Basic information
- CAS
621-59-0- Standard SMILES
COc1ccc(C=O)cc1O- InChIKey
JVTZFYYHCGSXJV-UHFFFAOYSA-N- Molecular formula
- C8H8O3
- Average molar mass
- 152.15 g/mol
- Monoisotopic mass
- 152.04734412
Overview
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 a HIV protease inhibitor, an antifungal agent, an antidiarrhoeal drug, an EC 1.2.3.1 (aldehyde oxidase) inhibitor, an animal metabolite and a plant metabolite. It is a member of benzaldehydes, a monomethoxybenzene and a member of phenols.
Names & identifiers
- Preferred name
- Isovanillin
- IUPAC
- 3-hydroxy-4-methoxybenzaldehyde
- English name
- Isovanillin
- Molecular formula
- C8H8O3
- Molecular weight
- 152.15
Names & synonyms
3-Hydroxy-4-methoxybenzaldehydeISOVANILLIN621-59-0Isovanilline5-Formylguaiacol3-Hydroxy-p-anisaldehydeBenzaldehyde, 3-hydroxy-4-methoxy-iso-Vanillin4A9N90H9X6NSC-82996RefChem:792444210-694-9
Show more names
ISOVANILINsovanillin3-Hydroxy-4-methoxyBenzaldehyde,3-hydroxy-4-methoxy-C8H8O3NSC 82996lsovanillin
Isovanicaline3-Hydroxy-4-methoxy-benzaldehydep-Anisaldehyde, 3-hydroxy-Oxy-3 methoxy-4 benzaldehyde3-hydroxy-4-anisaldehyde4-Methoxy-3-hydroxybenzaldehydeisovanilineMFCD00003369
Database identifiers
- CAS
621-59-0- PubChem CID
- 12127
- DTXSID
DTXSID7049423- ChEMBL
CHEMBL275563- ChEBI
CHEBI:193161- UNII
- 4A9N90H9X6
- EC Number
- 210-694-9
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 135
Experimental & physicochemical properties
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Food AdditivesFood
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 113 · 113-116 °C
- Boiling point
- 179 °C15 · 179 °C15 mm Hg(lit.)
- Density
- 1.2 · 1.20
- vapor pressure
- 0 Pa · 0Pa at 20℃
- refractive index
- 1.4945 · 1.4945 (estimate)
- Flash point
- 179 °C/15mm · 179°C/15mm
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Soluble in acetone and methanol.
- pka
- 1 · pK1:8.889 (25°C)
- form
- crystalline
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 13.3% (8 of 60) of reports.
Warning
H315 (86.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 28-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22519
Hazard Classes and CategoriesSkin Irrit. 2 (86.7%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CU6540000
- hs_code
- 29124900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36/37-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H335-H315-H319
- REACH Registrations
- Active
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Uses & manufacturing
General Manufacturing InformationBenzaldehyde, 3-hydroxy-4-methoxy-: ACTIVE
Applications
Uses3-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.
General Description3-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.
Preparation methods
PreparationSynthesis 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%.
Upstream & downstream products
Upstream raw materials
Related reactions
352 records
Compound notes
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