Α-Hexylcinnamaldehyde

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| 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

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|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

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|Section3={{Chembox Related

| OtherFunction_label = alkyl aldehydes

| OtherFunction = Isobutyraldehyde
Lilial
2-Methylundecanal

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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 }}

References