2'-Hydroxyacetophenone

Description

2'-Hydroxyacetophenone is a flavouring ingredient. It is a typical flavour additive for cherry kernel, cinnamon, rum, tobacco, coumarin, and tropical fruit. Moreover, it can be used as the intermediate or raw material in organic synthesis. Specifically, this chemical may act as the raw material to prepare a Schiff's base al-alkoxide initiator that facilitates the controlled polymerization of DL-lactide.¹ This substance can also function as the effective component in balsamic compounds for fabricating taste modifying compositions.² Additionally, this chemical has been employed to react with benzoyl chloride for generating 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran, which exhibits good performance for treating cancer and other proliferative diseases such as psoriasis and restenosis.³

Reference

1. Bhaw-Luximon, A.; Jhurry, D.; Spassky, N., Controlled polymerization of DL-lactide using a Schiff's base al-alkoxide initiator derived from 2-hydroxyacetophenone. Polym. Bull. 2000, 44, 31-38.
2. Johann Wonschick; Clemens M. Putter; Keepe, E., TASTE MODIFYING COMPOSITIONS PCT WO 2016/103183 A1 2016.
3. Alexander J Bridges; Saltiel, A. R., 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders US Patent US5525625 1996.

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

Uses

2'-Hydroxyacetophenone is used as pharmaceutical intermediate.

Uses

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

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is a monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group.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.

Preparation

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

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.