4-Anisaldehyde

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4-Anisaldehyde[1]
Structural formula of anisaldehyde
Ball-and-stick model of the anisaldehyde molecule
Ball-and-stick model of the anisaldehyde molecule
Space-filling 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.185 Edit this at Wikidata
EC Number
  • 204-602-6
KEGG
UNII
  • 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
  • COc1ccc(C=O)cc1
Properties
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:
GHS07: Exclamation mark
Warning
H302
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).
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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

  1. ^ 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.
  2. ^ a b c "p-Anisaldehyde". Sigma-Aldrich.
  3. ^ 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.
  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.
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