NO116435B - - Google Patents
Download PDFInfo
- Publication number
- NO116435B NO116435B NO16124866A NO16124866A NO116435B NO 116435 B NO116435 B NO 116435B NO 16124866 A NO16124866 A NO 16124866A NO 16124866 A NO16124866 A NO 16124866A NO 116435 B NO116435 B NO 116435B
- Authority
- NO
- Norway
- Prior art keywords
- isovaleric acid
- ester
- acid ester
- bond
- group
- Prior art date
Links
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical class CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 20
- -1 isovaleric acid ester Chemical class 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 16
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 238000010828 elution Methods 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 241000196324 Embryophyta Species 0.000 claims description 5
- 241000792902 Valerianaceae Species 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 101100129500 Caenorhabditis elegans max-2 gene Proteins 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
- 241000792914 Valeriana Species 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 235000020130 leben Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 235000017468 valeriana Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/84—Valerianaceae (Valerian family), e.g. valerian
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Alternative & Traditional Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Fremgangsmåte til utvinning av nye terapeutisk virksomme isovaleriansyreestere fra planter av familien Valerianaceae. Process for the extraction of new therapeutically active isovaleric acid esters from plants of the Valerianaceae family.
Foreliggende oppfinnelse angår isolering av to altt.il ikke beskrevne, terapeutisk virksomme isovaleriansyreeste-re av planter av familien Valerianaceae. De forbindelser har den folgende felles grunnstruktur: The present invention relates to the isolation of two not yet described, therapeutically active isovaleric acid esters from plants of the Valerianaceae family. The compounds have the following common basic structure:
hvor i isovaleriansyreesteren med bruttoformel C24H32^10 • 5,6-bindingen er en dobbeltbinding og den ene av gruppene R^ og . 1^ betegner en isovaleroxygruppe, og den andre en acetoxyisovaleroxV-gruppe, mena i isovaleriansyreesteren med bruttoformelen C22H32°0 5,6-bindlngen er en enkeltbinding, og de to grupper R-^ og R2hve:: betegner en isovaleroxygruppe. where in the isovaleric acid ester with gross formula C24H32^10 • the 5,6 bond is a double bond and one of the groups R^ and . 1^ denotes an isovaleroxy group, and the other an acetoxyisovaleroxyV group, meaning in the isovaleric acid ester with the gross formula C22H32°0 the 5,6 bond is a single bond, and the two groups R-^ and R2hve:: denote an isovaleroxy group.
Fra norsk patent nr. 113.067 er det kjent en isovalerianayns- From Norwegian patent no. 113,067 it is known an isovalerianayns-
eiastovear lmered ianbrsuyrtteoefsotremreen l mC^ed HjbqrOutqt, ofsoom rmhel ar C2s4amHm3e 2°1gr0u' nnt,osrt'rcfusket'tu't r frsa om^j begge grupper R-^og R2representerer en isovaleroxygruppe.!j eiastovear lmered ianbrsuyrtteoefsotremreen l mC^ed HjbqrOutqt, ofsoom rmhel ar C2s4amHm3e 2°1gr0u' nnt,osrt'rcfusket'tu't r frsa om^j both groups R-^and R2represent an isovaleroxy group.!j
Isovaleriansyreesteren med bruttoformel C^H^Ps■krys"fcal~ i liserer i form av hvite, lange nåler som smelter ved 62 - 63°C. Den optiske dreining [o]^ er -79° (i methanol), UV-maksimumet ligger i methanol ved 214 - 216 m ^°g er avhengig av konsentra-sjonen. Spektret i det infrarbde område og NMR-spektret er vist i fig. 1 og fig. 2. The isovaleric acid ester with the gross formula C^H^Ps■crys"fcal~ in the form of white, long needles melting at 62 - 63°C. The optical rotation [o]^ is -79° (in methanol), the UV maximum lies in methanol at 214 - 216 m ^°g depends on the concentration.The spectrum in the infrared region and the NMR spectrum are shown in Fig. 1 and Fig. 2.
Isovaleriansyreesteren med bruttoformel ^24^32^10 har e^ smeltepunkt på 83 - 84°C og en optisk dreining [ot]^ = + 163,7° The isovaleric acid ester with gross formula ^24^32^10 has a melting point of 83 - 84°C and an optical rotation [ot]^ = + 163.7°
(i methanol). UV-maksimumet ligger i methanol ved 256 m\i med en ekstinkajonskoeffisient (£= 16710). Spektret i det infrarbde område og kjerneresonansspektret er vist i fig. 3 og fig. 4. (in methanol). The UV maximum is in methanol at 256 m\i with an extinction coefficient (£= 16710). The spectrum in the infrared region and the nuclear resonance spectrum are shown in fig. 3 and fig. 4.
De ovennevnte, for forste gang isolerte og identifiserte isovalerianayreestere er sammen med den i norsk patent nr. The above-mentioned, for the first time isolated and identified isovaleriana reesters are, together with the one in Norwegian patent no.
[beskrevne-isovalerianayreester hovedbæreren j av den sedative virkning av vendelrot (Valeriana). Den terapeutiske virkning av de nye estere innskrenker seg imidlertid ikke bare ti,l ._. den sedative virkning. De ha.r praktisk talt samme virkning som de beroligende midler, bortsett fra. at de ikke forårsaJcer noen ubnsket matthet. [described-isovalerianareester is the main carrier j of the sedative effect of valerian root (Valeriana). However, the therapeutic effect of the new esters is not limited to just ti,l ._. the sedative effect. They have practically the same effect as the sedatives, except. that they do not cause any unwanted dullness.
De beskrevne isovaleriansyreestere utvinnes ved at man ekstranerer rotter eller rotstokker av planter av familien Valerianaceae ved en temperatur lavere enn 30°C med lipofile opplbsningsmidler i nærvær av surtvirkende stoffer i pH-området 3-7 The described isovaleric acid esters are extracted by extracting rhizomes or rhizomes of plants of the Valerianaceae family at a temperature lower than 30°C with lipophilic solvents in the presence of acidic substances in the pH range 3-7
i henhold til fremgangsmåten ifblge norsk patent nr. 109.348, hvoretter man opplbaer den inndampede ekstra.kt i carboxylsyrer, fjerner etheriake oljer, fett og hbyere hydrocarboner fra opp- | lbaningen ved behandling med lipofile opplbsningamidler, og man etter trinnvis fortynning av opplbsningen med vann ekatraherer del according to the method according to Norwegian patent no. 109,348, after which the evaporated extract is heated in carboxylic acids, ethereal oils, fats and higher hydrocarbons are removed from the the laban by treatment with lipophilic solvents, and after stepwise dilution of the solution with water, part is extracted
ovenfor beskrevne isovaleriansyreestere ved hjelp av lipofile opp-losningsmidler. I henhold til fremgangsmåten ifblge norsk patent nr. isoleres isovaleriansyreesteren m<q>d bruttoformel C22^30°8ved kromatografering på aluminiumoxyd som er blitt delvis inaktivert ved behandling med carboxylsyrer i vannfritt medium. isovaleric acid esters described above using lipophilic solvents. According to the method according to Norwegian patent no. the isovaleric acid ester with the gross formula C22^30°8 is isolated by chromatography on aluminum oxide which has been partially inactivated by treatment with carboxylic acids in an anhydrous medium.
Det har nu vist seg at man kan utvinne isovaleriansyreesterne med brutto formlene<C>22<H>j20g°8^24^32^10e^er ^en S8inine kromato-grafiske fremgangsmåte ut fra ikke-vandige ekstrakter av rbtter eller rotstokker av planter av familien Valerianaceae, når elueringen etter isoleringen av isovaleriansyreesteren C22Hjq0q utfbres med det samme opplbsningsmiddel, eventuelt ved tilsetning av opplbsningsmidler med sterkere elueringsvirkning. Por eluerin^; av isovaleriansyreesteren av bruttoformel C22Hj20g ^8n ^er foruton hexan også anvendes andre opplbsningsmidler av det fbrste område av den eluotrope rekke, såsom n-heptan eller cyclohexan, mens de]' for eluering av isovaleriansyreesteren av bruttoformel C^H^O^q er nbdvendig med tilsetning til opplbsningsmidlet av et keton eller en ester, f.eks. aceton. It has now been shown that it is possible to extract the isovaleric acid esters with the gross formulas <C>22<H>j20g°8^24^32^10e^er ^a S8inine chromatographic method from non-aqueous extracts of roots or rhizomes of plants of the family Valerianaceae, when the elution after the isolation of the isovaleric acid ester C22Hjq0q is carried out with the same solvent, possibly by adding solvents with a stronger elution effect. Por eluerin^; of the isovaleric acid ester of the gross formula C22Hj20g ^8n ^er besides hexane, other solvents of the first range of the eluotropic series are also used, such as n-heptane or cyclohexane, while they]' for elution of the isovaleric acid ester of the gross formula C^H^O^q are necessary with addition to the solvent of a ketone or an ester, e.g. acetone.
Man kan ved kromatograferingen også anvende en ekstrakt fra hvilken esteren C22H32°8allerede er fraskilt ved utkrystallisering. Man går i så fall frem på nbyaktig samme måte som ovenfor beskrevet, dvs. etter fraskillelse av esteren C22Hj008elueres af,n gjenværende mengde av esteren C22H32°8med et, .opplbsningsmiddel fra det fbrste område av den eluotrope rekke, hvoretter esteren G24<H>32°10elueres med samme opplbsningsmiddel etter tilsetning av et keton eller en ester. During the chromatography, you can also use an extract from which the ester C22H32°8 has already been separated by crystallization. In that case, one proceeds in almost the same way as described above, i.e. after separation of the ester C22H1008, the remaining amount of the ester C22H32°8 is eluted with a solvent from the first region of the eluotropic series, after which the ester G24<H> 32°10 is eluted with the same solvent after addition of a ketone or an ester.
Eksempel 1Example 1
60 kg malte vendelrbtter ble perkolert med eddikester som inneholdt 1 # iseddik, inntil det var erholdt totalt 190 liter perkolat. Dette ble så porsjonsvis vasket med 3 #-ig natriumbi-carbonatopplbsning og 5 #-ig koksaltopplbsning, klaret med kull, tUrket over natriumsulfat og inndampet inntil konstant vekt ved 30°C. Utbyttet av hbyviskbst, gulfarvet, uren esterblanding vår 3,15 kg (5*25 60 kg of ground beets were percolated with vinegar containing 1# of glacial acetic acid, until a total of 190 liters of percolate had been obtained. This was then washed in portions with 3 #g sodium bicarbonate solution and 5 #g sodium bicarbonate solution, clarified with charcoal, dried over sodium sulfate and evaporated to constant weight at 30°C. The yield of hbyviskbst, yellow colored, impure ester mixture our 3.15 kg (5*25
For å skille isovaleriansyreesterne fra de bvrige ubnskede stoffer ble de 3,15 kg uren esterblanding opplbst ved 10°C i 16 liter 96 #-ig eddiksyre og opplbeningen ekstrahert tre ganger mec porsjoner å 5 liter bensin son var avmettet med 90 %- ig eddiksyre. Deretter ble eddiksyrefasen fortynnet med 1 1/2 gang dens volum vann og ekstrahert seks gangen med porsjoner å. 15 liter bensin. In order to separate the isovaleric acid esters from the remaining unwanted substances, the 3.15 kg impure ester mixture was dissolved at 10°C in 16 liters of 96 # acetic acid and the solution was extracted three times with portions of 5 liters of gasoline that had been desaturated with 90% acetic acid . Then the acetic acid phase was diluted with 1 1/2 times its volume of water and extracted six times with portions of 15 liters of gasoline.
De sammenslåtte esterholdige bensinfaser' ble vasket syrefri med 0,25 fi- ig natronlut, torret over nåtriumsulfat, klaret med kull og inndampet til konsta.nt vekt i vakuum ved 30°C. Utbyttet av renset, lysegul esterolje var 0,7726 kg (1,29 %) beregnet på den torrede vare. 5 kg aluminiumoxyd ble etter inaktivering med en blanding av aceton, glycerinmonoaceta.t og propionsyre fylt i en soyle og va.sket med hexan. Deretter ble soylen tilsatt 0,25 kg av den lysegule esterolje fortynnet med 50 ml hexan. Elueringen ble utfort med totalt 20 liter hexan. De forste 3 liter av eluatet ble kastet. The combined ester-containing gasoline phases' were washed acid-free with 0.25 µg caustic soda, dried over sodium sulfate, clarified with charcoal and evaporated to constant weight in vacuum at 30°C. The yield of purified light yellow ester oil was 0.7726 kg (1.29%) calculated on the dried product. After inactivation with a mixture of acetone, glycerin monoacetate and propionic acid, 5 kg of aluminum oxide was filled into a soil and washed with hexane. Then 0.25 kg of the pale yellow ester oil diluted with 50 ml of hexane was added to the soy oil. The elution was carried out with a total of 20 liters of hexane. The first 3 liters of the eluate were discarded.
I de folgende 10 liter fikk man esteren med bruttoformlene<G>22<H>30°8' In the following 10 liters, the ester was obtained with the gross formulas<G>22<H>30°8'
Denne fraksjon ble inndampet, va.sket syrefri med natronlutThis fraction was evaporated, washed acid-free with caustic soda
og vann og torret-over natriumsulfa.t og kull. Etter inndampning i vakuum ble det erholdt 0,0935 kg ren ester med bruttoformel<C22H>30°8t37'4 ^° av ol3en)- and water and torret-over sodium sulpha.t and charcoal. After evaporation in vacuum, 0.0935 kg of pure ester with gross formula <C22H>30°8t37'4 ^° of ol3en)- was obtained
Molekylvekt, beregnet: 422,46 C beregnet: 62,54 H beregnet: 7,15 0 beregnet: 30,31 Molecular weight, calculated: 422.46 C calculated: 62.54 H calculated: 7.15 0 calculated: 30.31
Molekylvekt, funnet: 422,00 C funnet62,76 H funnet: 7,32Molecular weight, found: 422.00 C found 62.76 H found: 7.32
0 funnet: 29,920 found: 29.92
kryoskopisk i benzencryoscopically in benzene
ma.ks1= 204 m\ i é 4000 (i methanol)ma.ks1= 204 m\ in é 4000 (in methanol)
ma.ks2= 256 mn£16050 (i methanol)ma.ks2= 256 mn£16050 (in methanol)
20 20
n£<u>= 1,4906 n£<u>= 1.4906
[oc]^<1>= + 172,2° (i methanol)[oc]^<1>= + 172.2° (in methanol)
Av den folgende fra.ksjon på 2 liter ble der ved opparbeidelse som ovenfor beskrevet isolert 2,7 g av estere<n>^22^32^8'Som e^er omkrystallisering fra ether/hexan varkarakterisert vedde folgende fysikalske data.: sm.p. = 62 - 63°C (Kofler), [a]^° -79° (i methanol) Molekylvekt, beregnet: 424,5 9 beregnet: 62,24 H beregnet: 7,59 From the following fraction of 2 litres, 2.7 g of ester<n>^22^32^8', which was characterized by recrystallization from ether/hexane was characterized by the following physical data, was isolated by processing as described above.: sm .p. = 62 - 63°C (Kofler), [a]^° -79° (in methanol) Molecular weight, calculated: 424.5 9 calculated: 62.24 H calculated: 7.59
0 beregnet: 30,17 Molekylvekt, funnet: 413,0 G. funnet: .62,21 H funnet: 7,5,5 0 calculated: 30.17 Molecular weight, found: 413.0 G. found: .62.21 H found: 7.5.5
0 funnet:. 30,240 found:. 30,24
maks = 214 - 216 m^(konsentra.sjonsavhengig) ( i methanol)max = 214 - 216 m^(concentration dependent) (in methanol)
(Pig. 1 = IR-spektrum og fig. 2 = NMR-spektrum)(Pig. 1 = IR spectrum and Fig. 2 = NMR spectrum)
Por eluering av esteren ^ 2^~ 1>7p\ § l3^e hexane"k tilsatt aceton og det erholdte eluat inndampet i vakuum til konstant vekt. Det ble erholdt 30 g av et krystallisat som etter omkrystallisering fra. ether-petrolether hadde et smeltepunkt på 83 - 84°C (Kofler). Por elution of the ester ^ 2^~ 1>7p\ § l3^e hexane"k added to acetone and the resulting eluate evaporated in vacuum to constant weight. 30 g of a crystallisate was obtained which, after recrystallization from ether-petroleum ether, had a melting point of 83 - 84°C (Kofler).
Molekylvekt, beregnet: 480,52 C beregnet: 59,99 % H beregnet: 6,71 0 betegnet: 33,30 % Molecular weight, calculated: 480.52 C calculated: 59.99% H calculated: 6.71 0 expressed: 33.30%
Molekylvekt, funnet : 442,00 C funnet : 59,52 $ H funnet : 6,79 0 funnet: 33,83 % Molecular weight, found: 442.00 C found: $59.52 H found: 6.79 0 found: 33.83%
[a]^<4>=+ 163,7 (i methanol)[a]^<4>=+ 163.7 (in methanol)
maks-j^ = 204 m\i ( é = 4000) (i methanol)max-j^ = 204 m\i ( é = 4000) (in methanol)
maks2 = 256 myi ( ^ = 16710) (i methanol)max2 = 256 myi ( ^ = 16710) (in methanol)
(Pig. 3 - IR-spektrum og fig. 4 = NMR-spektrum). (Pig. 3 - IR spectrum and Fig. 4 = NMR spectrum).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1717101.6-4A DE1301433B (en) | 1965-01-15 | 1965-01-15 | Process for the production of therapeutically active compounds from Valerianaceae |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116435B true NO116435B (en) | 1969-03-24 |
Family
ID=7227325
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16124866A NO116435B (en) | 1965-01-15 | 1966-01-14 | |
| NO16973967A NO117492B (en) | 1965-01-15 | 1967-09-14 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16973967A NO117492B (en) | 1965-01-15 | 1967-09-14 |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE675165A (en) |
| BR (1) | BR6676415D0 (en) |
| CH (1) | CH530979A (en) |
| DE (1) | DE1301433B (en) |
| DK (1) | DK115347B (en) |
| FI (1) | FI44003B (en) |
| FR (1) | FR5640M (en) |
| GB (1) | GB1091695A (en) |
| IL (1) | IL24938A (en) |
| NL (1) | NL141186B (en) |
| NO (2) | NO116435B (en) |
| SE (2) | SE349940B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5211948A (en) * | 1988-10-12 | 1993-05-18 | Nestec S.A. | Process for the preparation of a powdered extract of valerian roots |
| IE61919B1 (en) * | 1988-10-12 | 1994-11-30 | Nestle Sa | "Process for the preparation of a powdered extract of valerian roots" |
-
1965
- 1965-01-15 DE DEP1717101.6-4A patent/DE1301433B/en active Pending
-
1966
- 1966-01-05 GB GB46666A patent/GB1091695A/en not_active Expired
- 1966-01-07 IL IL2493866A patent/IL24938A/en unknown
- 1966-01-14 NO NO16124866A patent/NO116435B/no unknown
- 1966-01-14 FI FI10166A patent/FI44003B/fi active
- 1966-01-14 BR BR17641566A patent/BR6676415D0/en unknown
- 1966-01-14 DK DK21166A patent/DK115347B/en unknown
- 1966-01-14 BE BE675165D patent/BE675165A/xx not_active IP Right Cessation
- 1966-01-14 SE SE51966A patent/SE349940B/xx unknown
- 1966-01-14 NL NL6600501A patent/NL141186B/en not_active IP Right Cessation
- 1966-01-15 FR FR46027A patent/FR5640M/fr not_active Expired
- 1966-01-17 CH CH58466A patent/CH530979A/en not_active IP Right Cessation
-
1967
- 1967-09-14 NO NO16973967A patent/NO117492B/no unknown
-
1968
- 1968-01-19 SE SE731/68A patent/SE343211B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI44003B (en) | 1971-04-30 |
| BR6676415D0 (en) | 1973-09-06 |
| NL141186B (en) | 1974-02-15 |
| BE675165A (en) | 1966-05-03 |
| NO117492B (en) | 1969-08-18 |
| SE349940B (en) | 1972-10-16 |
| NL6600501A (en) | 1966-07-18 |
| DE1301433B (en) | 1969-08-21 |
| CH530979A (en) | 1972-11-30 |
| IL24938A (en) | 1969-11-30 |
| FR5640M (en) | 1967-12-26 |
| GB1091695A (en) | 1967-11-22 |
| DK115347B (en) | 1969-09-29 |
| SE343211B (en) | 1972-03-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Strain et al. | Spectral absorption properties of ordinary and fully deuteriated chlorophylls a and b | |
| US4118508A (en) | Pharmacologically effective substance from plants belonging to the family of Labiatae | |
| Kass et al. | The elaidinization of linoleic acid | |
| NO151643B (en) | POWER MODULE WITH MONOPOLAR CELLS | |
| NO116435B (en) | ||
| Hall et al. | The volatile constituents of Valencia orange juice | |
| NO161248B (en) | DEVICE BY FARTOEY. | |
| Murray et al. | Studies of waxes. III. The alcohols of carnauba wax | |
| Clark | Deguelin. I. The preparation, purification and properties of deguelin, a constituent of certain tropical fish-poisoning plants | |
| Wallis et al. | The preparation of dehydroandrosterone from cholesterol | |
| Jacobson | Pellitorine Isomers. III. The Synthesis of N-Isobutyl-trans-4-trans-6-decadienamide and the Structure of Spilanthol1 | |
| Clark | Helenalin. I. Helenalin, the bitter sternutative substance occurring in Helenium Autumnale | |
| LaForge et al. | Constituents of Pyrethrum Flowers. 1 II. Isolation of Pyrethrin II | |
| Clark | Tephrosin. I. The composition of Tephrosin and its relation to Deguelin | |
| Fowler et al. | 719. Researches on acetylenic compounds. Part XXV. Synthesis of (±)-kawain | |
| Beroza | Epiasarinin, a diastereoisomer of sesamin and asarinin. Stereochemistry of 2, 6-diaryl-cis-3, 7-dioxabicyclo [3.3. 0] octane | |
| Knight et al. | Arizona flora: The sterols of Peniocereus greggii | |
| Murti et al. | A study of the chemical components of Decalepis Hamiltonii (Makali Veru) Part IV. Rasinols of Decalepis Hamiltonii and Hemidesmus indicus | |
| ROSE et al. | CONSTITUENTS OF PYRETHRUM FLOWERS. XI. CHRYSANTHIN | |
| US2498849A (en) | Extraction and recovery of rutin | |
| Rangaswami et al. | Chemical components of Plumieria alba Linn | |
| US3151125A (en) | Process to obtain visnagan by extraction of ammi visnaga l. | |
| NO122312B (en) | ||
| Fieser et al. | The Synthesis of Phenanthrene and Hydrophenanthrene Derivatives. III. Hydrocarbons of the Chrysene, Acechrysene, and 3, 4-Benzphenanthrene Series; 1, 2-Benzpyrene Derivatives | |
| Devine et al. | The preparation of β-carotene of a high degree of purity |