o-Anisaldehyde Chemical Properties

Melting point:

34-40 °C(lit.)

Boiling point:

238 °C(lit.)

Density 

1.127 g/mL at 25 °C(lit.)

refractive index 

1.5608

FEMA 

4077 | O-ANISALDEHYDE

Flash point:

244 °F

storage temp. 

2-8°C

solubility 

Solubility Slightly soluble in water; soluble in ethanol

form 

Low Melting Crystalline Mass

color 

Light yellow to pale brown

Specific Gravity

1.127

PH Range

Non1 uorescence (3.1) to green 1 uorescence (4.4)

Odor

at 10.00 % in propylene glycol. sweet powdery hawthorn guaiacol vanilla acetophenone almond

Odor Type

anisic

Water Solubility 

insoluble

Sensitive 

Air Sensitive

JECFA Number

2062

BRN 

606301

Major Application

Battery, hair dyes, bird repellents, cosmetics, antibacterial, antipyretic

LogP

1.72

CAS DataBase Reference

135-02-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 2-methoxy-(135-02-4)

EPA Substance Registry System

Benzaldehyde, 2-methoxy- (135-02-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/38

Safety Statements 

26-36-37/39

WGK Germany 

2

RTECS 

BZ2610000

F 

9-23

TSCA 

Yes

HS Code 

29124900

Toxicity

LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg

MSDS

• Language:English Provider:2-Methoxybenzaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

o-Anisaldehyde Usage And Synthesis

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

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

Chemical Properties

light yellow to pale brown

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.

o-Anisaldehyde(135-02-4)Related Product Information

• 4-Hydroxybenzaldehyde
• Benzaldehyde
• 2-Nitrobenzaldehyde
• Guaiacol
• Cuminaldehyde
• Veratraldehyde
• 2-Carboxybenzaldehyde
• 2-Formylbenzenesulfonic acid sodium salt
• 3,5-Dimethoxybenzaldehyde
• Anisole
• (Trifluoromethoxy)benzene
• 4-Dimethylaminobenzaldehyde
• 4-Methoxyphenol
• 2-BROMO-2'-METHOXYACETOPHENONE
• Salicylaldehyde
• o-Anisic acid
• 2-FLUOROCYCLOHEXANONE
• 2-Methoxycinnamic acid