Α-Hexylcinnamaldehyde: Difference between revisions

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			{{lowercasetitle}}
	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~443857463~~
			\| Watchedfields = changed
		⚫	\| verifiedrevid = 443858673
		⚫	\| Name = α-Hexylcinnamaldehyde
	\| ImageFile = Hexyl cinnamaldehyde.png		\| ImageFile = Hexyl cinnamaldehyde.png
			\| IUPACName = 2-Benzylideneoctanal
	\| ImageSize =
			\| OtherNames = Hexyl cinnamal<br>2-(Phenylmethylidene)octanal
	\| IUPACName = (''2E'')-2-benzylideneoctanal
		⚫	\|Section1={{Chembox Identifiers
	\| OtherNames =
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| Section1 = {{Chembox Identifiers
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 1267362		\| 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+		\| 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}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = GUUHFMWKWLOQMM-NTCAYCPXSA-N		\| StdInChIKey = GUUHFMWKWLOQMM-NTCAYCPXSA-N
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 101-86-0		\| CASNo = 101-86-0
⚫	\| PubChem = 1550884
	\| ~~ChEBI_Ref~~ = {{~~ebicite~~\|correct\|~~EBI~~}}		\| 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		\| ChEBI = 55365
	\| SMILES = O=C\C(=C\c1ccccc1)CCCCCC		\| SMILES = O=C\C(=C\c1ccccc1)CCCCCC
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| C=15\|H=20\|O=1		\| C=15 \| H=20 \| O=1
		⚫	\| Appearance =
	\| MolarMass = 216.319 g/mol
			\| Density = 0.95 g/mL
⚫	\| Appearance =
	\| ~~Density~~ =		\| MeltingPt =
	\| ~~MeltingPt~~ =		\| BoilingPtC = 308
		⚫	\| Solubility = 2.75 mg/L<ref name=goodscents>, thegoodscentscompany.com</ref>
	\| BoilingPt =
	\| Solubility = Insoluble
	}}		}}
	\| Section3 = {{Chembox Related		\|Section3={{Chembox Related
	\| ~~Function~~ = alkyl aldehydes		\| OtherFunction_label = alkyl aldehydes
	\| ~~OtherFunctn~~ = ]<br />		\| OtherFunction = ]<br />]<br />]
	]<br />
	]
	}}		}}
	}}		}}

	'''~~Hexyl ]~~'''~~, or~~ '''hexyl cinnamal''', is a common additive in perfume and cosmetic industry as aroma substance. It is found naturally in the ] of ].		'''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.

			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>
	==Properties==
	It is a pale yellow to yellow clear liquid to solid, which is insoluble in water but soluble in oils.

	==~~Toxicity~~==		==Synthesis==
	Hexyl cinnamaldehyde is a ~~class~~ B ~~allergen~~ ~~according~~ to ] ~~classification.~~ ~~It is also an irritant in concentrations higher than recommended~~.		Hexyl cinnamaldehyde is typically produced via crossed-] of ] and ].

			==Safety==
			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>

	==References==		==References==
			{{Reflist}}
	*
	*
⚫	* ~~(data sheet~~, ~~3-D Java applet showing the molecule~~.)

	]		]
	]		]
	]		]

	]
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Latest revision as of 01:44, 26 September 2024

α-Hexylcinnamaldehyde
Names

IUPAC name 2-Benzylideneoctanal
Other names Hexyl cinnamal 2-(Phenylmethylidene)octanal
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
Density	0.95 g/mL
Boiling point	308 °C (586 °F; 581 K)
Solubility in water	2.75 mg/L
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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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.

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.

References

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.

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