Hexyl cinnamaldehyde

Hexyl cinnamaldehyde
Names

IUPAC name 2-Benzylideneoctanal
Other names α-Hexyl cinnamaldehyde; 2-(Phenylmethylidene)octanal; alpha-hexyl cinnamaldehyde
Identifiers
CAS Number	101-86-0^Y 165184-98-5 (2E)^Y 364364-06-7 (2Z)^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:55365^Y
ChemSpider	1267362^Y
ECHA InfoCard	100.002.713
PubChem	1550884
UNII	7X6O37OK2I^Y E9947QRR9O (2E)^Y H2WS93I0OP (2Z)^Y
InChI InChI=1S/C15H20O/c1-2-3-4-6-11-15(13-16)12-14-9-7-5-8-10-14/h5,7-10,12-13H,2-4,6,11H2,1H3/b15-12+^Y Key: GUUHFMWKWLOQMM-NTCAYCPXSA-N^Y InChI=1/C15H20O/c1-2-3-4-6-11-15(13-16)12-14-9-7-5-8-10-14/h5,7-10,12-13H,2-4,6,11H2,1H3/b15-12+ Key: GUUHFMWKWLOQMM-NTCAYCPXBH
SMILES O=C\C(=C\c1ccccc1)CCCCCC
Properties
Chemical formula	C₁₅H₂₀O
Molar mass	216.32 g·mol⁻¹
Density	0.95 g/mL
Boiling point	308 °C (586 °F; 581 K)
Solubility in water	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).
Y verify (what is ^YN ?)
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

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

↑ alpha-hexyl cinnamaldehyde, thegoodscentscompany.com
↑ 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.
↑ 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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