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Isovanillin

CAS No.621-59-0
Chemical Name:Isovanillin
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)
FDA UNII 4A9N90H9X6
NIST Chemistry Reference Benzaldehyde, 3-hydroxy-4-methoxy-(621-59-0)
EPA Substance Registry System Benzaldehyde, 3-hydroxy-4-methoxy- (621-59-0)
UNSPSC Code 12352100
NACRES NA.22

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

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H335-H315-H319
Precautionary statements P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Isovanillin Price More Price(15)

Brand: Sigma-Aldrich(India)
Product number: 59940
Product name : Isovanillin
Purity: ≥95.0%
Packaging: 100G
Price: ₹8746.6
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 59940
Product name : Isovanillin
Purity: ≥95.0%
Packaging: 500G
Price: ₹34878.15
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 143685
Product name : 3-Hydroxy-4-methoxybenzaldehyde
Purity: 99%
Packaging: 25G
Price: ₹3691.33
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 143685
Product name : 3-Hydroxy-4-methoxybenzaldehyde
Purity: 99%
Packaging: 100G
Price: ₹8346.08
Updated: 2022/06/14
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Brand: ALFA India
Product number: ALF-A12866-22
Product name : 3-Hydroxy-4-methoxybenzaldehyde, 98%
Purity:
Packaging: 100g
Price: ₹7298
Updated: 2022/05/26
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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.