<i>Origanum bastetanum</i>Soc. Cultivated Specimens: Characterization of Its Essential Oil

Pérez-Galindo, Pilar; Martínez-Raya, Armando; Francia, José Ramón; Jiménez, J.; Navarro, C.

doi:10.1080/10412905.2005.9699024

Cited by 2 publications

(3 citation statements)

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“…(+)-Yabunikkeol ( 6 ) was described as an oxidation derivative of (−)-α-phellandrene, although the (4 R ,6 S ) absolute configuration was wrongly assigned, while p -cymene ( 7 ) and (+)-(4 S )-carvotanacetone ( 8 ) are widely reported as essential oil components. In addition, 7 has been considered a good-quality essential oil ingredient in Origanum species or a low-quality ingredient in lemon essential oil …”

Section: Resultsmentioning

confidence: 99%

“…In addition, 7 has been considered a good-quality essential oil ingredient in Origanum species 16 or a low-quality ingredient in lemon essential oil. 17 Since allylic alcohol intermediates 4−6 lead to aromatic 7, iodine was considered as the aromatization reagent. 18,19 Thus, p-menthenediol 4 was refluxed in the presence of iodine for 3 h to yield 8 and 9 (1:2), while aromatization for 5 h only provided carvacrol (9).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…9 In this paper the biomimetic transformations of 1 and 2 into aromatic monoterpene derivatives and other essential oil constituents, by dehydration and oxidation processes, are described. Dihydroxy-p-menthene derivatives 3−5, (+)-(4S,6R)-yabunikkeol (6), 1,5,6-triols 15 and 16, and the new (+)-(4S,5R,6S)-1 (7),2-menthadiene (17), as reaction intermediates in the formation of p-cymene (7) (9), were suggested. (+)-(4S)-Carvotanacetone (8) was also observed as a dehydration product of 4 and 5, while oxidation with iodine suggested that p-cymene (7) and carvacrol (9) could arise from a common precursor, 4.…”

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Biomimetic Transformation ofp-Menthene Glucosides intop-Cymenes and Carvotanacetone

et al. 2019

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A biomimetic transformation of p-menthene glucosides into aromatic monoterpenoids that alluded to mechanisms for essential oil metabolism, which lines up with the precepts of molecular economy, is described. Acid treatment of (−)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 3-O-β-d-glucopyranoside (1) and (−)-(3S,4R,5R,6S)-3,5,6-trihydroxy-1-menthene 3-O-β-d-glucopyranoside (2), from Ageratina glabrata, yielded p-cymene (7) and carvacrol (9). The stable oxidized intermediates (+)-(3S,4S,6R)-3,6-dihydroxy-1-menthene (3), (+)-(1S,4S,6R)-1,6-dihydroxy-2-menthene (4), (+)-(1R,4S,6R)-1,6-dihydroxy-2-menthene (5), (+)-(4S,6R)-yabunikkeol (6), (+)-(4S)-carvotanacetone (8), (+)-(1S,4S,5R,6R)-1,5,6-trihydroxy-2-menthene (15), (+)-(1R,4S,5R,6R)-1,5,6-trihydroxy-2-menthene (16), and the new (+)-(4S,5R,6S)-1(7),2-menthadiene (17) permitted establishment of the reaction mechanisms. The reactivity of the hydroxy groups of 4 and 5, as well as those of 15 and 16, was compared by acetylation reactions and supported by DFT calculations, revealing diminished reactivity in 4 and 15 due to the cis configuration of their hydroxy groups at C-1 and C-6. In addition, p-cymene (7) was detected as one of the major constituents of the essential oil of A. glabrata, which matches well with the biomimetic study.

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Section: Resultsmentioning

confidence: 99%