Α-Hexylcinnamaldehyde

α-Hexylcinnamaldehyde (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. It is a pale yellow to yellow 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. It is a derivative of cinnamaldehyde with a hexyl substituent.

α-Hexylcinnamaldehyde

Names
IUPAC name 2-Benzylideneoctanal
Other names Hexyl cinnamal 2-(Phenylmethylidene)octanal
Identifiers
CAS Number	101-86-0 Y 165184-98-5 (2E) Y 364364-06-7 (2Z) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:55365 Y
ChemSpider	1267362 Y
ECHA InfoCard	100.002.713
PubChem CID	1550884
UNII	7X6O37OK2I Y E9947QRR9O (2E) Y H2WS93I0OP (2Z) Y
CompTox Dashboard (EPA)	DTXSID4026684
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	216.324 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). N verify (what is YN ?) Infobox references

One supplier reported that its hexyl cinnamaldehyde (or "hexyl cinnamic aldehyde") contained at least 90% trans isomer.^[2]

Synthesis

Hexyl cinnamaldehyde is typically produced via crossed-aldol condensation of octanal and benzaldehyde.

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.^[3][4]