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Eugenol

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Name

Eugenol

EINECS 202-589-1
CAS No. 97-53-0 Density 1.05 g/cm3
PSA 29.46000 LogP 2.12930
Solubility slightly soluble in water Melting Point -5 - -20 °C(lit.)
Formula C10H12O2 Boiling Point 255 °C at 760 mmHg
Molecular Weight 164.22 Flash Point 119.8 °C
Transport Information Appearance Clear colorless pale yellow or amber-colored liquid
Safety 26-36-24/25-23 Risk Codes 22-36/37/38-42/43-38-40
Molecular Structure Molecular Structure of 97-53-0 (Eugenol) Hazard Symbols HarmfulXn
Synonyms

Synthetic eugenol;Phenol, 2-methoxy-4- (2-propenyl)-;EPA Pesticide Chemical Code 102701;Allylguaiacol;p-Allylguaiacol;2-Metoksy-4-allilofenol [Polish];Caryophyllic acid;2-Methoxy-4-(3-propenyl)phenol;Eugenic acid;1-Hydroxy-2-methoxy-4-allylbenzene;1-Hydroxy-2-methoxy-4-propenylbenzene;Engenol;2-Methoxy-4-(2-propenyl)phenol;FEMA No. 2467;2-Methoxy-4-prop-2-enylphenol;Phenol,2-methoxy-4-(2-propenyl)-;FEMA Number 2467;4-Allylcatechol 2-methyl ether;Eugenol (natural);4-06-00-06337 (Beilstein Handbook Reference);4-allyl-2-methoxyphenol;2-Hydroxy-5-allylanisole;Phenol, 2-methoxy-4-(2-propenyl)-;2-Methoxy-4-(2-propen-1-yl)phenol;

 

Eugenol Synthetic route

143654-03-9

4-allyl-2-methoxy-1-(methoxymethoxy)benzene

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry;96%
With p-toluenesulfonic acid monohydrate In dichloromethane Solvent;95.5%
With toluene-4-sulfonic acid In dichloromethane Solvent;95.5%
With bismuth(III) chloride In water; acetonitrile at 50℃; for 1h; chemoselective reaction;89%
144150-79-8

2-methoxy-4-(prop-2-en-1-yl)phenyl 4-methylbenzenesulfonate

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With magnesium In methanol for 6h; Ambient temperature;95%
4125-45-5

2-methoxy-4-allyl-1-(allyloxy)benzene

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
Stage #1: 4-allyl-(1-allyloxy)-2-methoxybenzene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2h; Inert atmosphere;
Stage #2: With methanol In diethyl ether; pentane at -78℃; Inert atmosphere;
92%
With ethylmagnesium chloride; iron(II) chloride In tetrahydrofuran; m-xylene at 20℃; for 1h;86%
2216-99-1

5-allyl-2-hydroxy-3-methoxybenzoic acid

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With lithium chloride In N,N-dimethyl-aniline at 190℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere;90%
With 2,3-Dimethylaniline at 160℃;
103552-63-2

4-Allyl-1-(1-ethoxy-ethoxy)-2-methoxy-benzene

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With diphosphorus tetraiodide In dichloromethane 0 degC, 25 min and room temp., 5 min;90%

4-Allyl-1-(2-ethoxy-ethoxy)-2-methoxy-benzene

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With diphosphorus tetraiodide In dichloromethane at 0℃; for 0.75h;90%
93-28-7

eugenol acetate

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With methanol; potassium permanganate at 25℃; chemoselective reaction;90%
With aluminium trichloride; potassium iodide In water; acetonitrile at 80℃; for 4h;83%
106-95-6

allyl bromide

156682-54-1

3-(benzyloxy)phenylboronic acid

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
Suzuki-Miyaura Coupling; Inert atmosphere;90%
4125-43-3

O-allyl guaiacol

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 276 - 300℃; for 0.025h; Irradiation;87%
With boron trifluoride diacetate at 68℃;
214330-24-2

3-[3-methoxy-4-(tert-butyldimethylsiloxy)phenyl]-1-propene

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With sodium tetrachloroaurate(III) dihydrate In methanol at 20℃; for 7h;87%
76513-64-9

[2-(4-Allyl-2-methoxy-phenoxymethoxy)-ethyl]-trimethyl-silane

A

50-00-0

formaldehyd

B

97-53-0

4-allylguaiacol

C

74-85-1

ethene

D

420-56-4

trimethylsilyl fluoride

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 45℃; for 10h;A n/a
B 85%
C n/a
D n/a
4125-43-3

O-allyl guaiacol

A

97-53-0

4-allylguaiacol

B

579-60-2

6-allylguaicol

Conditions
ConditionsYield
at 200℃; for 1.5h; Claisen Rearrangement;A 10%
B 84%
With 1-butyl-2,3-(trimethylene)imidazolium bistriflylimide at 250℃; for 0.025h; Claisen rearrangement; microwave irradiation;A 18%
B 64%
With bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.25h; Claisen rearrangement; Heating;A n/a
B 60%
6331-61-9

2-methoxy-4-(2-propenyl)phenoxyacetic acid

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-(2-propenyl)phenoxyacetic acid With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating;
Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.;
84%

eugenyl ferrocenecarboxylate

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran; methanol at 0 - 23℃; for 16h; Inert atmosphere;75%
16766-30-6

4-Chloroguaiacol

762-72-1

allyl-trimethyl-silane

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With caesium carbonate In 2,2,2-trifluoroethanol for 18h; Irradiation;73%
81391-19-7

1-<(4-hydroxy-3-methoxy)phenyl>-3-(trimethylsilyl)propan-1-ol

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With borontrifluoride acetic acid In dichloromethane at 25℃; for 0.0833333h;60%
1616917-77-1

2-(4-(allyloxy)-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A

97-53-0

4-allylguaiacol

B

4125-45-5

2-methoxy-4-allyl-1-(allyloxy)benzene

Conditions
ConditionsYield
With C14H16N6; palladium diacetate; calcium hydroxide In N,N-dimethyl acetamide; water at 50℃; for 24h; Inert atmosphere;A 57%
B 20%
5932-68-3

(E)-2-methoxy-4-(1-propenyl)phenol

A

97-53-0

4-allylguaiacol

B

51020-86-1

(+)-licarin A

D

121-33-5

vanillin

Conditions
ConditionsYield
With Pseudomonas putida NCIM 2176 for 144h; Microbiological reaction; Enzymatic reaction;A 3%
B 16%
C 10%
D 24%
917-64-6

methyl magnesium iodide

93-15-2

1,2-dimethoxy-4-(2-propenyl)benzene

A

97-53-0

4-allylguaiacol

B

501-19-9

chavibetol

Conditions
ConditionsYield
With diethyl ether; xylene Erhitzen des vom Aether befreiten Reaktionsgemisches auf 160-180grad;
2216-99-1

5-allyl-2-hydroxy-3-methoxybenzoic acid

121-69-7

N,N-dimethyl-aniline

97-53-0

4-allylguaiacol

85614-43-3

2-hydroxy-3-methoxy-5-(2-propeny)benzoic acid, methyl ester

62-53-3

aniline

97-53-0

4-allylguaiacol

123-75-1

pyrrolidine

93-28-7

eugenol acetate

A

4030-18-6

N-(acetyl)pyrrolidine

B

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
for 0.05h; Ambient temperature;
4125-43-3

O-allyl guaiacol

A

3345-11-7

2,3-Dihydro-7-methoxy-2-methylbenzofuran

B

97-53-0

4-allylguaiacol

C

579-60-2

6-allylguaicol

Conditions
ConditionsYield
With Y-zeolite 1.) n-pentane, r.t., 24 h, 2.) microwave irradiation, 5 min; Yield given. Multistep reaction. Yields of byproduct given;
68800-55-5

1-<(3-methylbut-2-enyl)oxyl>-2-methoxy-4-(2-propenyl)benzene

A

97-53-0

4-allylguaiacol

B

87893-16-1

4-allyl-2-methoxy-6-(3-methyl-2-butenyl)phenyl

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 190 - 200℃; for 4h;A 70 mg
B 25 mg
129664-76-2

2-methoxy-4-(2-propenylidene)-2,5-cyclohexadien-1-one, Z-isomer

97-53-0

4-allylguaiacol

129664-76-2

2-methoxy-4-(2-propenylidene)-2,5-cyclohexadien-1-one, Z-isomer

A

97-53-0

4-allylguaiacol

B

5932-68-3

(E)-2-methoxy-4-(1-propenyl)phenol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; tetrachloromethane Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
6-oxy-5-methoxy-3-allyl-benzoic acid methyl ester

6-oxy-5-methoxy-3-allyl-benzoic acid methyl ester

97-53-0

4-allylguaiacol

Conditions
ConditionsYield
With aniline
56-23-5

tetrachloromethane

60-29-7

diethyl ether

93-15-2

1,2-dimethoxy-4-(2-propenyl)benzene

1 mol methyl magnesium iodide

1 mol methyl magnesium iodide

A

97-53-0

4-allylguaiacol

B

501-19-9

chavibetol

Conditions
ConditionsYield
Erhitzen des vom Aether befreiten Reaktionsgemisches auf 160-180grad;
4125-43-3

O-allyl guaiacol

108-88-3

toluene

Fuller's earth

Fuller's earth

A

97-53-0

4-allylguaiacol

B

501-19-9

chavibetol

97-53-0

4-allylguaiacol

2785-87-7

2-methoxy-4-n-propylphenol

Conditions
ConditionsYield
With hydrogen In 2,2,4-trimethylpentane at 180℃; under 7500.75 - 37503.8 Torr; for 0.166667h; Inert atmosphere;100%
With 4,4'-di-tert-butylbiphenyl; lithium; isopropyl alcohol; nickel dichloride In tetrahydrofuran at 20 - 76℃; Inert atmosphere; chemoselective reaction;99%
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 1.5h;99.1%
97-53-0

4-allylguaiacol

108-24-7

acetic anhydride

93-28-7

eugenol acetate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 24h; Inert atmosphere;100%
With sodium acetate at 130℃; for 0.0111111h; Microwave irradiation;98%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;98%
97-53-0

4-allylguaiacol

100-39-0

benzyl bromide

57371-42-3

4-allyl-1-benzyloxy-2-methoxybenzene

Conditions
ConditionsYield
Stage #1: 4-allylguaiacol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0℃; for 1h;
100%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 55℃; Inert atmosphere;99%
With potassium carbonate In acetonitrile at 20℃; for 4h;98%
67-56-1

methanol

97-53-0

4-allylguaiacol

208-96-8

acenaphthylene

8-allyl-11,11-dimethoxy-6b,7,10,10a-tetrahydro-7,10-ethanofluoranthen-12-one

Conditions
ConditionsYield
Stage #1: methanol; 4-allylguaiacol With [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate In benzene at 0℃; for 0.166667h;
Stage #2: acenaphthylene In benzene at 20℃; for 22h; Diels-Alder reaction; stereoselective reaction;
100%
97-53-0

4-allylguaiacol

52204-65-6

4-n-propylcyclohexanol

Conditions
ConditionsYield
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 1.5h;99.9%
97-53-0

4-allylguaiacol

97-54-1

2-methoxy-4-propenylphenol

Conditions
ConditionsYield
With rhodium(III) chloride; ethanol at 140 - 145℃;99%
With tris(triphenylphosphine)ruthenium(II) chloride at 50 - 60℃; for 4h; Temperature;99%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; polydimethylsiloxane In methanol; water at 100℃; for 20h;82%
97-53-0

4-allylguaiacol

106-95-6

allyl bromide

4125-45-5

2-methoxy-4-allyl-1-(allyloxy)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; for 12h;99%
With sodium hydroxide In water; acetone for 8h; Reflux;96%
Stage #1: 4-allylguaiacol With potassium hydroxide In ethanol
Stage #2: With sodium carbonate In ethanol Reflux;
Stage #3: allyl bromide In ethanol Reflux;
94%
97-53-0

4-allylguaiacol

76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

76513-64-9

[2-(4-Allyl-2-methoxy-phenoxymethoxy)-ethyl]-trimethyl-silane

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 24h; Ambient temperature;99%
97-53-0

4-allylguaiacol

1126-61-0

4-allylpyrocatechol

Conditions
ConditionsYield
With pyridine; aluminium(III) iodide In acetonitrile at 80℃; for 18h; Reagent/catalyst; Solvent;99%
Stage #1: 4-allylguaiacol With pyridine; iodine; aluminium In acetonitrile for 18h; Reflux;
Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; Reagent/catalyst;
99%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h; Reagent/catalyst;99%
97-53-0

4-allylguaiacol

5932-68-3

(E)-2-methoxy-4-(1-propenyl)phenol

Conditions
ConditionsYield
With Grotjahn’s catalyst In [(2)H6]acetone at 25℃; for 0.0666667h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Glovebox; stereoselective reaction;99%
With platinum(II) chloride In methanol96%
With Grotjahn’s catalyst at 20℃; for 0.333333h; Catalytic behavior; Reagent/catalyst; Glovebox; Inert atmosphere; Green chemistry; diastereoselective reaction;95.9%
97-53-0

4-allylguaiacol

dichloro(methyl)(pentamethylcyclopentadienyl)titanium(IV)

259255-99-7

(Ti(C5(CH3)5)Cl2(O(C6H3(OCH3)(CH2CHCH2))))

Conditions
ConditionsYield
In toluene Ar atm., room temp.;99%

Schwartz's reagent

97-53-0

4-allylguaiacol

632354-19-9

CH2CHCH2C6H3(OCH3)OZr(C5H5)2Cl

Conditions
ConditionsYield
In tetrahydrofuran Ar atm.;99%
617-86-7

triethylsilane

97-53-0

4-allylguaiacol

1414854-49-1

((4-allyl-1,2-phenylene)bis(oxy))bis(triethylsilane)

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate at 20℃; for 3h; Inert atmosphere;99%
With tris(pentafluorophenyl)borate for 16h; Inert atmosphere;99%
With tris(pentafluorophenyl)borate at 20℃; for 0.166667h;99%
97-53-0

4-allylguaiacol

201230-82-2

carbon monoxide

106-99-0

buta-1,3-diene

C19H24O3

Conditions
ConditionsYield
With palladium diacetate; triphenylphosphine; benzoic acid In tetrahydrofuran at -40 - 80℃; under 15001.5 Torr; Autoclave; Inert atmosphere;99%
97-53-0

4-allylguaiacol

17875-55-7

1,1,5,5-tetramethyl-3,3-diphenyl-trisiloxane

C36H48O6Si3

Conditions
ConditionsYield
platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 80 - 120℃; for 2h;98.7%
97-53-0

4-allylguaiacol

591-87-7

Allyl acetate

4125-45-5

2-methoxy-4-allyl-1-(allyloxy)benzene

Conditions
ConditionsYield
With 5%-palladium/activated carbon; potassium carbonate; triphenylphosphine In water at 85 - 105℃; for 16h; Inert atmosphere;98.5%
With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether In water; toluene at 45℃; for 24h; Tsuji-Trost Allylation; Schlenk technique; Inert atmosphere; Sealed tube;77%
97-53-0

4-allylguaiacol

4433-08-3

5,5'-diallyl-2,2'-dihydroxy-3,3'-dimethoxybiphenyl

Conditions
ConditionsYield
Stage #1: 4-allylguaiacol With ammonium hydroxide In water; acetone for 0.166667h;
Stage #2: With potassium hexacyanoferrate(III) In water; acetone
98%
With ammonium hydroxide; air; potassium hexacyanoferrate(III) In water; acetone at 20℃;95%
With ammonium hydroxide; potassium hexacyanoferrate(III) at 20℃;95%
97-53-0

4-allylguaiacol

dehydrodieugenol

Conditions
ConditionsYield
With ammonium hydroxide; KFe(CN)6 In acetone98%
97-53-0

4-allylguaiacol

2380-78-1

homovanillyl alcohol

Conditions
ConditionsYield
Stage #1: 4-allylguaiacol With ozone In ethanol at -55℃;
Stage #2: With sodium tetrahydroborate In ethyl acetate at 20℃;
98%
Multi-step reaction with 2 steps
1: ozone / sodium hydrogencarbonate / dichloromethane; methanol / 2 h / -78 °C
2: sodium tetrahydroborate; methanol / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere
View Scheme
97-53-0

4-allylguaiacol

103-80-0

phenylacetyl chloride

10402-33-2

phenylacetic acid 4-allyl-2-methoxy-phenyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h; Reflux;98%
With potassium carbonate In acetone for 2h; Reflux;
70-49-5

DL-thiomalic acid

97-53-0

4-allylguaiacol

C14H18O6S

Conditions
ConditionsYield
With 2-hydroxy-2-methylpropiophenone In 1,4-dioxane; ethanol at 20℃; for 50h; UV-irradiation;98%
With benzoin dimethyl ether at 20℃; for 1h; UV-irradiation;
97-53-0

4-allylguaiacol

52000-32-5

7-mercaptoheptanoic acid

C17H26O4S

Conditions
ConditionsYield
With (2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone) In 1,4-dioxane; ethanol at 100℃; for 0.5h; UV-irradiation;98%
97-53-0

4-allylguaiacol

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

2-methoxy-4-allylphenyltrimethylsilyl ether

Conditions
ConditionsYield
for 4h; Reflux;98%
97-53-0

4-allylguaiacol

870-63-3

prenyl bromide

68800-55-5

1-<(3-methylbut-2-enyl)oxyl>-2-methoxy-4-(2-propenyl)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; for 12h;98%
97-53-0

4-allylguaiacol

60-24-2

2-hydroxyethanethiol

C12H18O3S

Conditions
ConditionsYield
With benzoin monomethyl ether In 1,4-dioxane; ethanol at 30℃; for 2h; Reagent/catalyst; Irradiation;97.5%
With 2,2-bis(hydroxymethyl)propionic acid UV-irradiation;
97-53-0

4-allylguaiacol

trieugenyl phosphate

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In ethyl acetate at 0 - 20℃; for 16.5h;97%
With triethylamine; trichlorophosphate In ethyl acetate at 0 - 20℃; for 24h;97%
With sodium hydroxide; trichlorophosphate extrahieren mit Aether;
Stage #1: 4-allylguaiacol With trichlorophosphate In dichloromethane at 0℃; for 4h;
Stage #2: With sodium hydroxide In dichloromethane; water Temperature; Reagent/catalyst; Solvent;
97-53-0

4-allylguaiacol

100-07-2

4-methoxy-benzoyl chloride

521960-43-0

4'-allyl-2'-methoxyphenyl 4-methoxybenzoate

Conditions
ConditionsYield
Stage #1: 4-allylguaiacol With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 4-methoxy-benzoyl chloride In dichloromethane at 0 - 20℃; for 24.75h; Inert atmosphere;
97%
With sodium hydroxide In water at 20℃; for 0.5h;85%
With sodium hydroxide In water at 20℃; for 0.5h;43%
With sodium hydroxide In water at 20℃; for 0.5h;
97-53-0

4-allylguaiacol

824-94-2

p-methoxybenzyl chloride

4-allyl-2-methoxy-1-(4-methoxybenzyloxy)benzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 25h;97%
97-53-0

4-allylguaiacol

3277-26-7

1,1,3,3-Tetramethyldisiloxane

6998-05-6

1,3-bis-[3-(4-hydroxy-3-methoxyphenyl)propyl]tetramethyldisiloxane

Conditions
ConditionsYield
With dihydrogen hexachloroplatinate In isopropyl alcohol at 60℃; for 4h;97%
97-53-0

4-allylguaiacol

17689-17-7

6-mercaptocaproic acid

C16H24O4S

Conditions
ConditionsYield
With 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-butan 1-one In 1,4-dioxane; ethanol at 80℃; for 10h; UV-irradiation;97%

Eugenol Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 36 (1985),p. 75.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NTP Carcinogenesis Studies (feed); Equivocal Evidence: mouse NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-223 ,1983. ; No Evidence: rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-223 ,1983. . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Eugenol Specification

The Eugenol is an organic compound with the formula C10H12O2. The IUPAC name of this chemical is 2-methoxy-4-prop-2-enylphenol. With the CAS registry number 97-53-0, it is also named as phenol, 2-methoxy-4-(2-propen-1-yl)-. The product's categories are Antioxidant; Biochemistry. Besides, it is a clear colorless pale yellow or amber-colored liquid, which should be stored in a dark and cool place.It will be darkens and thickens on exposure to air. Also darkens with age. Eugenol may decompose on exposure to light. Insoluble in water.It reacts with strong alkalis. Eugenol is incompatible with strong oxidizers. This includes ferric chloride and potassium permanganate.

The Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. It is also a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin. Eugenol is attractive to males of various species of orchid bees, so it is commonly used as bait to attract and collect these bees for study. Eugenol derivatives or methoxyphenol are used in formulating insect attractants and UV absorbers, biocides, analgesics, and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers.

Physical properties about Eugenol are:
(1)ACD/LogP: 2.20; (2)ACD/LogD (pH 5.5): 2.2; (3)ACD/LogD (pH 7.4): 2.2; (4)ACD/BCF (pH 5.5): 27.88; (5)ACD/BCF (pH 7.4): 27.85; (6)ACD/KOC (pH 5.5): 376.88; (7)ACD/KOC (pH 7.4): 376.41; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 29.46 Å2; (12)Index of Refraction: 1.535; (13)Molar Refractivity: 48.72 cm3; (14)Molar Volume: 156.2 cm3; (15)Polarizability: 19.31×10-24cm3; (16)Surface Tension: 36.5 dyne/cm; (17)Density: 1.05 g/cm3; (18)Flash Point: 119.8 °C; (19)Enthalpy of Vaporization: 51.24 kJ/mol; (20)Boiling Point: 255 °C at 760 mmHg; (21)Vapour Pressure: 0.0104 mmHg at 25°C.

Preparation of Eugenol:
The Eugenol can be prepared by 1-allyloxy-2-methoxy-benzene. This reaction will need reagent BF3+2 CH3COOH. The reaction temperature is 68 °C.
The Eugenol can be prepared by 1-allyloxy-2-methoxy-benzene. This reaction will need reagent BF3+2 CH3COOH. The reaction temperature is 68 °C.

Uses of Eugenol: 
It can be used to produce 2-Methoxy-4-propyl-phenol at temperature of 20 °C. It will need reagent H2, catalyst 10 percent Pd/C and solvent ethanol with reaction time of 5 hours. The yield is about 98%.
It can be used to produce 2-Methoxy-4-propyl-phenol at temperature of 20 °C. It will need reagent H2, catalyst 10 percent Pd/C and solvent ethanol with reaction time of 5 hours. The yield is about 98%.

When you are using Eugenol, please be cautious about it as the following:
It is harmful if swallowed and may cause sensitisation by inhalation and skin contact. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, Eugenol is irritating to eyes, respiratory system and skin and limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing, do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES:Oc1ccc(cc1OC)CC=C;
(2)Std. InChI:InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3;
(3)Std. InChIKey:RRAFCDWBNXTKKO-UHFFFAOYSA-N.

The toxicity data of Eugenol is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 500mg/kg (500mg/kg) BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Gastroenterology. Vol. 15, Pg. 481, 1950.
guinea pig LD50 oral 2130mg/kg (2130mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
hamster LD50 intratracheal 17mg/kg (17mg/kg) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Archives of Toxicology. Vol. 59, Pg. 78, 1986.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 250, Pg. 1148, 1960.
mouse LD50 intravenous 72mg/kg (72mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 30, 1966.
mouse LD50 oral 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LC inhalation > 2580mg/m3/4H (2580mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Archives of Toxicology. Vol. 62, Pg. 381, 1988.
rat LD50 intratracheal 11mg/kg (11mg/kg) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Archives of Toxicology. Vol. 59, Pg. 78, 1986.
rat LD50 oral 1930mg/kg (1930mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Proceedings of the Society for Experimental Biology and Medicine. Vol. 73, Pg. 148, 1950.
rat LDLo intraperitoneal 800mg/kg (800mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.
rat LDLo subcutaneous 5gm/kg (5000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.

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