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)

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 Information

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

MSDS

• Language:English Provider:Isovanillin
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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%.

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(621-59-0)Related Product Information

• Sodium 2-ethylhexanoate
• Isonicotinic acid
• 1-ADAMANTYL ISOCYANATE
• Isothiazolinones
• 3,5-Dimethoxybenzaldehyde
• 4-Hydroxybenzaldehyde
• 3-Methoxybenzaldehyde
• CHLOROPHOSPHONAZO III
• Veratraldehyde
• p-Anisaldehyde
• 3,7-Dimethyl-7-hydroxyoctanal
• Salicylaldehyde
• o-Anisaldehyde
• Benzaldehyde
• 2,6-Dimethoxybenzaldehyde
• 4-(3-Chloropropyl)morpholine
• 4-Chloro-3-fluoronitrobenzene
• 4-Chloro-3-fluoroaniline