6-Nonenal

Chemical compound From Wikipedia, the free encyclopedia

6-Nonenal is an organic compound with the formula C2H5CH=CH(CH2)4CHO. Other isomeric nonenal compounds are also known to exist naturally, e.g. 2-nonenal. The cis-isomer of 6-nonenal is often listed as the principal component in the aromas of muskmelon fruits.[1] The trans-isomer is listed as an off-flavor aroma of milk foams,[2] and thought to be a possible polypropylene odorant.[3]

Quick facts Names, Identifiers ...
6-Nonenal
cis-6-Nonenal
trans-6-Nonenal
Names
IUPAC names
(Z)-Non-6-enal
(E)-Non-6-enal
Other names
6-Nonenal
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1/C9H16O/c1-2-3-4-5-6-7-8-9-10/h3-4,9H,2,5-8H2,1H3
    Key: RTNPCOBSXBGDMO-UHFFFAOYAV
  • (E): InChI=1/C9H16O/c1-2-3-4-5-6-7-8-9-10/h3-4,9H,2,5-8H2,1H3/b4-3+
    Key: RTNPCOBSXBGDMO-ONEGZZNKBC
  • (Z): InChI=1/C9H16O/c1-2-3-4-5-6-7-8-9-10/h3-4,9H,2,5-8H2,1H3/b4-3-
    Key: RTNPCOBSXBGDMO-ARJAWSKDBN
  • O=CCCCCC=CCC
  • (E): O=CCCCC/C=C/CC
  • (Z): O=CCCCC/C=C\CC
Properties
C9H16O
Molar mass 140.226 g·mol−1
Appearance Colorless liquid
Density 0.841 g/cm3
Boiling point 62 to 63 °C (144 to 145 °F; 335 to 336 K) at 2 mmHg
Solubility in water 0.63 g/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
Flash point 113 °C (235 °F; 386 K)
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

6-Nonenal is thought to be biosynthesized from γ-lineolenic acid catalyzed by a lipoxygenase. The lipoxygenase converts alkene groups into hydroperoxides, which cleave by hydroperoxide lyase into the corresponding cis-aldehydes.[4] Consistent with this mechanism, the odor of muskmelons requires exposure to air. In the ripe, unmodified muskmelon, cis-6-nonenal exists in only low concentration. A steep increase in the concentration of 6-nonenal is noticed when the cells are lysed and exposed to air. This increase is attributed to rapid formation of hydroperoxides. Trans,cis-2,6-nonadienal is a related fragrance that arises via a similar pathway.

Laboratory synthesis

Either geometric isomer of this compound may be prepared by preparing by brominating 5-octene-1-ol, then preparing the appropriate Grignard reagent. Triethyl orthoformate is treated with this Grignard reagent, then hydrolyzed to give 6-nonenal.[5]

See also

References

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