Grundinformationen
- Standard-SMILES
O=C(O)Cc1ccc(O)cc1- InChIKey
XQXPVVBIMDBYFF-UHFFFAOYSA-N- Summenformel
- C8H8O3
- Durchschnittliche Molmasse
- 152,15 g/mol
- Monoisotopische Masse
- 152,04734412
Überblick
4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a mouse metabolite, a plant metabolite, a fungal metabolite and a human metabolite. It is a monocarboxylic acid and a member of phenols. It is functionally related to an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate.
Namen und Bezeichner
- Bevorzugter Name
- Hydroxyphenylacetic acid
- IUPAC
- 2-(4-hydroxyphenyl)acetic acid
- Lokaler Name
- p-Hydroxyphenylessigsure
- Englischer Name
- 4-Hydroxyphenylacetic acid
- Summenformel
- C8H8O3
- Molmasse
- 152.15
Namen und Synonyme
4-hydroxyphenylacetic acid156-38-7p-hydroxyphenylacetic acid(4-Hydroxyphenyl)acetic acid4-Hydroxybenzeneacetic acidbenzeneacetic acid, 4-hydroxy-(p-Hydroxyphenyl)acetic acid4-CarboxymethylphenolParahydroxy phenylacetic acidAcetic acid, (p-hydroxyphenyl)-3J9SHG0RCNNSC-25066
Weitere Namen anzeigen
2-(4-hydroxyphenyl)acetic acidPHPA4-Hydroxyphenylacetic4-hydrophenylacetic acid4-hydroxybenzeneaceticacidNSC 27460
NSC-27460DTXSID5059745CHEBI:18101para-hydroxyphenylacetic acidRefChem:524062DTXCID6035023205-851-3Hydroxyphenylacetic acid
Datenbank-Bezeichner
- CAS
156-38-7- PubChem CID
- 127
- DTXSID
DTXSID5059745- ChEMBL
CHEMBL1772- ChEBI
CHEBI:18101- UNII
- 3J9SHG0RCN
- EC Number
- 205-851-3
- Nikkaji
- J5.873D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,8
- Polarare Oberfläche (TPSA)
- 57,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 136
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Other Aromatic Compounds
SpringerMaterials PropertiesFusion temperature
LogP
0.75
1.26
Solubility60.7 mg/mL
Melting Point148 - 150 °C
Vapor Pressure0.0000555 [mmHg]
Physical Description
Off-white crystalline powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section
126.65 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
135.22 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
128.6 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
128.9 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 148 · 148-151 °C(lit.)
- Siedepunkt
- 234.6 °C · 234.6°C (rough estimate)
- Dichte
- 1.2143 · 1.2143 (rough estimate)
- Dampfdruck
- 0.007 Pa · 0.007Pa at 25℃
- Brechungsindex
- 1.4945 · 1.4945 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- 50 g/l · 50g/l
- pka
- 4.5 · 4.50±0.10(Predicted)
- Aggregatzustand
- Crystalline Powder
- Farbe
- White to cream or light tan
- PH
- 2 · 2.0-2.4 (30g/l, H2O, 20℃)
- Wasserlöslichkeit
- Soluble in dimethyl sulfoxide and methanol. Slightly soluble in water.
- BRN
- 1448766 · 1448766
- InChI
- 1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
- InChIKey
- XQXPVVBIMDBYFF-UHFFFAOYSA-N
- SMILES
- OC(=O)Cc1ccc(O)cc1
- LogP
- 0.75 at · 0.75 at 25℃
- CAS Datenbank
- 156 · 156-38-7(CAS DataBase Reference)
- NIST chemische Informationen
- 4 · Benzeneacetic acid, 4-hydroxy-(156-38-7)
- EPA chemische Informationen
- 4 · Benzeneacetic acid, 4-hydroxy- (156-38-7)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (97%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 233 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Benzeneacetic acid, 4-hydroxy-
Status: Cease Manufacture Update: 01-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22446
(4-Hydroxyphenyl)-acetic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryIntraperitoneal LD50 (mouse) = 3,500 mg/kg; [RTECS] An irritant; [Alfa Aesar MSDS] See Phenylacetic acid.
Hazard Classes and CategoriesSkin Irrit. 2 (97%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29182990
- RTECS-Nr.
- AI2680000
- risk_code
- 36/37/38
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36-24/25
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites4-hydroxyphenylacetic acid has known human metabolites that include 2-Phenylacetic acid.
MeSH Pharmacological ClassificationSubstances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Tissue LocationsBladder
Cellular LocationsCytoplasm
Metabolite PathwaysAlkaptonuria
Verwendung und Herstellung
General Manufacturing InformationBenzeneacetic acid, 4-hydroxy-: ACTIVE
Anwendungen
VerwendenA compound present in olive oil. An important fine chemical intermediate with broad prospects for application development.
Darstellung
synthetische4-Hydroxyphenylacetic acid is synthesized by diazotization and hydrolysis of 4-aminophenylacetic acid. 4-aminophenylacetic acid and alkali solution are prepared into sodium salt, and then sulfuric acid is added. Cool to 0°C, control the temperature at 0-5°C, and add sodium nitrate solution dropwise, and the reaction is completed for 0.5h. The obtained diazonium was added dropwise to dilute sulfuric acid at 90-95°C for about 1 hour, and the reaction was continued for 1 hour. The reaction solution was decolorized and filtered, cooled and extracted with ethyl acetate, and the extract was recovered with ethyl acetate to obtain 4-Hydroxyphenylacetic acid. The yield is about 85%.
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Ergänzende Hinweise
DefinitionChEBI: 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It derives from an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate.
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