2'-Hydroxyacetophenone
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Grundinformationen
- CAS
118-93-4- Standard-SMILES
CC(=O)c1ccccc1O- InChIKey
JECYUBVRTQDVAT-UHFFFAOYSA-N- Summenformel
- C8H8O2
- Durchschnittliche Molmasse
- 136,15 g/mol
- Monoisotopische Masse
- 136,0524295
Überblick
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is a monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group.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.
Namen und Bezeichner
- Bevorzugter Name
- 2'-Hydroxyacetophenone
- IUPAC
- 1-(2-hydroxyphenyl)ethanone
- Englischer Name
- 2'-Hydroxyacetophenone
- Summenformel
- C8H8O2
- Molmasse
- 136.15
Namen und Synonyme
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
Weitere Namen anzeigen
2-HYDROXYACETOPHENONE2-HYDROXYACETAMIDEFEMA 3548usafke-20USAF ke-20AKOS 90575O-ACETOPHENOL
NSC-169333E533Z76W0DTXCID5020285CHEBI:145716RefChem:908432204-288-02-hydroxy-1-phenyl-ethanone2-hydroxy-1-phenylethanone
Datenbank-Bezeichner
- CAS
118-93-4- PubChem CID
- 8375
- DTXSID
DTXSID7040285- ChEMBL
CHEMBL3187012- ChEBI
CHEBI:145716- UNII
- 3E533Z76W0
- EC Number
- 204-288-0
- Nikkaji
- J5.308B
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 1,9
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 131
Experimentelle und physikochemische Eigenschaften
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
Physikochemische Eigenschaften
- Schmelzpunkt
- 3 · 3-6 °C(lit.)
- Siedepunkt
- 213 °C717 · 213 °C717 mm Hg(lit.)
- Dichte
- 1.131 g/mL · 1.131 g/mL at 25 °C(lit.)
- Dampfdichte
- 4.7 · 4.7 (vs air)
- Dampfdruck
- 0.2 mm · ~0.2 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.558(lit.)
- FEMA
- 3548 · 3548 | 2-HYDROXYACETOPHENONE
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 0.2 g/l · 0.2g/l
- Aggregatzustand
- Liquid
- pka
- 10.06 · 10.06(at 25℃)
- Farbe
- Clear yellow to brown
- Geruch (Odor)
- 10 % · at 10.00 % in dipropylene glycol. phenolic sweet hawthorn tobacco honey herbal
- Geruchsart
- phenolic
- Biologische Quelle
- synthetic
- Explosionsgrenze
- 0.98 · 0.98-11.8%(V)
- Wasserlöslichkeit
- 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℃
- CAS Datenbank
- 118 · 118-93-4(CAS DataBase Reference)
- NIST chemische Informationen
- 1 · Ethanone, 1-(2-hydroxyphenyl)-(118-93-4)
- EPA chemische Informationen
- 2 · 2'-Hydroxyacetophenone (118-93-4)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
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%)
Toxikologische Informationen
Adverse EffectsDermatotoxin - Skin burns.
Sicherheitsdaten
- F
- 8
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29145000
- RTECS-Nr.
- AM8575000
- risk_code
- 36/37/38-36/38
- Toxizität
- LD50 orally in Rabbit: 2127 mg/kg LD50 dermal Rat > 2000 mg/kg
- hazard_code
- Xi
- hazard_note
- Harmful/Irritant
- safety_code
- 26-36-37/39
- Speicherklasse
- 10 - Combustible liquids
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites2'-Hydroxyacetophenone is a known human metabolite of 2'-methoxyacetophenone.
Cellular LocationsCytoplasm
Verwendung und Herstellung
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
Anwendungen
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
Verwenden2'-Hydroxyacetophenone is used as pharmaceutical intermediate.
Darstellung
synthetischePreparation by Fries rearrangement of phenyl acetate, with Lewis acids aluminium chloride.
Vor- und nachgelagerte Produkte
Nachgelagerte Produkte
Ergänzende Hinweise
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.
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