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Abstrakty
Lavandulol and its esters play a significant role in the perfume and cosmetics industry. Because of their biological activity they have recently become relevant in research on pheromones. Many natural sources of this important alcohol are known along with synthetic methods allowing to achieve either an optically pure product or a racemic mixture. The article presents a short overview on new natural resources of the alcohol, its sensory and pheromonal characteristics and synthesis of its racemic mixture and enantiomers.
Czasopismo
Rocznik
Tom
Strony
91--100
Opis fizyczny
Bibliogr. 27 poz., rys.
Twórcy
autor
- Institute of General Food Chemistry, Lodz University of Technology 90-924, Lodz, Poland
Bibliografia
- 1. Schintz H, Seidel CF. Uber Lavandulol, einen neuen Monotorpenalkohol aus Lavandelol. Helv. Chim. Acta 1942, 25, 1572-1591.
- 2. Sakauchi H, Kiyota H, Takigawa S, Oritani T, Kuwahara S. Enzymatic resolution and odor description of both enantiomers of lavandulol, a fragrance of lavender oil. Chem. Biodivers. J. 2005, 2, 1183-1186.
- 3. Zada A, Dunkelblum E. A convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic acid anhydride: simple preparation of enantiomerically pure (R)-lavandulol. Tetrahedron Assymetr. 2006, 17, 230-233.
- 4. Góra J, Lis A. Najcenniejsze olejki eteryczne. Wydawnictwo UMK Toruń 2004, 167, 171.
- 5. Weyerstahl P, Marschall H, Thefeld1 K, Rustaiyan A. Constituents of the essential oil of Tanacetum (syn. Chrysanthemum) fruticulosum Ledeb. from Iran. Flavour Fragr. J. 1999, 14, 112-120.
- 6. Kitchlu S, Bakshi SK, Kaul MK, Bhan MK, Thapa RK, Agarwal SG. Tanacetum gracile Hook. f & T. A new source of lavandulol from Ladakh Himalaya (India). Flavour Fragr. J. 2006, 21, 690-692.
- 7. Habibi Z, Biniyaz T, Ghodrati T, Masoudi S, Rustaiyan A. Volatile constituents of Tanacetum paradoxum Bornm. and Tanacetum tabrisianum (Boiss.) Sosn. et Takht., from Iran. J. Essent. Oil Res. 2007, 19, 11-13.
- 8. Cross JV, Hesketh H, Jay CN, Hall DH, Innocenzi PJ, Farman DI, Burgess CM. Exploiting the aggregation pheromone of strawberry blossom weevil Anthonomus rubi Herbst (Coleoptera: Curculionidae): Part 1. Development of lure and trap. Crop Prot. 2006, 25, 144-154.
- 9. Hamilton JGC, Hall DR, Kirk WDJ. Identification of a male-produced aggregation pheromone in the western flower thrips Frankliniella occidentalis. J. Chem. Ecol. 2005, 31, 6, 1369-1379.
- 10. Alfonso I, Hernandez E, Velazquez Y, Navarro I, Primo J. Identification of the sex pheromone of the mealybug Dysmicoccus grassii Leonardi. J. Agr Food Chem. 2012, 60, 11959-11964.
- 11. Francis A, Bloem KA, Roda AL, Laponie SL, Hang A, Onokpise O. Development of trapping methods with a synthetic sex pheromone of the pink hibiscus mealybug, Maconellicoccus Hirsutus (Hemiptrera: Pseudococcidae). Fla. Entomol. 2007, 90, 3, 440-446.
- 12. Zhang A, Amalin D, Shirali S, Serrano MS, Franqui RA, Oliver JE, Klun JA, Aldrich JR, Meyerdirk DE, Lapointe SL. Sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, contains an unusual cyclobutanoid monoterpene. PNAS 2004, 101, 26, 9601-9606.
- 13. Ho Y, Su Y, Ko CH, Tsai MY. Identification and Synthesis of the sex pheromone of the Madeira mealybug, Phenacoccus Madeirensis Green. J Chem Ecol 2009, 35, 24-732.
- 14. Hinkens DM, McElfresh JS, Millar JG. Identification and synthesis of the sex pheromone of the vine mealybug, Planococcus ficus. Tetrahedron Lett. 2001, 42, 1619-1621.
- 15. Matsui M, Stalla-Bourdillon B. New attempt at the synthesis of lavandulol by a Claisen type rearrangement. Agr. Biol. Chem. 1968, 32, 10, 1246-1249.
- 16. Ueno Y, Aoki S, Okawara M. Synthesis of (±)-lavandulol and its related homoallylic alcohol via allyl transfer form sulphur to tin. J. S. C. Chem. Comm. 1980, 680-684.
- 17. Imai T, Nishida S. A new type of catalysis by copper (I) salts in the barbier-type aldehyde allylation with tin (II) chloride. Short synthesis of (±)-lavandulol and this γ,δ-dihydro derivate. J. Chem. Soc., Chem. Commun. 1994, 277-278.
- 18. Fleming I, Lee D. Conjugate Addition of silyl groups to β-unsubstitued enoes, & Si-to-OH conversion: a synthesis of (±)-lavandulol. Tetrahedron Lett. 1996, 37, 38, 6929-6930.
- 19. Mino T, Fukui S, Yamashito M. Hydrolysis of β,γ-unsaturated aldehyde dimethylhydrazones with copper dichloride: a new synthesis of lavandulol. J. Org. Chem. 1997, 62, 734-735.
- 20. Mehta G, Karmakar S, Chattopadhyay SK. Grob-type fragmentation of a carvon derived β-hydroxymesylate: application to the synthesis of chiral lavandulol derivatives. Tetrahedron 2004, 60, 5013-5017.
- 21. Kim HJ, Su L, Jung H, Koo S. Selective deoxygenaton of allylic alcohol: stereocontrolled synthesis of lavandulol. Organic Lett. 2011, 13, 10, 2682-2685.
- 22. Fernandes RA, Chowdhury AK. A synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate, and (+)-lavandulyl senecioate through orthoester Johnson - Claisen rearrangement. Eur. J. Org. Chem. 2013, 5165-5170.
- 23. Araki S, Kambe S, Kameda K, Hirashita T. A new synthesis of lavandulol via Indium/Palladium-mediated umpolung of vinyloxirane. Synth. 2003, 5, 751-754.
- 24. Cardillo G, D'Amico A, Orena M, Sandri S. Diastereoselective alkylation of 3-acylimidazolidin-2-ones: synthesis of (R)- and (S)-lavandulol. J. Org. Chem. 1988, 53, 2354-2356.
- 25. Piva O. Enantio- and diastereoselective protonation of photodienols: total synthesis of (R)-(-)-lavandulol. J. Org. Chem. 1995, 60, 7879-7883.
- 26. Gliszczyńska A, Bonikowski R, Kula J, Wawrzeńczyk C, Ciołak K. Chemomicrobial synthesis of R- and S-lavandulol. Tetrahedron Lett. 2011, 52, 34, 4462-4463.
- 27. Kula J, Podlejski J. Synthesis of (-)-isohomolavandulol from (+)-limonene. Liebigs Ann. Chem. 1985, 2098-2100.
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Bibliografia
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