PROPENYL GUAETHOL
PROPENYL GUAETHOL
  • CAS No.:94-86-0
Other grades of this product :
PROPENYL GUAETHOL Basic information
Product Name:PROPENYL GUAETHOL
Synonyms:VANITROPE;TRANS-2-ETHOXY-5-(1-PROPENYL)PHENOL;PROPENYL GUAETHOL;2-ETHOXY-5-(1-PROPENYL)PHENOL;2-ETHOXY-5-PROP-1-ENYLPHENOL;2-ETHOXY-5-PROPENYLPHENOL;5-PROPENYLGUAETHOL;6-ETHOXY-M-ANOL
CAS:94-86-0
MF:C11H14O2
MW:178.23
EINECS:202-370-0
Product Categories:Alphabetical Listings;Flavors and Fragrances;O-P
Mol File:94-86-0.mol
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
form powder to crystal
pka10.02±0.10(Predicted)
color White to Almost white
JECFA Number1264
InChIKeyRADIRXJQODWKGQ-HWKANZROSA-N
CAS DataBase Reference94-86-0(CAS DataBase Reference)
EPA Substance Registry SystemPhenol, 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 Information
ProviderLanguage
SigmaAldrich English
PROPENYL GUAETHOL Usage And Synthesis
Chemical PropertiesFree-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 PropertiesPROPENYL 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 PropertiesPropenylguaethol has a vanilla-like odor and flavor.
Usestrans-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.
UsesArtificial vanilla flavoring, flavor enhancer.
PreparationBy 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 valuesDetection: 400 ppb. Aroma characteristics at 1.0%: vanilla, sweet, spicy, slightly phenolic with a heliotropine- like creaminess.
Taste threshold valuesTaste 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 ActionsTaste at 25 ppm
PROPENYL GUAETHOL Preparation Products And Raw materials
Raw materialsAllylbenzene
Preparation ProductsEthyl vanillin-->ISOEUGENOL

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