Isovanillin
- CAS No.
- 621-59-0
- Chemical Name:
- Isovanillin
- Synonyms
- 3-HYDROXY-4-METHOXYBENZALDEHYDE;ISOVANILIN;sovanillin;5-Formylguaiacol;3-Hydroxy-4-methoxy;Benzaldehyde,3-hydroxy-4-methoxy-;NSC 82996;ISOVANILLIN;lsovanillin;AKOS B022473
- CBNumber:
- CB0705725
- Molecular Formula:
- C8H8O3
- Molecular Weight:
- 152.15
- MOL File:
- 621-59-0.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/17 21:30:02
| 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) |
| Flash point | 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H335-H315-H319 | |||||||||
| Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | |||||||||
| 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 | |||||||||
| NFPA 704 |
|
Isovanillin price More Price(15)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | 59940 | Isovanillin ≥95.0% | 621-59-0 | 100G | ₹8746.6 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 59940 | Isovanillin ≥95.0% | 621-59-0 | 500G | ₹34878.15 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 143685 | 3-Hydroxy-4-methoxybenzaldehyde 99% | 621-59-0 | 25G | ₹3691.33 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 143685 | 3-Hydroxy-4-methoxybenzaldehyde 99% | 621-59-0 | 100G | ₹8346.08 | 2022-06-14 | Buy |
| ALFA India | ALF-A12866-22 | 3-Hydroxy-4-methoxybenzaldehyde, 98% | 621-59-0 | 100g | ₹7298 | 2022-05-26 | Buy |
Isovanillin Chemical Properties,Uses,Production
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%.
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.
Source
Isovanillin is a natural product found in many plant species like Pluchea sagittalis, Pycnocycla spinose, Mondia whitei, Benincasa hispida, Arum Palaestinum, Thalictrum przewalskii, Valeriana officinalis var. latifolia[1].
Purification Methods
Crystallise isovaniline from H2O or *C6H6. The oxime has m 147o. [Beilstein 8 IV 1764.]
References
[1] Ana C. de Carvalho . “Understanding the cytotoxic effects of new isovanillin derivatives through phospholipid Langmuir monolayers.” Bioorganic Chemistry 83 (2019): Pages 205-213.
[2] V. Balachandran , K. Parimala. “Vanillin and isovanillin: Comparative vibrational spectroscopic studies, conformational stability and NLO properties by density functional theory calculations.” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 95 (2012): Pages 354-368.
Isovanillin Preparation Products And Raw materials
Raw materials
Preparation Products
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| Supplier | Advantage |
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| GLR Innovations | 58 |
| chromsynth pvt ltd | 58 |
| ANJI BIOSCIENCES | 58 |
| SVH BIOSCIENCES | 58 |
| Vihita Chem Private Limited | 58 |
| Hyderabad | 58 |
| SynthoCascade Research Laboratories | 58 |
| JSK Chemicals | 58 |
| Clarion Drugs Ltd | 58 |
| Stereokem Pvt Ltd | 58 |