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Basic Information
CAS No.: 621-59-0
Name: Isovanillin
Article Data: 113
Molecular Structure:
Molecular Structure of 621-59-0 (Isovanillin)
Formula: C8H8O3
Molecular Weight: 152.15
Synonyms: Isovanillin(6CI);p-Anisaldehyde, 3-hydroxy- (7CI,8CI);2-Methoxy-5-formylphenol;3-Hydroxy-4-anisaldehyde;3-Hydroxy-4-methoxybenzaldehyde;3-Hydroxy-p-anisaldehyde;4-Methoxy-3-hydroxybenzaldehyde;5-Formyl-2-methoxyphenol;5-Formylguaiacol;Isovanillic aldehyde;Benzaldehyde,3-hydroxy-4-methoxy-;
EINECS: 210-694-9
Density: 1.231 g/cm3
Melting Point: 113-116 °C
Boiling Point: 308.1 °C at 760 mmHg
Flash Point: 119.9 °C
Solubility: 2.27g/L at 20℃
Appearance: light tan cyrstalline solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37-36
PSA: 46.53000
LogP: 1.21330
Synthetic route
4383-06-6

3-hydroxy-4-methoxybenzyl alcohol

621-59-0

isovanillin

Conditions
ConditionsYield
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane100%
With oxygen In toluene at 80℃; under 760.051 Torr; for 24h;99%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 16h; Ambient temperature;97%
132638-47-2

4-methoxy-5-methoxycarbonyloxy-2-methylbenzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature;100%
6346-05-0

3-benzyloxy-4-methoxybenzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
With iron(III) chloride on silica In neat (no solvent) at 30℃; for 1h;99%
With sodium hydrogen sulfate; silica gel; methoxybenzene at 115℃; for 3h;87%
With magnesium iodide for 10h; neat (no solvent);87%
With sulfosuccinic acid functionalized mesoporous silica In ethanol at 100℃;
5779-98-6

O-methoxymethylisovanillin

621-59-0

isovanillin

Conditions
ConditionsYield
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation;99%
H6P2W18O62; silica gel In tetrahydrofuran; methanol at 65℃; for 1h;95%
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;95%
106852-87-3

4-methoxy-3-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation;99%
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;94%
881-57-2

isovanillin acetate

621-59-0

isovanillin

Conditions
ConditionsYield
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation;99%
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;98%

C15H16N2O4S

621-59-0

isovanillin

Conditions
ConditionsYield
With water; phosphorus pentoxide for 0.00861111h; microwave irradiation;98%
With phosphoric acid for 0.00833333h; microwave irradiation;68%

Sodium; hydroxy-(3-hydroxy-4-methoxy-phenyl)-methanesulfonate

621-59-0

isovanillin

Conditions
ConditionsYield
With Montmorillonite KSF clay for 0.00277778h; Elimination; microwave irradiation;96%
With ammonium acetate for 0.0105556h; microwave irradiation;93%
78515-24-9

5-formyl-2-methoxyphenyl 4-methylbenzenesulfonate

621-59-0

isovanillin

Conditions
ConditionsYield
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;96%
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation;70%
77-78-1

dimethyl sulfate

139-85-5

3,4-dihydroxybenzaldehyde

A

621-59-0

isovanillin

B

121-33-5

vanillin

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 55 - 60℃; for 1.58333h;A 93.5%
B 5.8%
With MES buffer In ethanol; water at 37℃; Kinetics; Thermodynamic data; O-methylation in the absence or in the presence of metal ion, ΔH(excit.), ΔS(excit.);
With HCl methanol buffer; BIS-TRIS at 37℃; Rate constant; Thermodynamic data; Kinetics; other divalent metal ions catalysts, var. temperat.; Ea, ΔH(excit.), ΔS(excit.);
With sodium hydroxide In dichloromethane; water at 55 - 60℃; for 5h;A 8 %Chromat.
B 77.5 %Chromat.
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Chemistry


IUPAC Name: 3-Hydroxy-4-methoxybenzaldehyde
Molecular Formula: C8H8O3
Molecular Weight: 152.14 g/mol
SMILES: O=Cc1ccc(OC)c(O)c1 Copy 
InChI: InChI=1/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3 
EINECS: 210-694-9
Classification Code: Mutation data
Product Categories: FINE Chemical & INTERMEDIATES; Aromatic Aldehydes & erivatives substituted); BenzaldehydeDerivative; Benzaldehyde; Aromatics
Index of Refraction: 1.587 
Molar Refractivity: 41.56 cm
Molar Volume: 123.5 cm3
Surface Tension: 47.3 dyne/cm 
Density: 1.231 g/cm
Flash Point: 119.9 °C 
Enthalpy of Vaporization: 57.06 kJ/mol 
Boiling Point: 308.1 °C at 760 mmHg 
Melting Point: 113-116 °C
Sensitive: Air Sensitive
Vapour Pressure of Isovanillin (CAS NO.621-59-0): 0.000384 mmHg at 25 °C

Uses

 Isovanillin (CAS NO.621-59-0) is used as flavor chemical and pharmaceutical intermediate.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 1470mg/kg (1470mg/kg)   Annales Pharmaceutiques Francaises. Vol. 14, Pg. 456, 1956.
rat LD50 intraperitoneal 1276mg/kg (1276mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 243, Pg. 609, 1956.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: IrritantXi
R36/37/38:Irritating to eyes, respiratory system and skin. Risk Statements: 36/37/38
Safety Statements: 26-36/37-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: CU6540000
Hazard Note of Isovanillin (CAS NO.621-59-0): Irritant

Specification

  Isovanillin (CAS NO.621-59-0), its Synonyms are 3-Hydroxy-4-methoxybenzaldehyde ; 3-Hydroxy-p-anisaldehyde ; Isovanilline ; Oxy-3 methoxy-4 benzaldehyde ; Benzaldehyde, 3-hydroxy-4-methoxy- ; p-Anisaldehyde, 3-hydroxy- (8CI) . It is light tan cyrstalline solid.