Zapach siana, który koi nerwy; kumaryny w medycynie przemyśle perfumeryjnym

• Autorzy: Szwaczko Katarzyna , Lipa Agnieszka

Warianty tytułu

EN

The smell of hay that soothes the nerves; coumarins in medicine and perfumery

• Języki publikacji: PL

Abstrakty

PL

Kumaryna to jeden z najpopularniejszych związków organicznych w wyrobach perfumeryjnych nadający im delikatny zapach siana ze słodką nutą migdałów. To pierwotne źródło nowoczesnej perfumerii, które pozwoliło perfumiarzom odciąć się od przeszłości i zwrócić oczy w stronę nowoczesnej abstrakcji. Po raz pierwszy została wykorzystana w przełomowym Fougère Royale (Houbigant), który to zapach całkowicie zrewolucjonizował świat perfum i wyznaczył nowe kierunki we współczesnej perfumerii. Kumaryna to niezwykła molekuła o wielu obliczach. Jest podstawowym materiałem w przemyśle perfumeryjnym, znajdziemy ją w wielu produktach do ciała i kosmetykach. Jej liczne naturalne i syntetyczne pochodne posiadają natomiast właściwości antyoksydacyjne, antykoagulacyjne, przeciwzapalne, antybakteryjne, antygrzybiczne, a nawet anty-HIV, czy antynowotworowe. W niniejszym artykule przedstawimy krótką charakterystykę kumaryny, jej zastosowanie w medycynie i przemyśle kosmetycznym.

EN

Coumarin is one of the most popular organic compounds in perfumery, giving them a delicate scent of hay with a sweet hint of almonds. It is the original source of modern perfumery, which has allowed perfumers to cut themselves off from the past and turn their eyes towards modern abstraction. It was first used in the groundbreaking Fougère Royale (Houbigant), a fragrance that completely revolutionized the world of perfumes and set new directions in contemporary perfumery. Coumarin is an unusual molecule with many faces. It is a staple material in the perfume industry and can be found in many body products and cosmetics. Its numerous natural and synthetic derivatives have antioxidant, anticoagulant, antiinflammatory, antibacterial, antifungal, and even anti-HIV or anti-cancer properties. In this article, we will present a brief description of coumarin, its use in medicine and the cosmetics industry.

Słowa kluczowe

PL

kumaryna; perfumy; akord fougère; fasola tonka; warfaryna; reakcja Perkina; reakcja Pechmanna; kondensacja

EN

coumarin; perfume; fougere accord; tonka beans; warfarin; Perkin reaction; Pechmann reaction; condensation

• Wydawca: ELAMED Media Group
• Czasopismo: Laboratorium - Przegląd Ogólnopolski
• Rocznik: 2021
• Tom: nr 4
• Strony: 36--41
• Opis fizyczny: Bibliogr. 42 poz., fot., rys.

Twórcy

autor

Szwaczko Katarzyna

• Katedra Chemii Organicznej Instytutu Nauk Chemicznych UMCS w Lublinie

autor

Lipa Agnieszka

• Wydział Chemii UMCS w Lublinie

Bibliografia

• 1. Hoult J.R.S., Paya M.: Pharmacological and biochemical actions of simple coumarins:
• Natural products with therapeutic potential. "General Pharmacology: The Vascular System.", 1996, 27, 713-722.
• 2. Vogel A.: Darstellung von Benzoesäure aus der Tonka-Bohne und aus den Meliloten- oder Steinklee-Blumen [Preparation of benzoic acid from tonka beans and from the flowers of melilot or sweet clover]. (in German) "Annalen der Physik", 1820, 64, 161-166.
• 3. Guibourt N.J.B.G.: Histoire Abrégée des Drogues Simples [Abridged History of Simple Drugs]. (in French) L. Colas, 1820, 2, 160-161.
• 4. Perkin W.H.: On the artificial production of coumarin and formation of its homologues. "Journal of the Chemical Society", 1868, 21, 53-63.
• 5. Lončar M., Jakovljević M., Šubarić D., Pavlić M., Služek V.B., Cindrić I., Molnar M.: Coumarins in Food and Methods of Their Determination - literature review. "Foods", 2020, 9, 645.
• 6. http://www.thegoodscentscompany.com/data/rw1003832.html
• 7. IUPAC: Nomenclature of OrganicChemistry. Pergamon Press: Oxford, 1979.
• 8. Ansary I., Taher A.: One-Pot Synthesis of Coumarin Derivatives. In "Phytochemicals in Human Health", Rao V., Mans D., Rao L., IntechOpen, 2020.
• 9. Perkin W.H.: On the hydride of aceto-salicyl. "Journal of the Chemical Society", 1868, 21, 181-186.
• 10. Perkin W.H.: On the formation of coumarin and of cinnamic and of other analogous acids from the aromatic aldehydes. "Journal of the Chemical Society", 1877, 31, 388-427.
• 11. J. O'Neil M.J.: The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th edition, Merck & Co, 2006.
• 12. von Pechmann H., Duisberg C.: Ueber die Verbindungen der Phenole mit Acetessigäther. Berichte der Deutschen Chemischen Gesellschaft. "Berichte Der Deutschen Chemischen Gesellschaft", 1883, 16, 2119-2128.
• 13. von Pechmann H.: Neue Bildungsweise der Cumarine. Synthese des Daphnetins. I. "Berichte der Deutschen Chemischen Gesellschaft", 1884, 17, 929-979.
• 14. Panetta J.A., Rapaport H. : New syntheses of coumarins. "The Journal of Organic Chemistry", 1982, 47, 946-950.
• 15. Woods L.L., Sapp J.: A new one-step synthesis of substituted coumarins. "The Journal of Organic Chemistry", 1962, 27, 3703-3705.
• 16. Sethna S.M., Shah N.M., Shah R.C.: Aluminium chloride, a new reagent for the condensation of β-ketonic esters with phenols. Part I. The condensations of methyl β-resorcylate, β-resorcylic acid, and resacetophenone with ethyl acetoacetate. "Journal of the Chemical Society", 1938, 228-232.
• 17. Corrie J.E.T.: A convenient synthesis of N-(7-dimethylamino-4 -methylcoumarin-3-yl) -maleimide incorporating a novel variant of the Pechmann reaction. "Journal of the Chemical Society Perkin Transactions 1", 1990, 7, 2151-2152.
• 18. Smitha G., Reddy S.C.: ZrC/4- catalyzed Pechmann reaction: Synthesis of coumarins under solvent -free conditions. "Synthetic Communications", 2004,34,3997-4003.
• 19. Smitha G., Reddy S.C. ZrCl4 - catalyzed Pechmann reaction: Synthesis of coumarins under solvent-free conditions. "Synthetic Communications", 2004, 34, 3997-4003.
• 20. John E.V.O., Israelstam S.S.: Notes. Use of cation exchange resins in organic reactions. l. The Von Pechmann reaction. "The Journal of Organic Chemistry", 1961, 26, 240-242.
• 21. Laufer M.C., Hausmann H., Hölderich W.F.: Synthesis of 7-hydroxycoumarins by Pechmann reaction using Nafion resin/silica nanocomposites as catalysts. "Journal of Catalysis", 2003, 218, 315-320.
• 22. Hoefnagel A.J., Gunnewegh E.A., Downing R.S., v. Bekkum H.: Synthesis of 7-hydroxycoumarins catalysed by solid acid catalysts. "Journal of the Chemical Society, Chemical Communications", 1995, 2, 225-226.
• 23. Knoevenagel E.: Condensationen zwischen Malonester und Aldehyden unter dem Einfluss von Ammoniak und organischen Aminen. "Berichte Der Deutschen Chemischen Gesellschaft", 1898, 31, 2585-2595.
• 24. Knoevenagel E.: Ueber die condensirende Wirkung organischer Basen. "Berichte Der Deutschen Chemischen Gesellschaft", 1904, 37, 4461-4463.
• 25. KeshavarzipourF., Tavakol H.: The synthesis of coumarin derivatives using choline chloride/zinc chloride as a deep eutectic solvent. "Journal of the Iranian Chemical Society", 2015, 13, 149-153.
• 26. Sugino T., Tanaka K.: Solvent-Free Coumarin Synthesis. "Chemistry Letters", 2001,30, 110-111.
• 27. Phadtare B., Shankarling G.S.: Greener coumarin synthesis by Knoevenagel condensation using biodegradable choline chloride. "Environmental Chemistry Letters", 2012, 10, 363-368.
• 28. Jayaseelan D., Ganapathi M., Guhanathan S.A.: A Conventional and Microwave Assisted Synthesis of 3-(3-(4-chlorophenyl)acryloyl)-2H-chromen-2-one Using Eco-Friendly Catalyst And Its Characterisation. "SOJ Materials Science and Engineering", 2015, 3, 1-6.
• 29. Zhu J.-J., Jiang J.-G.: Pharmacological and Nutritional Effects of Natural Coumarins and Their Structure-Activity Relationships." Molecular Nutrition and Food Research", 2018, 62.
• 30. Stefanachi A., Leonetti F., Pisani L., Catto M., Carotti, A.: Coumarin: A natural, privileged and versatile scaffold for bioactive compounds - literature review. "Molecules", 2018, 23, 250.
• 31. Lin C.-M., Huang S.-T., Lee F.-W., Kuo H.-S., Lin M.-H.: 6-Acyl-4-aryl/alkyl-5,7-dihydroxycoumarins as anti-inflammatory agents. "Bioorganic and Medicinal Chemistry", 2006,14, 4402-4409.
• 32. Wang T., Zhao Y., Shi M., Wu F.: The synthesis of novel coumarin dyes and the study of their photoreaction properties. "Dyesand Pigments", 2007, 75,104-110.
• 33. Sundt T.M., Anderson R.E.J.: Umbelliferone as an Intracellular pH-sensitive fluorescent indicator and blood-brain barrier probe: instrumentation, calibration, and analysis. "Neurophysiol", 1980, 44, 60-75.
• 34. Bielawska K., Malinowska M., Cyuńczyk M.: Wpływ kumaryn na organizm człowieka. "Bromatologia i Chemia Toksykologiczna" - XLVII", 2014, 2, 213-221.
• 35. Srikrishna D., Godugu C., Dubey P.K.: A Review on Pharmacological Properties of Coumarins. "Mini-Reviews in Medicinal Chemistry" 2018, 18, 113-141.
• 36. Annunziata F., Pinna C., Dallavalle S., Tamborini L., Pinto A.: An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities - literature review. "International Journal of Molecular Sciences" 2020, 21, 4618.
• 37. Sharma S., Agarwal N.: A review on herbs with antidepressant properties. "International Journal of Pharmacy and Therapeutics",2011, 2, 24-36.
• 38. Changwong N., Sabphon C., Ingkaninan K., Sawasdee P.: Acetyl- and Butyryl-cholinesterase Inhibitory Activities of Mansorins and Mansonones. "Phytotherapy Research", 2012, 26, 392-396.
• 39. Santra H.K., Banerjee D.: Natural Products as Fungicide and Their Role in Crop Protection. In "Natural Bioactive Products in Sustainable Agriculture" Singh J., Yadav A., Springer, 2020, 131-219.
• 40. Hazleton L.W., Tusing T.W., Zeitlin B.R., Thiessen R.Jr., Murer H.K.: Toxicity of coumarin. "Journal of Pharmacology and Experimental Therapeutics", 1956, 118, 348-358.
• 41. European Commission. European Parliament and Council Directive No. 1334/2008 on the flavourings and certain food ingredients with flavouring properties for use in and on food and amending Council Regulation (EEC) No.1601/91, Regulations (EC) No. 2232/96 and (EC) No. 110/2008 and Directive 2000/13/EC. O. J. Eur. Commun. 2008, L354, 34-50.
• 42. Notification of the 49th Amendment to the IFRA Code of Practice January 10, 2020 (https://ifrafragrance.org).

Uwagi

PL

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2021).