Basic information
- Standard SMILES
CC(=O)c1ccccc1O- InChIKey
JECYUBVRTQDVAT-UHFFFAOYSA-N- Molecular formula
- C8H8O2
- Average molar mass
- 136.15 g/mol
- Monoisotopic mass
- 136.0524295
Overview
2-acetylphenol is a monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group.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.
Names & identifiers
- Preferred name
- 2'-Hydroxyacetophenone
- IUPAC
- 1-(2-hydroxyphenyl)ethanone
- English name
- 2'-Hydroxyacetophenone
- Molecular formula
- C8H8O2
- Molecular weight
- 136.15
Names & synonyms
2'-Hydroxyacetophenone118-93-41-(2-Hydroxyphenyl)ethanone2-AcetylphenolO-HYDROXYACETOPHENONE1-(2-Hydroxyphenyl)Ethan-1-Oneo-Hydroxyphenyl methyl ketone2-Hydroxyphenyl methyl ketoneEthanone, 1-(2-hydroxyphenyl)-Methyl 2-hydroxyphenyl ketoneFEMA No. 3548DTXSID7040285
Show more names
2-HYDROXYACETOPHENONE2-HYDROXYACETAMIDEFEMA 3548usafke-20USAF ke-20AKOS 90575O-ACETOPHENOL
NSC-169333E533Z76W0DTXCID5020285CHEBI:145716RefChem:908432204-288-02-hydroxy-1-phenyl-ethanone2-hydroxy-1-phenylethanone
Database identifiers
- CAS
118-93-4- PubChem CID
- 8375
- DTXSID
DTXSID7040285- ChEMBL
CHEMBL3187012- ChEBI
CHEBI:145716- UNII
- 3E533Z76W0
- EC Number
- 204-288-0
- Nikkaji
- J5.308B
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 131
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aromatic Ketones
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (2-Hydroxyacetophenone) -> IFRA transparency List
LogP1.92
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.127-1.133
Flavoring AgentsEU Flavoring substances
Solubility
slightly soluble in water; soluble in fat
miscible (in ethanol)
Boiling Point
213.00 °C. @ 717.00 mm Hg
215-220 °C
Melting Point4 - 6 °C
Vapor Pressure0.00748 [mmHg]
Refractive Index1.556-1.560
Physicochemical properties
- Melting point
- 3 · 3-6 °C(lit.)
- Boiling point
- 213 °C717 · 213 °C717 mm Hg(lit.)
- Density
- 1.131 g/mL · 1.131 g/mL at 25 °C(lit.)
- vapor density
- 4.7 · 4.7 (vs air)
- vapor pressure
- 0.2 mm · ~0.2 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.558(lit.)
- FEMA
- 3548 · 3548 | 2-HYDROXYACETOPHENONE
- FLAVIS Number
- 7.124 · 07.124 | 2-Hydroxyacetophenone
- Flash point
- 230 °F · >230 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.2 g/l · 0.2g/l
- form
- Liquid
- pka
- 10.06 · 10.06(at 25℃)
- color
- Clear yellow to brown
- Odor
- 10 % · at 10.00 % in dipropylene glycol. phenolic sweet hawthorn tobacco honey herbal
- Odor Type
- phenolic
- biological source
- synthetic
- explosive limit
- 0.98 · 0.98-11.8%(V)
- Water Solubility
- slightly soluble
- JECFA Number
- 727 · 727
- BRN
- 386123 · 386123
- Henry's Law Constant
- 1 · 1.0×100 mol/(m3Pa) at 25℃, Ji et al. (2008)
- Major Application
- flavors and fragrances
- InChI
- 1S/C8H8O2/c1-6(9)7-4-2-3-5-8(7)10/h2-5,10H,1H3
- InChIKey
- JECYUBVRTQDVAT-UHFFFAOYSA-N
- SMILES
- CC(=O)c1ccccc1O
- LogP
- 1.92 · 1.92-1.97 at 25℃
- Dissociation constant
- 10.06 · 10.06-10.25 at 20-25℃
- CAS DataBase Reference
- 118 · 118-93-4(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 2 · 2-HYDROXYACETOPHENONE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3 E533Z76W0 · 3E533Z76W0
- NIST Chemistry Reference
- 1 · Ethanone, 1-(2-hydroxyphenyl)-(118-93-4)
- EPA Substance Registry System
- 2 · 2'-Hydroxyacetophenone (118-93-4)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-36/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- RTECS
- 8575000 · AM8575000
- F
- 8 · 8
- Hazard Note
- Harmful/Irritant
- TSCA
- TSCA listed
- HS Code
- 29145000 · 29145000
- Storage Class
- 10 · 10 - Combustible liquids
- Toxicity
- 50 orally · LD50 orally in Rabbit: 2127 mg/kg LD50 dermal Rat > 2000 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 70.5% (177 of 251) of all reports.
Warning
H302 (10.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 251 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Ethanone, 1-(2-hydroxyphenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 1-(2-hydroxyphenyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 1-(2-hydroxyphenyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 11-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/19594
Ethanone, 1-(2-hydroxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Intraperitoneal LD50 (mouse) = 100 mg/kg; [RTECS] Safe when used as a flavoring agent in food; [EFSA] A skin and strong eye irritant; Depending on severity of exposure, effects range from mild irritation to destruction of tissue; [Sigma-Aldrich MSDS] See Acetophenone.
Hazard Classes and CategoriesAcute Tox. 4 (10.4%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 8
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AM8575000
- hs_code
- 29145000
- Toxicity
- LD50 orally in Rabbit: 2127 mg/kg LD50 dermal Rat > 2000 mg/kg
- risk_code
- 36/37/38-36/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Harmful/Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
Metabolism/Metabolites2'-Hydroxyacetophenone is a known human metabolite of 2'-methoxyacetophenone.
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
U.S. Production2023: 250,000 - <550,000 lb
Consumer UsesOther
Industry UsesOther
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Ethanone, 1-(2-hydroxyphenyl)-: ACTIVE
Applications
Description2'-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
OccurrenceReported 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
Uses2'-Hydroxyacetophenone is used as pharmaceutical intermediate.
Uses2’Hydroxyacetophenone is a phenolic compound used in the synthesis of potential anti-myobacterial and anticancer agents.
General Description2'-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.
Preparation methods
PreparationPreparation by Fries rearrangement of phenyl acetate, with Lewis acids aluminium chloride.
Upstream & downstream products
Downstream products
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes
DefinitionChEBI: 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.
Related reactions
166 records
Linked notes
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