Grundinformationen
- Standard-SMILES
CC(=O)c1ccc(O)cc1- InChIKey
TXFPEBPIARQUIG-UHFFFAOYSA-N- Summenformel
- C8H8O2
- Durchschnittliche Molmasse
- 136,15 g/mol
- Monoisotopische Masse
- 136,0524295
Überblick
4'-hydroxyacetophenone is a monohydroxyacetophenone carrying a hydroxy substituent at position 4'. It has a role as a mouse metabolite, a plant metabolite and a fungal metabolite.
Namen und Bezeichner
- Bevorzugter Name
- 4'-Hydroxyacetophenone
- IUPAC
- 1-(4-hydroxyphenyl)ethanone
- Lokaler Name
- 4'-Hydroxyacetophenon
- Englischer Name
- 4'-Hydroxyacetophenone
- Summenformel
- C8H8O2
- Molmasse
- 136.15
Namen und Synonyme
4'-Hydroxyacetophenone99-93-44-Hydroxyacetophenone1-(4-Hydroxyphenyl)ethanoneP-HYDROXYACETOPHENONE4-Acetylphenolp-Hydroxyphenyl methyl ketoneEthanone, 1-(4-hydroxyphenyl)-Methyl p-hydroxyphenyl ketonepara-Hydroxyacetophenone(4-Hydroxyphenyl)ethan-1-oneHYDROXYACETOPHENONE, PARA
Weitere Namen anzeigen
PiceolPOBP-HYDROXYBENZOPHENONEACETYLPHENOLp-Acetylphenolp-Oxyacetophenone
DTXSID0029133G1L3HT4CMHNSC-3698DTXCID209133FEMA NO. 4330CHEBI:28032RefChem:523982CHEBI:24668
Datenbank-Bezeichner
- CAS
99-93-4- PubChem CID
- 7469
- DTXSID
DTXSID0029133- ChEMBL
CHEMBL201083- ChEBI
CHEBI:28032- UNII
- G1L3HT4CMH
- EC Number
- 202-802-8
- Nikkaji
- J2.233.995H、J4.976J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,4
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 123
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Aromatic Ketones
CosmeticsCosmetic ingredients (Hydroxyacetophenone) -> CIR (Cosmetic Ingredient Review)
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (4-Hydroxyacetophenone) -> IFRA transparency List
LogP1.45
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
Practically insoluble or insoluble in water
Soluble (in ethanol)
Vapor Pressure0.00748 [mmHg]
Physical Description
Other Solid; Liquid
White or off-white powder; [Alfa Aesar MSDS]
White to off-white crystals, chips or chunks; Slight berry to sweet balsam aroma
Collision Cross Section125.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0029133]
Physikochemische Eigenschaften
- Schmelzpunkt
- 132 · 132-135 °C(lit.)
- Siedepunkt
- 147 · 147-148 °C3 mm Hg(lit.)
- Dichte
- 1.109 · 1.109
- Dampfdruck
- 0.002 Pa · 0.002Pa at 20℃
- Brechungsindex
- 1.5577 · 1.5577 (estimate)
- FEMA
- 4330 · 4330 | 4-HYDROXYACETOPHENONE
- Flammpunkt
- 166 °C · 166 °C
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 0.1 g/mL, · methanol: 0.1 g/mL, clear
- Aggregatzustand
- Crystalline Powder
- pka
- 8.05 · 8.05(at 25℃)
- Farbe
- Almost white to beige
- Wichte
- 1.109 · 1.109
- Geruch (Odor)
- 10 % · at 10.00 % in dipropylene glycol. mild sweet hawthorn balsam mimosa
- Geruchsart
- floral
- Wasserlöslichkeit
- 10 g/L · 10 g/L (22 ºC)
- JECFA Number
- 2040 · 2040
- BRN
- 774355 · 774355
- Kosmetik-Inhaltsstoffe Funktionen
- ANTIOXIDANT
- InChI
- 1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3
- InChIKey
- TXFPEBPIARQUIG-UHFFFAOYSA-N
- SMILES
- CC(=O)c1ccc(O)cc1
- LogP
- 1.35 at · 1.35 at 25℃
- CAS Datenbank
- 99 · 99-93-4(CAS DataBase Reference)
- NIST chemische Informationen
- 4 · Acetophenone, 4'-hydroxy-(99-93-4)
- EPA chemische Informationen
- 4 · 4-Hydroxyacetophenone (99-93-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 3.9% (11 of 279) of reports.
Warning
H302 (45.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, 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 279 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Ethanone, 1-(4-hydroxyphenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 1-(4-hydroxyphenyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 1-(4-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: 12-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11354
Ethanone, 1-(4-hydroxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummarySafe when used as a flavoring agent in food; [EFSA] A skin and strong eye irritant; Toxic by ingestion; [Alfa Aesar MSDS] See 2'-Hydroxyacetophenone, 3'-Hydroxyacetophenone, and Acetophenone.
EPA Safer ChemicalChemical: 4-Hydroxyacetophenone
Hazard Classes and CategoriesAcute Tox. 4 (45.2%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29145000
- RTECS-Nr.
- PC4959775
- risk_code
- 36/37/38-22
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36/37-37/39-24/25-22-36
- Speicherklasse
- 13 - Non Combustible Solids
- Hazard Classifications
- Aquatic Chronic 3Eye Irrit. 2
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites4-Hydroxyacetophenone has known human metabolites that include (2S,3S,4S,5R)-6-(4-acetylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid.
Verwendung und Herstellung
Uses
CIR ingredient: Hydroxyacetophenone
A flavoring agent that naturally occurs in cloudberry, coffee, mango, sherry, and in trace amounts in cranberry; [EFSA] Used as an intermediate for plastics, cosmetics, and pharmaceuticals; [ECHA REACH Registrations]
U.S. Production2023: 1,000,000 - <5,000,000 lb
Consumer UsesAntioxidant
Industry UsesAntioxidant
Use Classification
EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants
Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
All Other Chemical Product and Preparation Manufacturing
Ethanone, 1-(4-hydroxyphenyl)-: ACTIVE
Anwendungen
OccurrenceReported found in cloudberry, coffee, cranberry, mango, sherry, and wort.
Verwenden4-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.
Darstellung
synthetischePreparation by Fries rearrangement of phenyl acetate with Lewis acidsaluminium chloridein nitrobenzene at 20–25° or at 50–60°in chlorobenzene between 45° and 65°, sealed tube and subjected to high power microwave irradiation for 2 min only (36%) in nitroethane at 60° (44%)in carbon disulfide at 45° (40%)in petroleum ether at 50° (20%) but between 130° and 175° (40–60%)aluminium chloride–sodium chloride mixture at 240–250° (10%) boron trifluoride at 90° (56%) scandium tris(trifluoromethanesulfonate), in nitromethane, at 50° (39%)titanium tetrachloride at 90–100° (34%)ferric chloride at 65° (25%)zinc chloride at 125° (8%) hydrofluoric acid, between 20° and 100° (94%) polyphosphoric acid, between 20° and 100° (69%) (50–53%)(44%)Nafion-XR 500, sulfonic acid type at 100°ZSM-5, in sulfolane, at 180° (28%)H-ZSM-5 at 400° or at 210° (6%) H-Nu-2 at 170° (15%)HY (Si/Al = 3) or fluorided alumina (Al2O3-F; 3 % wt. F), at 400°.
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Ergänzende Hinweise
DefinitionChEBI: A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.
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