ISOEUGENOL supplier | CasNO.97-54-1

Name
ISOEUGENOL
EINECS 202-590-7
CAS No. 97-54-1
Article Data66
CAS DataBase
Density 1.074 g/cm³
Solubility
Melting Point -10 °C
Formula C₁₀H₁₂O₂
Boiling Point 266.64 °C at 760 mmHg
Molecular Weight 164.204
Flash Point 122.907 °C
Transport Information
Appearance light yellow-green viscous liquid
Safety 26-36-36/37
Risk Codes 22-36/37/38-43
Molecular Structure
Hazard Symbols Xn
Synonyms Phenol,2-methoxy-4-(1-propenyl)- (9CI);Phenol, 2-methoxy-4-propenyl- (8CI);1-(3-Methoxy-4-hydroxyphenyl)-1-propene;2-Methoxy-4-(1-propenyl)phenol;2-Methoxy-4-propenylphenol;3-Methoxy-4-hydroxy-1-propenylbenzene;4-Hydroxy-3-methoxy-1-propenylbenzene;4-Hydroxy-3-methoxy-b-methylstyrene;4-Propenylguaiacol;NSC 6769;iso-Eugenol;
PSA 29.46000
LogP 2.43390

Synthetic route

: 97-53-0
4-allylguaiacol

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
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%

: 1-(4-hydroxy-3-methoxyphenyl)prop-1-yl acetate

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 2h;	94%

: 1350619-56-5
2-methoxy-4-(1-propenyl)phenyl tetrahydro-2H-pyran-2-yl ether

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With iron(III) p-toluenesulfonate hexahydrate In methanol at 20℃; for 2h;	76%

: 97-53-0
4-allylguaiacol

: 124-38-9
carbon dioxide

A: 97-54-1
2-methoxy-4-propenylphenol

B: (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-enoic acid

Conditions

Conditions	Yield
With trimethylaluminum; cesium fluoride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; cobalt acetylacetonate In N,N-dimethyl acetamide; toluene at 60℃; under 760.051 Torr; for 12h; Inert atmosphere; Sealed tube; regioselective reaction;	A 25 %Spectr. B 72%

...Expand

: 1530-32-1
ethyltriphenylphosphonium bromide

: 121-33-5
vanillin

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With potassium carbonate In water for 1.5h;	68%
With potassium carbonate In water at 25℃; for 1.5h; Product distribution; var. temp. and solvents;

: 97-53-0
4-allylguaiacol

: 201230-82-2
carbon monoxide

A: 97-54-1
2-methoxy-4-propenylphenol

B: 91142-61-9
5,6-Dihydro-3-methoxy-naphth-2-ol

C: 40275-47-6
3-(4-hydroxy-3-methoxyphenyl)-2-methylpropanal

Conditions

Conditions	Yield
With acetylacetonatodicarbonylrhodium(l); phosphoric acid; hydrogen; methoxybenzene; triphenylphosphine In dichloromethane at 110℃; under 15514.9 Torr; for 2h; Autoclave;	A 21 %Chromat. B 60% C n/a

...Expand

: 4-(1-acetoxypropyl)-2-methoxyphenyl pivalate

A: 97-54-1
2-methoxy-4-propenylphenol

B: isoeugenyl pivaloate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 31h;	A 25.2% B 41.3%

: 4-(1-acetoxypropyl)-2-methoxyphenyl benzoate

A: 97-54-1
2-methoxy-4-propenylphenol

B: 2-methoxy-4-(prop-1-enyl)phenyl acetate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 12h;	A 36% B 9%

: 95316-34-0
3-Hydroxy-1-methoxy-2-(2-methoxy-phenoxy)-1-(4-hydroxy-3-methoxy-phenyl)-propan

A: 2785-87-7
2-methoxy-4-n-propylphenol

B: 97-54-1
2-methoxy-4-propenylphenol

C: 90-05-1
2-methoxy-phenol

Conditions

Conditions	Yield
With 10% nickel/activated carbon; hydrogen In 1,4-dioxane at 150℃; under 15001.5 Torr; for 2h; Autoclave;	A 5.5% B 14.2% C 19.3%

...Expand

: 95316-34-0
3-Hydroxy-1-methoxy-2-(2-methoxy-phenoxy)-1-(4-hydroxy-3-methoxy-phenyl)-propan

A: 97-54-1
2-methoxy-4-propenylphenol

B: 90-05-1
2-methoxy-phenol

Conditions

Conditions	Yield
With 10% nickel/activated carbon; hydrogen In tetrahydrofuran at 150℃; under 15001.5 Torr; for 1h; Autoclave;	A 9.4% B 12.2%

: methyl ferulic acid

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With cucumber juice at 30 - 35℃; for 24h; Inert atmosphere; Green chemistry;	10%

: 7784-67-0
ethyl isoeugenol

A: 97-54-1
2-methoxy-4-propenylphenol

B: 94-86-0
2-ethoxy-5-propenylphenol

Conditions

Conditions	Yield
With sodium hydroxide; 18-crown-6 ether In ethylene glycol at 200℃; for 3h; Irradiation;	A 2% B 70 % Chromat.
With potassium tert-butylate; 18-crown-6 ether In ethylene glycol at 228℃; for 1h; Product distribution; Irradiation; further reagents and catalysts, other times and temperatures, without irradiation, without solvent;	A 3 % Chromat. B 56 % Chromat.

: 99865-71-1
α-methyl-(E)-ferulic acid

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With methyllithium; calcium carbonate

: 7452-03-1
pinoresinol

A: 93-51-6
2-Methoxy-4-methylphenol

B: 97-54-1
2-methoxy-4-propenylphenol

C: 90-05-1
2-methoxy-phenol

Conditions

Conditions	Yield
Bei der trockenen Destillation;

...Expand

: 10467-10-4
ethylmagnesium iodide

: 121-33-5
vanillin

: 97-54-1
2-methoxy-4-propenylphenol

: 925-90-6
ethylmagnesium bromide

: 121-33-5
vanillin

: 97-54-1
2-methoxy-4-propenylphenol

: 138252-41-2
Acetic acid 4-(2-hydroxy-propyl)-2-methoxy-phenyl ester

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 50℃; for 6h; Yield given;

: 7784-67-0
ethyl isoeugenol

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With potassium tert-butylate; 18-crown-6 ether at 139℃; for 0.333333h; Irradiation;	82 % Chromat.

: 2-methoxy-4-(prop-1-enyl)phenyl acetate

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With piperidine In 1,4-dioxane at 25℃; Kinetics; Deacetylation;

wood: wood

A: 91-10-1
1,3-dimethoxy-2-hydroxy-benzene

B: 934-00-9
3-methocycatechol

C: 97-54-1
2-methoxy-4-propenylphenol

D: 2785-89-9
4-Ethylguaiacol

Conditions

Conditions	Yield
With air Oxidation; Formation of xenobiotics; Further byproducts given;

...Expand

: 97-53-0
4-allylguaiacol

ethanolic KOH-solution: ethanolic KOH-solution

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
at 130 - 140℃; unter Druck;
at 130 - 140℃; unter Druck;

: 97-53-0
4-allylguaiacol

: 7732-18-5
water

potash: potash

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
at 200 - 230℃; beim Schmelzen;

...Expand

: 97-53-0
4-allylguaiacol

potassium hydroxide: potassium hydroxide

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
durch Schmelzen;

: 97-53-0
4-allylguaiacol

: 71-41-0
pentan-1-ol

potassium hydroxide: potassium hydroxide

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
at 140℃;
at 140℃;

...Expand

: 97-53-0
4-allylguaiacol

potassium hydroxide: potassium hydroxide

lead peroxide: lead peroxide

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
beim Verschmelzen;

...Expand

: 97-53-0
4-allylguaiacol

potassium hydroxide: potassium hydroxide

sodium hydroxide: sodium hydroxide

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
durch Schmelzen;

...Expand

: 97-53-0
4-allylguaiacol

: 71-41-0
pentan-1-ol

sodium: sodium

: 97-54-1
2-methoxy-4-propenylphenol

...Expand

: 97-53-0
4-allylguaiacol

cinnamon leaves-oil: cinnamon leaves-oil

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With potassium hydroxide; paraffin oil at 244℃;
With potassium hydroxide; phenol at 150 - 170℃;

: 97-53-0
4-allylguaiacol

clove-oil: clove-oil

: 97-54-1
2-methoxy-4-propenylphenol

Conditions

Conditions	Yield
With potassium hydroxide; paraffin oil at 244℃;
With potassium hydroxide; phenol at 150 - 170℃;

: 97-54-1
2-methoxy-4-propenylphenol

: 2785-87-7
2-methoxy-4-n-propylphenol

Conditions

Conditions	Yield
With hydrogen In toluene at 100℃; under 22502.3 Torr; for 0.25h; Catalytic behavior; Temperature; Reagent/catalyst; Flow reactor;	99.9%
With methanol; nickel boride; diborane for 0.5h; Ambient temperature;	98.2%
With hydrogen In methanol at 20℃; for 20h; chemoselective reaction;	98%

: 97-54-1
2-methoxy-4-propenylphenol

: 108-24-7
acetic anhydride

: 2-methoxy-4-(prop-1-enyl)phenyl acetate

Conditions

Conditions	Yield
With sodium carbonate at 100 - 150℃; for 3h; Reagent/catalyst; Temperature;	99%
indium(III) chloride at 20℃; for 0.25h;	95%
With sodium acetate at 120℃; for 1.5h;	63.08%
With triethylamine In dichloromethane at 0℃; for 4h;

: 97-54-1
2-methoxy-4-propenylphenol

: (1R,2R,3R)-1-ethyl-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2-methylindane

Conditions

Conditions	Yield
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 78℃; under 760.051 Torr; for 16h; Green chemistry; chemoselective reaction;	99%

: 103-11-7
2-Ethylhexyl acrylate

: 97-54-1
2-methoxy-4-propenylphenol

: (E)-2-ethylhexyl ferulate

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;	98%

: 97-54-1
2-methoxy-4-propenylphenol

: 2680-81-1, 23518-29-8, 23518-30-1, 51020-86-1, 64870-40-2, 69744-09-8, 72274-58-9, 72274-59-0, 83377-50-8, 88034-58-6, 127000-67-3
dehydrodiisoeugenol

Conditions

Conditions	Yield
With dihydrogen peroxide; horseradish peroxidase In aq. phosphate buffer; water; acetone at 50℃; for 2h; pH=5.83;	95.3%
With urea hydrogen peroxide adduct; horseradish peroxidase In water; acetone at 20℃; for 1h; Enzymatic reaction;	32%
With calli of Bouvardia ternifolia In acetone at 25℃; for 120h;	23%

: 97-54-1
2-methoxy-4-propenylphenol

: 106-96-7
propargyl bromide

: propargylated isoeugenol

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; toluene for 12h;	91%
With potassium carbonate In N,N-dimethyl-formamide; toluene for 12h;	73%

: 135-67-1
phenoxazine

: 97-54-1
2-methoxy-4-propenylphenol

: 62-53-3
aniline

: 4-(2-(10H-phenoxazin-10-yl)-1-(phenylamino)propyl)-2-methoxyphenol

Conditions

Conditions	Yield
With copper diacetate In ethyl acetate at 20℃; for 12h; Inert atmosphere;	91%

...Expand

: 97-54-1
2-methoxy-4-propenylphenol

: 1835-12-7
3-methoxy-4-benzyloxy-α-bromoacetophenone

: 1523436-79-4
3-methoxy-4-benzyloxy-α-(2-methoxy-4-(1-propenyl)phenol)-acetophenone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Microwave irradiation;	90.6%

: 97-54-1
2-methoxy-4-propenylphenol

: 292638-85-8
acrylic acid methyl ester

: 2309-07-1
Methyl ferulate

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;	90%

: 97-54-1
2-methoxy-4-propenylphenol

: 98-88-4
benzoyl chloride

: 531-26-0
2-methoxy-4-allylphenyl benzoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 3h;	90%

: 97-54-1
2-methoxy-4-propenylphenol

: d5-isoeugenol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); (S)-Mandelic acid; water-d2; tricyclohexylphosphine In toluene at 120℃; for 16h; Inert atmosphere;	90%

: 97-54-1
2-methoxy-4-propenylphenol

: 67914-60-7, 89929-31-7
N-acetyl-N'-(4-hydroxyphenyl)piperazine

: 1-(4-(2-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,3-dihydrobenzofuran-5-yl)piperazin-1-yl)ethan-1-one

Conditions

Conditions	Yield
With copper diacetate at 20℃; for 3h;	90%

: 59-02-9
vitamin E

: 97-54-1
2-methoxy-4-propenylphenol

: 62-53-3
aniline

: 2-methoxy-4-(1-(phenylamino)-2-((2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman-6-yl)oxy)propyl)phenol

Conditions

Conditions	Yield
With copper diacetate In ethyl acetate at 20℃; for 12h; Inert atmosphere;	90%

...Expand

: 6291-23-2
4-(4-morpholinyl)phenol

: 97-54-1
2-methoxy-4-propenylphenol

: 2-methoxy-4-(3-methyl-5-morpholino-2,3-dihydrobenzofuran-2-yl)phenol

Conditions

Conditions	Yield
With copper diacetate at 20℃; for 3h;	88%

: 31643-49-9
4-Nitrophthalonitrile

: 97-54-1
2-methoxy-4-propenylphenol

: C18H14N2O2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	85.6%

: 97-54-1
2-methoxy-4-propenylphenol

: 75-36-5
acetyl chloride

: 93-28-7
eugenol acetate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 12h;	85%

: 97-54-1
2-methoxy-4-propenylphenol

: 120-80-9
benzene-1,2-diol

Conditions

Conditions	Yield
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Sealed tube; Inert atmosphere;	85%
With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Sealed tube; Inert atmosphere;	62%

: 2127-03-9
2,2'-dipyridyldisulphide

: 97-54-1
2-methoxy-4-propenylphenol

: trans-3-(4-hydroxy-3-methoxyphenyl)-2-methyl-2H,3H-[1,3]thiazolo[3,2-]pyridin-4-ium chloride

Conditions

Conditions	Yield
Stage #1: 2,2'-dipyridyldisulphide With sulfuryl dichloride In chloroform at 20℃; for 0.166667h; Stage #2: 2-methoxy-4-propenylphenol In chloroform at 20℃; for 12h; Reflux; regioselective reaction;	85%

: 103-14-0
4-(benzylamino)phenol

: 97-54-1
2-methoxy-4-propenylphenol

: 4-(5-(benzylamino)-3-methyl-2,3-dihydrobenzofuran-2-yl)-2-methoxyphenol

Conditions

Conditions	Yield
With copper diacetate at 20℃; for 3h;	84%

: 97-54-1
2-methoxy-4-propenylphenol

: 619-60-3
4-(N,N-dimethylamino)phenol

: 104-94-9
4-methoxy-aniline

: 4-(2-(4-(dimethylamino)phenoxy)-1-((4-methoxyphenyl)amino)propyl)-2-methoxyphenol

Conditions

Conditions	Yield
With copper diacetate In ethyl acetate at 20℃; for 12h; Inert atmosphere;	83%

...Expand

ISOEUGENOL Chemical Properties

Synonyms: 4-PROPENYLGUAIACOL;4-PROPENYL-2-METHOXYPHENOL;4-HYDROXY-3-METHOXY-1-PROPENYLBENZENE;3-METHOXY-4-HYDROXYPROPENYLBENZENE;2-METHOXY-4-PROPENYLPHENOL;2-METHOXY-4-((E)-PROPENYL)-PHENOL;
ISOEUGENOL is the chemical compound with the formula C₁₀H₁₂O₂ .Its Molecular Weight is 164.2 .
Melting point:-10 °C
Boiling point:266 °C
density:1.082 g/mL at 25 °C
vapor density:>1 (vs air)
vapor pressure:<0.01 mm Hg ( 20 °C)
refractive index n20/D 1.575(lit.)
Flash point:>230 °F
storage temp.:0-6°C

ISOEUGENOL Uses

ISOEUGENOL's used as flavor intermediates.

ISOEUGENOL Toxicity Data With Reference

1.	skn-man 16 mg/48H MOD	CTOIDG Cosmetics and Toiletries. 94 (8)(1979),41.
2.	skn-rbt 100 mg/24H SEV	CTOIDG Cosmetics and Toiletries. 94 (8)(1979),41.
3.	skn-gpg 100 mg/24H SEV	CTOIDG Cosmetics and Toiletries. 94 (8)(1979),41.
4.	sce-hmn:lym 250 µmol/L	MUREAV Mutation Research. 169 (1986),129.
5.	orl-rat LD50:1560 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),378.
6.	orl-gpg LD50:1410 mg/kg	FCTXAV Food and Cosmetics Toxicology. 2 (1964),327.

ISOEUGENOL Consensus Reports

Reported in EPA TSCA Inventory.

ISOEUGENOL Safety Profile

Moderately toxic by ingestion. A moderate human skin irritant. Human mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and fumes. See also EUGENOL.

ISOEUGENOL's Hazard Codes:Xn
ISOEUGENOL's Risk Statements:
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
43:May cause sensitization by skin contact
ISOEUGENOL's Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany:2

Product Name

ISOEUGENOL

Synthetic route

ISOEUGENOL Chemical Properties

ISOEUGENOL Uses

ISOEUGENOL Toxicity Data With Reference

ISOEUGENOL Consensus Reports

ISOEUGENOL Safety Profile

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