4-Anisaldehyde, or p-Anisaldehyde, is an organic compound with the formula CH3OC6H4CHO. The molecule consists of a benzene ring with a formyl and a methoxy 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, ortho-anisaldehyde and meta-anisaldehyde. They are less commonly encountered.
Anisaldehyde is prepared commercially by oxidation of 4-methoxytoluene (p-cresyl methyl ether) using manganese dioxide to convert a methyl group to the aldehyde group. It can also be produced by oxidation of anethole, a related fragrance that is found in some alcoholic beverages, by oxidative cleavage of an alkene.[3]
Usesedit
Being structurally related to vanillin, 4-anisaldehyde is a widely used in the fragrance and flavor industry.[3] It is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery. The related ortho isomer has a scent of licorice.
A solution of para-anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography.[4] Different chemical compounds on the plate can give different colors, allowing easy distinction.
DNA breakageedit
Anisaldehyde in combination with copper (II) can induce single- and double-strand breaks in double stranded DNA.[5]
Referencesedit
^Budavari, Susan, ed. (1994). The Merck index: an encyclopedia of chemicals, drugs, and biologicals (11. ed., 4. print ed.). Rahway, NJ: Merck. p. 693. ISBN978-0-911910-28-5.
^Becker, T. W.; Krieger, G.; Witte, I. (1996). "DNA Single and Double Strand Breaks Induced by Aliphatic and Aromatic Aldehydes in Combination with Copper(II)". Free Radical Research. 24 (5): 325–332. doi:10.3109/10715769609088030. PMID 8733936.
May 02, 2024
anisaldehyde, anisaldehyde, organic, compound, with, formula, ch3oc6h4cho, molecule, consists, benzene, ring, with, formyl, methoxy, group, colorless, liquid, with, strong, aroma, provides, sweet, floral, strong, aniseed, odor, isomers, anisaldehyde, known, or. 4 Anisaldehyde or p Anisaldehyde is an organic compound with the formula CH3OC6H4CHO The molecule consists of a benzene ring with a formyl and a methoxy 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 ortho anisaldehyde and meta anisaldehyde They are less commonly encountered 4 Anisaldehyde 1 Ball and stick model of the anisaldehyde molecule Space filling model of the anisaldehyde molecule Names Preferred IUPAC name 4 Methoxybenzaldehyde Systematic IUPAC name 4 Methoxybenzenecarbaldehyde Other names 4 Anisaldehydep Anisaldehydepara AnisaldehydeAnisic aldehydeAnise aldehyde Identifiers CAS Number 123 11 5 Y 3D model JSmol Interactive image ChEBI CHEBI 28235 ChEMBL ChEMBL161598 N ChemSpider 28984 Y21105937 ECHA InfoCard 100 004 185 EC Number 204 602 6 KEGG C10761 PubChem CID 31244 UNII 9PA5V6656V Y CompTox Dashboard EPA DTXSID2026997 InChI InChI 1S C8H8O2 c1 10 8 4 2 7 6 9 3 5 8 h2 6H 1H3Key ZRSNZINYAWTAHE UHFFFAOYSA NInChI 1 C8H8O2 c1 10 8 4 2 7 6 9 3 5 8 h2 6H 1H3Key ZRSNZINYAWTAHE UHFFFAOYAA SMILES COc1ccc C O cc1 Properties Chemical formula C 8H 8O 2 Molar mass 136 150 g mol 1 Density 1 119 g cm3 2 Melting point 1 C 30 F 272 K 2 Boiling point 248 C 478 F 521 K 2 Hazards GHS labelling Pictograms Signal word Warning Hazard statements H302 Precautionary statements P264 P270 P301 P312 P330 P501 Flash point 108 C 226 F 381 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Production 2 Uses 3 DNA breakage 4 ReferencesProduction editAnisaldehyde is prepared commercially by oxidation of 4 methoxytoluene p cresyl methyl ether using manganese dioxide to convert a methyl group to the aldehyde group It can also be produced by oxidation of anethole a related fragrance that is found in some alcoholic beverages by oxidative cleavage of an alkene 3 Uses editBeing structurally related to vanillin 4 anisaldehyde is a widely used in the fragrance and flavor industry 3 It is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery The related ortho isomer has a scent of licorice A solution of para anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography 4 Different chemical compounds on the plate can give different colors allowing easy distinction DNA breakage editAnisaldehyde in combination with copper II can induce single and double strand breaks in double stranded DNA 5 References edit Budavari Susan ed 1994 The Merck index an encyclopedia of chemicals drugs and biologicals 11 ed 4 print ed Rahway NJ Merck p 693 ISBN 978 0 911910 28 5 a b c p Anisaldehyde Sigma Aldrich a b Karl Georg Fahlbusch Franz Josef Hammerschmidt Johannes Panten Wilhelm Pickenhagen Dietmar Schatkowski Kurt Bauer Dorothea Garbe Horst Surburg 2003 Flavors and Fragrances Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a11 141 ISBN 978 3527306732 Stains for Developing TLC Plates Becker T W Krieger G Witte I 1996 DNA Single and Double Strand Breaks Induced by Aliphatic and Aromatic Aldehydes in Combination with Copper II Free Radical Research 24 5 325 332 doi 10 3109 10715769609088030 PMID 8733936 Retrieved from https en wikipedia org w index php title 4 Anisaldehyde amp oldid 1184991086, wikipedia, wiki, book, books, library,
