2'-Hydroxyacetophenone

Chemical properties

2-Hydroxyacetophenone is a clear yellow to brown liquid that has a sweet, heavy floral, herbaceous odor, reminiscent of mown hay or hawthorn.

Occurrence

Reported found in beef, cassia oil, cocoa, cocoa powder, coffee, Jamaican rum, tomato, Scotch whiskey, sherry, tea, mountain papaya, papaya, roasted almond and black choke berry

The Uses of 2'-Hydroxyacetophenone

2'-Hydroxyacetophenone is used as pharmaceutical intermediate.

The Uses of 2'-Hydroxyacetophenone

2’Hydroxyacetophenone is a phenolic compound used in the synthesis of potential anti-myobacterial and anticancer agents.

Preparation

Preparation by Fries rearrangement of phenyl acetate, with Lewis acids aluminium chloride.

Definition

ChEBI: 2'-Hydroxyacetophenone is a monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group. It has a role as a flavouring agent. It is a monohydroxyacetophenone and a member of phenols.

Aroma threshold values

Detection: 5.5 ppm; aroma characteristics at 2.0%: phenolic, sharp, benzaldehyde, cherry pit, tropical, melon with a tobacco afternote

Taste threshold values

Taste characteristics at 5.0 ppm: naphthyl, cinnamon, cherry pit, coumarin, phenolic, tobacco and honey.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 377, 1983 DOI: 10.1016/S0040-4039(00)81412-4

General Description

2'-Hydroxyacetophenone, also known as O-acetylphenol, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2'-Hydroxyacetophenone is a sweet, hawthorne, and herbal tasting compound. 2'-Hydroxyacetophenone has been detected, but not quantified in, several different foods, such as green tea, arabica coffees (Coffea arabica), chinese cinnamons (Cinnamomum aromaticum), cocoa beans (Theobroma cacao), and cocoa and cocoa products. This could make 2'-hydroxyacetophenone a potential biomarker for the consumption of these foods.