NO135770B - - Google Patents
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- Publication number
- NO135770B NO135770B NO4674/72A NO467472A NO135770B NO 135770 B NO135770 B NO 135770B NO 4674/72 A NO4674/72 A NO 4674/72A NO 467472 A NO467472 A NO 467472A NO 135770 B NO135770 B NO 135770B
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- group
- propanone
- sweetener
- formula
- Prior art date
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- 235000003599 food sweetener Nutrition 0.000 claims description 12
- 239000003765 sweetening agent Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 206010013911 Dysgeusia Diseases 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 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 4
- 235000013305 food Nutrition 0.000 description 4
- -1 methoxy, ethoxy Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229960004793 sucrose Drugs 0.000 description 4
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 229940109275 cyclamate Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 235000019204 saccharin Nutrition 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000276498 Pollachius virens Species 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- GVSPXQVUXHMUMA-MDWZMJQESA-N (e)-3-(3,5-ditert-butyl-4-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)\C=C\C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GVSPXQVUXHMUMA-MDWZMJQESA-N 0.000 description 1
- GLSHEJRXROUYLB-UHFFFAOYSA-N 2-[3-hydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)propanoyl]phenoxy]acetic acid Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C1=CC=C(OCC(O)=O)C=C1O GLSHEJRXROUYLB-UHFFFAOYSA-N 0.000 description 1
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Chemical class 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000003085 diluting agent Substances 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 description 1
- 229940052490 naringin Drugs 0.000 description 1
- 229930019673 naringin Natural products 0.000 description 1
- ARGKVCXINMKCAZ-UZRWAPQLSA-N neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 description 1
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 210000005182 tip of the tongue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Saccharide Compounds (AREA)
Description
For å minske carbohydratinnholdet henholdsvis kaloriinn-holdet av levnetsmidler, hvilket er av betydning for dem som lider av sukkersyke, har der i mange år vært anvendt kunstige søtningsmidler. De midler som anvendes for dette formål, må til-fredsstille mange fordringer. Den ønskede søtningseffekt må nåes under inntagelse av et vesentlig mindre kaloriinnhold, og søt -
heten av slike midler må være mange ganger sterkere enn rør-sukkerets søthet. Toksisitet eller andre bivirkninger må ikke oppstå efter mange års bruk. Søtningsmidlet må være tilstrekke-
lig oppløselig i vann, og ved fremstilling av matvarer må søt-ningsmidlet ikke beskadiges av varme, og må heller ikke gi noen bi- eller eftersmak.
Fra faglitteraturen er kjent et antall forbindelser som er anvendbare som søtningsmiddel. Av disse stoffer har kun to forbindelser, nemlig "saccharin" og "cyclamat", fått utbredt anvendelse i praksis. Disse to produkter tilfredsstiller ikke fullt ut de ønskede fordringer. Saccharin er tungt oppløselig i vann og gir en ubehagelig bismak. For cyclamat er der ved dyreforsøk vist at det efter lengre tids administrasjon utøver en carcinogen virkning. Derfor ble anvendelse av cyclamat som søtningsmiddel forbudt i U.S.A.
Ifølge US patentskrift nr. 3.087-821 kan også dehydrocal-conforbindelsen av den generelle formel:
anvendes som søtningsmiddel , i hvilken formel.
R har betydningen en hydroxylgruppe,
R"<*>" et hydrogenatom, en hydroxy- eller methoxygruppe, og -
R er en 2-0-(a-L-ramnosyl)-0-D-glycosyl-(neohesperidosyl)-
gruppe eller en glycosilgruppe.
Litteraturstedene J. Agr. Food. Chem. 16, 108 (1968) og
J. Food. Sei. 34, 101 (1969) og US patentskrift nr. 1.189i,573-vedrører også forbindelser av den generelle formel IV, hvori R er en hydroxylgruppe, R"*" er en methoxy-, ethoxy- eller propoxygruppe,
og R <2> er en neohesperidoxylgruppe.
Ulempen ved anvendelse av disse forbindelser som søtnings-middel består i at de utviser en mentholeftersmak. Forbindelsene fremstilles fra naringin, neohesperidin eller.runin ved spaltning,
med lut, hvorefter det erholdte substituerte acetofenon omsettes med et egnet benzaldehydderivat. Det dannede calconderivat' v
•' -V
hydreres til det tilsvarende dihydrocalcon.:;-* '•■^
Utgangsmaterialet uttrekkes av planteråmaterialer^og er derfor meget vanskelig tilgjengelig. >i
Foreliggende oppfinnelse angår søtningsmidler som inne-
holder l-(2-hydroxy-/f-carboxymethoxyf enyl)-3-(3-hydroxy-4~ 7 methoxyfenyl)-propanon-1 med formelen:
og/eller salter derav.
Forbindelsene med formel I kan f. eks . f remst illes ved at man: (a) reduserer 1-(2-hydroxy-4-carboxymethoxyfenyl)-3-(2-hydroxy-3-methoxyf enyl)-2-propen-l-onmed formelen:
>■ ■.
(b) i 1-^/fdihydroxyfenyl)-3-(3-hydroxy-4-methoxyfenyl)-propanon-1 med formelen:
omdanner 4-hydroxygruppen på fenylgruppen i 1-stillingen på propanon-1 til en carboxymethoxygruppe,
og at eventuelt en erholdt forbindelse med formel I omdannes til et salt derav.
Ifølge en fordelaktig fremgangsmåte utføres reduksjonen av calcon av den generelle formel II ved katalytisk hydrogenering. Som katalysator anvendes fortrinnsvis palladium. Hydrogeneringen kan.utføres i et organisk oppløsningsmiddel som eddiksyre, aceton, alkohol eller x en oppløsningsmiddelblanding som en blanding av dimethylformamid og alkohol, eller også i et vandig, alkalisk medium. Reaksjonen kan akselereres ved oppvarmning.
Omdannelsen av 4-hydroxygruppen på fenylgruppen i 1-stillingen på propanon-1 kan utføres med alkylhalogenider, epoxyfor-bindelser, alkylsulfater, alkylhalogenider, eventuelt substi-tuert med en sulfonyl-, dialkylamino- eller trialkylammonium-gruppe, halogenerte carboxylsyrer eller deres estere, eller halogenerte én- eller flerverdige alkoholer, og hvor reaksjonen utføres i et vandig, alkalisk medium eller i nærvær av et vann-fritt, organisk oppløsningsmiddel i nærvær av en syrebindende forbindelse. Som oppløsningsmiddel anvendes fortrinnsvis aceton eller diethylformamid, og som syrebindende middel kan eksempelvis anvendes calciumcarbonat. De erholdte estere kan så omdannes til de tilsvarende syrer.
Når reaksjonen utføres med en beregnet mengde av reaksjons-komponenten, tar kun 4-hydroxygruppen på fenylgruppen i 1-stillingen på propanon-1 del i reaksjonen som følge av den større aktivitet av denne hydroxylgruppe.
Forbindelsen som anvendes ifølge oppfinnelsen, er ugiftig, intenst søt og har ingen bismak. Fra denne forbindelse kan dannes salter som er godt oppløselige i vann. Spesielt fordel-aktige er alkalisalter, slik som natrium-, kalium- eller ammoniumsalter, eksempelvis er natriumsaltet av 1 -(2-h<y>droxy-4~ carboxymethoxyf enyl)-3-(3-hydroxy-4-methoxyf enyl)-propan-1-on 180 ganger søtere enn rørsukker og er oppløselig i en 20 ganger mengde koldt vann.
Søtningsverdien av den aktive forbindelse ifølge oppfinnelsen ble bestemt av et utvalg på 6 medlemmer. Til sammenlign-ing ble anvendt en 1%-ig saccharoseoppløsning.
To medlemmer av utvalget fant søtningsmidlet lOO ganger søtere enn sammenligningsoppløsningen, og 4 medlemmer fant det 300 ganger søtere enn sammenligningsoppløsningen. Medlemmene som satte søtningsverdien til lOO ganger søtere, bestemte denne verdi med en relativ spredning på 10%. Den relative spredning var 30% ved bestemmelse av den høyere verdi.
I henhold til utvalget kan smaken av foreliggende søt-ningsmiddel ikke bare oppfattes med spissen av tungen, men også med roten av den. Utviklingen av søtfølelsen var forsinket sammenlignet med den for saccharose, men varer lengre og blir kvalmende. Dette gjør smakingen vanskeligere og mere usikker, og forklarer bestemmelsen av forskjellige verdier.
Søtningsmidlene ifølge oppfinnelsen kan inneholde biologisk nøytrale bærermidler eller ernæringsmidler, eller også andre søtningsmidler, eksempelvis saccharin. Som tilsetningsmidler er fortynningsmidler, oppløsningsmidler og formstoffer anvendbare.
Fremstillingen av den aktive forbindelse som anvendes ifølge oppfinnelsen, belyses ved de følgende utførelses-eksempler.
Eksempel 1
11,9 g 2-hydroxy-4-carbethoxymethoxyacetofenon [Ann. Chim.
(Roma) 49, 1632 (1959) ] og 7,6 g isovanilin omrøres med en blanding av 25 ml ethanol og 50 ml 60%<*>s natriumhydroxyd i 24 timer, hvorefter blandingen kokes under tilbakeløp i 4 timer. Blandingen avkjøles og surgjøres med 10%'2 saltsyreoppløsning, og det utfelte presipitat avfiltreres. Produktet vaskes med en liten mengde varmt vann, avfiltreres erg tørkes. Der erholdes 6,75 g 2',3-dihydroxy-4-raethoxy-4'-carbethoxymethoxycalcon, smp. 220 - 223°C. Det erholdte produkt hydrogeneres i aceton i nærvær av palladium-på-benkull-katalysator. Efter opptagelse av en ekvi-
molar mengde hydrogen, frafiltreres katalysatoren. Det erholdte l-(2-hydroxy-4-carbethoxymethoxyfenyl)-3-(3-hydroxy-4~methoxy-fenyl)-propanon-1 omkrystalliseres fra eddiksyre; hvorved man får 1-(2-hydroxy-4-carboxymethoxyfeny1)-3-(3~hydroxy-4-methoxy-fenyl)-propanon-1 med smp. 177 - 180°C. Det erholdte produkt overføres til det vannoppløselige natriumsalt.
Eksempel 2
2,88 g l-(2,4-dihydroxyfenyl)-3-(3-hydroxy-4-methoxyfenyl)-propanon-1, smp. 115 - ll6°c, oppløses i 30 ml aceton og kokes 8 timer under tilbakeløp med 1,3 ml kloreddiksyreethylester i nærvær av 2 g kaliumcarbonat. Acetonet avdestilleres, og 5 ml vann tilsettes til residuet, hvorefter blandingen kokes 30 min-utter. Efter avkjøling av reaksjonsblandingen utkrystalliseres kaliumsaltet av l-(2-hydroxy-4-carboxymethoxyfenyl)-3-(3-hydroxy-4-methoxyf enyl)-propanon-1.
Utgangsmaterialet fremstilles fra 2',4* >*ihydroxy-4-methoxy-calcon, smp. 206 - 208°C [P. R. Rao, T. R. Seshadri, Proe. Indian Acad. Sei. l4A, 29 (1941)] ved katalytisk hydrogenering som i eksempel 1.
Claims (1)
- Søtningsmiddel, karakterisert ved at det inneholder 1-(2-hydroxy-4-carboxymethoxyfenyl)-3-(3-hydroxy-4-methoxyfenyl)-propanon-1 med formelen:og/eller salter derav.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1196A HU163394B (no) | 1971-12-20 | 1971-12-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135770B true NO135770B (no) | 1977-02-21 |
| NO135770C NO135770C (no) | 1977-06-01 |
Family
ID=10994426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4674/72A NO135770C (no) | 1971-12-20 | 1972-12-19 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3956375A (no) |
| JP (1) | JPS5726256B2 (no) |
| AR (1) | AR195990A1 (no) |
| AT (1) | AT321277B (no) |
| AU (1) | AU471895B2 (no) |
| CA (1) | CA1048535A (no) |
| CH (1) | CH583166A5 (no) |
| CS (1) | CS168916B1 (no) |
| DD (1) | DD104287A1 (no) |
| DE (1) | DE2258304A1 (no) |
| ES (1) | ES409567A1 (no) |
| FI (1) | FI58489C (no) |
| FR (1) | FR2164676B1 (no) |
| GB (1) | GB1418305A (no) |
| HU (1) | HU163394B (no) |
| IL (1) | IL41003A (no) |
| IN (1) | IN139923B (no) |
| NL (1) | NL7216684A (no) |
| NO (1) | NO135770C (no) |
| SE (1) | SE409854B (no) |
| SU (1) | SU451235A3 (no) |
| YU (1) | YU318172A (no) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4092346A (en) * | 1974-02-19 | 1978-05-30 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Acyl-phenoxy-propanesulfoacids and salts, and artificial sweetening compositions containing the same |
| US4190671A (en) * | 1977-03-17 | 1980-02-26 | Biorex Laboratories Limited | Chalcone derivatives |
| US4219569A (en) * | 1978-10-10 | 1980-08-26 | The Upjohn Company | Process for treating inflammation |
| US4226804A (en) * | 1979-03-09 | 1980-10-07 | Dynapol | Alpha amino acid dihydrochalcones |
| US4267165A (en) * | 1979-03-09 | 1981-05-12 | Dynapol | Comestibles sweetened with alpha amino acid dihydrochalcones |
| US4283434A (en) * | 1980-04-14 | 1981-08-11 | Dubois Grant E | Sulfamo dihydrochalcone sweeteners |
| US4348333A (en) * | 1981-10-09 | 1982-09-07 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | β-Ketocarboxyl and phosphonate dihydro-chalcone sweeteners |
| JPS59167550U (ja) * | 1983-04-26 | 1984-11-09 | 西村 備章 | 安全ベルト |
| JPS602552U (ja) * | 1983-06-20 | 1985-01-10 | 佐藤工業株式会社 | 安全帯装置 |
| US5637618A (en) * | 1990-06-01 | 1997-06-10 | Bioresearch, Inc. | Specific eatable taste modifiers |
| IL118657A0 (en) * | 1996-06-14 | 1996-10-16 | Arad Dorit | Inhibitors for picornavirus proteases |
| KR100270410B1 (ko) * | 1997-03-06 | 2000-11-01 | 성재갑 | 타이로시네이즈 활성 저해능을 갖는 신규 1,3-디페닐프로판 유도체 및 그의 제조방법 |
| IL122591A0 (en) | 1997-12-14 | 1998-06-15 | Arad Dorit | Pharmaceutical compositions comprising cystein protease inhibitors |
| US6789391B2 (en) | 2001-05-21 | 2004-09-14 | B. Eric Graham | Modular apparatus and method for shipping super frozen materials |
| US8715761B2 (en) | 2008-02-25 | 2014-05-06 | Givaudan S.A. | Flavor molecules |
| US8449936B2 (en) * | 2008-02-25 | 2013-05-28 | Givaudan Sa | Flavor molecules |
| KR101849695B1 (ko) * | 2008-07-21 | 2018-04-17 | 유니젠, 인크. | 일련의 피부-화이트닝(라이트닝) 화합물 |
| EP2451781B1 (en) * | 2009-07-10 | 2013-09-18 | Givaudan SA | Pyridine derivatives with umami flavour |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087821A (en) * | 1961-11-28 | 1963-04-30 | Robert M Horowitz | Dihydrochalcone derivatives and their use as sweetening agents |
-
1971
- 1971-12-20 HU HUCI1196A patent/HU163394B/hu unknown
-
1972
- 1972-11-29 DE DE19722258304 patent/DE2258304A1/de active Pending
- 1972-11-29 AT AT1014472A patent/AT321277B/de not_active IP Right Cessation
- 1972-12-04 AU AU49568/72A patent/AU471895B2/en not_active Expired
- 1972-12-04 US US05/311,666 patent/US3956375A/en not_active Expired - Lifetime
- 1972-12-05 IL IL41003A patent/IL41003A/en unknown
- 1972-12-07 DD DD167363A patent/DD104287A1/xx unknown
- 1972-12-08 NL NL7216684A patent/NL7216684A/xx not_active Application Discontinuation
- 1972-12-13 CS CS8559A patent/CS168916B1/cs unknown
- 1972-12-13 ES ES409567A patent/ES409567A1/es not_active Expired
- 1972-12-15 SE SE7216483A patent/SE409854B/xx unknown
- 1972-12-15 FI FI3558/72A patent/FI58489C/fi active
- 1972-12-18 SU SU1858002A patent/SU451235A3/ru active
- 1972-12-19 FR FR7245184A patent/FR2164676B1/fr not_active Expired
- 1972-12-19 CA CA72159419A patent/CA1048535A/en not_active Expired
- 1972-12-19 CH CH1850072A patent/CH583166A5/xx not_active IP Right Cessation
- 1972-12-19 NO NO4674/72A patent/NO135770C/no unknown
- 1972-12-19 JP JP12758772A patent/JPS5726256B2/ja not_active Expired
- 1972-12-20 YU YU03181/72A patent/YU318172A/xx unknown
- 1972-12-20 GB GB5885772A patent/GB1418305A/en not_active Expired
- 1972-12-20 AR AR245738A patent/AR195990A1/es active
-
1973
- 1973-05-22 IN IN1200/CAL/73A patent/IN139923B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2258304A1 (de) | 1973-07-05 |
| CA1048535A (en) | 1979-02-13 |
| FR2164676B1 (no) | 1977-08-05 |
| SU451235A3 (ru) | 1974-11-25 |
| HU163394B (no) | 1973-08-28 |
| AU4956872A (en) | 1974-06-06 |
| NL7216684A (no) | 1973-06-22 |
| FR2164676A1 (no) | 1973-08-03 |
| IN139923B (no) | 1976-08-21 |
| GB1418305A (en) | 1975-12-17 |
| JPS4868552A (no) | 1973-09-18 |
| CH583166A5 (no) | 1976-12-31 |
| IL41003A (en) | 1976-09-30 |
| SE409854B (sv) | 1979-09-10 |
| NO135770C (no) | 1977-06-01 |
| DD104287A1 (no) | 1974-03-05 |
| IL41003A0 (en) | 1973-02-28 |
| CS168916B1 (no) | 1976-06-29 |
| AT321277B (de) | 1975-03-25 |
| AU471895B2 (en) | 1976-05-06 |
| US3956375A (en) | 1976-05-11 |
| ES409567A1 (es) | 1975-12-01 |
| YU318172A (en) | 1980-10-31 |
| FI58489C (fi) | 1981-02-10 |
| AR195990A1 (es) | 1973-11-23 |
| JPS5726256B2 (no) | 1982-06-03 |
| FI58489B (fi) | 1980-10-31 |
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