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Revision as of 13:15, 27 October 2009 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of chemical identifiers from ChemSpider for the Chem/Drugbox validation project.← Previous edit		Latest revision as of 17:25, 5 January 2025 edit undo2405:201:5003:881b:35bb:7ceb:d774:5f60 (talk) Updated short descriptionTags: Mobile edit Mobile app edit Android app edit App description change
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			{{Short description|Chemical compound}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| Reference=<ref>''Merck Index'', 11th Edition, '''693'''</ref>
			| verifiedrevid = 387721524
⚫	| Name = Anisaldehyde
			| Reference=<ref>{{Cite book |title=The Merck index: an encyclopedia of chemicals, drugs, and biologicals |date=1994 |publisher=Merck |isbn=978-0-911910-28-5 |editor-last=Budavari |editor-first=Susan |edition=11. ed., 4. print |location=Rahway, NJ |pages=693}}</ref>
	| ImageFile = Anisaldehyde.svg
		⚫	| Name = 4-Anisaldehyde
	| ImageSize = 100px
	| ImageName = Anisaldehyde		| ImageFile1 = Anisaldehyde-2D-structure.svg
			| ImageName1 = Structural formula of anisaldehyde
⚫	| IUPACName = 4-Methoxybenzaldehyde
			| ImageFileL2 = Anisaldehyde-from-xtal-Mercury-3D-bs.png
⚫	| Section1 = {{Chembox Identifiers
			| ImageNameL2 = Ball-and-stick model of the anisaldehyde molecule
⚫	| ChemSpiderID = 28984
			| ImageSizeL2 = 200px
			| ImageFileR2 = Anisaldehyde-from-xtal-Mercury-3D-sf.png
			| ImageNameR2 = Space-filling model of the anisaldehyde molecule
			| ImageSizeR2 = 200px
		⚫	| PIN = 4-Methoxybenzaldehyde
			| SystematicName = 4-Methoxybenzenecarbaldehyde
			| OtherNames = {{bulletedlist|4-Anisaldehyde|''p''-Anisaldehyde|''para''-Anisaldehyde|Anisic aldehyde | Anise aldehyde}}
		⚫	|Section1={{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| ChemSpiderID = 28984
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 9PA5V6656V
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 123-11-5		| CASNo = 123-11-5
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫	| PubChem = 31244
			| ChEMBL = 161598
⚫	| SMILES = O=CC1=CC=C(OC)C=C1
		⚫	| PubChem = 31244
			| ChemSpiderID1 = 21105937
			| EC_number = 204-602-6
			| ChEBI = 28235
			| KEGG = C10761
			| 3DMet =
		⚫	| SMILES = COc1ccc(C=O)cc1
			| InChI = 1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
			| InChIKey = ZRSNZINYAWTAHE-UHFFFAOYAA
			| StdInChI = 1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
			| StdInChIKey = ZRSNZINYAWTAHE-UHFFFAOYSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=8|H=8|O=2
	| Formula = C<sub>8</sub>H<sub>8</sub>O<sub>2</sub>
			| Density = 1.119 g/cm<sup>3</sup><ref name="Aldrich">{{Cite web |title=p-Anisaldehyde |url=http://www.sigmaaldrich.com/catalog/product/aldrich/a88107?lang=en |publisher=]}}</ref>
	| MolarMass = 136.15 g/mol
			| MeltingPtC = -1
	| Density = 1.119 g/cm³ at 15 °C
			| MeltingPt_ref = <ref name=Aldrich/>
	| MeltingPt = 0 °C
	| BoilingPt = 248 °C		| BoilingPtC = 248
			| BoilingPt_ref = <ref name=Aldrich/>
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| FlashPt = 108 °C		| FlashPtC = 108
			| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|302}}
			| PPhrases = {{P-phrases|264|270|301+312|330|501}}
	}}		}}
	}}		}}
	'''Anisaldehyde''', or anisic aldehyde, is an ] that consists of a benzene ring substituted with an ] and a ] group. It is a clear colorless liquid with a strong aroma. It comes in 3 varieties, ''ortho'', ''meta'', and ''para'' in which the two functional groups (methoxy and aldehyde) are alpha, beta, and gamma, respectively to each other. The unmodified term ''anisaldehyde'' generally refers to the ''para'' isomer.		'''4-Anisaldehyde''', or '''''p''-Anisaldehyde''', is an ] with the formula CH<sub>3</sub>OC<sub>6</sub>H<sub>4</sub>CHO. The molecule consists of a benzene ring with a ] and a ] group. It is a colorless liquid with a strong aroma. It provides sweet, floral and strong aniseed odor. Two isomers of 4-anisaldehyde are known, ] and ''meta''-anisaldehyde. They are less commonly encountered.
			== Production ==
	Anisaldehyde is found in ], from which it gets its name. It is similar in structure to ].
			Anisaldehyde is prepared commercially by oxidation of 4-] (''p''-cresyl methyl ether) using ] to convert a ] to the ]. It can also be produced by oxidation of ], a related fragrance that is found in some alcoholic beverages, by oxidative cleavage of an ].<ref name=Ullmann/>
			== Uses ==
	Anisaldehyde is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery, particularly ''ortho''-anisaldehyde, which has a scent of licorice.
			Being structurally related to ], 4-anisaldehyde is a widely used in the fragrance and flavor industry.<ref name="Ullmann">{{Ullmann|author1=Karl-Georg Fahlbusch |author2=Franz-Josef Hammerschmidt |author3=Johannes Panten |author4=Wilhelm Pickenhagen |author5=Dietmar Schatkowski |author6=Kurt Bauer |author7=Dorothea Garbe |author8=Horst Surburg |title=Flavors and Fragrances|year=2003|doi=10.1002/14356007.a11_141}}</ref> It is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery. The related ] has a scent of licorice.
	A solution of ''para''-anisaldehyde in acid and ethanol is frequently used to stain ] plates. It is a particularly useful stain because different spots on the plate can be stained different colors allowing easy distinction.		A solution of ''para''-anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography.<ref></ref> Different chemical compounds on the plate can give different colors, allowing easy distinction.
			==DNA breakage==
			Anisaldehyde in combination with copper (II) can induce single- and double-strand breaks in double stranded ].<ref>{{Cite journal |last=Becker |first=T. W. |last2=Krieger |first2=G. |last3=Witte |first3=I. |year=1996 |title=DNA Single and Double Strand Breaks Induced by Aliphatic and Aromatic Aldehydes in Combination with Copper(II) |journal=Free Radical Research |volume=24 |issue=5 |pages=325–332 |doi=10.3109/10715769609088030 |pmid=8733936}}</ref>
	== References ==		== References ==
	{{reflist}}		{{reflist}}
			{{DEFAULTSORT:Anisaldehyde, 4-}}
	]		]
	]		]
	]
	]
	]
	]
	]