Distribution of piperitone oxide stereoisomers in Mentha and Micromeria species and their chemical syntheses

Flavour and Fragrance Journal

Volumn 22, Issue 4, 2007, Pages 328-333

  Larkov, Olga ^a   Matasyoh, Josphat C ^b   Dudai, Nativ ^a   Lewinsohn, Efraim ^a   Mayer, Alfred A ^c   Ravid, Uzi ^a  

^a VOLCANI CENTER   (Israel)

^b EGERTON UNIVERSITY   (Kenya)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Alkaline epoxidation; Diastereomers; Enantiomers; Keto enol tautomerism; Mentha longifolia L.; Micromeria fruticosa (L.) Druce; Trans and cis piperitone oxide

Indexed keywords

ALKALINE EPOXIDATION; PIPERITONE OXIDE; RACEMIZATION;

CHIRALITY; ENANTIOMERS; EPOXIDATION; PLANTS (BOTANY); SYNTHESIS (CHEMICAL);

STEREOCHEMISTRY;

PIPERITONE DERIVATIVE; TERPENOID; UNCLASSIFIED DRUG;

ALKALINITY; ANGIOSPERM; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENANTIOMER; EPOXIDATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MENTHA; MICROMERIA; PHYTOCHEMISTRY; RACEMIZATION; SPECIES DIFFERENCE; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MENTHA; MENTHA LONGIFOLIA; MICROMERIA; MICROMERIA FRUTICOSA;

EID: 34447580190     PISSN: 08825734     EISSN: 10991026     Source Type: Journal    
DOI: 10.1002/ffj.1801     Document Type: Article

References (41)

1. Ravid U, Putievsky E, Katzir I. Flavour Fragr. J. 1994; 9: 85-87.
2. Ravid U, Putievsky E, Katzir I, Weinstein V, Ikan R. Flavour Fragr. J. 1992; 7: 289-292.
3. Ravid U, Putievsky E, Katzir I. Flavour Fragr. J. 1994; 9: 139-142.
4. Ravid U, Putievsky E, Katzir I. Flavour Fragr. J. 1994; 9: 205-207.
5. Ravid U, Putievsky E, Katzir I. Flavour Fragr. J. 1995; 10: 281-284.
6. Ravid U. Perfum. Flavor. 1998; 23(4): 25-30.
7. Kokkalou E, Stefanou E. Flavour Fragr. J. 1990; 5: 23-26.
8. Lawrence BM. In Advances in Labiatae Science, Harley RM, Reynolds T (eds). Royal Botanic Gardens: Kew, 1992; 399-436.
9. Baldovini N, Ristorcelli D, Tomi F, Casanova J. Flavour Fragr. J. 2000; 15: 50-54.
10. Kitic D, Palic R, Ristic M, Sojanovic G, Jovanovic T. Flavour Fragr. J. 2001; 16: 257-258.
11. Shah GC, Bhandari R, Mathela CG. J. Essent. Oil Res. 1992; 4: 57-59.
12. Brophy JJ, Goldsack RJ, Forster PI, Fookes CJR. J. Essent. Oil Res. 1997; 9: 459-461.
13. Croteau R, Karp F, Wagschal KC, Satterwhite DM, Hyatt DC, Scotland CB. Plant Physiol. 1991; 96: 744-752.
14. Başer KHC, Kirimer N, Duman H. Flavour Fragr. J. 1997; 12: 289-291.
15. Fleisher A, Fleisher G. J. Essent. Oil Res. 1991; 3: 57-58.
16. Ghoulami S, Idrissi AI, Fkih-Tetouani S. Fitoterapia 2001; 72: 596-598.
17. Kokkini S, Karousou R, Lanaras T. Bot. Acta 1997; 110: 184-189.
18. Umemoto K. Nat. Prod. Lett. 1998; 11: 161-165.
19. Reitsema RH. J. Am. Pharm. Assoc. 1958; 4: 267-269.
20. De Pooter HL, De Buyck LF, Schamp NM. Phytochemistry 1986; 25: 691-694.
21. Kokkini S, Papageorgiou VP. Flavour Fragr. J. 1987; 2: 119-121.
22. Abu-Al-Futuch IM, Abdelmageed OH, Jamil RM, Avato P. J. Essent. Oil Res. 1995, 12: 530-532.
23. Tumen G, Başer KHC, Kurkcuoglu, Demircakmak B. J. Essent. Oil Res. 1995, 7: 679-680.
24. Kokdil G. Flavour Fragr. J. 1998; 13: 170-172.
25. Fraternale D, Giamperi L, Ricca D, Manunta A. J. Essent. Oil Res. 1998, 10: 568-570.
26. Oumzil H, Ghoulami S, Rhajaoui M et al. Phytother. Res. 2002; 16: 727-731.
27. Reitsema RN, Varnis JV. J. Am. Chem. Soc. 1956; 78: 3792-3794.
28. Shimizu S, Katsuhara J, Inouye Y. Agr. Biol. Chem. 1966; 1: 89-90.
29. Shimizu S. Bull. Agr. Chem. Soc. Japan 1957; 2: 107-114.
30. Klein E, Ohloff G. Tetrahedron 1963; 19: 1091-1099.
31. House HO. Modern Synthetic Reactions. W.A. Benjamin Inc.: Menlo Park, CA, 1972.
32. Elings JA, Lempers HEB, Sheldon RA. Eur. J. Org. Chem. 2000; 1905-1911.
33. Mahmoud SS, Croteau RB. Proc. Natl Acad. Sci. USA 2003; 100: 14481-14486.
34. Connoly JD, Hill RA. Dictionary of Terpenoids, vol. l. Chapman and Hall: London, 1991.
35. Dudai N, Larkov O, Chaimovitsh D, Lewinsohn E, Freiman L, Ravid U. Flavour Fragr. J. 2003; 18: 334-337.
36. Larkov O, Dunkelblum E, Zada A et al. Flavour Fragr. J. 2005; 20: 109-114.
37. Adams RP. Identification of Essential Oil Compounds by Gas Chromatography/Quadrupole Mass Spectroscopy. Allured: Carol Stream, IL, 2001.
38. Erman WF. Chemistry of the Monoterpenes. Marcel Dekker: New York, 1985; 670-675.
39. Mori K. The Total Synthesis of Natural Products, vol. 9. Ap Simon J. (ed.). John Wiley; New York, 1992; 320-326.
40. Guenther E. The Essential Oils, vol. 2. Van Nostxand-Reinhold: New York, 1949; 396-399.
41. Croteau RB, Davis EM, Ringer KL, Widung MR. Naturwissenschaften 2005; 92: 562-567.