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Cas Database

Name	Vanillylacetone	EINECS	204-548-3
CAS No.	122-48-5	Density	1.111 g/cm³
PSA	46.53000	LogP	1.92240
Solubility	N/A	Melting Point	40-41 °C(lit.)
Formula	C₁₁H₁₄O₃	Boiling Point	323 °C at 760 mmHg
Molecular Weight	194.23	Flash Point	123.7 °C
Transport Information	N/A	Appearance	Clear slightly yellow liquid.
Safety	26-36	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	N/A
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;	Article Data	43

Vanillylacetone Synthetic route

: 1080-12-2
Dehydrozingerone

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: C18H19O3Pol

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
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

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / 20 °C 2: H2; AcOH / Pd/C / ethanol View Scheme

Vanillylacetone Chemical Properties

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 .

Vanillylacetone 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.

Vanillylacetone Consensus Reports

Reported in EPA TSCA Inventory.

Vanillylacetone 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

Vanillylacetone Standards and Recommendations

DOT Classification: 3; Label: Flammable Liquid

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