Natural acetylenes. Part XXVIII. C17-polyacetylenic alcohols from the Umbellifer Daucus carota L. (carrot) : alkylation of benzene by acetylenyl(vinyl)carbinols in the presence of toluene-p-sulphonic acid

Bentley, R. K.; Bhattacharjee, D.; Jones, E. R. H.; Thaller, V.

doi:10.1039/j39690000685

Cited by 23 publications

(21 citation statements)

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“…Analysis of whole peeled carrots (cv Irnperator) stored for 1 to 3 weeks vacuum packed in plastic shrink bags showed that, in addition to three of the polyacetylenes previously identified by Bentley et al (1969) 15 acetylenic other compounds were present.…”

Section: Resultsmentioning

confidence: 99%

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Acetylenic compounds in stored packaged carrots

Lund¹,

Bruemmer²

1991

J Sci Food Agric

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Stored carrots vacuum packed in plastic shrink bags showed signijkant variations in the concentration of certain important secondary compounds.in the acetylene group, 18 compounds were isolated and measured. Only eight of these compounds have previously been reported as carrot constituents. The concentrations of 10 of the 18 increased with storage time, and six were present only in stored samples.

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Section: Resultsmentioning

confidence: 99%

“…The concentration/time curves for the two are also very similar. The only previous value reported for the concentration of falcarindiol-3-monoacetate was 5 mg kg-l (Bentley et al 1969).…”

Section: Resultsmentioning

confidence: 99%

Acetylenic compounds in stored packaged carrots

Lund¹,

Bruemmer²

1991

J Sci Food Agric

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“…From this, it was concluded that falcarinol is the major elicitor of allergic contact dermatitis in Schefflera arboricola and that falcarinol does not react in its oxidized form. Falcarinol is chemically very reactive (15), and it seems reasonable to propose it as an alkylating agent. If its hydroxy group, helped by a proton, is removed, as the leaving group, an extremely stable carbocation is formed which can easily react with mercapto and amino groups in proteins, forming haptens.…”

Section: Discussionmentioning

confidence: 99%

Allergic contact dermatitis from falcarinol isolated from Schefflera arboricola

Hansen¹,

Hammershøy

Boll³

1986

Contact Dermatitis

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From the plant Schefflera arboricola, which has been reported to cause allergic contact dermatitis, we have isolated and determined the elicitor of allergic contact dermatitis as falcarinol, heptadeca-1,9(Z)-diene-4,6-diyne-3-ol. Three polyacetylenes closely related to falcarinol, namely falcarindiol, falcarinone and dehydrofalcarinone were tested simultaneously. Falcarinol, but not falcarindiol, falcarinone and dehydrofalcarinone, elicited allergic contact dermatitis in a 38-year-old female plant-nursery worker.

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“…These include four compounds: falcarinol (R, -OH, R,-H), falcarindiol (R, -OH, R,-OH), falcarindiol-3-monoacetate (R, -OAc, R,-OH) and falcarinolone (carbonyl at R, position) (Bentley et al 1969).…”

Section: Introduction E D Lund J M Whitementioning

confidence: 99%

Polyacetylenes in normal and waterstressed ‘Orlando Gold’ carrots (Daucus carota)

Lund¹,

White

1990

J Sci Food Agric

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The effect of water stress on the polyacetylenic constituents of carrots (Daucus carota L, cv 'Orlando Gold') was studied by liquid chromatographic analysis. Eleven polyacetylenes were isolated fiom plants grown in the greenhouse under normal conditions and under conditions simulating drought or waterlogging. Three compounds were ident$ed. These include the known carrot polyacetylenes falcarinol (cis-heptadeca-1,9-diene-4,6-diyn-3-01), falcarindiol (cis-heptadeca-l,9-diene-4,6-diyn-3,8-diol), and falcarindiol-3-monoacetate (cis-3-acetoxyheptadeca-l,9-diene-4,6-diyn-8-o1). Three of the eight unidentified compounds were produced only by one or both stressed samples. The other eight (including the three knowns) were less concentrated in the stressed samples than in the control.

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Natural acetylenes. Part XXVIII. C17-polyacetylenic alcohols from the Umbellifer Daucus carota L. (carrot) : alkylation of benzene by acetylenyl(vinyl)carbinols in the presence of toluene-p-sulphonic acid

Cited by 23 publications

References 0 publications

Acetylenic compounds in stored packaged carrots

Acetylenic compounds in stored packaged carrots

Allergic contact dermatitis from falcarinol isolated from Schefflera arboricola

Polyacetylenes in normal and waterstressed ‘Orlando Gold’ carrots (Daucus carota)

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