CA1237141A

CA1237141A - Carboxylates aliphatiques 3-hydroxy-4- alcoyloxyphenyliques

Carboxylates aliphatiques 3-hydroxy-4- alcoyloxyphenyliques

Info

Publication number: CA1237141A
Authority: CA; Canada
Prior art keywords: hydroxy; methoxyphenyl; group; integer; sweetening agent
Prior art date: 1983-12-29
Legal status : Expired

Application number

CA000469307A

Other languages

English (en)

Inventor

Ronald E. Barnett

Jed A. Riemer

Paul R. Zanno

Current Assignee

General Foods Corp

Original Assignee

General Foods Corp

Priority date

1983-12-29

Filing date

1984-12-04

Publication date

1988-05-24

1984-12-04 Application filed by General Foods Corp filed Critical General Foods Corp

1988-05-24 Application granted granted Critical

1988-05-24 Publication of CA1237141A publication Critical patent/CA1237141A/fr

Status Expired legal-status Critical Current

Links

-1 aliphatic carboxylates Chemical class 0.000 title claims abstract description 26
235000003599 food sweetener Nutrition 0.000 claims abstract description 56
239000003765 sweetening agent Substances 0.000 claims abstract description 56
150000001875 compounds Chemical class 0.000 claims description 71
239000000203 mixture Substances 0.000 claims description 67
238000000034 method Methods 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000002993 cycloalkylene group Chemical group 0.000 claims description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
HOSWFPOUZAVPLW-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) 2-methylpropanoate Chemical compound COC1=CC=C(OC(=O)C(C)C)C=C1O HOSWFPOUZAVPLW-UHFFFAOYSA-N 0.000 claims description 6
MKXXAPIXRKJORN-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OC1=CC=C(OC)C(O)=C1 MKXXAPIXRKJORN-UHFFFAOYSA-N 0.000 claims description 5
GKWIJLPSSJJMAA-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1C(C=C2)CC2C1 GKWIJLPSSJJMAA-UHFFFAOYSA-N 0.000 claims description 5
TVMDGHNFYHKOJL-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) butanoate Chemical compound CCCC(=O)OC1=CC=C(OC)C(O)=C1 TVMDGHNFYHKOJL-UHFFFAOYSA-N 0.000 claims description 5
KUCSBHMRHGAGCB-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) cyclobutanecarboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1CCC1 KUCSBHMRHGAGCB-UHFFFAOYSA-N 0.000 claims description 5
FDYQGPLJYMKSHI-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) cyclohex-3-ene-1-carboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1CC=CCC1 FDYQGPLJYMKSHI-UHFFFAOYSA-N 0.000 claims description 5
KIMZZLUKFQSSKT-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) cyclopentanecarboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1CCCC1 KIMZZLUKFQSSKT-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
235000013361 beverage Nutrition 0.000 claims description 5
150000001993 dienes Chemical group 0.000 claims description 5
235000011852 gelatine desserts Nutrition 0.000 claims description 5
MXWCKGAJOOCOFR-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) 2-(cyclopenten-1-yl)acetate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)CC1=CCCC1 MXWCKGAJOOCOFR-UHFFFAOYSA-N 0.000 claims description 4
UDQSMCAYKNHTGI-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) 2-cyclopentylacetate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)CC1CCCC1 UDQSMCAYKNHTGI-UHFFFAOYSA-N 0.000 claims description 4
RIUZCPXVMYIXLO-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) 3,3-dimethylbutanoate Chemical compound COC1=CC=C(OC(=O)CC(C)(C)C)C=C1O RIUZCPXVMYIXLO-UHFFFAOYSA-N 0.000 claims description 4
QZPKJBYCMDNPNU-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) 3-methylbut-2-enoate Chemical compound COC1=CC=C(OC(=O)C=C(C)C)C=C1O QZPKJBYCMDNPNU-UHFFFAOYSA-N 0.000 claims description 4
LMJHTILIEUVNLH-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) bicyclo[2.2.1]heptane-3-carboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1C(C2)CCC2C1 LMJHTILIEUVNLH-UHFFFAOYSA-N 0.000 claims description 4
TZJFGRJBSBCYDB-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) cycloheptanecarboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1CCCCCC1 TZJFGRJBSBCYDB-UHFFFAOYSA-N 0.000 claims description 4
NIGNNXYPOVOUFQ-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) cyclohexanecarboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1CCCCC1 NIGNNXYPOVOUFQ-UHFFFAOYSA-N 0.000 claims description 4
PQNZCMPXSJKINV-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=C(OC)C(O)=C1 PQNZCMPXSJKINV-UHFFFAOYSA-N 0.000 claims description 4
SODLPGWOFRWFNL-UHFFFAOYSA-N (3-hydroxy-4-propoxyphenyl) butanoate Chemical compound CCCOC1=CC=C(OC(=O)CCC)C=C1O SODLPGWOFRWFNL-UHFFFAOYSA-N 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
235000011962 puddings Nutrition 0.000 claims description 4
230000008447 perception Effects 0.000 claims description 3
235000013336 milk Nutrition 0.000 claims description 2
239000008267 milk Substances 0.000 claims description 2
210000004080 milk Anatomy 0.000 claims description 2
QVXJMBYONUHSTM-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) 2-methylbutanoate Chemical compound CCC(C)C(=O)OC1=CC=C(OC)C(O)=C1 QVXJMBYONUHSTM-UHFFFAOYSA-N 0.000 claims 3
PXRCITKZFWXYNV-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) pent-4-enoate Chemical compound COC1=CC=C(OC(=O)CCC=C)C=C1O PXRCITKZFWXYNV-UHFFFAOYSA-N 0.000 claims 3
MUAYRPPKUKMKDL-UHFFFAOYSA-N (4-ethoxy-3-hydroxyphenyl) butanoate Chemical compound CCCC(=O)OC1=CC=C(OCC)C(O)=C1 MUAYRPPKUKMKDL-UHFFFAOYSA-N 0.000 claims 3
JBVGNTBYGVCNJJ-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) cyclopentene-1-carboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1=CCCC1 JBVGNTBYGVCNJJ-UHFFFAOYSA-N 0.000 claims 2
150000007942 carboxylates Chemical class 0.000 abstract description 2
229930006000 Sucrose Natural products 0.000 description 44
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 44
239000005720 sucrose Substances 0.000 description 44
239000000047 product Substances 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
239000007864 aqueous solution Substances 0.000 description 18
GUYAGMJZETTWMM-UHFFFAOYSA-N 4-methoxy-3-phenylmethoxyphenol Chemical compound COC1=CC=C(O)C=C1OCC1=CC=CC=C1 GUYAGMJZETTWMM-UHFFFAOYSA-N 0.000 description 17
238000005481 NMR spectroscopy Methods 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 11
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
235000011167 hydrochloric acid Nutrition 0.000 description 10
229960000443 hydrochloric acid Drugs 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
235000019605 sweet taste sensations Nutrition 0.000 description 9
JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 8
235000013305 food Nutrition 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000002253 acid Substances 0.000 description 5
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
108010011485 Aspartame Proteins 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
239000008122 artificial sweetener Substances 0.000 description 4
235000021311 artificial sweeteners Nutrition 0.000 description 4
239000000605 aspartame Substances 0.000 description 4
235000010357 aspartame Nutrition 0.000 description 4
229960003438 aspartame Drugs 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
238000002156 mixing Methods 0.000 description 4
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
NNRZTJAACCRFRV-UHFFFAOYSA-N 2-(2-cyclopentenyl)-ethanoic acid Chemical compound OC(=O)CC1CCC=C1 NNRZTJAACCRFRV-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
235000005979 Citrus limon Nutrition 0.000 description 3
244000131522 Citrus pyriformis Species 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000872 buffer Substances 0.000 description 3
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
235000009508 confectionery Nutrition 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
IQZZFVDIZRWADY-UHFFFAOYSA-N isocoumarin Chemical compound C1=CC=C2C(=O)OC=CC2=C1 IQZZFVDIZRWADY-UHFFFAOYSA-N 0.000 description 3
HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 3
235000019204 saccharin Nutrition 0.000 description 3
229940081974 saccharin Drugs 0.000 description 3
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
241000167854 Bourreria succulenta Species 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
206010013911 Dysgeusia Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000019693 cherries Nutrition 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229940109275 cyclamate Drugs 0.000 description 2
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
235000011850 desserts Nutrition 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 2
PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
TVHBMXJAQHVCSA-UHFFFAOYSA-N ethyl carbamimidate;hydrochloride Chemical compound [Cl-].CCOC(N)=[NH2+] TVHBMXJAQHVCSA-UHFFFAOYSA-N 0.000 description 2
235000021554 flavoured beverage Nutrition 0.000 description 2
230000006870 function Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
150000008163 sugars Chemical class 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
UYXMBPVOGLUKIV-UHFFFAOYSA-N (2-methoxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=CC=C1OC UYXMBPVOGLUKIV-UHFFFAOYSA-N 0.000 description 1
NTWSIWWJPQHFTO-AATRIKPKSA-N (2E)-3-methylhex-2-enoic acid Chemical compound CCC\C(C)=C\C(O)=O NTWSIWWJPQHFTO-AATRIKPKSA-N 0.000 description 1
NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical class C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
FWSSVEORJJNSIS-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) 2-methylcyclopropane-1-carboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1C(C)C1 FWSSVEORJJNSIS-UHFFFAOYSA-N 0.000 description 1
NUYHPASJJHDMNW-UHFFFAOYSA-N (3-hydroxy-4-methoxyphenyl) cyclopropanecarboxylate Chemical compound C1=C(O)C(OC)=CC=C1OC(=O)C1CC1 NUYHPASJJHDMNW-UHFFFAOYSA-N 0.000 description 1
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