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97-54-1

Basic Information
CAS No.: 97-54-1
Name: ISOEUGENOL
Article Data: 66
Molecular Structure:
Molecular Structure of 97-54-1 (ISOEUGENOL)
Formula: C10H12O2
Molecular Weight: 164.204
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;
EINECS: 202-590-7
Density: 1.074 g/cm3
Melting Point: -10 °C
Boiling Point: 266.64 °C at 760 mmHg
Flash Point: 122.907 °C
Appearance: light yellow-green viscous liquid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38-43
Safety: 26-36-36/37
PSA: 29.46000
LogP: 2.43390
Synthetic route
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%

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

97-54-1

2-methoxy-4-propenylphenol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
1530-32-1

ethyltriphenylphosphonium bromide

121-33-5

vanillin

97-54-1

2-methoxy-4-propenylphenol

Conditions
ConditionsYield
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
ConditionsYield
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

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

A

97-54-1

2-methoxy-4-propenylphenol

B

isoeugenyl pivaloate

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
With 10% nickel/activated carbon; hydrogen In tetrahydrofuran at 150℃; under 15001.5 Torr; for 1h; Autoclave;A 9.4%
B 12.2%
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    Isoeugenol CAS No:97-54-1

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Chemistry

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

Uses

ISOEUGENOL's used as  flavor intermediates.

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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