4-Anisaldehyde, or ''p''-Anisaldehyde, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula CH₃OC₆H₄CHO. The molecule consists of a benzene ring with an formyl and a

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position as ...

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 Methoxytoluenes (methylanisoles or cresyl methyl ethers) are a group of three isomeric organic compounds with the formula CH3OC6H4CH3. They consist of a disubstituted benzene ring with methoxy group and one methyl group. All three are colorless ...

(''p''-cresyl methyl ether) using

manganese dioxide Manganese dioxide is the inorganic compound with the formula . This blackish or brown solid occurs naturally as the mineral pyrolusite, which is the main ore of manganese and a component of manganese nodules. The principal use for is for dry-cell ...

to convert a

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

to the

aldehyde group In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group ...

. It can also be produced by oxidation of

anethole Anethole (also known as anise camphor) is an organic compound that is widely used as a flavoring substance. It is a derivative of phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils. It is in the class of p ...

, a related fragrance that is found in some alcoholic beverages, by oxidative cleavage of an

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

Uses

Being structurally related to

vanillin Vanillin is an organic compound with the molecular formula . It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used ...

, 4-anisaldehyde is a widely used in the fragrance and flavor industry. 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. 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.

References

{{DEFAULTSORT:Anisaldehyde, 4- Flavors Benzaldehydes