2'-Hydroxyacetophenone Property

Melting point:

3-6 °C(lit.)

Boiling point:

213 °C717 mm Hg(lit.)

Density 

1.131 g/mL at 25 °C(lit.)

vapor density 

4.7 (vs air)

vapor pressure 

~0.2 mm Hg ( 20 °C)

refractive index 

n20/D 1.558(lit.)

FEMA 

3548 | 2-HYDROXYACETOPHENONE

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

0.2g/l

form 

Liquid

pka

10.06(at 25℃)

color 

Clear yellow to brown

Odor

at 10.00 % in dipropylene glycol. phenolic sweet hawthorn tobacco honey herbal

Odor Type

phenolic

explosive limit

0.98-11.8%(V)

Water Solubility 

slightly soluble

JECFA Number

727

BRN 

386123

LogP

1.92-1.97 at 25℃

Dissociation constant

10.06-10.25 at 20-25℃

CAS DataBase Reference

118-93-4(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(2-hydroxyphenyl)-(118-93-4)

EPA Substance Registry System

2'-Hydroxyacetophenone (118-93-4)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

AM8575000

F 

8

Hazard Note 

Harmful/Irritant

TSCA 

Yes

HS Code 

29145000

Toxicity

LD50 orally in Rabbit: 2127 mg/kg LD50 dermal Rat > 2000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2'-Hydroxyacetophenone Chemical Properties,Usage,Production

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.