Grundinformationen
- Standard-SMILES
O=C(O)Cc1ccc(O)c(O)c1- InChIKey
CFFZDZCDUFSOFZ-UHFFFAOYSA-N- Summenformel
- C8H8O4
- Durchschnittliche Molmasse
- 168,15 g/mol
- Monoisotopische Masse
- 168,04225874
Überblick
(3,4-dihydroxyphenyl)acetic acid is a dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine. It has a role as a human metabolite. It is a member of catechols and a dihydroxyphenylacetic acid. It is functionally related to a phenylacetic acid. It is a conjugate acid of a (3,4-dihydroxyphenyl)acetate.
Namen und Bezeichner
- Bevorzugter Name
- Dopac
- IUPAC
- 2-(3,4-dihydroxyphenyl)acetic acid
- Lokaler Name
- 3,4-Dihydroxyphenylessigsure
- Englischer Name
- 3,4-Dihydroxyphenylacetic acid
- Summenformel
- C8H8O4
- Molmasse
- 168.15
Namen und Synonyme
3,4-Dihydroxyphenylacetic acid102-32-9Dopac2-(3,4-DIHYDROXYPHENYL)ACETIC ACIDHomoprotocatechuic acidDopacetic acidBenzeneacetic acid, 3,4-dihydroxy-Acetic acid, (3,4-dihydroxyphenyl)-BA 2773KEX5N0R4N5NSC-73191DTXSID9074430
Weitere Namen anzeigen
N,N-DIMETHYL-P-PHENYLENEDIAMINE SULFATE3,4-DihydroxyphenyLba2773dopaceticacid
HMDB013363,4 Dihydroxyphenylacetic AcidRefChem:486240DTXCID3032676203-024-13,4-Dihydroxybenzeneacetic acidDihydroxyphenylacetic acid(3,4-DIHYDROXYPHENYL)ACETIC ACID
Datenbank-Bezeichner
- CAS
102-32-9- PubChem CID
- 547
- DTXSID
DTXSID9074430- ChEMBL
CHEMBL1284- ChEBI
CHEBI:41941- UNII
- KEX5N0R4N5
- EC Number
- 203-024-1
- Nikkaji
- J804D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,5
- Polarare Oberfläche (TPSA)
- 77,8 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 168
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LogP
0.98
0.98
Solubility4 mg/mL
Melting Point168 °C
Vapor Pressure0.00000082 [mmHg]
Physical Description
Off-white powder; [Alfa Aesar MSDS]
Solid
Dissociation Constants4.25 (at 30 °C)
Collision Cross Section
139.9 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
125.7 Ų [M-H2O-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
140.4 Ų [M-2H+Na]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 127 · 127-130 °C (lit.)
- Siedepunkt
- 257.07 °C · 257.07°C (rough estimate)
- Dichte
- 1.3037 · 1.3037 (rough estimate)
- Brechungsindex
- 1.509 · 1.5090 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- 50 mg/mL, · water: soluble50mg/mL, clear, almost colorless
- pka
- 4.42 · 4.42±0.10(Predicted)
- Aggregatzustand
- Powder, Crystals or Lumps
- Farbe
- White to off-white
- Wasserlöslichkeit
- Soluble in water and methanol.
- BRN
- 2211017 · 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
- 0.98 · 0.980
- CAS Datenbank
- 102 · 102-32-9(CAS DataBase Reference)
- NIST chemische Informationen
- Acetic acid, (3,4-dihydroxyphenyl)-,(102-32-9)
- EPA chemische Informationen
- 3 · 3,4-Dihydroxyphenylacetic acid (102-32-9)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (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.
Gefahrenhinweise
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Sicherheitsdaten
- F
- 10-23
- wgk
- 3
- hs_code
- 29182900
- RTECS-Nr.
- AH0590000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites3,4-dihydroxyphenylacetic acid has known human metabolites that include 3-hydroxyphenylacetic acid, 4-hydroxyphenylacetic acid, and Protocatehuic acid.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysAlkaptonuria
Verwendung und Herstellung
UsesA deaminated metabolite of LEVODOPA. [ChemIDplus]
Anwendungen
Beschreibung3,4-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
Verwenden3,4-Dihydroxyphenylacetic Acid is a metabolite of Dopamine (D533782).
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