ChemicalBook > CAS DataBase List > Isovanillin

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
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
143685
Product name
3-Hydroxy-4-methoxybenzaldehyde
Purity
99%
Packaging
25g
Price
$70.4
Updated
2025/07/31
Sigma-Aldrich
Product number
143685
Product name
3-Hydroxy-4-methoxybenzaldehyde
Purity
99%
Packaging
100g
Price
$102
Updated
2025/07/31
TCI Chemical
Product number
H0263
Product name
Isovanillin
Purity
>98.0%(T)
Packaging
25g
Price
$59
Updated
2025/07/31
TCI Chemical
Product number
H0263
Product name
Isovanillin
Purity
>98.0%(T)
Packaging
250g
Price
$251
Updated
2025/07/31
Sigma-Aldrich
Product number
59940
Product name
Isovanillin
Purity
≥95.0%
Packaging
100g
Price
$115
Updated
2025/07/31
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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

Vanillin Dimethyl sulfate

Preparation Products

Tetrahydrocurcumin 2-Chloroveratraldehyde 6-HYDROXY-7-METHOXYCOUMARIN 3-CYCLOPENTYLOXY-4-METHOXYBENZALDEHYDE 3-HYDROXY-4-METHOXYPHENETHYLAMINE HYDROCHLORIDE Fenoldopam COMBRETASTATIN A-4
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Isovanillin Suppliers

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View Lastest Price from Isovanillin manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
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
Hebei Chuanghai Biotechnology Co., Ltd
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
Hebei Zhuanglai Chemical Trading Co.,Ltd
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

621-59-0, IsovanillinRelated Search:

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

  • ISOVANILIN
  • ISOVANILLIN
  • 3-HYDROXY-4-ANISALDEHYDE
  • 3-HYDROXY-4-METHOXYBENZALDEHYDE
  • 3-HYDROXYANISALDEHYDE
  • 3-HYDROXY-P-ANISALDEHYDE
  • AKOS B022473
  • AKOS BBS-00003278
  • TIMTEC-BB SBB008245
  • 2-Methoxy-5-formylphenol
  • 4-METHOXY-3-HYDROXYBENZALDEHYDE
  • 3-Hydroxy-4-methoxybenzaL
  • 3-Hydroxy-4-methoxybenzaldehyd
  • p-Anisaldehyde,3-hydroxy-
  • 3-Hydorxy-4-Methoxy Benzoic Acid
  • 3-Hydroxy-4-methylhoxy benzaldehyde
  • 3-Hydroxy-4-methoxy
  • ISOVANILLIN, MATRIX SUBSTANCE FOR MALDI- MS
  • Isovanilllin
  • Isovanillin, 3-Hydroxyanisaldehyde
  • Isovanillin, 3-Hydroxy-p-anisaldehyde, 5-Formylguaiacol, 5-Formyl-2-methoxyphenol
  • 3-Hydroxy-4-Methoxybenzaldehyde, 97+%
  • Extraordinary fragrance LanSu
  • Isovanillin Synonyms 3-Hydroxy-4-methoxybenzaldehyde
  • Isovanillin >=95.0%
  • 3-hydroxy-4-methoxy-benzaldehyd
  • 3-hydroxy-p-anisaldehyd
  • sovanillin
  • Benzaldehyde,3-hydroxy-4-m
  • 3-HYDROXY-4-METHOXYBENZALDEHYDE / ISOVANILLIN
  • 3-HYDROXY-4-METHOXYBENZALDEHYDE 99+%
  • ISOVANILLIN (3-HYDROXY-4-METHOXYBENZALDEHYDE)
  • NSC 82996
  • 3-Hydroxy-4-methoxybenzaldehyde 4-Methoxy-3-hydroxybenzaldehyde
  • 3-Hydroxy-4-methoxybenzaldehyde, 98+%
  • 3-Hydroxyanisaldehyde, Isovanillin
  • 3-Hydroxy-4-methoxybenzaldehyde, 3-Hydroxyanisaldehyde
  • 3-Hydroxy-para-anisaldehyde
  • 5-Formyl-2-methoxyphenol
  • 5-Formylguaiacol
  • Benzaldehyde,3-hydroxy-4-methoxy-
  • Isovanicaline
  • Isovanillicaldehyde
  • Isovanilline
  • Oxy-3 methoxy-4 benzaldehyde
  • oxy-3methoxy-4benzaldehyde
  • p-Anisaldehyde, 3-hydroxy-
  • 3-Hydroxy-4-Methoxybenzaldehyde, 98% 5GR
  • Isovanillin&gt
  • 3-Hydroxy-4-methoxybenzaldehyde, 99%, for synthesis
  • Isovanillin,>98%
  • Gefitinib Impurity 42 (Isovanillin)
  • Gefitinib Impurity 91
  • 3-Hydroxy-4-methoxybenzaldehyde USP/EP/BP
  • Entacapone Impurity 79
  • Bloom Tech Chemical Reagent Isovanillin CAS?621-59-0
  • ISOVANILINE Extra Pure
  • 11 Dihydrocarbamezer