Long chain conjugated alkadienes; a new component of plant waxes

Stoianova-Ivanova, B.; Mladenova, Kirilka; Malova, I.

doi:10.1016/s0031-9422(00)89900-8

Cited by 9 publications

(7 citation statements)

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“…Thus, in common with the barley monoenoic alkenes, those from other plant waxes are characterized by a series of positional isomers and homologue distributions that differ from those of the n ‐alkanes. Dienoic alkenes were also identified in early studies, for example in flower wax of R. damascene , but double bond positions were not characterized (Stoianova‐Ivanova et al. , 1971).…”

Section: Resultsmentioning

confidence: 99%

Analyses of barley spike mutant waxes identify alkenes, cyclopropanes and internally branched alkanes with dominating isomers at carbon 9

Wettstein-Knowles

2006

The Plant Journal

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SummaryAbout 15% of the epidermal wax on Hordeum vulgare cv. Bonus barley spikes is n-alkanes. Longer homologues are greatly reduced in the eceriferum mutants, cer-a 6 , cer-e 8 , cer-n 26 , cer-n 53 , cer-n 985 , cer-x 60 , cer-yc 135 and cer-yl 187 . Simultaneously hydrocarbons accounting for only traces in the wild-type become prominent in the mutants, although their chain-length distributions remain unchanged. Accordingly several new hydrocarbon series were identified. The two major ones were C 23 -C 35 cis monoenoic alkenes (the major 9-ene isomer was part of a homologous series including 11, 13 and 15-enes), and the novel C 27 -C 31 cyclopropanes (the ring carbons of major isomers were 9,10 and 11,12 with lesser amounts of 13,14). Three minor series included 2-and 3-methylalkanes plus C 25 -C 33 internally branched alkanes (methyls on carbons 9, 11, 13, 15 or 17; shorter homologues dominated by the 9 isomer, longer homologues by 11, 13 or 15 isomers). Acyl chains destined for spike waxes are synthesized via acyl and polyketide elongase systems plus associated reductive and decarbonylative/decarboxylative enzyme systems. Both elongation systems are defective in synthesizing C 32 acyl chains in all nine mutants. The similarities in the position of the chemical groups (primarily on carbon 9, secondarily on carbon 11) of the alkenes, cyclopropanes and internally branched methyl alkanes imply an origin from a common, hitherto unrecognized associated pathway in barley, designated the enoic pathway. The elongation system leading to the enoic derived hydrocarbons differs from the known elongation systems by inclusion of a mechanism for introducing a double bond.

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Section: Resultsmentioning

confidence: 99%

Analyses of barley spike mutant waxes identify alkenes, cyclopropanes and internally branched alkanes with dominating isomers at carbon 9

Wettstein-Knowles

2006

The Plant Journal

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“…Almost 200 peaks were detected, and ninety percent of the chromatogram total area were identified. 2,7,12,[15][16][17]19,[23][24][25][26][27][28]33,34 On Figure 1, the main compounds of rose absolutes were identified with the peaks from A to H. The detailed characteristic fragmentations are provided in Figure 2.…”

Section: Initial Work On Rose Absolutes With Lrms and Hrmsmentioning

confidence: 99%

“…In addition, from a toxicological point of view, the lack of knowledge of an ingredient significantly reduces its use to avoid any risk for the consumer. There are several published works on the composition of rose absolutes from Rosa damascena (CAS: 8007‐01‐0) and Rosa centifolia (CAS: 84604‐12‐6) 2,7,12,15‐28 . They referred the main compounds to be phenylethyl alcohol, citronellol, geraniol, methyl eugenol, limonene, neryl acetate, geranyl acetate, nerol, α‐terpineol, benzyl alcohol, nonadecane, (9 Z )‐nonadecene and ( E,E ) ‐ farnesol.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, more than 200 minor compounds are cited in the literature. Stoianova‐Ivanova et al 19 contributed to the identification of long chain alkenes that have only been reported after by Garnero 28 . Wollrab identified some long chained alcohols (C ≥ 20) in the concrete 29 .…”

Section: Introductionmentioning

confidence: 99%

“…There are several published works on the composition of rose absolutes from Rosa damascena (CAS: 8007-01-0) and Rosa centifolia (CAS: 84604-12-6). 2,7,12,[15][16][17][18][19][20][21][22][23][24][25][26][27][28] They referred the main compounds to be phenylethyl alcohol, citronellol, geraniol, methyl eugenol, limonene, neryl acetate, geranyl acetate, nerol, α-terpineol, benzyl alcohol, nonadecane, (9Z)-nonadecene and (E,E)-farnesol. In addition, more than 200 minor compounds are cited in the literature.…”

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confidence: 99%

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Identification of novel compounds in rose absolute with gas chromatography/high‐resolution mass spectrometry

Remy

Sarrazin²,

Pérès³

et al. 2022

Flavour & Fragrance J

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Roses have beautiful shapes and colors, which make them attractive for horticultural purposes, and more than 18,000 varieties have been created by crossings. 1 Rose is also one of the major sources of natural ingredients for the fragrance industry. Indeed, the Queen of the flowers brings exceptional facets to perfume compositions. Among the 200 rose species, Rosa centifolia and Rosa damascena are the two main species used by the fragrance industry. 1 Rosa centifolia is mainly farmed in France and Morocco, 2,3 while Rosa damascena is mainly farmed in Bulgaria, Turkey, China, India and Egypt. 2,3 Rosa damascena is used to produce essential oil (yield: 0.03%), concrete (yield: 0.17%-0.40%), and absolute (yield: 50%-65% from concrete extraction), whereas Rosa centifolia is only used for concrete and absolute, and is not economically viable for essential oil. 4 Due to its rarity Rosa centifolia is one of the most precious species used in perfumery for absolute. Obtention of rose concrete from fresh rose flowers is a well-known process. Rose concrete is produced by solvent extraction, generally using petroleum ether and/or "generic" hexane. 2,[5][6][7][8] In contrast with recent allegations, 9 various mixtures of C6 hydrocarbons with low n-hexane content are preferred, rather than pure n-hexane, a CMR and neurotoxic substance. Benzene is no longer used for solvent extraction due to his high toxicity. 10 Moreover, to date extraction of fresh rose flowers with liquefied gases or supercritical CO 2 have not reached any significant importance. Rose concrete is a waxy, semi-solid material, that is, hardly soluble in ethanol. So, concrete is poorly used in its native form for fragrances and is further transformed into absolute using ethanol. Concrete is dissolved in hot ethanol (between 35 and 40°C) and then filtered at glacial temperature (−20°C). Ethanol is finally evaporated under vacuum to get the absolute. 2,6,11,12 Rose absolute is a dark red liquid with a typical rose odor. Rose absolute is considered to represent the more genuine character of rose fragrance. Indeed,

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Rosa damascena Mill. (R. damascena f. Trigintipetala)

Azimova¹,

Glushenkova²

2012

Lipids, Lipophilic Components and Essential Oils From Plant Sources

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Long chain conjugated alkadienes; a new component of plant waxes

Cited by 9 publications

References 1 publication

Analyses of barley spike mutant waxes identify alkenes, cyclopropanes and internally branched alkanes with dominating isomers at carbon 9

Analyses of barley spike mutant waxes identify alkenes, cyclopropanes and internally branched alkanes with dominating isomers at carbon 9

Identification of novel compounds in rose absolute with gas chromatography/high‐resolution mass spectrometry

Rosa damascena Mill. (R. damascena f. Trigintipetala)

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