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