4-Hydroxy-3-methoxystyrene

Description

4-Vinylguaiacol, or 2-methoxy-4-vinylphenol, is the aroma component of buckwheat. The aroma can remind people of apples, spices, peanuts, wine, clove, or curry. Brewing yeasts such as Saccharomyces delbrueckii produce 4-vinylguaiacol to give wheat beers their clove flavor.

Chemical properties

2-Methoxy-4-vinylphenol has a powerful, spicy, apple, rum, roasted peanut aroma.

Occurrence

Reported found among the steam-distillable phenols from the alcoholic fermentation of cereal grains, especially corn; probably formed from ferulic acid. Reported found in tobacco, beans, coffee, malt, apple, grapefruit juice, grapes, raspberry, strawberry, asparagus, kohlrabi, carrot, celery, tomato, rye bread, smoked fish, cured pork, beer, cognac, rum, cider, sherry, grape wines, coffee, tea, peanut, popcorn,soybean, passion fruit, beans,starfruit,sesame seed, mango, cauliflower, tamarind, fig, corianderseed, rice, quince, rhubarb, dill, lovage root, corn oil, sweet corn, malt, wort, Texas sage, okra, cuttlefish and Chinese quince.

The Uses of 4-Hydroxy-3-methoxystyrene

p-Vinylguaiacol is an aromatic substance and one of the compounds responsible for the natural aroma of buckwheat. It is also one of the major pyrolytic products of (E)-N-[(4-hydroxy-3-methoxy)-phenethyl]-3-[(3-methoxy-4-O-β-D-glucopyranosyloxy) phenyl] acrylamide; a new gycloside in tobacco.

What are the applications of Application

2-Methoxy-4-vinylphenol is an aromatic substance resembling buckwheat

Definition

ChEBI: A member of the class of phenols that is guaiacol in which the hydrogen para- to the hydroxy group is replaced by a vinyl group.

Preparation

From vanillin by reacting with acetic anhydride and sodium acetate yielding 3-methoxy-4-hydroxycinnamic acid on sub sequent hydrolysis; the latter, heated with quinoline in the presence of hydroquinone, is decarboxylated to 4-vinylguaiacol.

Aroma threshold values

Detection; 0.75 to 3 ppb

General Description

2-Methoxy-4-vinylphenol is one of the key volatile aroma compounds of buckwheat and okra.