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trans,cis-2,6-Nonadienal

Chemical compound From Wikipedia, the free encyclopedia

trans,cis-2,6-Nonadienal (also known as (E,Z)-2,6-nonadienal or "cucumber aldehyde") is an organic compound that is classified as a doubly unsaturated derivative of nonanal. The molecule consists of a α,β-unsaturated aldehyde with an isolated alkene group. The compound having an odour described as "green, fatty, dry, cucumber, violet leaf, melon",[1] has attracted attention as the essence of cucumbers,[2][3] but it is also found in bread crust[4] and freshly cut watermelon.

Quick facts Names, Identifiers ...
trans,cis-2,6-Nonadienal
Names
Preferred IUPAC name
(2E,6Z)-Nona-2,6-dienal
Other names
(E,Z)-2,6-Nonadienal
Violet leaf aldehyde
Cucumber aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.345 Edit this at Wikidata
UNII
  • InChI=1S/C9H14O/c1-2-3-4-5-6-7-8-9-10/h3-4,7-9H,2,5-6H2,1H3/b4-3-,8-7+
    Key: HZYHMHHBBBSGHB-ODYTWBPASA-N
  • CC/C=C\CC/C=C/C=O
Properties
C9H14O
Molar mass 138.210 g·mol−1
Appearance Colorless oil
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H317
P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis

Isotopic labeling has indicated that nonadienal is formed from α-linolenic acid.[5] Such reactions are typically catalyzed by hydroperoxide lyases.

See also

  • 2-Nonenal - Structurally related, aroma of cucumber
  • 6-Nonenal - Structurally related, aroma of cantaloupe

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