2-Nonenal

Last updated
2-Nonenal
2-Nonenal.png
2-Nonenal-3D-balls.png
Names
Preferred IUPAC name
Non-2-enal
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.017.784 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 242-609-6(trans)
  • 219-562-5
PubChem CID
UNII
  • InChI=1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7+ Yes check.svgY
    Key: BSAIUMLZVGUGKX-BQYQJAHWSA-N Yes check.svgY
  • 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
Properties
C9H16O
Molar mass 140.226 g·mol−1
AppearanceColorless 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:
GHS-pictogram-exclam.svg
Warning
H315
P264, P280, P302+P352, P321, P332+P313, P362
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

Odor characteristics

The odor of this substance is perceived as orris, fat and cucumber. [4] Its odor has been associated with human body odor alterations during aging. [5]

Related Research Articles

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Buckwheat, or common buckwheat, is a flowering plant in the knotweed family Polygonaceae cultivated for its grain-like seeds and as a cover crop. The name "buckwheat" is used for several other species, such as Fagopyrum tataricum, a domesticated food plant raised in Asia.

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<span class="mw-page-title-main">Aroma compound</span> Chemical compound that has a smell or odor

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<span class="mw-page-title-main">4-Hydroxynonenal</span> Chemical compound

4-Hydroxynonenal, or 4-hydroxy-2-nonenal or 4-HNE or HNE,, is an α,β-unsaturated hydroxyalkenal that is produced by lipid peroxidation in cells. 4-HNE is the primary α,β-unsaturated hydroxyalkenal formed in this process. It is a colorless oil. It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events. 4-HNE has been hypothesized to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion.

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<span class="mw-page-title-main">Furaneol</span> Chemical compound

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(E,E)-2,4-Decadienal is an aromatic substance found in butter, cooked beef, fish, potato chips, roasted peanut, buckwheat and wheat bread crumb. In an isolated state, it smells of deep fat flavor, characteristic of chicken aroma (at 10ppm). At lower concentration, it has the odor of citrus, orange or grapefruit. It might be carcinogenic. It has been used as aroma in the EU, but use restrictions apply until the required data have been submitted.

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<span class="mw-page-title-main">3-Deoxyglucosone</span> Chemical compound

3-Deoxyglucosone (3DG) is a sugar that is notable because it is a marker for diabetes. 3DG reacts with protein to form advanced glycation end-products (AGEs), which contribute to diseases such as the vascular complications of diabetes, atherosclerosis, hypertension, Alzheimer's disease, inflammation, and aging.

<span class="mw-page-title-main">Miquelianin</span> Chemical compound

Miquelianin is a flavonol glucuronide, a type of phenolic compound present in wine, in species of St John's wort, like Hypericum hirsutum, in Nelumbo nucifera or in green beans.

<span class="mw-page-title-main">Dimethyl trisulfide</span> Chemical compound

Dimethyl trisulfide (DMTS) is an organic chemical compound and the simplest organic trisulfide, with the chemical formula CH3SSSCH3. It is a flammable liquid with a foul odor, which is detectable at levels as low as 1 part per trillion.

<span class="mw-page-title-main">6-Nonenal</span> Chemical compound

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. The trans-isomer is listed as an off-flavor aroma of milk foams, and thought to be a possible polypropylene odorant.

References

  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. "2-nonenal CAS 60784-31-8". Flavornet.
  5. 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