o-Anisaldehyde

o-Anisaldehyde Basic information
Description References
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:135-02-4
MF:C8H8O2
MW:136.15
EINECS:205-171-7
Product Categories:aldehyde;Fluorescent;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Pyridines
Mol File:135-02-4.mol
o-Anisaldehyde Structure
o-Anisaldehyde Chemical Properties
Melting point 34-40 °C(lit.)
Boiling point 238 °C(lit.)
density 1.127 g/mL at 25 °C(lit.)
FEMA 4077 | O-ANISALDEHYDE
refractive index 1.5608
Fp 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 Gravity1.127
PH RangeNon1 uorescence (3.1) to green 1 uorescence (4.4)
Odorat 10.00 % in propylene glycol. sweet powdery hawthorn guaiacol vanilla acetophenone almond
Odor Typeanisic
Water Solubility insoluble
Sensitive Air Sensitive
JECFA Number2062
BRN 606301
Major ApplicationBattery, hair dyes, bird repellents, cosmetics, antibacterial, antipyretic
LogP1.72
CAS DataBase Reference135-02-4(CAS DataBase Reference)
NIST Chemistry ReferenceBenzaldehyde, 2-methoxy-(135-02-4)
EPA Substance Registry SystemBenzaldehyde, 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
9-23
TSCA Yes
HS Code 29124900
ToxicityLD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg
MSDS Information
ProviderLanguage
2-Methoxybenzaldehyde English
SigmaAldrich English
ACROS English
ALFA English
o-Anisaldehyde Usage And Synthesis
DescriptionO-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/
Descriptiono-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 PropertiesColorless to cream amber crystalline powder; sweet powdery hawthorn guaiacol vanilla acetophenone almond aroma.
Chemical Propertieslight yellow to pale brown
OccurrenceReported found in Cassia oil, cinnamon bark, and Cinnamon bark oil (Cinnamomum zeylanicum Blume), Sri Lanka (0.09–0.15%)
UsesIntermediate.
Uses2-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.
Uses2-Methoxybenzaldehyde has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.
DefinitionChEBI: 2-Methoxybenzaldehyde is a carbonyl compound.
Aroma threshold valuesMedium strength odor; anisic type; recommend smelling in a 10.00% solution or less.
Taste threshold valuesSweet 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 ActionsNaturally-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 ProfileModerately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
2,6-Dimethoxybenzaldehyde 2,4-Dimethoxybenzaldehyde Guaiacol 4-Dimethylaminobenzaldehyde Anisole (Trifluoromethoxy)benzene 2,5-Dimethoxybenzaldehyde 4-Hydroxybenzaldehyde Benzaldehyde 2-Carboxybenzaldehyde Veratraldehyde p-Anisaldehyde 4-Methoxyphenol 3,5-Dimethoxybenzaldehyde 2-Nitrobenzaldehyde 2-Formylbenzenesulfonic acid sodium salt Cuminaldehyde 3-ANISALDEHYDE

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