(3Z)-Nonenal

(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
Boiling point	105 °C (221 °F; 378 K) (20 mmHg)
Hazards
	GHS labelling:
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

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

Occurrence

(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]

References

^ ^a ^b "(Z)-3-Nonenal". 2023-08-27. {{cite web}}: Missing or empty |url= (help)
^ ^a ^b ^c Tadahiko Kajiwara, Yoshinobu Odake, Akikazu Hatanaka (1975). "Synthesis of 3Z-Nonenal and 3Z,6Z-Nonadienal". Agricultural and Biological Chemistry. 39 (8): 1617–1621. doi:10.1080/00021369.1975.10861815.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ^a ^b S. F. Vaughn, H. W. Gardner (1993-10-01). "Lipoxygenase-derived aldehydes inhibit fungi pathogenic on soybean". Journal of Chemical Ecology. 19 (10): 2337–2345. Bibcode:1993JCEco..19.2337V. doi:10.1007/BF00979668. PMID 24248580.
^ ^a ^b Nathalie Tijet, Claus Schneider, Bernard L. Muller, Alan R. Brash (2001-02-01). "Biogenesis of Volatile Aldehydes from Fatty Acid Hydroperoxides: Molecular Cloning of a Hydroperoxide Lyase (CYP74C) with Specificity for both the 9- and 13-Hydroperoxides of Linoleic and Linolenic Acids". Archives of Biochemistry and Biophysics. 386 (2): 281–289. doi:10.1006/abbi.2000.2218. PMID 11368353.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Akikazu Hatanaka, Tadahiko Kajiwara, Takahiro Harada (1975-12-01). "Biosynthetic pathway of cucumber alcohol: Trans-2,cis-6-nonadienol via cis-3,cis-6-nonadienal". Phytochemistry. 14 (12): 2589–2592. Bibcode:1975PChem..14.2589H. doi:10.1016/0031-9422(75)85230-7.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ^a ^b ^c David R. Phillips, Jennifer A. Matthew, John Reynolds, G.Roger Fenwick (1979-01-01). "Partial purification and properties of a cis-3: trans-2-enal isomerase from cucumber fruit". Phytochemistry. 18 (3): 401–404. Bibcode:1979PChem..18..401P. doi:10.1016/S0031-9422(00)81874-9.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ^a ^b Kangsadan Boonprab, Kenji Matsui, Yoshihiko Akakabe, Norishige Yotsukura, Tadahiko Kajiwara (2003-07-01). "Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3- and (E)-2-nonenal formation in Laminaria angustata". Phytochemistry. 63 (6): 669–678. Bibcode:2003PChem..63..669B. doi:10.1016/S0031-9422(03)00026-8. PMID 12842139.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ^a ^b Kangsadan Boonprab, Kenji Matsui, Yoshihiko Akakabe, Miyuki Yoshida, Norishige Yotsukura, Anong Chirapart, Tadahiko Kajiwara (2006-11-27). "Formation of Aldehyde Flavor (n-hexanal, 3Z-nonenal and 2E-nonenal) in the Brown Alga, Laminaria Angustata". Journal of Applied Phycology. 18 (3–5): 409–412. Bibcode:2006JAPco..18..409B. doi:10.1007/s10811-006-9038-6.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ^a ^b Estelle Delort, Alain Jaquier, Christian Chapuis, Mark Rubin, Christian Starkenmann (2012-11-28). "Volatile Composition of Oyster Leaf (Mertensia maritima (L.) Gray)". Journal of Agricultural and Food Chemistry. 60 (47): 11681–11690. Bibcode:2012JAFC...6011681D. doi:10.1021/jf303395q. PMID 23140514.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[MSDS-1] "(Z)-3-Nonenal". 2023-08-27. {{cite web}}: Missing or empty |url= (help)

[Tadahiko_Kajiwara-2] Tadahiko Kajiwara, Yoshinobu Odake, Akikazu Hatanaka (1975). "Synthesis of 3Z-Nonenal and 3Z,6Z-Nonadienal". Agricultural and Biological Chemistry. 39 (8): 1617–1621. doi:10.1080/00021369.1975.10861815.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[:1-3] S. F. Vaughn, H. W. Gardner (1993-10-01). "Lipoxygenase-derived aldehydes inhibit fungi pathogenic on soybean". Journal of Chemical Ecology. 19 (10): 2337–2345. Bibcode:1993JCEco..19.2337V. doi:10.1007/BF00979668. PMID 24248580.

[:2-4] Nathalie Tijet, Claus Schneider, Bernard L. Muller, Alan R. Brash (2001-02-01). "Biogenesis of Volatile Aldehydes from Fatty Acid Hydroperoxides: Molecular Cloning of a Hydroperoxide Lyase (CYP74C) with Specificity for both the 9- and 13-Hydroperoxides of Linoleic and Linolenic Acids". Archives of Biochemistry and Biophysics. 386 (2): 281–289. doi:10.1006/abbi.2000.2218. PMID 11368353.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[5] Akikazu Hatanaka, Tadahiko Kajiwara, Takahiro Harada (1975-12-01). "Biosynthetic pathway of cucumber alcohol: Trans-2,cis-6-nonadienol via cis-3,cis-6-nonadienal". Phytochemistry. 14 (12): 2589–2592. Bibcode:1975PChem..14.2589H. doi:10.1016/0031-9422(75)85230-7.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[:3-6] David R. Phillips, Jennifer A. Matthew, John Reynolds, G.Roger Fenwick (1979-01-01). "Partial purification and properties of a cis-3: trans-2-enal isomerase from cucumber fruit". Phytochemistry. 18 (3): 401–404. Bibcode:1979PChem..18..401P. doi:10.1016/S0031-9422(00)81874-9.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[:4-7] Kangsadan Boonprab, Kenji Matsui, Yoshihiko Akakabe, Norishige Yotsukura, Tadahiko Kajiwara (2003-07-01). "Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3- and (E)-2-nonenal formation in Laminaria angustata". Phytochemistry. 63 (6): 669–678. Bibcode:2003PChem..63..669B. doi:10.1016/S0031-9422(03)00026-8. PMID 12842139.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[:5-8] Kangsadan Boonprab, Kenji Matsui, Yoshihiko Akakabe, Miyuki Yoshida, Norishige Yotsukura, Anong Chirapart, Tadahiko Kajiwara (2006-11-27). "Formation of Aldehyde Flavor (n-hexanal, 3Z-nonenal and 2E-nonenal) in the Brown Alga, Laminaria Angustata". Journal of Applied Phycology. 18 (3–5): 409–412. Bibcode:2006JAPco..18..409B. doi:10.1007/s10811-006-9038-6.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[:0-9] Estelle Delort, Alain Jaquier, Christian Chapuis, Mark Rubin, Christian Starkenmann (2012-11-28). "Volatile Composition of Oyster Leaf (Mertensia maritima (L.) Gray)". Journal of Agricultural and Food Chemistry. 60 (47): 11681–11690. Bibcode:2012JAFC...6011681D. doi:10.1021/jf303395q. PMID 23140514.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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