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2-Nonenal

From Wikipedia, the free encyclopedia
2-Nonenal
Skeletal formula of 2-nonenal
Ball-and-stick model of the 2-nonenal molecule
Names
Preferred IUPAC name
Non-2-enal
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.017.784 Edit this at Wikidata
EC Number
  • 242-609-6 (trans)
  • 219-562-5
UNII
  • InChI=1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7+ checkY
    Key: BSAIUMLZVGUGKX-BQYQJAHWSA-N checkY
  • InChI=1/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7+
    Key: BSAIUMLZVGUGKX-BQYQJAHWBS
  • O=C/C=C/CCCCCC (E)
    O=C/C=\/CCCCCC (Z)
    O=CC=CCCCCCC (unspecified)
Properties
C9H16O
Molar mass 140.226 g·mol−1
Appearance Colorless liquid
Boiling point 188.00 to 190.00 °C (370.40 to 374.00 °F; 461.15 to 463.15 K) at 760.00 mmHg
Hazards[1]
GHS labelling:
GHS07: Exclamation mark
Warning
H315
P264, P280, P302+P352, P321, P332+P313, P362
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 79 °C (174 °F; 352 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

2-Nonenal is an unsaturated aldehyde. The colorless liquid is an important aroma component of aged beer[2] and buckwheat, and is insoluble in water.[3]

2-Nonenal reacts with the Wittig reagent methylenetriphenylphosphorane to give hexyl-1,3-butadiene.[4]

Odor characteristics

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The odour of the mixed isomers is perceived as "fatty, green, waxy, cucumber, melon".[5] The odour of the (Z)-isomer is "orris, fatty, waxy, cucumber"[6] whilst that of the (E)-isomer is "fatty, green, cucumber, aldehydic".[7] Its odor has been associated with human body odor alterations during aging.[8]

See also

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References

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  1. ↑ "2-Nonenal". pubchem.ncbi.nlm.nih.gov.
  2. ↑ Santos, J. R.; Carneiro, J. R.; Guido, L. F.; Almeida, P. J.; Rodrigues, J. A.; Barros, A. A. (2008). "Determination of E-2-nonenal by high-performance liquid chromatography with UV detection - Assay for the evaluation of beer ageing". Journal of Chromatography A. 985 (1–2): 395–402. doi:10.1016/S0021-9673(02)01396-1. PMID 12580508.
  3. ↑ Janeš, D.; Kantar, D.; Kreft, S.; Prosen, H. (2008). "Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS". Food Chemistry. 112 (1): 120–4. doi:10.1016/j.foodchem.2008.05.048.
  4. ↑ Ely, Robert J.; Morken, James P. (2011). "Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes". Organic Syntheses. 88: 342. doi:10.15227/orgsyn.088.0342.
  5. ↑ "2-nonenal". scentsandflavors.com. Retrieved 2 August 2026.
  6. ↑ "(Z)-2-nonenal". scentsandflavors.com. Retrieved 2 August 2026.
  7. ↑ "(E)-2-nonenal". scentsandflavors.com. Retrieved 2 August 2026.
  8. ↑ Haze, S.; Gozu, Y.; Nakamura, S.; Kohno, Y.; Sawano, K.; Ohta, H.; Yamazaki, K. (2001). "2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging". Journal of Investigative Dermatology. 116 (4): 520–4. doi:10.1046/j.0022-202x.2001.01287.x. PMID 11286617.

Further reading

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