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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 322330683 |
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| verifiedrevid = 387721524 |
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| Reference=<ref>''Merck Index'', 11th Edition, '''693'''</ref> |
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| 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> |
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| Name = Anisaldehyde |
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| ImageFile = Anisaldehyde.svg |
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| Name = 4-Anisaldehyde |
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| ImageFile1 = Anisaldehyde-2D-structure.svg |
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| ImageSize = 100px |
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| ImageName1 = Structural formula of anisaldehyde |
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| ImageName = Anisaldehyde |
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| ImageFileL2 = Anisaldehyde-from-xtal-Mercury-3D-bs.png |
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| IUPACName = 4-Methoxybenzaldehyde |
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| ImageNameL2 = Ball-and-stick model of the anisaldehyde molecule |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID = 28984 |
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| ImageSizeL2 = 200px |
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| ImageFileR2 = Anisaldehyde-from-xtal-Mercury-3D-sf.png |
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| ImageNameR2 = Space-filling model of the anisaldehyde molecule |
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| ImageSizeR2 = 200px |
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| PIN = 4-Methoxybenzaldehyde |
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| SystematicName = 4-Methoxybenzenecarbaldehyde |
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| OtherNames = {{bulletedlist|4-Anisaldehyde|''p''-Anisaldehyde|''para''-Anisaldehyde|Anisic aldehyde | Anise aldehyde}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 28984 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9PA5V6656V |
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| UNII = 9PA5V6656V |
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| CASNo_Ref = {{cascite}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 123-11-5 |
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| CASNo = 123-11-5 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| PubChem = 31244 |
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| ChEMBL = 161598 |
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| SMILES = O=CC1=CC=C(OC)C=C1 |
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| PubChem = 31244 |
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| ChemSpiderID1 = 21105937 |
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| EC_number = 204-602-6 |
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| ChEBI = 28235 |
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| KEGG = C10761 |
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| 3DMet = |
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| SMILES = COc1ccc(C=O)cc1 |
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| InChI = 1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3 |
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| InChIKey = ZRSNZINYAWTAHE-UHFFFAOYAA |
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| StdInChI = 1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3 |
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| StdInChIKey = ZRSNZINYAWTAHE-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8|H=8|O=2 |
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| Formula = C<sub>8</sub>H<sub>8</sub>O<sub>2</sub> |
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| 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> |
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| MolarMass = 136.15 g/mol |
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| MeltingPtC = -1 |
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| Density = 1.119 g/cm³ at 15 °C |
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| MeltingPt_ref = <ref name=Aldrich/> |
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| MeltingPt = 0 °C |
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| BoilingPt = 248 °C |
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| BoilingPtC = 248 |
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| BoilingPt_ref = <ref name=Aldrich/> |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| FlashPt = 108 °C |
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| FlashPtC = 108 |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|302}} |
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| PPhrases = {{P-phrases|264|270|301+312|330|501}} |
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'''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. |
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'''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. |
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== Production == |
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Anisaldehyde is found in ], from which it gets its name. It is similar in structure to ]. |
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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/> |
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== Uses == |
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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. |
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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. |
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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. |
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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. |
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==DNA breakage== |
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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> |
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== References == |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{DEFAULTSORT:Anisaldehyde, 4-}} |
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