Α-Hexylcinnamaldehyde
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{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443858673
| Name = α-Hexylcinnamaldehyde
| ImageFile = Hexyl cinnamaldehyde.png
| IUPACName = 2-Benzylideneoctanal
| OtherNames = Hexyl cinnamal
2-(Phenylmethylidene)octanal
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1267362
| 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+
| InChIKey = GUUHFMWKWLOQMM-NTCAYCPXBH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GUUHFMWKWLOQMM-NTCAYCPXSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 101-86-0
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 165184-98-5
| CASNo1_Comment = (2E)
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 364364-06-7
| CASNo2_Comment = (2Z)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7X6O37OK2I
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = E9947QRR9O
| UNII1_Comment = (2E)
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = H2WS93I0OP
| UNII2_Comment = (2Z)
| PubChem = 1550884
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 55365
| SMILES = O=C\C(=C\c1ccccc1)CCCCCC
}}
|Section2={{Chembox Properties
| C=15 | H=20 | O=1
| Appearance =
| Density = 0.95 g/mL
| MeltingPt =
| BoilingPtC = 308
| Solubility = 2.75 mg/L[http://www.thegoodscentscompany.com/data/rw1005971.html alpha-hexyl cinnamaldehyde], thegoodscentscompany.com
}}
|Section3={{Chembox Related
| OtherFunction_label = alkyl aldehydes
| OtherFunction = Isobutyraldehyde
Lilial
2-Methylundecanal
}}
}}
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.
One supplier reported that its hexyl cinnamaldehyde (or "hexyl cinnamic aldehyde") contained at least 90% trans isomer.{{cite web |title=Hexyl Cinnamic Aldehyde |url=http://www.iff.com/Ingredients.nsf/0/8A7C28F4050F32428025699300390223 |archive-url=https://web.archive.org/web/20100513221012/http://www.iff.com/Ingredients.nsf/0/8A7C28F4050F32428025699300390223 |archive-date=2010-05-13 |publisher=International Flavors & Fragrances Inc. |date=2010}}
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.{{cite journal|last1=Schnuch|first1=Axel|last2=Uter|first2=Wolfgang|last3=Geier|first3=Johannes|last4=Lessmann|first4=Holger|last5=Frosch|first5=Peter J|title=Sensitization to 26 fragrances to be labelled according to current European regulation.|journal=Contact Dermatitis|volume=57|issue=1|year=2007|pages=1–10|issn=0105-1873|doi=10.1111/j.1600-0536.2007.01088.x|pmid=17577350|doi-access=free}}{{cite journal|last1=Frosch|first1=Peter J.|last2=Pirker|first2=Claudia|last3=Rastogi|first3=Suresh C.|last4=Andersen|first4=Klaus E.|last5=Bruze|first5=Magnus|last6=Svedman|first6=Cecilia|last7=Goossens|first7=An|last8=White|first8=Ian R.|last9=Uter|first9=Wolfgang|last10=Arnau|first10=Elena Gimenez|last11=Lepoittevin|first11=Jean-Pierre|last12=Menne|first12=Torkil|last13=Johansen|first13=Jeanne Duus|title=Patch testing with a new fragrance mix detects additional patients sensitive to perfumes and missed by the current fragrance mix|journal=Contact Dermatitis|volume=52|issue=4|year=2005|pages=207–215|issn=0105-1873|doi=10.1111/j.0105-1873.2005.00565.x|pmid=15859993 |s2cid=20219911 }}