3,4-Dihydroxyphenylessigsure
DOPAC · 2-(3,4-dihydroxyphenyl)acetic acid · 3,4-Dihydroxybenzeneacetic acid · N,N-DIMETHYL-P-PHENYLENEDIAMINE SULFATE · Dihydroxyphenylacetic acid · 3,4-DihydroxyphenyL · HOMOPROTOCATECHUIC ACID · ba2773
Identifikatoren & physikalische Daten
| CAS No. | 102-32-9 |
|---|---|
| Summenformel | C8H8O4 |
| Durchschnittliche Molmasse | 168,15 g/mol |
| Monoisotopische Masse | 168,04225874 g/mol |
| SMILES | O=C(O)Cc1ccc(O)c(O)c1 |
| InChIKey | CFFZDZCDUFSOFZ-UHFFFAOYSA-N |
| PubChem CID | 547 |
| ChEMBL | CHEMBL1284 |
| ChEBI | CHEBI:41941 |
| EC No. | 203-024-1 |
| DTXSID | DTXSID9074430 |
| Lokaler Name | 3,4-Dihydroxyphenylessigsure |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 77,8 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 168 |
| Stoffklassen | Other Classes -> Organic Acids |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 0.98 |
| Löslichkeit | 4 mg/mLwater: soluble50mg/mL, clear, almost colorlessSoluble in water and methanol. |
| Schmelzpunkt | 168 °C127-130 °C (lit.) |
| Dampfdruck | 0.00000082 [mmHg] |
| Physical Description | Off-white powder[Alfa Aesar MSDS]Solid |
| Dissociation Constants | 4.25 (at 30 °C) |
| Collision Cross Section | 139.9 Ų [M+Na-2H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]125.7 Ų [M-H2O-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]140.4 Ų [M-2H+Na]- |
| Siedepunkt | 257.07°C (rough estimate) |
| Dichte | 1.3037 (rough estimate) |
| Brechungsindex | 1.5090 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| pKa (Säurekonstante) | 4.42±0.10(Predicted) |
| Aggregatzustand | Powder, Crystals or Lumps |
| Farbe | White to off-white |
| BRN | 2211017 |
| InChI | InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) |
| InChIKey | CFFZDZCDUFSOFZ-UHFFFAOYSA-N |
| SMILES | C1(CC(O)=O)=CC=C(O)C(O)=C1 |
| LogP (Verteilungskoeffizient) | 0.980 |
| CAS Datenbank | 102-32-9(CAS DataBase Reference) |
| NIST chemische Informationen | Acetic acid, (3,4-dihydroxyphenyl)-,(102-32-9) |
| EPA chemische Informationen | 3,4-Dihydroxyphenylacetic acid (102-32-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): 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 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Gefahrenübersicht | A skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| F | 10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29182900 |
| RTECS-Nr. | AH0590000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2 |
Anwendungen & Verwendung
Beschreibung
3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine. Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is 3-methoxytyramine (3-MT). Both of these substances are degraded to form homovanillic acid (HVA). Both degradations involve the enzymes monoamine oxidase (MAO) and catechol-O-methyl transferase (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is norepinephrine (noradrenaline).DOPAC can be oxidized by hydrogen peroxide, leading to the formation of toxic metabolites which destroy dopamine storage vesicles in the substantia nigra. This may contribute to the failure of levodopa treatment of Parkinson's disease. A MAO-B inhibitor such as selegiline or rasagiline can prevent this from happening.wikipedia
Verwenden
3,4-Dihydroxyphenylacetic Acid is a metabolite of Dopamine (D533782).