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{{lowercasetitle}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 443857463 |
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| Watchedfields = changed |
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| verifiedrevid = 443858673 |
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| Name = α-Hexylcinnamaldehyde |
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| ImageFile = Hexyl cinnamaldehyde.png |
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| ImageFile = Hexyl cinnamaldehyde.png |
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| IUPACName = 2-Benzylideneoctanal |
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| ImageSize = |
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| OtherNames = Hexyl cinnamal<br>2-(Phenylmethylidene)octanal |
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| IUPACName = (''2E'')-2-benzylideneoctanal |
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|Section1={{Chembox Identifiers |
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| OtherNames = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 1267362 |
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| ChemSpiderID = 1267362 |
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| 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+ |
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| 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+ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GUUHFMWKWLOQMM-NTCAYCPXSA-N |
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| StdInChIKey = GUUHFMWKWLOQMM-NTCAYCPXSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 101-86-0 |
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| CASNo = 101-86-0 |
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| PubChem = 1550884 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 165184-98-5 |
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| CASNo1_Comment = (2E) |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2 = 364364-06-7 |
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| CASNo2_Comment = (2Z) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 7X6O37OK2I |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = E9947QRR9O |
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| UNII1_Comment = (2E) |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = H2WS93I0OP |
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| UNII2_Comment = (2Z) |
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| PubChem = 1550884 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 55365 |
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| ChEBI = 55365 |
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| SMILES = O=C\C(=C\c1ccccc1)CCCCCC |
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| SMILES = O=C\C(=C\c1ccccc1)CCCCCC |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=15|H=20|O=1 |
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| C=15 | H=20 | O=1 |
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| Appearance = |
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| MolarMass = 216.319 g/mol |
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| Density = 0.95 g/mL |
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| Appearance = |
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| Density = |
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| MeltingPt = |
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| MeltingPt = |
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| BoilingPtC = 308 |
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| Solubility = 2.75 mg/L<ref name=goodscents>, thegoodscentscompany.com</ref> |
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| BoilingPt = |
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| Solubility = Insoluble |
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| Section3 = {{Chembox Related |
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|Section3={{Chembox Related |
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| Function = alkyl aldehydes |
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| OtherFunction_label = alkyl aldehydes |
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| OtherFunctn = ]<br /> |
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| OtherFunction = ]<br />]<br />] |
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]<br /> |
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'''Hexyl ]''', or '''hexyl cinnamal''', is a common additive in perfume and cosmetic industry as aroma substance. It is found naturally in the ] of ]. |
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'''α-Hexylcinnamaldehyde''' ('''hexyl cinnamal''') is a common additive in the ] and ] as ]. It is found naturally in the ] of ]. 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 ] with a ] substituent. |
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One supplier reported that its hexyl cinnamaldehyde (or "hexyl cinnamic aldehyde") contained at least 90% ] isomer.<ref>{{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}}</ref> |
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==Properties== |
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It is a pale yellow to yellow clear liquid to solid, which is insoluble in water but soluble in oils. |
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==Toxicity== |
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==Synthesis== |
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Hexyl cinnamaldehyde is a class B allergen according to ] classification. It is also an irritant in concentrations higher than recommended. |
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Hexyl cinnamaldehyde is typically produced via crossed-] of ] and ]. |
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==Safety== |
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Hexyl cinnamaldehyde is known to cause contact allergies in some individuals but the rate of incidence is low, with ]s indicating ~0.1% of people to be susceptible.<ref name="SchnuchUter2007">{{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}}</ref><ref name="FroschPirker2005">{{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 }}</ref> |
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==References== |
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==References== |
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{{Reflist}} |
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* (data sheet, 3-D Java applet showing the molecule.) |
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