavored syrup and preparation method thereof - Google Patents
Flavored syrup and preparation method thereof Download PDFInfo
- Publication number
- CN114208928B CN114208928B CN202111581842.7A CN202111581842A CN114208928B CN 114208928 B CN114208928 B CN 114208928B CN 202111581842 A CN202111581842 A CN 202111581842A CN 114208928 B CN114208928 B CN 114208928B
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- CN
- China
- Prior art keywords
- syrup
- phloretin
- stirring
- reaction
- carrying
- Prior art date
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- 235000020375 flavoured syrup Nutrition 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 55
- 235000020357 syrup Nutrition 0.000 claims abstract description 52
- 239000006188 syrup Substances 0.000 claims abstract description 52
- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 claims abstract description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000003755 preservative agent Substances 0.000 claims abstract description 37
- 230000002335 preservative effect Effects 0.000 claims abstract description 36
- 239000000796 flavoring agent Substances 0.000 claims abstract description 31
- 235000019634 flavors Nutrition 0.000 claims abstract description 31
- 235000021552 granulated sugar Nutrition 0.000 claims abstract description 30
- 238000001914 filtration Methods 0.000 claims abstract description 26
- 238000002156 mixing Methods 0.000 claims abstract description 26
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 235000021433 fructose syrup Nutrition 0.000 claims abstract description 12
- 229940105902 mint extract Drugs 0.000 claims abstract description 10
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims abstract description 6
- 235000005979 Citrus limon Nutrition 0.000 claims abstract description 6
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims abstract description 6
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001768 carboxy methyl cellulose Substances 0.000 claims abstract description 6
- 235000021579 juice concentrates Nutrition 0.000 claims abstract description 6
- 239000001630 malic acid Substances 0.000 claims abstract description 6
- 235000011090 malic acid Nutrition 0.000 claims abstract description 6
- 239000000049 pigment Substances 0.000 claims abstract description 6
- 239000008213 purified water Substances 0.000 claims abstract description 6
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims abstract description 6
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims abstract description 6
- 230000001954 sterilising effect Effects 0.000 claims abstract description 6
- 239000000230 xanthan gum Substances 0.000 claims abstract description 6
- 229920001285 xanthan gum Polymers 0.000 claims abstract description 6
- 229940082509 xanthan gum Drugs 0.000 claims abstract description 6
- 235000010493 xanthan gum Nutrition 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 112
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 88
- VGEREEWJJVICBM-UHFFFAOYSA-N phloretin Chemical compound C1=CC(O)=CC=C1CCC(=O)C1=C(O)C=C(O)C=C1O VGEREEWJJVICBM-UHFFFAOYSA-N 0.000 claims description 78
- 238000006243 chemical reaction Methods 0.000 claims description 57
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 34
- 235000019441 ethanol Nutrition 0.000 claims description 34
- 238000010438 heat treatment Methods 0.000 claims description 27
- ZWTDXYUDJYDHJR-UHFFFAOYSA-N (E)-1-(2,4-dihydroxyphenyl)-3-(2,4-dihydroxyphenyl)-2-propen-1-one Natural products OC1=CC(O)=CC=C1C=CC(=O)C1=CC=C(O)C=C1O ZWTDXYUDJYDHJR-UHFFFAOYSA-N 0.000 claims description 24
- YQHMWTPYORBCMF-UHFFFAOYSA-N Naringenin chalcone Natural products C1=CC(O)=CC=C1C=CC(=O)C1=C(O)C=C(O)C=C1O YQHMWTPYORBCMF-UHFFFAOYSA-N 0.000 claims description 24
- 229920001542 oligosaccharide Polymers 0.000 claims description 23
- 150000002482 oligosaccharides Chemical class 0.000 claims description 23
- 238000001816 cooling Methods 0.000 claims description 22
- 239000008367 deionised water Substances 0.000 claims description 22
- 229910021641 deionized water Inorganic materials 0.000 claims description 22
- 238000002390 rotary evaporation Methods 0.000 claims description 22
- 238000000967 suction filtration Methods 0.000 claims description 22
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 22
- 239000000706 filtrate Substances 0.000 claims description 19
- 238000010992 reflux Methods 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 238000001291 vacuum drying Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 17
- 230000001681 protective effect Effects 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 acyl chloride phloretin derivative Chemical class 0.000 claims description 14
- 238000004321 preservation Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 13
- 239000013067 intermediate product Substances 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 235000020737 peppermint extract Nutrition 0.000 claims description 10
- 230000001105 regulatory effect Effects 0.000 claims description 10
- 238000000502 dialysis Methods 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 7
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 claims description 7
- KPFPCGFKQNSWSQ-UHFFFAOYSA-N ethyl 4-hydroxy-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(O)C=C1C KPFPCGFKQNSWSQ-UHFFFAOYSA-N 0.000 claims description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 7
- 239000012286 potassium permanganate Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 244000131522 Citrus pyriformis Species 0.000 claims description 5
- 244000246386 Mentha pulegium Species 0.000 claims description 5
- 235000016257 Mentha pulegium Nutrition 0.000 claims description 5
- 235000004357 Mentha x piperita Nutrition 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 5
- 238000004108 freeze drying Methods 0.000 claims description 5
- 235000001050 hortel pimenta Nutrition 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 238000010298 pulverizing process Methods 0.000 claims description 5
- 238000007873 sieving Methods 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 238000010025 steaming Methods 0.000 claims description 5
- 238000004659 sterilization and disinfection Methods 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 2
- 238000002137 ultrasound extraction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 3
- 244000248349 Citrus limon Species 0.000 abstract 1
- 239000008236 heating water Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 73
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 20
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000001953 sensory effect Effects 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 235000013305 food Nutrition 0.000 description 8
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- WJAXXWSZNSFVNG-UHFFFAOYSA-N 2-bromoethanamine;hydron;bromide Chemical compound [Br-].[NH3+]CCBr WJAXXWSZNSFVNG-UHFFFAOYSA-N 0.000 description 6
- PNHHVOISKCAJLC-UHFFFAOYSA-N benzaldehyde;methanol Chemical compound OC.O=CC1=CC=CC=C1 PNHHVOISKCAJLC-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 4
- 238000000944 Soxhlet extraction Methods 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910001961 silver nitrate Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000009210 therapy by ultrasound Methods 0.000 description 4
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000004302 potassium sorbate Substances 0.000 description 3
- 235000010241 potassium sorbate Nutrition 0.000 description 3
- 229940069338 potassium sorbate Drugs 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 206010058667 Oral toxicity Diseases 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 231100000418 oral toxicity Toxicity 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000235342 Saccharomycetes Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000607764 Shigella dysenteriae Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000001339 gustatory effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000012009 microbiological test Methods 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000015541 sensory perception of touch Effects 0.000 description 1
- 229940007046 shigella dysenteriae Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical group [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
- A23G3/48—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing plants or parts thereof, e.g. fruits, seeds, extracts
-
- 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
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
- A23G3/364—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
-
- 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
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
- A23G3/42—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
-
- 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
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3562—Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/90—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in food processing or handling, e.g. food conservation
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Nutrition Science (AREA)
- Botany (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Abstract
The invention relates to a flavor syrup and a preparation method thereof, belonging to the technical field of syrup production, and comprising the following raw materials in percentage by mass: 40-50% of white granulated sugar, 5-10% of fructose syrup, 10-20% of brown granulated sugar, 3-5% of mint extract, 0.1-1% of lemon juice concentrate, 0.01-0.1% of citric acid, 0.01-0.1% of malic acid, 0.01-0.1% of xanthan gum, 0.01-0.1% of sodium carboxymethyl cellulose, 0.1-2% of edible essence, 0.01-0.1% of pigment, 0.04-0.1% of chitosan oligosaccharide-based preservative and the balance of purified water; heating water to 85 ℃, adding white granulated sugar, stirring, transferring to a heat-preserving tank, adding high fructose syrup and brown granulated sugar, preserving heat, stirring, adding the rest raw materials, mixing for 1-2h, sterilizing, filtering to obtain flavored syrup, and endowing the syrup with good flavor and storage performance by adding a chitosan oligosaccharide-based preservative and a mint extract.
Description
Technical Field
The invention belongs to the technical field of syrup production, and particularly relates to a flavored syrup and a preparation method thereof.
Background
The flavor syrup is a compound syrup with various specific flavors, which is formed by taking white granulated sugar as a basic raw material and adding auxiliary materials such as flavor, color and acidity regulating substances, and the like, is widely applied to instant drinks such as coffee, wine preparation, milk tea and the like as a main raw material, and has very wide application prospect.
The syrup is easy to be polluted by mould, saccharomycete or other microorganisms in the preparation process because of containing nutrient components such as sugar, protein and the like, so that the standard of the hygiene index of the syrup cannot meet the requirement. In order to prevent mildew, artificial preservative is usually added in the production to inhibit and delay the proliferation of microorganisms, so that the quality of syrup meets the food safety requirement. The common preservatives used in syrup formulations are benzoic acids, nipagins, potassium sorbate and the like. Benzoic acid and nipagin preservatives have small water solubility and are easy to dissolve in ethanol, and the conventional method for assisting in dissolution by using organic solvents in production is to dissolve nipagin ethyl ester and benzoic acid in ethanol to prepare a pre-formulation, and the pre-formulation is prepared into syrup by stirring while adding, so that the nipagin ethyl ester and the benzoic acid are dispersed and dissolved rapidly. However, when the preservative ethanol solution and the syrup are mixed, because the polarities of the preservative ethanol solution and the syrup are different, turbidity occurs at the part contacted with the syrup, the preservative is easy to crystallize and separate out, redissolution is difficult, the preservative effect of the syrup is affected, and the ethanol for dissolving the preservative is brought into the syrup, so that the color, the smell and the taste of the syrup are affected, and the potassium sorbate is a chemical preservative although the water solubility is higher, and can generate certain toxic and side effects on a human body, so that the flavor syrup added with the safe and natural preservative with good solubility and high activity is a technical problem to be solved at present.
Disclosure of Invention
In order to solve the technical problems mentioned in the background art, the invention provides a flavor syrup and a preparation method thereof.
The aim of the invention can be achieved by the following technical scheme:
a flavor syrup comprises the following raw materials in percentage by mass: 40-50% of white granulated sugar, 5-10% of fructose syrup, 10-20% of brown granulated sugar, 3-5% of mint extract, 0.1-1% of lemon juice concentrate, 0.01-0.1% of citric acid, 0.01-0.1% of malic acid, 0.01-0.1% of xanthan gum, 0.01-0.1% of sodium carboxymethyl cellulose, 0.1-2% of edible essence, 0.01-0.1% of pigment, 0.04-0.1% of chitosan oligosaccharide-based preservative and the balance of purified water;
the flavor syrup is prepared by the following steps:
adding water into a digester, heating to 85 ℃, adding white granulated sugar, and stirring until the white granulated sugar is completely dissolved to obtain main syrup;
transferring the main syrup into a heat preservation tank, adding high fructose syrup and brown granulated sugar, preserving heat and stirring for 20-30min, adding the rest raw materials, stirring and mixing for 1-2h, transferring into a heat preservation and sterilization tank, preserving heat at 90 ℃ for 15min, and filtering by a 80-mesh filter after the treatment is finished to obtain the flavor syrup.
Further, the peppermint extract is prepared by the following steps:
drying herba Menthae at 60deg.C to constant weight, pulverizing, sieving with 80 mesh sieve, adding into 50% ethanol solution, power 400W, ultrasonic extracting at 50deg.C for 30-60min, cooling to room temperature, filtering, concentrating filtrate to 1/10 of original volume, and preserving in-20deg.C refrigerator to obtain herba Menthae extract.
Wherein, the dosage ratio of the peppermint to the ethanol solution is 1g:20mL, ethanol solution is used as extraction solvent, and ultrasonic treatment is adopted to obtain the peppermint extract.
Further, the chitosan oligosaccharide-based preservative is prepared by the following steps:
step A1, placing a phloretin derivative in a three-neck flask, adding thionyl chloride and DMF, heating to reflux reaction for 3 hours, and removing DMF and redundant thionyl chloride by rotary evaporation after the reaction is finished to obtain an acyl chloride phloretin derivative;
wherein the dosage ratio of the phloretin derivative, the thionyl chloride and the DMF is 0.05mol:20-25mL:120-150mL, and performing acyl chlorination on the phloretin derivative by using thionyl chloride to obtain the acyl chloride phloretin derivative, wherein the structural formula is as follows:
step A2, placing chitosan oligosaccharide into acetic acid solution with the mass fraction of 1%, adding methanol, uniformly stirring, transferring to a three-neck flask, heating to 60 ℃, dropwise adding methanol solution of benzaldehyde, carrying out heat preservation reaction for 2 hours, cooling to room temperature, adding sodium hydroxide solution with the mass fraction of 5% to adjust the pH value to 7.0, continuously stirring until flocculent precipitate is not generated any more, carrying out suction filtration, collecting precipitate, carrying out Soxhlet extraction on the precipitate with absolute ethyl alcohol for 12 hours, washing to neutrality, and carrying out vacuum drying at 60 ℃ to constant weight to obtain amino protective shell oligosaccharide;
wherein, the dosage ratio of the chitosan oligosaccharide to the acetic acid solution to the methanol solution of methanol and benzaldehyde is 10-12g:120mL:100mL:120mL, wherein the methanol solution of benzaldehyde is prepared from benzaldehyde and methanol according to a volume ratio of 1:10, performing condensation reaction on amino groups of the chitosan oligosaccharide and aldehyde groups of benzaldehyde to protect the amino groups of the chitosan oligosaccharide to obtain amino protective shell oligosaccharide;
step A3, uniformly mixing an acyl chloride phloretin derivative and DMF, dropwise adding a DMF solution of amino protective shell oligosaccharide into the mixture, adding pyridine after the dropwise addition, stirring the mixture at 25 ℃ for reaction for 6 hours, adding acetone to terminate the reaction to precipitate a product, carrying out suction filtration, extracting a filter cake with acetone for 12 hours, and carrying out vacuum drying at 60 ℃ to constant weight to obtain phloretin grafted chitosan oligosaccharide;
wherein, the dosage ratio of the DMF solution of the acyl chloride phloretin derivative, the DMF, the pyridine and the amino protective shell oligosaccharide is 0.02mol:250-300mL:0.04mol:100mL of a DMF solution of the amino-protecting oligosaccharide was prepared from the amino-protecting oligosaccharide and DMF at 10g:100mL of the mixture; under an alkaline environment, enabling an acyl chloride phloretin derivative and an alcohol hydroxyl group of amino protective shell oligosaccharide to undergo elimination HCl reaction to obtain phloretin grafted chitosan oligosaccharide;
and A4, placing phloretin grafted chitosan oligosaccharide in an ethanol hydrochloric acid solution, stirring for 12 hours at room temperature, regulating the pH value to be neutral by using a sodium carbonate solution with the mass fraction of 10%, washing by using acetone, carrying out suction filtration, carrying out vacuum drying, dialyzing the dried product in deionized water for 4 days by using a cellulose dialysis bag, replacing the deionized water during the dialysis, detecting by using silver nitrate every time the deionized water is replaced until no white precipitate is generated in the deionized water, and then carrying out freeze drying to obtain the chitosan oligosaccharide-based preservative.
Wherein, the dosage ratio of the phloretin grafted chitosan oligosaccharide to the ethanol solution of hydrochloric acid is 10g:110-150mL, hydrochloric acid ethanol solution is formed by mixing hydrochloric acid solution with the concentration of 0.25mol/L and ethanol according to the volume ratio of 1:4, and in the hydrochloric acid solution, the phloretin grafted chitosan oligosaccharide is subjected to deprotection to release amino active groups, so that the chitosan oligosaccharide-based preservative is obtained.
Further, the phloretin derivative is prepared by the following steps:
step B1, dissolving 4-hydroxy-2-methylbenzoic acid ethyl ester and hydrazine hydrate with the mass fraction of 85% into absolute ethyl alcohol, heating to reflux for 10 hours, after the reaction is finished, performing rotary evaporation to 1/3 of the original volume, cooling to form white precipitate, performing suction filtration, recrystallizing the ethanol, performing suction filtration, and drying to obtain an intermediate product 1;
wherein the dosage ratio of the ethyl 4-hydroxy-2-methylbenzoate, the hydrazine hydrate and the absolute ethyl alcohol is 0.05mol:20mL:80-100mL of ethyl 4-hydroxy-2-methylbenzoate and hydrazine hydrate are subjected to chemical reaction to obtain an intermediate product 1, and the structural formula is as follows:
step B2, adding the intermediate product 1 and DMF into a reaction kettle, adding potassium permanganate and 17% hydrochloric acid solution by mass fraction, then heating to 65-68 ℃, stirring for reaction for 4-5h, cooling to room temperature, filtering, and steaming the filtrate to obtain a hydrazide compound;
wherein, the dosage ratio of the intermediate product 1, DMF, potassium permanganate and hydrochloric acid solution is 0.05mol:50-80mL:0.8-1.3g:20-30mL, and oxidizing methyl on benzene ring of intermediate product 1 into carboxyl by using potassium permanganate as oxidant to obtain hydrazide compound with the following structural formula:
step B3, placing anhydrous potassium carbonate into DMF, stirring for 20min, adding phloretin and 2-bromoethylamine hydrobromide, refluxing and stirring for 1-3h, naturally cooling to room temperature after the reaction is finished, filtering, removing DMF by rotary evaporation of filtrate, recrystallizing the rotary evaporation product with deionized water twice, and drying in vacuum at 60 ℃ to constant weight to obtain the aminated phloretin;
wherein, the dosage ratio of anhydrous potassium carbonate, DMF, phloretin and 2-bromoethylamine hydrobromide is as follows: 0.1mol:300-350mL:0.05mol: the phloretin and 2-bromoethylamine hydrobromide undergo elimination of halogenated hydrogen to react to obtain the amino phloretin, and the structural formula is as follows:
step B4, placing the aminated phloretin and the hydrazide compound in a three-neck flask, adding absolute ethyl alcohol, stirring for 20min, sequentially adding toluene and p-toluenesulfonic acid, heating to reflux reaction for 48-50h, filtering after the reaction is finished, performing rotary evaporation on the filtrate, separating by using a 200-300 mesh silica gel column chromatography, performing dry sample loading, mixing ethyl acetate and petroleum ether according to a volume ratio of 1:1, collecting and concentrating a target product by using an eluent, and performing vacuum drying at 60 ℃ until the weight is constant to obtain the phloretin derivative;
wherein the dosage ratio of the amino phloretin to the hydrazide compound to the absolute ethanol to the toluene to the p-toluenesulfonic acid is 0.05mol:0.05mol:250-300mL:40-50mL:0.7-0.9g, and reacting aminated phloretin with hydrazide compound to obtain phloretin derivative with the following structural formula:
the invention has the beneficial effects that:
the invention provides a flavor syrup, which is endowed with unique cool flavor by adding a mint extract, wherein the main components of the mint extract are L-menthol and flavonoid substances, the mint extract has the effects of resisting tumor, resisting inflammation and easing pain, has important regulating functions on a central nervous system, a digestive system and an antibacterial and anti-inflammatory system, and aims to solve the problems that the existing preservative has poor compatibility with syrup, is easy to precipitate and crystallize and affects the color and the smell of the syrup; under an alkaline environment, enabling an acyl chloride phloretin derivative and an alcohol hydroxyl group of amino protective shell oligosaccharide to undergo elimination HCl reaction to obtain phloretin grafted chitosan oligosaccharide; in hydrochloric acid solution, the phloretin grafted chitosan oligosaccharide is deprotected to release amino active groups to obtain the chitosan oligosaccharide-based preservative, wherein the chitosan oligosaccharide-based preservative not only has higher antibacterial activity, but also is grafted with phloretin derivatives, contains a plurality of phenolic hydroxyl groups, hydrophilic amino groups and other groups, has better water solubility, thermal stability and oxidation resistance, and is safe, nontoxic and higher in antibacterial activity after being tested, so that the chitosan oligosaccharide-based preservative can better play a role in preserving when being added into flavor syrup.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
The embodiment provides a chitosan oligosaccharide-based preservative, which is prepared by the following steps:
step A1, placing 0.05mol of phloretin derivative into a three-neck flask, adding 20mL of thionyl chloride and 120mL of DMF, heating to reflux for 3h, and removing the DMF and the redundant thionyl chloride by rotary evaporation after the reaction is finished to obtain the phloretin derivative;
step A2, placing 10g of chitosan oligosaccharide into 120mL of acetic acid solution with the mass fraction of 1%, adding 100mL of methanol, uniformly stirring, transferring to a three-neck flask, heating to 60 ℃, dropwise adding 120mL of benzaldehyde methanol solution, carrying out heat preservation reaction for 2h, cooling to room temperature after the reaction is finished, adding 5% of sodium hydroxide solution with the mass fraction of regulating the pH value to 7.0, continuously stirring until no flocculent precipitate is generated, carrying out suction filtration, collecting the precipitate, carrying out Soxhlet extraction on the precipitate with absolute ethyl alcohol for 12h, washing to neutrality, and carrying out vacuum drying at 60 ℃ until the weight is constant, thereby obtaining the amino-protective shell oligosaccharide, wherein the benzaldehyde methanol solution is prepared from benzaldehyde and methanol according to the volume ratio of 1:10, mixing;
step A3, uniformly mixing 0.02mol of acyl chloride phloretin derivative and 250mL of DMF, dropwise adding 100mL of DMF solution of amino protective shell oligosaccharide into the mixture, adding 0.04mol of pyridine after the dropwise addition, stirring the mixture at 25 ℃ for reaction for 6 hours, adding acetone to terminate the reaction to precipitate a product, carrying out suction filtration, extracting a filter cake with acetone for 12 hours, and carrying out vacuum drying at 60 ℃ until the constant weight to obtain phloretin grafted chitosan oligosaccharide, wherein the DMF solution of the amino protective shell oligosaccharide is prepared from 10g of amino protective shell oligosaccharide and DMF: 100mL of the mixture;
and A4, placing 10g of phloretin grafted chitosan oligosaccharide in 110mL of ethanol hydrochloride solution, stirring for 12 hours at room temperature, regulating the pH value to be neutral by using a sodium carbonate solution with the mass fraction of 10%, washing by using acetone, carrying out suction filtration, carrying out vacuum drying, dialyzing the dried product in deionized water for 4 days by using a cellulose dialysis bag, replacing the deionized water during the dialysis, detecting by using silver nitrate when the deionized water is replaced once until no white precipitate is generated in the deionized water, and then freeze-drying to obtain the chitosan oligosaccharide-based preservative, wherein the ethanol hydrochloride solution is prepared by mixing a hydrochloric acid solution with the concentration of 0.25mol/L and ethanol according to the volume ratio of 1:4.
Wherein the phloretin derivative is prepared by the following steps:
step B1, dissolving 0.05mol of 4-hydroxy-2-methylbenzoic acid ethyl ester and 20mL of hydrazine hydrate with the mass fraction of 85% into 80mL of absolute ethyl alcohol, heating to reflux for reaction for 10h, after the reaction is finished, performing rotary evaporation to 1/3 of the original volume, cooling to form white precipitate, performing suction filtration, recrystallizing the ethanol, performing suction filtration, and drying to obtain an intermediate product 1;
step B2, adding 0.05mol of intermediate product 1 and 50mL of DMF into a reaction kettle, adding 0.8g of potassium permanganate and 20mL of 17% hydrochloric acid solution by mass fraction, heating to 65 ℃, stirring for reaction for 4 hours, cooling to room temperature, filtering, and steaming filtrate to obtain a hydrazide compound;
step B3, placing 0.1mol of anhydrous potassium carbonate into 300mL of DMF, stirring for 20min, adding 0.05mol of phloretin and 0.05mol of 2-bromoethylamine hydrobromide, refluxing and stirring for 1h, naturally cooling to room temperature after the reaction is finished, filtering, removing DMF by rotary evaporation of filtrate, recrystallizing the rotary evaporation product with deionized water twice, and drying in vacuum at 60 ℃ to constant weight to obtain the aminated phloretin;
and B4, placing 0.05mol of aminated phloretin and 0.05mol of hydrazide compound into a three-necked flask, adding 250mL of absolute ethyl alcohol, stirring for 20min, sequentially adding 40mL of toluene and 0.7g of p-toluenesulfonic acid, heating to reflux reaction for 48h, filtering after the reaction is finished, performing chromatographic separation on filtrate by using a 200-mesh silica gel column after rotary evaporation, performing dry sample loading, mixing ethyl acetate and petroleum ether according to a volume ratio of 1:1 as an eluent, collecting and concentrating a target product, and performing vacuum drying at 60 ℃ until the weight is constant to obtain the phloretin derivative.
Example 2
The embodiment provides a chitosan oligosaccharide-based preservative, which is prepared by the following steps:
step A1, placing 0.05mol of phloretin derivative into a three-neck flask, adding 22mL of thionyl chloride and 140mL of DMF, heating to reflux for 3h, and removing the DMF and the redundant thionyl chloride by rotary evaporation after the reaction is finished to obtain the phloretin derivative;
step A2, placing 11g of chitosan oligosaccharide into 120mL of acetic acid solution with the mass fraction of 1%, adding 100mL of methanol, uniformly stirring, transferring to a three-neck flask, heating to 60 ℃, dropwise adding 120mL of benzaldehyde methanol solution, carrying out heat preservation reaction for 2h, cooling to room temperature after the reaction is finished, adding 5% of sodium hydroxide solution with the mass fraction of regulating the pH value to 7.0, continuously stirring until no flocculent precipitate is generated, carrying out suction filtration, collecting the precipitate, carrying out Soxhlet extraction on the precipitate with absolute ethyl alcohol for 12h, washing to neutrality, and carrying out vacuum drying at 60 ℃ until the weight is constant, thereby obtaining the amino-protective shell oligosaccharide, wherein the benzaldehyde methanol solution is prepared by mixing benzaldehyde and methanol according to the volume ratio of 1:10, mixing;
step A3, uniformly mixing 0.02mol of acyl chloride phloretin derivative and 280mL of DMF, dropwise adding 100mL of DMF solution of amino protective shell oligosaccharide into the mixture, adding 0.04mol of pyridine after the dropwise addition, stirring the mixture at 25 ℃ for reaction for 6 hours, adding acetone to terminate the reaction to precipitate a product, carrying out suction filtration, extracting a filter cake with acetone for 12 hours, and carrying out vacuum drying at 60 ℃ until the constant weight to obtain phloretin grafted chitosan oligosaccharide, wherein the DMF solution of the amino protective shell oligosaccharide is prepared from 10g of amino protective shell oligosaccharide and DMF: 100mL of the mixture;
and A4, placing 10g of phloretin grafted chitosan oligosaccharide in 120mL of ethanol solution of hydrochloric acid, stirring for 12 hours at room temperature, regulating the pH value to be neutral by using 10% sodium carbonate solution by mass fraction, washing by using acetone, carrying out suction filtration, carrying out vacuum drying, dialyzing the dried product in deionized water for 4 days by using a cellulose dialysis bag, replacing the deionized water during the dialysis, detecting by using silver nitrate when the deionized water is replaced once until no white precipitate is generated in the deionized water, and then freeze-drying to obtain the chitosan oligosaccharide-based preservative, wherein the ethanol solution of hydrochloric acid is prepared by mixing 0.25mol/L hydrochloric acid solution and ethanol according to a volume ratio of 1:4.
Wherein the phloretin derivative is prepared by the following steps:
step B1, dissolving 0.05mol of 4-hydroxy-2-methylbenzoic acid ethyl ester and 20mL of hydrazine hydrate with the mass fraction of 85% into 90mL of absolute ethyl alcohol, heating to reflux for reaction for 10h, after the reaction is finished, performing rotary evaporation to 1/3 of the original volume, cooling to form white precipitate, performing suction filtration, recrystallizing the ethanol, performing suction filtration, and drying to obtain an intermediate product 1;
step B2, adding 0.05mol of intermediate product 1 and 70mL of DMF into a reaction kettle, adding 1.0g of potassium permanganate and 25mL of 17% hydrochloric acid solution by mass fraction, heating to 67 ℃, stirring and reacting for 4.5h, cooling to room temperature, filtering, and steaming filtrate to obtain a hydrazide compound;
step B3, placing 0.1mol of anhydrous potassium carbonate into 320mL of DMF, stirring for 20min, adding 0.05mol of phloretin and 0.05mol of 2-bromoethylamine hydrobromide, refluxing and stirring for 2h, naturally cooling to room temperature after the reaction is finished, filtering, removing DMF by rotary evaporation of filtrate, recrystallizing the rotary evaporation product with deionized water twice, and drying in vacuum at 60 ℃ to constant weight to obtain the aminated phloretin;
and B4, placing 0.05mol of aminated phloretin and 0.05mol of hydrazide compound into a three-necked flask, adding 280mL of absolute ethyl alcohol, stirring for 20min, sequentially adding 45mL of toluene and 0.8g of p-toluenesulfonic acid, heating to reflux reaction for 49h, filtering after the reaction is finished, performing chromatographic separation on the filtrate by using a 250-mesh silica gel column after rotary evaporation, performing dry sample loading, mixing ethyl acetate and petroleum ether according to a volume ratio of 1:1 as an eluent, collecting and concentrating a target product, and performing vacuum drying at 60 ℃ until the weight is constant to obtain the phloretin derivative.
Example 3
The embodiment provides a chitosan oligosaccharide-based preservative, which is prepared by the following steps:
step A1, placing 0.05mol of phloretin derivative into a three-neck flask, adding 25mL of thionyl chloride and 150mL of DMF, heating to reflux for 3h, and removing the DMF and the redundant thionyl chloride by rotary evaporation after the reaction is finished to obtain the phloretin derivative;
step A2, placing 12g of chitosan oligosaccharide into 120mL of acetic acid solution with the mass fraction of 1%, adding 100mL of methanol, uniformly stirring, transferring to a three-neck flask, heating to 60 ℃, dropwise adding 120mL of benzaldehyde methanol solution, carrying out heat preservation reaction for 2h, cooling to room temperature after the reaction is finished, adding 5% of sodium hydroxide solution with the mass fraction of regulating the pH value to 7.0, continuously stirring until no flocculent precipitate is generated, carrying out suction filtration, collecting the precipitate, carrying out Soxhlet extraction on the precipitate with absolute ethyl alcohol for 12h, washing to neutrality, and carrying out vacuum drying at 60 ℃ until the weight is constant, thereby obtaining the amino-protective shell oligosaccharide, wherein the benzaldehyde methanol solution is prepared by mixing benzaldehyde and methanol according to the volume ratio of 1:10, mixing;
step A3, uniformly mixing 0.02mol of acyl chloride phloretin derivative and 300mL of DMF, dropwise adding 100mL of DMF solution of amino protective shell oligosaccharide into the mixture, adding 0.04mol of pyridine after the dropwise addition, stirring the mixture at 25 ℃ for reaction for 6 hours, adding acetone to terminate the reaction to precipitate a product, carrying out suction filtration, extracting a filter cake with acetone for 12 hours, and carrying out vacuum drying at 60 ℃ until the constant weight to obtain phloretin grafted chitosan oligosaccharide, wherein the DMF solution of the amino protective shell oligosaccharide is prepared from 10g of amino protective shell oligosaccharide and DMF: 100mL of the mixture;
and A4, placing 10g of phloretin grafted chitosan oligosaccharide in 150mL of ethanol hydrochloride solution, stirring for 12 hours at room temperature, regulating the pH value to be neutral by using 10% sodium carbonate solution by mass fraction, washing by using acetone, carrying out suction filtration, carrying out vacuum drying, dialyzing the dried product in deionized water for 4 days by using a cellulose dialysis bag, replacing the deionized water during the dialysis, detecting by using silver nitrate when the deionized water is replaced once until no white precipitate is generated in the deionized water, and then freeze-drying to obtain the chitosan oligosaccharide-based preservative, wherein the ethanol hydrochloride solution is prepared by mixing 0.25mol/L hydrochloric acid solution and ethanol according to a volume ratio of 1:4.
Wherein the phloretin derivative is prepared by the following steps:
step B1, dissolving 0.05mol of 4-hydroxy-2-methylbenzoic acid ethyl ester and 20mL of hydrazine hydrate with the mass fraction of 85% into 100mL of absolute ethyl alcohol, heating to reflux for reaction for 10h, after the reaction is finished, performing rotary evaporation to 1/3 of the original volume, cooling to form white precipitate, performing suction filtration, recrystallizing the ethanol, performing suction filtration, and drying to obtain an intermediate product 1;
step B2, adding 0.05mol of intermediate product 1 and 80mL of DMF into a reaction kettle, adding 1.3g of potassium permanganate and 30mL of 17% hydrochloric acid solution by mass fraction, heating to 68 ℃, stirring for reaction for 5h, cooling to room temperature, filtering, and steaming filtrate to obtain a hydrazide compound;
step B3, placing 0.1mol of anhydrous potassium carbonate into 350mL of DMF, stirring for 20min, adding 0.05mol of phloretin and 0.05mol of 2-bromoethylamine hydrobromide, refluxing and stirring for 3h, naturally cooling to room temperature after the reaction is finished, filtering, removing DMF by rotary evaporation of filtrate, recrystallizing the rotary evaporation product with deionized water twice, and drying in vacuum at 60 ℃ to constant weight to obtain the aminated phloretin;
and B4, placing 0.05mol of aminated phloretin and 0.05mol of hydrazide compound into a three-necked flask, adding 300mL of absolute ethyl alcohol, stirring for 20min, sequentially adding 50mL of toluene and 0.9g of p-toluenesulfonic acid, heating to reflux reaction for 50h, filtering after the reaction is finished, performing chromatographic separation on filtrate by using a 300-mesh silica gel column after rotary evaporation, performing dry sample loading, mixing an eluent of ethyl acetate and petroleum ether according to a volume ratio of 1:1, collecting and concentrating a target product by using an eluent, and performing vacuum drying at 60 ℃ until the weight is constant to obtain the phloretin derivative.
Comparative example 1
The comparative example is chitosan sold by Shandong Fengtai Biotechnology Co.
Comparative example 2
The comparative example is sodium benzoate sold by Hangzhou Dingyan chemical industry Co.
Comparative example 3
The comparative example was potassium sorbate sold by the company Nantong acetate chemical engineering Co.
The substances of examples 1-3 and comparative examples 1-3 were subjected to an oral toxicity test according to the standard GB15193.13-2015, 90 day oral toxicity test, and test results show that the substances are safe and can be used as food additives in reasonable dosage, and then subjected to a solubility test and an antibacterial activity test:
dissolution performance: accurately weighing 0.1g of each group of reagent, adding into a test tube containing 1mL of distilled water, stirring, observing and recording the dissolution phenomenon, if the solution is not clear, continuously adding 1mL of distilled water to dilute until the solution is completely dissolved, and recording the amount of a sample dissolved in 1mL of water;
antibacterial activity: preparing each group of reagents into 2.5mg/mL solution, filtering with a microporous filter membrane with 0.22um to obtain an antibacterial agent, culturing and mixing 1mL of initial bacterial solution with 98mL of sterilized nutrient broth, adding 1mL of the antibacterial agent, taking 1mL of deionized water as a blank instead of the antibacterial agent solution, performing shake culture at 37 ℃, taking out 1mL of culture solution after 8 hours in the culture process, performing multiple dilution, and calculating colony number by a coating plate method, wherein each sample is repeated for 3 times. The antibacterial rate I is calculated according to the following formula:
I(％)＝(N1-N2)/N1x100％
wherein, N1: total number of colonies in the initial culture; n2: the total number of colonies in the culture solution containing the antibacterial agent; inhibiting the concentration of the antibacterial agent on the abscissaThe preparation rate is plotted on the ordinate to obtain the IC 50 The values, test strains were staphylococcus aureus, streptococcus pyogenes, bacillus subtilis, salmonella typhimurium, shigella dysenteriae and escherichia coli, and the test results are shown in table 1:
TABLE 1
As can be seen from Table 1, the chitosan-based preservative of examples 1-3 has significantly better solubility in water than chitosan and has higher antibacterial activity than comparative examples 1-3, so that the chitosan-based preservative prepared by the invention has higher water solubility and higher antibacterial activity.
Example 4
A flavor syrup comprises the following raw materials in percentage by mass: 40% of white granulated sugar, 10% of high fructose syrup, 10% of brown granulated sugar, 3% of mint extract, 0.1% of lemon juice concentrate, 0.05% of citric acid, 0.05% of malic acid, 0.01% of xanthan gum, 0.01% of sodium carboxymethyl cellulose, 0.1% of edible essence, 0.01% of pigment, 0.04% of chitosan oligosaccharide-based preservative of example 1 and the balance of purified water;
the flavor syrup is prepared by the following steps:
adding water into a digester, heating to 85 ℃, adding white granulated sugar, and stirring until the white granulated sugar is completely dissolved to obtain main syrup;
transferring the main syrup into a heat preservation tank, adding high fructose syrup and brown granulated sugar, preserving heat and stirring for 20min, adding the rest raw materials, stirring and mixing for 1h, transferring into a heat preservation and sterilization tank, preserving heat at 90 ℃ for 15min, and filtering by a 80-mesh filter after the treatment is finished to obtain the flavor syrup.
Wherein the peppermint extract is prepared by the following steps:
drying herba Menthae at 60deg.C to constant weight, pulverizing, sieving with 80 mesh sieve, adding into 50% ethanol solution, power 400W, ultrasonic extracting at 50deg.C for 30min, cooling to room temperature, filtering, concentrating filtrate to 1/10 of original volume, and storing in refrigerator at-20deg.C to obtain herba Menthae extract.
Wherein, the dosage ratio of the peppermint to the ethanol solution is 1g:20mL, ethanol solution is used as extraction solvent, and ultrasonic treatment is adopted to obtain the peppermint extract.
Example 5
A flavor syrup comprises the following raw materials in percentage by mass: 45% of white granulated sugar, 8% of high fructose syrup, 15% of brown granulated sugar, 4% of mint extract, 0.5% of lemon juice concentrate, 0.08% of citric acid, 0.06% of malic acid, 0.05% of xanthan gum, 0.05% of sodium carboxymethyl cellulose, 0.6% of edible essence, 0.05% of pigment, 0.06% of chitosan oligosaccharide-based preservative of example 2 and the balance of purified water;
the flavor syrup is prepared by the following steps:
adding water into a digester, heating to 85 ℃, adding white granulated sugar, and stirring until the white granulated sugar is completely dissolved to obtain main syrup;
transferring the main syrup into a heat preservation tank, adding high fructose syrup and brown granulated sugar, preserving heat and stirring for 25min, adding the rest raw materials, stirring and mixing for 1.5h, transferring into a heat preservation and sterilization tank, preserving heat at 90 ℃ for 15min, and filtering by a 80-mesh filter after the treatment is finished to obtain the flavor syrup.
Wherein the peppermint extract is prepared by the following steps:
drying herba Menthae at 60deg.C to constant weight, pulverizing, sieving with 80 mesh sieve, adding into 50% ethanol solution, power 400W, ultrasonic extracting at 50deg.C for 40min, cooling to room temperature, filtering, concentrating filtrate to 1/10 of original volume, and storing in refrigerator at-20deg.C to obtain herba Menthae extract.
Wherein, the dosage ratio of the peppermint to the ethanol solution is 1g:20mL, ethanol solution is used as extraction solvent, and ultrasonic treatment is adopted to obtain the peppermint extract.
Example 6
A flavor syrup comprises the following raw materials in percentage by mass: 50% of white granulated sugar, 10% of high fructose syrup, 10% of brown granulated sugar, 3% of mint extract, 0.1% of lemon juice concentrate, 0.01% of citric acid, 0.1% of malic acid, 0.01% of xanthan gum, 0.1% of sodium carboxymethyl cellulose, 0.15% of edible essence, 0.08% of pigment, 0.06% of chitosan oligosaccharide-based preservative of example 3 and the balance of purified water;
the flavor syrup is prepared by the following steps:
adding water into a digester, heating to 85 ℃, adding white granulated sugar, and stirring until the white granulated sugar is completely dissolved to obtain main syrup;
transferring the main syrup into a heat preservation tank, adding high fructose syrup and brown granulated sugar, preserving heat and stirring for 30min, adding the rest raw materials, stirring and mixing for 2h, transferring into a heat preservation and sterilization tank, preserving heat at 90 ℃ for 15min, and filtering by a 80-mesh filter after the treatment is finished to obtain the flavor syrup.
Wherein the peppermint extract is prepared by the following steps:
drying herba Menthae at 60deg.C to constant weight, pulverizing, sieving with 80 mesh sieve, adding into 50% ethanol solution, power 400W, ultrasonic extracting at 50deg.C for 60min, cooling to room temperature, filtering, concentrating filtrate to 1/10 of original volume, and storing in refrigerator at-20deg.C to obtain herba Menthae extract.
Wherein, the dosage ratio of the peppermint to the ethanol solution is 1g:20mL, ethanol solution is used as extraction solvent, and ultrasonic treatment is adopted to obtain the peppermint extract.
Comparative example 4
The peppermint extract of example 4 was removed, and the remaining materials and preparation process were unchanged.
Comparative example 5
The chitosan oligosaccharide based preservative of example 5 was replaced with the preservative of comparative example 2 in equal amount.
Comparative example 6
The chitosan oligosaccharide based preservative of example 6 was replaced with the preservative of comparative example 3 in equal amount.
Sensory evaluation of flavor syrup: an evaluation group consisting of 18 experienced evaluators was carried out, and their visual sense, olfactory sense, gustatory sense and tactile sense were in accordance with the requirement of the basic ability of the sensory evaluation of foods, and were trained and examined by a special sensory method. Through sensory evaluation work, indexes with great change in the storage process of the flavor syrup are defined, wherein the indexes comprise 6 sensory indexes including color, wall-hanging degree, transparency, main characteristic flavor, sweetness and sourness, and meanwhile, the sensory evaluation standard of the flavor syrup is formed, the specific sensory score standard is shown in a table 2, and the weight ratio of the characteristic flavor in the sensory total score is highest. And the sensory total score is obtained after the index scores are summed, the total score is between 0 and 100, and the sensory evaluation is better when the score is higher.
TABLE 2
(II) microbiological test: test samples were prepared according to the formula, according to the methods in GB/T4789.2-2016 (food safety national standard food microbiology test colony count determination), GB 4789.3-2016 (food safety national standard food microbiology test coliform count) and GB 4789.15-2016 (food safety national standard food microbiology test mold and yeast count), respectively at 0, 45d at 27 ℃,37 ℃ under storage conditions, the increase rate of the sample coliform count and mold count = (45 d colony count-0 d colony count)/0 d colony count × 100%, the test results are shown in table 3:
TABLE 3 Table 3
As can be seen from table 3, the flavor syrups of examples 4-6 have a higher sensory score and a longer lasting bacteriostatic effect, and therefore, have a longer shelf life and are more favored by consumers.
In the description of the present specification, the descriptions of the terms "one embodiment," "example," "specific example," and the like, mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present invention. In this specification, schematic representations of the above terms do not necessarily refer to the same embodiments or examples. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is merely illustrative and explanatory of the invention, as various modifications and additions may be made to the particular embodiments described, or in a similar manner, by those skilled in the art, without departing from the scope of the invention or exceeding the scope of the invention as defined in the claims.
Claims (4)
1. The flavor syrup is characterized by comprising the following raw materials in percentage by mass: 40-50% of white granulated sugar, 5-10% of fructose syrup, 10-20% of brown granulated sugar, 3-5% of mint extract, 0.1-1% of lemon juice concentrate, 0.01-0.1% of citric acid, 0.01-0.1% of malic acid, 0.01-0.1% of xanthan gum, 0.01-0.1% of sodium carboxymethyl cellulose, 0.1-2% of edible essence, 0.01-0.1% of pigment, 0.04-0.1% of chitosan oligosaccharide-based preservative and the balance of purified water;
wherein the chitosan oligosaccharide-based preservative is prepared by the following steps:
placing phloretin grafted chitosan oligosaccharide into ethanol hydrochloride solution, stirring for 12 hours at room temperature, regulating the pH value to be neutral by sodium carbonate, washing, carrying out suction filtration, carrying out vacuum drying, dialyzing the dried product in deionized water for 4 days by using a cellulose dialysis bag, and then carrying out freeze drying to obtain the chitosan oligosaccharide-based preservative;
the phloretin grafted chitosan oligosaccharide is prepared by the following steps:
mixing an acyl chloride phloretin derivative with DMF, dropwise adding a DMF solution of amino protective shell oligosaccharide into the mixture, adding pyridine after dropwise adding, stirring at 25 ℃ for reaction for 6 hours, adding acetone for terminating reaction, carrying out suction filtration, extracting a filter cake with acetone for 12 hours, and carrying out vacuum drying at 60 ℃ until the weight is constant to obtain phloretin grafted chitosan oligosaccharide;
the acid chloride phloretin derivative is prepared by the following steps:
placing the phloretin derivative into a three-neck flask, adding thionyl chloride and DMF, carrying out reflux reaction for 3 hours, and carrying out rotary evaporation to obtain an acyl chloride phloretin derivative;
the phloretin derivative is prepared by the following steps:
mixing the aminated phloretin and the hydrazide compound, adding absolute ethyl alcohol, stirring, sequentially adding toluene and p-toluenesulfonic acid, carrying out reflux reaction for 48-50h, filtering after the reaction is finished, carrying out rotary evaporation on the filtrate, and separating by silica gel column chromatography to obtain phloretin derivatives;
the hydrazide compound is prepared by the following steps:
step B1, dissolving 4-hydroxy-2-methylbenzoic acid ethyl ester and hydrazine hydrate with the mass fraction of 85% into absolute ethyl alcohol, and heating to reflux for reaction for 10 hours to obtain an intermediate product 1;
step B2, adding the intermediate product 1 and DMF into a reaction kettle, adding potassium permanganate and hydrochloric acid solution, heating to 65-68 ℃, stirring for reaction for 4-5h, cooling to room temperature, filtering, and steaming the filtrate to obtain a hydrazide compound;
the peppermint extract is prepared by the following steps:
drying herba Menthae at 60deg.C to constant weight, pulverizing, sieving with 80 mesh sieve, adding into 50% ethanol solution, performing ultrasonic extraction at power of 400W and temperature of 50deg.C for 30-60min, cooling to room temperature, filtering, concentrating filtrate to 1/10 of original volume, and preserving in-20deg.C refrigerator to obtain herba Menthae extract;
wherein, the dosage ratio of the peppermint to the ethanol solution is 1g:20mL.
2. A flavored syrup according to claim 1, wherein the ethanol solution of hydrochloric acid is mixed with ethanol at a concentration of 0.25mol/L at a volume ratio of 1:4.
3. A flavor syrup according to claim 1, characterized in that the DMF solution of the amino-protecting oligosaccharide is prepared from the amino-protecting oligosaccharide and DMF at a ratio of 10g:100mL of the mixture.
4. A method of preparing a flavored syrup according to claim 1, comprising the steps of:
adding water into a digester, heating to 85 ℃, adding white granulated sugar, and stirring until the white granulated sugar is completely dissolved to obtain main syrup;
transferring the main syrup into a heat preservation tank, adding high fructose syrup and brown granulated sugar, preserving heat and stirring for 20-30min, adding the rest raw materials, stirring and mixing for 1-2h, transferring into a heat preservation and sterilization tank, preserving heat at 90 ℃ for 15min, and filtering by a 80-mesh filter after the treatment is finished to obtain the flavor syrup.
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