DEP0021789DA - Preparations with azulene - Google Patents
Preparations with azuleneInfo
- Publication number
- DEP0021789DA DEP0021789DA DEP0021789DA DE P0021789D A DEP0021789D A DE P0021789DA DE P0021789D A DEP0021789D A DE P0021789DA
- Authority
- DE
- Germany
- Prior art keywords
- oil
- blue
- oils
- preparations
- azulene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 title description 8
- 239000003921 oil Substances 0.000 claims description 19
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 3
- 210000004209 hair Anatomy 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 239000000341 volatile oil Substances 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- -1 fatty acid esters Chemical class 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000419 plant extract Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000001993 wax Substances 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 18
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical compound CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 7
- PMRJYBALQVLLSJ-UHFFFAOYSA-N chamazulene Natural products CCC1=CC2=C(C)CCC2=CC=C1 PMRJYBALQVLLSJ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000001545 azulenes Chemical class 0.000 description 5
- APVKGMMYGFJZHY-UHFFFAOYSA-N vetivazulene Chemical compound C1=CC=C(C)C2=CC(C(C)C)=CC2=C1C APVKGMMYGFJZHY-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000010628 chamomile oil Substances 0.000 description 2
- 235000019480 chamomile oil Nutrition 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002884 skin cream Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 229940070641 chamomile flowers Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000010634 clove oil Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000010642 eucalyptus oil Substances 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 239000010670 sage oil Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
Description
Es ist bekannt, dass den Kamillenblüten entzündungswidrige und desodorierende Wirkungen zukommen. Nach neueren Erkenntnissen ist das Chamazulen der Träger dieser Eigenschaften, und zwar sowohl in freier Form als auch als Addukt, derzeit noch unbekannter Zusammensetzung, das in der Blüte vorgebildet ist.It is known that chamomile flowers have anti-inflammatory and deodorant effects. According to more recent findings, chamazulene is the carrier of these properties, both in free form and as an adduct, currently of a still unknown composition, which is preformed in the flower.
Es wurde nun gefunden, dass gewisse synthetische Azulene die gleichen Eigenschaften wie das Chamazulen aufweisen, insbesondere reine Blauöle wie z. B. das S-Guajazulen. Diese Feststellung ist neu und war nicht vorauszusehen. Ch. Pommer (Naundyn-Schmiedebergs Archiv f. exper. Pathologie u. Pharmakologie 199,74 (1942)) konnte nachweisen, dass das synthetische Grundazulen C(sub)10H(sub)8 und das nach Pfau und Plattner hergestellte Vetivazulen C(sub)16H(sub)16 (Chem. Zentralblatt 1939, I, 2995 und ebenda 1941, II, 2933) keine Wirkung bei der Senfölchemosis am Meerschweinchenauge besitzt. Im Gegensatz hierzu konnten Heubner und Mitarbeiter, wie andere, die entzündungswidrige Eigenschaft des Chamazulens wiederholt beobachten oder bestätigen. Daraus ist zu ersehen, dass nicht allen Azulenen eine günstige pharmakologische Wirkung innewohnt.It has now been found that certain synthetic azulenes have the same properties as chamazulene, in particular pure blue oils such. B. the S-guaia poultry. This finding is new and could not have been foreseen. Ch. Pommer (Naundyn-Schmiedebergs Archiv f. Exper.pathologie u. Pharmakologie 199,74 (1942)) was able to prove that the synthetic basic azulene C (sub) 10H (sub) 8 and the vetivazulene manufactured according to Pfau and Plattner C (sub ) 16H (sub) 16 (Chem. Zentralblatt 1939, I, 2995 and ibid. 1941, II, 2933) has no effect on the mustard oil dose on guinea pigs' eyes. In contrast, Heubner and co-workers, like others, were able to repeatedly observe or confirm the anti-inflammatory properties of chamazulene. It can be seen from this that not all azulenes have a beneficial pharmacological effect.
Es wurde nun gefunden, dass alle violetten, rotvioletten oder violettblauen Azulene unwirksam oder weniger wirksam sind. Nur die reinen Blauöle zeigen eine befriedigende Wirkung.It has now been found that all purple, red-purple, or purple-blue azulenes are ineffective or less effective. Only the pure blue oils show a satisfactory effect.
Die pharmakologische Prüfung eines reinen Blauöles, das künstlich durch Dehydrierung von Gurjen in bekannter Weise erhalten wurde, ergab bei der Inhalation an Menschen keine Schleimhautreizungen und im Tierversuch zeigte sich bei der künstlich gesetzten Konjunktivitis in 60% ein positiver entzündungswidriger Erfolg.The pharmacological test of a pure blue oil, which was artificially obtained by dehydration of Gurjen in a known manner, showed no irritation of the mucous membranes when inhaled on humans and in animal experiments a positive anti-inflammatory success was shown in 60% of the artificially created conjunctivitis.
Da nun Chamazulen die bekannten günstigen Eigenschaften entfaltet, Vetivazulen und manche anderen synthetischen Azulene nicht, so ist die Feststellung der Wirksamkeit synthetisch hergestellter Blauöle, die mit Chamazulen nicht identisch sind, eine Neuerung und ein beachtlicher Fortschritt.Since chamazulene now develops the well-known beneficial properties, vetivazulene and some other synthetic azulenes do not, the determination of the effectiveness of synthetically produced blue oils, which are not identical to chamazulene, is an innovation and a considerable advance.
Die reinblauen oder fast reinblauen synthetischen Blauöle (Azulene) können als solche oder in Form ihrer Addukte z. B. als Addukt aus Azulen und Maleinsäureanhydrid bestehend oder in teilweiser hydrierter, chlorierter, bromierter, jodierter oder rhodinierter Form zur Anwendung gelangen. Sowohl einfache Lösungen in Alkoholen, Ölen, Fetten, Kohlenwasserstoffen als auch Emulsionen aller Art dienen als Grundlagen zur weiteren Verarbeitung zu Salben, Cremes, Haarwässern, Mundpflegemitteln, antiseptischen Mitteln und dergleichen.The pure blue or almost pure blue synthetic blue oils (azulenes) can be used as such or in the form of their adducts, for. B. as an adduct of azulene and maleic anhydride or in partially hydrogenated, chlorinated, brominated, iodized or rhodium-plated form for use. Both simple solutions in alcohols, oils, fats, hydrocarbons and emulsions of all kinds serve as the basis for further processing into ointments, creams, hair lotions, oral care products, antiseptics and the like.
Bekanntlich entfalten viele ätherische Öle und Riechstoffe hautreizende Wirkungen. Durch Zugabe von etwa 0,5-10% Blauöl wird die Reizwirkung vermindert oder aufgehoben. In dieser Hinsicht sind Kombinationen mit Nelkenöl (Eugenol), Pfefferminzöl (Menthol), Eukalyptusölen, Fichtennadelölen, Rosmarinöl, Thymianöl, Citronenöl, Orangenschalenöl, Lavendelöl, Hydroxycitronellal u. a. erwähnenswert. Ferner können Produkte aller Art, die auf der Wirkung der echten Kamille vorzugsweise aufgebaut sind, durch Zugabe eines synthetischen Blauöles oder eines Adduktes oder Derivates in der Wirkung standardisiert werden, denn der Gehalt an Chamazulen ist in der Droge erheblichen Schwankungen unterworfen. Ebenso kann das echte Kamillenöl durch Zugabe von Blauöl standardisiert und so wesentlich verbessert werden.It is well known that many essential oils and fragrances have skin-irritating effects. The irritation is reduced or eliminated by adding about 0.5-10% blue oil. In this regard, combinations with clove oil (eugenol), peppermint oil (menthol), eucalyptus oils, spruce needle oils, rosemary oil, thyme oil, lemon oil, orange peel oil, lavender oil, hydroxycitronellal and the like are. worth mentioning. Furthermore, products of all kinds, which are preferably based on the effect of real chamomile, can be standardized in the effect by adding a synthetic blue oil or an adduct or derivative, because the content of chamazulene in the drug is subject to considerable fluctuations. The real chamomile oil can also be standardized by adding blue oil and thus be significantly improved.
Verwendungsbeispiele:Usage examples:
1. Ätherisches Kamillenöl mit geringen Mengen Chamazulen wird durch Zugabe von S-Guajazulen auf 5% Gehalt eingestellt und damit in der Wirkung verbessert und standardisiert.1. Essential chamomile oil with small amounts of chamazulene is adjusted to a content of 5% by adding S-guajazulene and thus its effect is improved and standardized.
2. Ein ätherischer Kamillenblütenauszug wird nach der Entfernung des Äthers im Vakuum mit 3% Blauöl versetzt.2. An essential chamomile blossom extract is mixed with 3% blue oil after the ether has been removed in a vacuum.
3. Haaröl:3. Hair oil:
Eine Mischung, bestehend aus gleichen Teilen Paraffinöl, Isopropylpalmitat und Buckeckernöl oder fetten Senföl, wird mit 1% Azulen (synthetisches Blauöl) versetzt.A mixture consisting of equal parts of paraffin oil, isopropyl palmitate and buckecker oil or fatty mustard oil is mixed with 1% azulene (synthetic blue oil).
4. Hautcreme:4. Skin cream:
3% Wollwachs3% wool wax
4% Paraffin4% paraffin
10% Vaselin10% petroleum jelly
15% Weissöl geruchlos15% white oil odorless
2% Lanolin wasserfrei2% lanolin anhydrous
0,2% Cholesterin0.2% cholesterol
0,3% Guajazulen (Blauöl)0.3% guajazulene (blue oil)
65,5% Wasser65.5% water
werden in bekannter Art emulgiert. Man erhält eine Hautcreme, die zur Behandlung geröteter oder entzündeter Haut geeignet ist.are emulsified in a known manner. A skin cream is obtained which is suitable for treating reddened or inflamed skin.
5. 85 Tl. Polyäthylenoxydsorbitanmonolaurat werden mit 15 Tl. einer Mischung, bestehend aus 15 Tl. Salbeiöl, 15 Tl. Lavendelöl und 70 Tl. Blauöl, vermengt und anschliessend mit Wasser oder verdünntem Alkohol versetzt. Die erhaltenen stabilen Emulsionen ergeben brauchbare Spülungsmittel.5. 85 parts of polyethylene oxide sorbitan monolaurate are mixed with 15 parts of a mixture consisting of 15 parts of sage oil, 15 parts of lavender oil and 70 parts of blue oil and then mixed with water or diluted alcohol. The stable emulsions obtained make useful flushing agents.
Claims (1)
Family
ID=
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