Hexyl cinnamaldehyde

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Hexyl cinnamaldehyde
Hexyl cinnamaldehyde.png
Names
IUPAC name
2-Benzylideneoctanal
Other names
α-Hexyl cinnamaldehyde; 2-(Phenylmethylidene)octanal; alpha-hexyl cinnamaldehyde
Identifiers
101-86-0 YesY
165184-98-5 (2E) YesY
364364-06-7 (2Z) YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:55365 YesY
ChemSpider 1267362 YesY
ECHA InfoCard 100.002.713
PubChem 1550884
UNII 7X6O37OK2I YesY
E9947QRR9O (2E) YesY
H2WS93I0OP (2Z) YesY
Properties
C15H20O
Molar mass 216.32 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

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

Synthesis[edit]

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

Properties[edit]

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[edit]

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[edit]

  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. 
  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.