(3Z)-Nonenal

(3Z)-Nonenal is an unsaturated aldehyde that occurs naturally in various plants.

(3Z)-Nonenal

Structural formula of (3Z)-nonenal
Names
Other names (Z)-3-Nonenal (Z)-Non-3-enal cis-3-Nonenal
Identifiers
CAS Number	31823-43-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:191226
ChemSpider	4936380
PubChem CID	6431042
InChI InChI=1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h6-7,9H,2-5,8H2,1H3/b7-6- Key: YXEAENVLZOODMT-SREVYHEPSA-N
SMILES CCCCC/C=C\CC=O
Properties
Chemical formula	C9H16O
Molar mass	140.226 g·mol−1
Appearance	Colorless oil[1]
Boiling point	105 °C (221 °F; 378 K) (20 mmHg)[2]
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Occurrence

The oysterplant, also known as sea bluebells, contains (3Z)-nonenal

(3Z)-Nonenal is a flavor component in various plants, such as cucumber, honeydew melon, and soy.^[3][4][5][6] It is the biosynthetic precursor to (2E)-nonenal, formed by isomerases.^[6] It also occurs in the brown algae Laminaria angustata.^[7][8] In the oysterplant, it contributes to its oyster-like taste.^[9]

Biosynthesis

In various plants such as cucumbers and melons, (3Z)-nonenal is formed from linoleic acid to 9-hydroperoxy-10,12-octadecadienoic acid and its splitting.^{[4][6][clarification needed]} In Laminaria angustata, formation also occurs via arachidonic acid and its 12-hydroperoxide.^[7][8][how?]

Synthesis

(3Z)-Nonenal can be synthesized by oxidation of (3Z)-nonen-1-ol with pyridinium chlorochromate.^[2] The compound can also be obtained through a multi-step reaction starting from 1,4-butanediol.^[2][how?]

Properties

The scent is described as fruity, melony, or maritime in low concentrations.^[9] In an in vitro study, (3Z)-nonenal acted as a fungicide against various types of fungi.^[3]