4-Anisaldehyde

4-Anisaldehyde^[1]

Names
IUPAC name 4-Methoxybenzaldehyde
Other names p-Anisaldehyde para-Anisaldehyde Anisic aldehyde Anise aldehyde
Identifiers
CAS Number	123-11-5 Y
3D model (JSmol)	Interactive image
ChemSpider	28984 Y 21105937
ECHA InfoCard	100.004.185
PubChem CID	31244
UNII	9PA5V6656V Y
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	136.15 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
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 YN ?)
Infobox references

4-Anisaldehyde (p-anisaldehyde, anisic aldehyde, or anise aldehyde) is an organic compound that is commonly encountered in fragrances, both synthetic and natural. The compound consists of a benzene ring with an aldehyde and a methoxy group. It is a clear liquid with a strong aroma. Two related isomers, ortho-anisaldehyde and meta-anisaldehyde, are also known but less commonly encountered. It provides sweet, floral and strong aniseed odor.

Production

Anisaldehyde is prepared commercially by oxidation of methoxytoluene (p-cresyl methyl ether) using manganese dioxide. It can also be produced by oxidation of anethole, a related fragrance that is found in some alcoholic beverages.^[3]

Uses

Being structurally related to vanillin, anisaldehyde is a widely used in the fragrance and flavor industry.^[3] Anisaldehyde is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery. ortho-Anisaldehyde 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.

Drugs

Drugs made from 4-Anisaldehyde include:

1. PMA & PMMA
2. 4-Hydroxyamfetamine
3. Dasantafil
4. Tomoxiprole
5. Benzestrol
6. Meobentine (via p-methoxybenzylamine made via reduction of the oxime).
7. Ambucetamide
8. Metostilenol

References