Isovanillin

Synonym(s):3-Hydroxy-4-methoxybenzaldehyde;3-Hydroxyanisaldehyde;Isovanillin

CAS NO.：621-59-0
Empirical Formula: C8H8O3
Molecular Weight: 152.15
MDL number: MFCD00003369
EINECS: 210-694-9
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-01 18:09:03

What is Isovanillin?

Chemical properties

Light Tan Cyrstalline Solid

The Uses of Isovanillin

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.

What are the applications of 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

Purification Methods

Crystallise isovaniline from H2O or *C6H6. The oxime has m 147o. [Beilstein 8 IV 1764.]

Properties of Isovanillin

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.
form	crystalline
pka	pK1:8.889 (25°C)
color	faintly brown
Water Solubility	2.27g/L at 20℃
Sensitive	Air Sensitive
BRN	1073021
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 information for Isovanillin

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.