PROPENYL GUAETHOL Chemical Properties

Melting point:

86-88 °C(lit.)

Boiling point:

116°C/2mmHg(lit.)

Density 

1.0196 (rough estimate)

refractive index 

1.5670 (estimate)

FEMA 

2922 | PROPENYLGUAETHOL

storage temp. 

2-8°C

Water Solubility 

Insoluble in water

solubility 

10% soluble in alcohol, 4 % soluble in Propylene glycol, 4 % soluble in Polysorbate 80, 20% soluble in Benzylalcohol, soluble in most perfume and flavor oils.

form 

powder to crystal

pka

10.02±0.10(Predicted)

color 

White to Almost white

Odor

at 10.00 % in dipropylene glycol. sweet vanilla woody tobacco spicy phenolic powdery

Odor Type

vanilla

JECFA Number

1264

InChIKey

RADIRXJQODWKGQ-HWKANZROSA-N

LogP

2.90

CAS DataBase Reference

94-86-0(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 2-ethoxy-5-(1-propenyl)- (94-86-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

2

RTECS 

SL3850000

HS Code 

2909500090

MSDS

• Language:English Provider:SigmaAldrich

PROPENYL GUAETHOL Usage And Synthesis

Chemical Properties

Free-flowing, white powder; odor and taste similar to vanilla, but much more powerful.Very soluble in fats, edible solvents, and essential oils; very slightly soluble in water.

Chemical Properties

PROPENYL GUAETHOL exists in (Z)- (mp 35–36°C), [876306-58-0], and in (E)- (mp 86°C), [63477-41-8] forms. The (E)-isomer has a sweet vanilla-like odor. Propenylguethol can be prepared from isosafrole by reaction with methylmagnesium chloride or by ethylation of isoeugenol followed by selective demethylation with alkali .

Chemical Properties

Propenylguaethol has a vanilla-like odor and flavor.

Uses

trans-2-Ethoxy-5-(1-propenyl)phenol was used in the synthesis of 2S-((E)-2-ethoxy-5-propenyl-phenoxy)-1-(3,4,5-trimethoxy-phenyl)-propane-1-one.

Uses

Artificial vanilla flavoring, flavor enhancer.

Definition

ChEBI: 2-Ethoxy-5-(1-propenyl)phenol is an aromatic ether.

Preparation

By alkaline hydrolysis of 1-ethoxy-2-methoxy-4-propenyl benzene in ethanol or methanol solution at 150 to 190°C under pressure; or in ethylene glycol solution at the same temperature under atmospheric pressure; by saponification and contemporary transposition of the double bond starting from 1-ethoxy-2-methoxy-4-allyl benzene.

Aroma threshold values

Detection: 400 ppb. Aroma characteristics at 1.0%: vanilla, sweet, spicy, slightly phenolic with a heliotropine- like creaminess.

Taste threshold values

Taste characteristics at 25 ppm: vanilla, spicy, sweet nutty, anisic with a biting creaminess.

Synthesis Reference(s)

Synthetic Communications, 21, p. 379, 1991 DOI: 10.1080/00397919108016759

Biochem/physiol Actions

Taste at 25 ppm

PROPENYL GUAETHOL(94-86-0)Related Product Information

• 4-ACETOXY-3-METHOXYCINNAMIC ACID
• 4-BENZYLOXY-3-METHOXYCINNAMIC ACID
• 1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE
• ISOEUGENYL PHENYLACETATE
• LUTEOLIN-4'-O-GLUCOSIDE
• PROPENYL GUAETHOL
• ELEUTHEROSIDE B
• 1-Benzyloxy-2-methoxy-4-propenylbenzene
• Guaiacol
• Vanillin
• 3-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)ACRYLIC ACID
• 2-methoxy-4-prop-1-enylphenetole
• (2E)-3-(4-ethoxy-3-methoxyphenyl)acrylic acid
• 3-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)-1-(5-FLUORO-2-HYDROXYPHENYL)PROP-2-EN-1-ONE
• 3-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)-1-(2-HYDROXY-5-METHYLPHENYL)PROP-2-EN-1-ONE
• 1-(4-CHLORO-2-HYDROXYPHENYL)-3-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)PROP-2-EN-1-ONE
• 1-(5-CHLORO-2-HYDROXYPHENYL)-3-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)PROP-2-EN-1-ONE
• 3-(4-ETHOXY-3-METHOXYPHENYL)-1-(2-NITROPHENYL)PROP-2-EN-1-ONE