Lipoxygenase-catalyzed peroxidative decomposition of unsaturated fatty acids occurs within seconds when diatoms are crushed or eaten, producing alkyls.1 DDA is a prominent member of this class of reactive compounds. Common ω-6 fatty acids such as linoleic acid, dihomo-γ-linolenic acid, and arachidonic acid can give rise to DDA. DDA reduces the hatching rate and has a strong teratogenic effect on the eggs of pelagic copepods, at concentrations around 1 µM.2 In human carcinoma Caco2 cells, DDA induces cell growth arrest at around 15 µM. DDA appears to be a natural defensive chemical designed to limit the reproductive success of copepods, the main predators of diatoms. It may also be a more general inducer of apoptosis.
1
Miralto, A., Barone, G., Romano, G., et al. The insidious effect of diatoms on copepod reproduction. Nature402173-176(1999).
2
Ianora, A., Miralto, A., Poulet, S.A., et al. Aldehyde suppression of copepod recruitment in blooms of a ubiquitous planktonic diatom. Nature429403-407(2004).
Synonyms
trans-2,4-Decadien-1-al
Decadienealdehyde
Formal Name
2E,4E-decadienal
CAS Number
25152-84-5
Molecular Formula
C10H16O
Formula Weight
152.2
Formulation
A yellow liquid
Purity
≥98%
λmax
273 nm
Stability
2 years
Storage
-20°C
Shipping
Wet ice
in continental US; may vary elsewhere
SMILES
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CCCCC\C=C\C=C/C=O
Background Reading
Miralto, A., Barone, G., Romano, G., et al. The insidious effect of diatoms on copepod reproduction. Nature402173-176(1999).
Ianora, A., Miralto, A., Poulet, S.A., et al. Aldehyde suppression of copepod recruitment in blooms of a ubiquitous planktonic diatom. Nature429403-407(2004).
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