135-02-4

Basic information

• Product Name: o-Anisaldehyde
• Synonyms: o-Anisaldehyde：2-Methoxybenzaldehyde;o-Anisaldehyde, 98% 100GR;o-Anisaldehyde, 98% 5GR;2-Methoxybenzaldehyde Salicylaldehyde Methyl Ether;Adjacent Methoxy benzene forMaldehyde;o-Anisaldehyde 〔o-Methoxybenzaldehyde〕;2-methoxy-benzaldehyd;2-Methoxybenzenecarboxaldehyde
• CAS NO: 135-02-4
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• EINECS: 205-171-7
• Product Categories: aldehyde;Pyridines;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Fluorescent
• Mol File: 135-02-4.mol
• Article Data: 407

Chemical Properties

• Melting Point: 34-40 °C(lit.)
• Boiling Point: 238 °C(lit.)
• Flash Point: 244 °F
• Appearance: Light yellow to pale brown/Low Melting Crystalline Mass
• Density: 1.127 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00128mmHg at 25°C
• Refractive Index: 1.5608
• Storage Temp.: Store below +30°C.
• Solubility: Solubility Slightly soluble in water; soluble in ethanol
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 606301
• CAS DataBase Reference: o-Anisaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: o-Anisaldehyde(135-02-4)
• EPA Substance Registry System: o-Anisaldehyde(135-02-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: BZ2610000
• F: 9-23
• TSCA: Yes
• Hazardous Substances Data: 135-02-4(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 135-02-4 differently. You can refer to the following data:
1. 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.
2. 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.

References

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

Chemical Properties

Different sources of media describe the Chemical Properties of 135-02-4 differently. You can refer to the following data:
1. Colorless to cream amber crystalline powder; sweet powdery hawthorn guaiacol vanilla acetophenone almond aroma.
2. 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

Different sources of media describe the Uses of 135-02-4 differently. You can refer to the following data:
1. 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.
2. Intermediate.
3. 2-Methoxybenzaldehyde has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.

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.5570110616Tetrahedron 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.

InChI:InChI=1/C8H8O2/c1-10-8-5-3-2-4-7(8)6-9/h2-6H,1H3

Upstream product

• 6609-56-9 2-methoxy-benzonitrile 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 90-02-8 salicylaldehyde 
• 578-57-4 2-bromoanisole 
• 201230-82-2 carbon monoxide 
• 556-63-8 lithium formate 
• 141-53-7 sodium formate 
• 529-28-2 4-iodoanisol 
• 1011-54-7 2-methoxycinnamic acid 
• 120445-51-4 2-methoxybenzaldehyde semicarbazone 
• 74-83-9 methyl bromide 
• 101005-06-5 1-Dibutoxymethyl-2-methoxy-benzene 
• 132407-64-8 trifluoromethanesulphonyloxy-methylene-N,N-dimethyliminium trifluoromethanesulphonate 
• 100-66-3 methoxybenzene 

Downstream Products

• 10172-73-3 3,3'?(2?methoxyphenylmethylene)?bis(4?hydroxy?2H?chromen?2?one) 
• 110876-09-0 4-(2-methoxy-trans-styryl)-benzo[h]chromen-2-one 
• 408310-12-3 2-ethoxycarbonyl-2-hydroxy-2-(2-methoxylphenyl)-acetonitrile 
• 1011-54-7 2-methoxycinnamic acid 
• 7401-52-7 1,1-diacetoxy-1-(2-methoxyphenyl)methane 
• 1005138-56-6 4-hydroxy-2-(2-methoxy-phenyl)-4-methyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester 
• 42972-42-9 diethyl 1,4-dihydro-4-(2-methoxyphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate 
• 26971-96-0 3-(2-methoxy-phenyl)-2-(4-nitro-phenyl)-acrylonitrile 
• 34082-43-4 2-methoxybenzil 
• 74552-54-8 2-Hydroxy-2-(2-methoxyphenyl)-1-phenylethanone 
• 89549-73-5 benzoyloxy-(2-methoxy-phenyl)-acetonitrile 
• 71937-07-0 4-[(2-methoxybenzylidene)amino]benzoic acid 
• 64380-46-7 2-((2-methoxybenzylidene)amino)benzoic acid 
• 18176-35-7 salicylic acid-(2-methoxy-benzylidenehydrazide) 

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