o-Anisaldehyde

Description

O-Anisaldehyde (also 2-methoxybenzaldehyde) is found in cassia oil, cinnamon bark, and cinnamon bark oil. It is a clear colorless liquid with a strong aroma.
O-Anisaldehyde is used as a flavor agent in foods including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, Jams, jellies, and milk products. O-Anisaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus and to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.

References

[1] George A. Burdock (2016) Fenraoli’s Handbook of Flavor Ingredients, Sixth Edition.
[2] https://www.alfa.com/en/catalog/A10770/

Description

o-Methoxybenzaldehyde has a faint, sweet, floral odor. It blends well with cassia. It has a spice-like flavor, quite bitter above 30 - 40 ppm. May be prepared from salicylaldehyde and dimethyl sulfate in weak alkaline solution.

Chemical Properties

light yellow to pale brown

Chemical Properties

Colorless to cream amber crystalline powder; sweet powdery hawthorn guaiacol vanilla acetophenone almond aroma.

Occurrence

Reported found in Cassia oil, cinnamon bark, and Cinnamon bark oil (Cinnamomum zeylanicum Blume), Sri Lanka (0.09–0.15%)

Uses

2-Methoxybenzaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus. It has also been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.

Uses

2-Methoxybenzaldehyde has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.

Uses

Intermediate.

Definition

ChEBI: 2-Methoxybenzaldehyde is a carbonyl compound.

Aroma threshold values

Medium strength odor; anisic type; recommend smelling in a 10.00% solution or less.

Taste threshold values

Sweet powdery guaiacol musty vanilla floral almond taste at 50 ppm in water.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 11, p. 943, 1974 DOI: 10.1002/jhet.5570110616
Tetrahedron Letters, 25, p. 1843, 1984 DOI: 10.1016/S0040-4039(01)90056-5

Biochem/physiol Actions

Naturally-occurring aromatic aldehyde with acaricidal activity. May condense with L-tryptophan in foods to form the corresponding phenolic tetrahydro-β-carboline-3-carboxylic acid which is a potent antioxidant.

Safety Profile

Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.