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122-48-5

Basic Information
CAS No.: 122-48-5
Name: Vanillylacetone
Article Data: 43
Molecular Structure:
Molecular Structure of 122-48-5 (Vanillylacetone)
Formula: C11H14O3
Molecular Weight: 194.23
Synonyms: Zingiberone;Zingerone;NSC 15335;Gingerone;4-Hydroxy-3-methoxybenzylacetone;4-(4-Hydroxy-3-methoxyphenyl)-2-butanone;3-Methoxy-4-hydroxybenzylacetone;(4-Hydroxy-3-methoxyphenyl)ethylmethyl ketone;
EINECS: 204-548-3
Density: 1.111 g/cm3
Melting Point: 40-41 °C(lit.)
Boiling Point: 323 °C at 760 mmHg
Flash Point: 123.7 °C
Appearance: Clear slightly yellow liquid.
Risk Codes: 36/37/38
Safety: 26-36
PSA: 46.53000
LogP: 1.92240
Synthetic route
1080-12-2

Dehydrozingerone

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions
ConditionsYield
With diphenyl sulfide; palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h;94%
With N-benzylammonium trifluoroacetate; 1,4-dihydro-2,6-dimethyl-3,5-bis<(methylamino)carbonyl>pyridine In tetrahydrofuran at 70℃; for 16h; Sealed tube;93%
With palladium on activated charcoal; hydrogen; acetic acid In ethanol at 20℃; under 760.051 Torr;87%
1080-12-2, 22214-42-2

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions
ConditionsYield
With Rh/Al2O3; hydrogen In methanol at 20℃; under 750.075 Torr; for 2h;100%
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 4h; Time;97%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃;97%
1080-12-2, 22214-42-2

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one

A

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

B

39728-80-8

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen In methanol at 0 - 30℃; under 760.051 Torr; Reflux; Inert atmosphere;A 98%
B 2%
With diphenyl diselenide; hypophosphorous acid In glycerol at 90℃; for 0.5h; Inert atmosphere; chemoselective reaction;A 68%
B 19%
With hydrogen; palladium on activated charcoal In ethyl acetate
121-33-5

vanillin

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 63 percent / aq. NaOH / 48 h / Ambient temperature
2: 43 percent / H2 / 10percent Pd/C / 3 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: aq. NaOH
2: H2 / Pd-C / CHCl3
View Scheme
Multi-step reaction with 2 steps
1: aq. alkali
2: H2 / Raney-Ni
View Scheme

4-((tert-butyldiphenylsilyl)oxy)-3-methoxybenzyl 3-oxobutanoate

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; zinc(II) chloride In tetrahydrofuran; toluene at 20℃; for 0.75h;70%
121-33-5

vanillin

iron (II)-chloride

iron (II)-chloride

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. NaOH / 20 °C
2: aq. HCl / 20 °C
3: H2; AcOH / Pd/C / ethanol
View Scheme
Multi-step reaction with 2 steps
1: NaOH; water / 20 °C
2: H2 / Pd/C / ethyl acetate
View Scheme
Multi-step reaction with 2 steps
1: 83 percent / NaOH / H2O / 3 h
2: H2 / 10 percent Pd/C / ethyl acetate
View Scheme
1080-12-2

Dehydrozingerone

A

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

B

39728-80-8

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; acetic acid In methanol at 20℃; for 24h;A 58%
B 37%
With ethanol; palladium Hydrogenation;
78-94-4

methyl vinyl ketone

90-05-1

2-methoxy-phenol

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions
ConditionsYield
With amberlyst-15 In toluene at 20 - 40℃;36.6%

C18H19O3Pol

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; solid phase reaction;12 mg
61152-59-8

4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone

122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HCl / 20 °C
2: H2; AcOH / Pd/C / ethanol
View Scheme
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    Product Name: Vanillylacetone CAS: 122-48-5 MF: C11H14O3 MW: 194.23 EINECS: 204-548-3 Mol File: 122-48-5.mol Vanillylacetone Structure Vanillylacetone Chemical Properties Melting point 40-41 °C(lit.) Boiling point 141

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    Product Name: Vanillylacetone Synonyms: (0)-paradol;[0]-Paradol;3-Methoxy-4-hydroxybenzylacetone;3-methoxy-4-hydroxy-benzylacetone;4-(3-methoxy-4-hydroxyphenyl)-2-butanone;4-(4-hydroxy-3;4-(4-hydroxy-3-methoxyphenyl)-2-b

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Chemistry

Product Name: Vanillyl acetone (122-48-5)


Molecular Formula: C11H14O3
Molecular Weight: 194.23g/mol
Mol File: 122-48-5.mol
Einecs: 204-548-3
Melting Point: 40-41 °C(lit.)
Boiling point: 141 °C0.5 mm Hg(lit.)
Flash Point: >230 °F
Density: 1.14 g/mL at 25 °C(lit.)
Refractive index: n20/D 1.541(lit.)
Product Categories: Miscellaneous Natural Products
Synonyms of  Vanillyl acetone (122-48-5): (0)-paradol ; [0]-Paradol ; 3-Methoxy-4-hydroxybenzylacetone ; 3-methoxy-4-hydroxy-benzylacetone ; 4-(3-methoxy-4-hydroxyphenyl)-2-butanone ; 4-(4-hydroxy-3 ; 4-(4-hydroxy-3-methoxyphenyl)-2-butanon ; Gingerone .

Toxicity Data With Reference

Moderately toxic by ingestion. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Chemical Toxicology. Vol. 20, Pg. 851, 1982.
rat LD50 oral 2580mg/kg (2580mg/kg)   Food and Chemical Toxicology. Vol. 20, Pg. 851, 1982.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of  Vanillyl acetone (122-48-5):
Risk Statements: 36/37/38
36:  Irritating to the eyes 
37:  Irritating to the respiratory system 
38:  Irritating to the skin  
Safety Statements: 26-36
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing  

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid