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| Isovanillin Basic information |
| Isovanillin Chemical Properties |
| Melting point | 113-116 °C | | Boiling point | 179 °C15 mm Hg(lit.) | | density | 1.20 | | vapor pressure | 0Pa at 20℃ | | refractive index | 1.4945 (estimate) | | Fp | 179°C/15mm | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Soluble in acetone and methanol. | | pka | pK1:8.889 (25°C) | | form | crystalline | | color | faintly brown | | Water Solubility | 2.27g/L at 20℃ | | Sensitive | Air Sensitive | | BRN | 1073021 | | InChIKey | JVTZFYYHCGSXJV-UHFFFAOYSA-N | | LogP | 0.95 at 20℃ | | CAS DataBase Reference | 621-59-0(CAS DataBase Reference) | | NIST Chemistry Reference | Benzaldehyde, 3-hydroxy-4-methoxy-(621-59-0) | | EPA Substance Registry System | Benzaldehyde, 3-hydroxy-4-methoxy- (621-59-0) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/37-36 | | WGK Germany | 3 | | RTECS | CU6540000 | | Hazard Note | Irritant | | TSCA | Yes | | HS Code | 29124900 |
| Isovanillin Usage And Synthesis |
| Chemical Properties | Light Tan Cyrstalline Solid | | Uses | 3-Hydroxy-4-methoxybenzaldehyde was used as starting reagent during the two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 and glycitein synthesis. | | Application | Isovanillin is a kind of fragrance and isomer of vanillin. it has unique properties than vanillin, its fragrance can change with the change of ambient temperature, so it is especially suitable for special cosmetics and some special fragrance industries. Isovanillin is a selective inhibitor of aldehyde oxidase. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid, which could make it a candidate drug for use in alcohol aversion therapy. | | Preparation | Synthesis of isovanillin: 4-Hydroxybenzaldehyde is used as raw material, firstly react with bromine to obtain 3-bromo-4-hydroxybenzaldehyde, then react with methyl iodide to obtain 3-bromo-4-methoxybenzaldehyde, and then hydrolyzed under the action of sodium hydroxide and cuprous chloride to produce isovanillin. The yield was 64.1%. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 45, p. 1596, 1980 DOI: 10.1021/jo01297a010 | | General Description | 3-Hydroxy-4-methoxybenzaldehyde on condensation with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide yields Schiff-bases. It undergoes condensation reaction with1-azabicyclo[2.2.2]octan-3-one to give (Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one. | | Flammability and Explosibility | Notclassified | | Purification Methods | Crystallise isovaniline from H2O or *C6H6. The oxime has m 147o. [Beilstein 8 IV 1764.] |
| Isovanillin Preparation Products And Raw materials |
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