Hexyl cinnamaldehyde

Hexyl cinnamaldehyde (hexyl cinnamal) is a common additive in the perfume and cosmetic industry as aroma substance. It is found naturally in the essential oil of chamomile.

Hexyl cinnamaldehyde
Names
IUPAC name
2-Benzylideneoctanal
Other names
α-Hexyl cinnamaldehyde; 2-(Phenylmethylidene)octanal; alpha-hexyl cinnamaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.713
UNII
Properties
C15H20O
Molar mass 216.324 g·mol−1
Density 0.95 g/mL
Boiling point 308 °C (586 °F; 581 K)
2.75 mg/L[1]
Related compounds
Related alkyl aldehydes
Isobutyraldehyde
Lilial
2-Methylundecanal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis

Hexyl cinnamaldehyde is typically produced via a crossed-aldol condensation reaction between octanal and benzaldehyde.

Properties

It is a pale yellow to yellow clear liquid to solid, which is nearly insoluble in water but soluble in oils. The commercial material often contains low levels of 2,6-di-tert-butyl-4-methoxyphenol as a stabilizer.

Safety

Hexyl cinnamaldehyde is known to cause contact allergies in some individuals but the rate of incidence is low, with patch tests indicating ~0.1% of people to be susceptible.[2][3]

References

  1. alpha-hexyl cinnamaldehyde, thegoodscentscompany.com
  2. Schnuch, Axel; Uter, Wolfgang; Geier, Johannes; Lessmann, Holger; Frosch, Peter J (2007). "Sensitization to 26 fragrances to be labelled according to current European regulation". Contact Dermatitis. 57 (1): 1–10. doi:10.1111/j.1600-0536.2007.01088.x. ISSN 0105-1873. PMID 17577350.
  3. Frosch, Peter J.; Pirker, Claudia; Rastogi, Suresh C.; Andersen, Klaus E.; Bruze, Magnus; Svedman, Cecilia; Goossens, An; White, Ian R.; Uter, Wolfgang; Arnau, Elena Gimenez; Lepoittevin, Jean-Pierre; Menne, Torkil; Johansen, Jeanne Duus (2005). "Patch testing with a new fragrance mix detects additional patients sensitive to perfumes and missed by the current fragrance mix". Contact Dermatitis. 52 (4): 207–215. doi:10.1111/j.0105-1873.2005.00565.x. ISSN 0105-1873.
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