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.
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| Names | |
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| IUPAC name
2-Benzylideneoctanal
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| Other names
Hexyl cinnamal
2-(Phenylmethylidene)octanal | |
| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.002.713 |
PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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| 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
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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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One supplier reported that its hexyl cinnamaldehyde (or "hexyl cinnamic aldehyde") contained at least 90% trans isomer.[2]
Synthesis
editHexyl cinnamaldehyde is typically produced via crossed-aldol condensation of octanal and benzaldehyde.
Safety
editHexyl 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]
References
edit- ^ alpha-hexyl cinnamaldehyde, thegoodscentscompany.com
- ^ "Hexyl Cinnamic Aldehyde". International Flavors & Fragrances Inc. 2010. Archived from the original on 2010-05-13.
- ^ 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. PMID 15859993. S2CID 20219911.