4-Anisaldehyde

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-Anisaldehyde; p-Anisaldehyde; para-Anisaldehyde; Anisic aldehyde; Anise aldehyde;
Identifiers
CAS Number	123-11-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28235;
ChEMBL	ChEMBL161598 ;
ChemSpider	28984 ; 21105937;
ECHA InfoCard	100.004.185
EC Number	204-602-6;
KEGG	C10761;
PubChem CID	31244;
UNII	9PA5V6656V ;
CompTox Dashboard (EPA)	DTXSID2026997 ;
	InChI InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3 Key: ZRSNZINYAWTAHE-UHFFFAOYSA-N; InChI=1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3 Key: ZRSNZINYAWTAHE-UHFFFAOYAA;
	SMILES COc1ccc(C=O)cc1;
Properties
Chemical formula	C8H8O2
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). verify (what is ?) Infobox references

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.

Production

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]

Uses

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 breakage

Anisaldehyde in combination with copper (II) can induce single- and double-strand breaks in double stranded DNA.[5]

References

Merck Index, 11th Edition, 693
"p-Anisaldehyde". Sigma-Aldrich.
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.
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.

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[1] Merck Index, 11th Edition, 693

[Aldrich-2] "p-Anisaldehyde". Sigma-Aldrich.

[Ullmann-3] 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.

[4] Stains for Developing TLC Plates

[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.