METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE supplier

Name
4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE
EINECS
CAS No. 1080-12-2
Article Data108
CAS DataBase
Density 1.154g/cm3
Solubility
Melting Point 125-130oC
Formula C11H12 O3
Boiling Point 348.2oC at 760 mmHg
Molecular Weight 192.214
Flash Point 136.9oC
Transport Information
Appearance
Safety Moderately toxic by intraperitoneal route. Slightly toxic by ingestion. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating vapors.
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms 3-Methoxy-4-hydroxybenzalacetone;4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one;4-Hydroxy-3-methoxybenzylideneacetone; 4-Hydroxy-3-methoxystyryl methyl ketone;Dehydro[0]-paradol; Dehydrogingerone; Dehydrozingerone; Feruloylmethane; NSC26613; NSC 4019; NSC 44708; NSC 45411; NSC 5316; Vanillalacetone; [0]-Paradol,dehydro-
PSA 46.53000
LogP 2.00300

Synthetic route

: 121-33-5
vanillin

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 10 - 20℃;	95%
With sodium hydroxide In acetone at 20℃; for 12h;

: 121-33-5
vanillin

: 67-64-1
acetone

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water for 0.00833333h; Claisen Condensation; Microwave irradiation;	92%
With sodium hydroxide for 0.25h; Irradiation;	88%
With sodium hydroxide In ethanol; water at 20℃;	87%

: 121-33-5
vanillin

: 106-96-7
propargyl bromide

A: 1080-12-2
Dehydrozingerone

B: 132927-15-2
4-(1-hydroxybut-3-ynyl)-2-methoxyphenol

Conditions

Conditions	Yield
With tin In tetrahydrofuran; water; hydrogen bromide for 2h; Ambient temperature; Yield given. Yields of byproduct given;
With tin; hydrogen bromide In tetrahydrofuran for 2h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 1833-53-0
2-(Trimethylsilyloxy)propene

: 121-33-5
vanillin

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane

: 121-33-5
vanillin

: 67-64-1
acetone

aqueous alcoholic alkaline solution: aqueous alcoholic alkaline solution

: 1080-12-2
Dehydrozingerone

...Expand

glycosidovanillal acetone: glycosidovanillal acetone

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
With emulsin

: 61152-59-8
4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
With hydrogenchloride at 20℃;

: 121-33-5
vanillin

iron (II)-chloride: iron (II)-chloride

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / 20 °C 2: aq. HCl / 20 °C View Scheme

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

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
With eugenol oxidase from Rhodococcus jostii RHA1 In dimethyl sulfoxide at 20℃; for 12h; pH=8; Enzymatic reaction;

: 458-37-7
curcumin

A: 1135-24-6
3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B: 1080-12-2
Dehydrozingerone

C: 121-33-5
vanillin

D: 67-64-1
acetone

Conditions

Conditions	Yield
With water at 29.84℃; pH=7; Kinetics; Reagent/catalyst;

...Expand

: 5533-00-6
3-methoxy-4-methoxymethoxy-benzaldehyde

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethanol / 1 h / 20 °C 2: hydrogenchloride / methanol / 18 h / 50 °C View Scheme

: C13H16O4

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 50℃; for 18h;

: 121-33-5
vanillin

: 1439-36-7
1-triphenylphosphoranylidene-2-propanone

: 1080-12-2
Dehydrozingerone

Conditions

Conditions	Yield
In toluene for 15h; Reflux;

: 1080-12-2
Dehydrozingerone

: 71597-85-8
(p-hydroxyphenyl)boronic acid

: (S)-4-(4-hydroxy-3-methoxyphenyl)-4-(4-hydroxyphenyl)butan-2-one

Conditions

Conditions	Yield
With C50H56Cl2O4Rh2 In ethanol at 60℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry; enantioselective reaction;	99%

: 109-65-9
1-bromo-butane

: 1080-12-2
Dehydrozingerone

: 4-(4-buthoxy-3-methoxyphenyl)-but-3-en-2-one

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux; Inert atmosphere;	96%

: 1080-12-2
Dehydrozingerone

: 75-33-2
2-propanethiol

: C14H20O3S

Conditions

Conditions	Yield
With C38H54ClFeN2O2 In 1,2-dichloro-ethane at -5℃; for 38h; enantioselective reaction;	95%

: 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
Dehydrozingerone

: 95-92-1
oxalic acid diethyl ester

: ethyl-2-hydroxy-4-((E)-2-(4’-hydroxy-3’-methoxyphenyl)vinyl)-4-oxo-2-butenoate

Conditions

Conditions	Yield
Stage #1: Dehydrozingerone; oxalic acid diethyl ester With sodium ethanolate In diethyl ether; ethanol at -10℃; Cooling; Stage #2: In diethyl ether; ethanol at 20℃; for 0.5h;	93%

: 1080-12-2
Dehydrozingerone

: 105-58-8
Diethyl carbonate

: ethyl 5-(4-hydroxy-3-methoxyphenyl)-3-oxopent-4-enoate

Conditions

Conditions	Yield
With sodium hydride Reflux;	90%

: 1080-12-2
Dehydrozingerone

: 2409-61-2
di(p-tolyl)phosphine oxide

: 1354655-18-7
4-[bis(4-methylphenyl)phosphinyl]-4-[4-hydroxy-3-methoxyphenyl]butan-2-one

Conditions

Conditions	Yield
at 130℃; for 0.583333h; phospha-Michael addition; Neat (no solvent); Inert atmosphere; Microwave irradiation;	82%

: 1080-12-2
Dehydrozingerone

: 99-90-1
para-bromoacetophenone

: C19H18O4

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Heck Reaction; Irradiation; Inert atmosphere; stereoselective reaction;	82%

: 1080-12-2
Dehydrozingerone

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 1-(3,4-dimethoxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water for 0.00833333h; Claisen Condensation; Microwave irradiation;	81%

: 1080-12-2
Dehydrozingerone

: 100-44-7
benzyl chloride

: 75335-47-6
(E)-4-[4-(benzyloxy)-3-methoxyphenyl]but-3-en-2-one

Conditions

Conditions	Yield
In acetone for 6h; Heating;	78%

: 1080-12-2
Dehydrozingerone

: 60118-15-2, 95591-54-1
2,4-bis(phenylthio)-1,3-dithia-2λ5,4λ5-diphosphetane 2,4-disulphide

: (Z)4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-thione

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 10h;	75%

: 91066-18-1
3-(7-chloroquinolin-4-ylamino)propyl alcohol

: 1080-12-2
Dehydrozingerone

: 4-{4-[2-(7-chloroquinolin-4-ylamino)ethoxy]-3-methoxyphenyl}but-3-en-2-one

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 6h; Mitsunobu reaction; Inert atmosphere;	73%

: 1080-12-2
Dehydrozingerone

: 39844-41-2
2-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]ethanol

: 4-(4-{2-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]ethoxy}-3-methoxyphenyl)but-3-en-2-one

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 6h; Mitsunobu reaction; Inert atmosphere;	68%

: 1080-12-2
Dehydrozingerone

: 73818-55-0, 15596-07-3
Bestmann ylide

: 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-(triphenylphosphoran- ylidene)-3,6-dihydro-2H-pyran-2-one

Conditions

Conditions	Yield
In toluene for 8h; Reflux;	67%

: 50-00-0
formaldehyd

: 1080-12-2
Dehydrozingerone

: 17544-03-5
4,4'-trimethylenedipiperidine dihydrochloride

: 5,5'-(4,4'-(propane-1,3-diyl)bis(piperidine-4,1-diyl))bis(1-(4-hydroxy-3-methoxyphenyl)pent-1-en-3-one) dihydrochloride

Conditions

Conditions	Yield
In ethanol for 2h; Mannich Aminomethylation; Reflux;	65%

...Expand

: 1080-12-2
Dehydrozingerone

: 95-92-1
oxalic acid diethyl ester

: 113465-70-6
ethyl 6-(4-hydroxy-3-methoxyphenyl)-2,4-dioxo-5-hexenoate

Conditions

Conditions	Yield
In ethanol	63%
In ethanol	63%
With sodium ethanolate 1.) EtOH, RT, 10 min, 2.) RT, 5 h; Yield given. Multistep reaction;

: 186534-02-1
3,5,6-trimethyl-pyrazine-2-carbaldehyde

: 1080-12-2
Dehydrozingerone

: (1E,4E)-1-(4-hydroxy-3-methoxyphenyl)-5-(3,5,6-trimethylpyrazin-2-yl)penta-1,4-dien-3-one

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In 1,4-dioxane at 20 - 101℃; Claisen-Schmidt Condensation; Inert atmosphere;	63%

: 1080-12-2
Dehydrozingerone

: 6783-05-7
trans-2-phenylvinylboronic acid

: (E)-4-(4-hydroxy-3-methoxyphenyl)-6-phenylhex-5-en-2-one

Conditions

Conditions	Yield
With C30H20N2O2; C32H64F6O6P4Pd2S2; magnesium 2-methylpropan-2-olate In acetonitrile for 10h; Inert atmosphere; Reflux; Molecular sieve; enantioselective reaction;	62%

: 1080-12-2
Dehydrozingerone

: 1-[5-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Conditions

Conditions	Yield
With hydrazine hydrate; acetic acid for 5h; Reflux;	61%

: 1080-12-2
Dehydrozingerone

: 61152-59-8
4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone

Conditions

Conditions	Yield
With water In ethanol for 2h; Reflux;	60%

: 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;

: 50-00-0
formaldehyd

: 1080-12-2
Dehydrozingerone

: 837-52-5
7-chloro-4-piperazinylquinoline

: 4-{3-[4-(7-chloroquinolin-4-yl)piperazin-1-ylmethyl]-4-hydroxy-5-methoxyphenyl}but-3-en-2-one

Conditions

Conditions	Yield
In ethanol; water at 110℃; for 12h; Mannich reaction;	58%

...Expand

: 1080-12-2
Dehydrozingerone

: 1571-08-0
methyl 4-formylbenzoate

: 4-[(1E,4E)-5-(3-methoxy-4-hydroxyphenyl)-3-carbonyl-1,4-pentadienyl]benzoic acid

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 72h;	50%

: 64448-06-2, 21385-80-8
(N-phenyliminovinylidene)triphenylphosphorane

: 1080-12-2
Dehydrozingerone

: 2-methoxy-4-(6-methyl-2-(phenylimino)-2Hpyran-4-yl)phenol

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h;	45%

: 1080-12-2
Dehydrozingerone

: 1447701-63-4
C14H10N2O5

: C25H20N2O7

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In 1,4-dioxane at 50℃;	25%

: 25016-11-9
1-methylpyrazole-4-carbaldehyde

: 1080-12-2
Dehydrozingerone

: (1E,4E)-1-(4-hydroxy-3-methoxyphenyl)-5-(1-methyl-1H-pyrazol-4-yl) penta-1,4-dien-3-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃;	14.1%

: 658703-33-4
5-ethoxy-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

: 1080-12-2
Dehydrozingerone

: (1E,4E)-1-(5-ethoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-5-(4-hydroxy-3-methoxyphenyl) penta-1,4-dien-3-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃;	12.6%

: 947-95-5
5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole

: 1080-12-2
Dehydrozingerone

: C22H19ClN2O3

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃;	11.5%

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Chemical Properties

Product Name: Methyl-3-methoxy-4-hydroxy styryl ketone (CAS NO.1080-12-2)

Molecular Formula: C₁₁H₁₂O₃
Molecular Weight: 192.21g/mol
Mol File: 1080-12-2.mol
Einecs: 214-096-9
Melting Point: 125-130 °C
Boiling point: 348.2 °C at 760 mmHg
Flash Point: 136.9 °C
Density: 1.154 g/cm³
Surface Tension: 43.1 dyne/cm
Enthalpy of Vaporization: 61.59 kJ/mol
Vapour Pressure: 2.55E-05 mmHg at 25°C
XLogP3: 1.7
H-Bond Donor: 1
H-Bond Acceptor: 3
Product Categories: Aromatic Ketones (substituted)

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	610mg/kg (610mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 37, Pg. 708, 1987.
mouse	LDLo	oral	> 2gm/kg (2000mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 37, Pg. 708, 1987.
rat	LD	oral	> 1gm/kg (1000mg/kg)	Indian Journal of Pharmaceutical Sciences. Vol. 43, Pg. 226, 1981.

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Consensus Reports

Reported in EPA TSCA Inventory.

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Safety Profile

Moderately toxic by intraperitoneal route. Slightly toxic by ingestion. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating vapors.
Safety Information of Methyl-3-methoxy-4-hydroxy styryl ketone (CAS NO.1080-12-2):
Risk Statements: 36/37/38
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements: 26-36/37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Standards and Recommendations

DOT Classification: 3; Label: Flammable Liquid

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Specification

Methyl-3-methoxy-4-hydroxy styryl ketone ,its CAS NO. is 1080-12-2,the synonyms is Vanillylidenacetone ; Vanillylideneacetone ; Vanillylidine acetone ; 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one ; 4-(4-Hydroxy-3-methoxyphenyl)-3-butene-2-one ; 4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one ; Fema 3738 ; Dehydrozingerone .

Product Name

4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE

Synthetic route

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Chemical Properties

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Toxicity Data With Reference

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Consensus Reports

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Safety Profile

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Standards and Recommendations

METHYL-3-METHOXY-4-HYDROXY STYRYL KETONE Specification

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