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 ; 165184-98-5 (2E) ; 364364-06-7 (2Z) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:55365 ;
ChemSpider	1267362 ;
ECHA InfoCard	100.002.713
PubChem CID	1550884;
UNII	7X6O37OK2I ; E9947QRR9O (2E) ; H2WS93I0OP (2Z) ;
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+ Key: GUUHFMWKWLOQMM-NTCAYCPXSA-N ; 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).
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	Infobox references

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.

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. PMID 17577350.
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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[goodscents-1] -hexyl cinnamaldehyde, thegoodscentscompany.com

[SchnuchUter2007-2] 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.

[FroschPirker2005-3] 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.