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| CAS No.: | 120-14-9 |
|---|---|
| Name: | Veratraldehyde |
| Article Data: | 569 |
| Cas Database | |
| Molecular Structure: | |
|
|
|
| Formula: | C9H10O3 |
| Molecular Weight: | 166.177 |
| Synonyms: | 3,4-Dimethoxybenzaldehyde;3,4-Dimethoxybenzenecarbonal;4-O-Methylvanillin;Methylvanillin;NSC 24521;NSC 8500;Protocatechualdehydedimethyl ether;Protocatechuic aldehyde dimethyl ether;Vanillin methyl ether;Veratral;Veratric aldehyde;Veratrum aldehyde;Veratryl aldehyde;3,4-Dimethoxy-benzaldehyde;Benzaldehyde,3,4-dimethoxy-; |
| EINECS: | 204-373-2 |
| Density: | 1.114 g/cm3 |
| Melting Point: | 42-45 ºC |
| Boiling Point: | 281 ºC at 760 mmHg |
| Flash Point: | 110.4ºC |
| Solubility: | water: <0.1 g/100 mL at 22 ºC |
| Appearance: | needle-shaped crystal |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36/37/38 |
| Safety: | 26-22-24/25 |
| Transport Information: | N/A |
| PSA: | 35.53000 |
| LogP: | 1.51630 |
| Conditions | Yield |
|---|---|
| With polymer supported perruthenate reagent In dichloromethane | 100% |
| With benzyltriphenylphosphonium peroxymonosulfate for 0.0833333h; Oxidation; | 100% |
| With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.5h; Heating; | 100% |
3,4-Dimethoxy-benzaldehyde oxime
3,4-dimethoxy-benzaldehyde
| Conditions | Yield |
|---|---|
| With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate In acetonitrile for 0.25h; Oxidation; Heating; | 100% |
| With benzyltriphenylphosphonium dichromate; silica gel for 0.0833333h; | 100% |
| With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate In acetonitrile for 0.25h; Heating; | 99% |
2-(3,4-dimethoxyphenyl)-1,3-dithiane
3,4-dimethoxy-benzaldehyde
| Conditions | Yield |
|---|---|
| With silver(I) nitrite; iodine In tetrahydrofuran for 1.5h; Ambient temperature; | 100% |
| With bismuth(III) nitrate; water In benzene at 20℃; for 5h; | 93% |
| With eosin y In water; acetonitrile at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Irradiation; | 92% |
| With dipotassium peroxodisulfate; 1-n-butyl-3-methylimidazolim bromide at 60 - 70℃; for 0.166667h; | 80% |
| Conditions | Yield |
|---|---|
| With laccase at 20℃; Reagent/catalyst; Green chemistry; Enzymatic reaction; | 100% |
| With laccase from Trametes versicolor; oxygen; benzotriazol-1-ol In water at 45℃; for 22h; pH=4.5; | 99% |
| With laccase of Pleurotus ostreatus MTCC-1801; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt In 1,4-dioxane at 20℃; pH=4.5; Enzymatic reaction; | 98% |
1,1-diacetoxy-1-(3,4-dimethoxyphenyl)methane
3,4-dimethoxy-benzaldehyde
| Conditions | Yield |
|---|---|
| With water; titanium(IV) fluoride at 60℃; for 1.3h; screw-capped vial; | 100% |
| With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.0833333h; | 96% |
| With rice husk supported FeCl3 nanoparticles In ethanol at 70℃; for 0.05h; | 92% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In acetone at 20℃; for 1.5h; | 100% |
| With potassium carbonate In acetone at 60 - 70℃; for 17h; Reflux; | 99.3% |
| With 18-crown-6 ether; potassium carbonate | 96% |
((3,4-dimethoxybenzyl)oxy)trimethylsilane
3,4-dimethoxy-benzaldehyde
| Conditions | Yield |
|---|---|
| With nitrogen dioxide at 20℃; for 0.166667h; | 100% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In acetone at 20℃; for 1.5h; Reflux; | 99% |
| With potassium carbonate In acetone | 95% |
| With potassium hydroxide In water at 20 - 23℃; for 6h; | 90% |
| Conditions | Yield |
|---|---|
| With potassium dichromate; aluminium trichloride for 0.0333333h; | 98% |
| With lithium chloride In water; dimethyl sulfoxide at 90℃; for 6h; | 95% |
| With CuCl2*2H2O In acetonitrile for 0.5h; Ambient temperature; | 93% |
| With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol for 12h; Reflux; chemoselective reaction; | 88% |
| With K5 In acetone for 0.166667h; Heating; | 97 % Chromat. |
| Conditions | Yield |
|---|---|
| With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccasefrom Trametes versicolor; oxygen In water at 30℃; for 24h; pH=4.5; Enzymatic reaction; | 98% |
| With immobilised amine transaminase from the moderate halophilic bacterium Halomonas elongata; sodium pyruvate In aq. phosphate buffer; toluene at 45℃; under 760.051 Torr; for 5h; pH=8; | 96% |
| With sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; acetic acid; trifluoroacetic acid In water; acetonitrile for 20h; | 75% |
| Multi-step reaction with 3 steps 1: N-chloro-succinimide / 0.17 h / 20 °C / Milling 2: triethylamine / 0.17 h / 20 °C / Milling 3: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C View Scheme |
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1. Introduction of Veratraldehyde
Veratraldehyde is derivative of vanillin, widely used as a flavorant and odorant. The IUPAC name of Veratraldehyde is 3,4-dimethoxybenzaldehyde, it is off-white crystalline solid. It is also called 3,4-dimethoxy-benzaldehyd ; 4-O-Methylvanillin ; Benzaldehyde, 3,4-dimethoxy-veratraldehyde ; Protocatechuecaldehyde dimethyl ether ; Protocatechuecaldehydedimethylether ; P-Veratric aldehyde ; P-veratricaldehyde and so on.
2. Properties of Veratraldehyde
Veratraldehyde is incompatible with strong oxidizing agents and strong bases.Veratraldehyde is an aldehyde. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction).
Physical properties about Veratraldehyde are:
Appearance: off-white crystalline solid
Nominal Mass: 166 Da
Average Mass: 166.1739 Da
Monoisotopic Mass: 166.062994 Da
Index of Refraction: 1.534
Molar Refractivity: 46.36 cm3
Molar Volume: 149.1 cm3
Surface Tension: 36.1 dyne/cm
Density: 1.114 g/cm3
Flash Point: 110.4 °C
Enthalpy of Vaporization: 51.98 kJ/mol
Boiling Point: 281 °C at 760 mmHg
Vapour Pressure: 0.00366 mmHg at 25°C
Water Solubility: <0.1 g/100 mL at 22 ºC
Sensitive: Air Sensitive
Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
3. Toxicity of Veratraldehyde
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | oral | 3200mg/kg (3200mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: ATAXIA GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION | National Technical Information Service. Vol. OTS0533446, |
| rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Cosmetics Toxicology. Vol. 13, Pg. 923, 1975. | |
| rat | LD50 | oral | 2gm/kg (2000mg/kg) | Food and Cosmetics Toxicology. Vol. 13, Pg. 923, 1975. |
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Xn6. Preparation of Veratraldehyde
Veratraldehyde has been prepared by treatment of veratrole with hydrogen cyanide in the presence of aluminum chloride; by condensing veratrole with formylpiperidine and hydrolyzing the product; and by methylating vanillin with methyl iodide, methyl sulfate, methyl p-toluenesulfonate, or trimethylphenylammonium hydroxide.
7. Other details of Veratraldehyde
Personal Protection:
Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure.
Fire Fighting:Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. To extinguish fire, use water fog, dry chemical, carbon dioxide, or regular foam.
