Isovanillin
- Product Name
- 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
- Formula Weight
- 152.15
- MOL File
- 621-59-0.mol
Isovanillin Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 143685
- Product name
- 3-Hydroxy-4-methoxybenzaldehyde
- Purity
- 99%
- Packaging
- 25g
- Price
- $70.4
- Updated
- 2025/07/31
- Product number
- 143685
- Product name
- 3-Hydroxy-4-methoxybenzaldehyde
- Purity
- 99%
- Packaging
- 100g
- Price
- $102
- Updated
- 2025/07/31
- Product number
- H0263
- Product name
- Isovanillin
- Purity
- >98.0%(T)
- Packaging
- 25g
- Price
- $59
- Updated
- 2025/07/31
- Product number
- H0263
- Product name
- Isovanillin
- Purity
- >98.0%(T)
- Packaging
- 250g
- Price
- $251
- Updated
- 2025/07/31
- Product number
- 59940
- Product name
- Isovanillin
- Purity
- ≥95.0%
- Packaging
- 100g
- Price
- $115
- Updated
- 2025/07/31
Isovanillin Chemical Properties,Usage,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%.
Definition
ChEBI: Isovanillin is a member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase. It has a role as an EC 1.2.3.1 (aldehyde oxidase) inhibitor, a plant metabolite, an antidiarrhoeal drug, an antifungal agent, a HIV protease inhibitor and an animal metabolite. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes.
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
Not classified
target
5-HT Receptor | AChR
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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View Lastest Price from Isovanillin manufacturers
- Product
- 4-METHOXY-3-HYDROXYBENZALDEHYDE 621-59-0
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-01
- Product
- Isovanillin 621-59-0
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-10-31
- Product
- 3-Hydroxy-p-anisaldehyde 621-59-0
- Price
- US $30.00/kg
- Min. Order
- 1kg
- Purity
- 99
- Supply Ability
- 5000
- Release date
- 2024-04-24