ChemicalBook Product Catalog Flavors and fragrances Synthetic fragrances Phenols, ethers and epoxides Phenols PROPENYL GUAETHOL

PROPENYL GUAETHOL

Product NamePROPENYL GUAETHOL
CAS94-86-0
MFC11H14O2
MW178.23
EINECS202-370-0
MOL File94-86-0.mol

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
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.
Water Solubility	Insoluble in water
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
biological source	synthetic
JECFA Number	1264
Cosmetics Ingredients Functions	PERFUMING
InChI	1S/C11H14O2/c1-3-5-9-6-7-11(13-4-2)10(12)8-9/h3,5-8,12H,4H2,1-2H3/b5-3+
InChIKey	RADIRXJQODWKGQ-HWKANZROSA-N
SMILES	CCOc1ccc(\C=C\C)cc1O
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
TSCA	TSCA listed
HS Code	2909500090
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Propenylguaethol has a vanilla-like odor and flavor.

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 .

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

Preparation Products And Raw materials

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