Basic information
- Standard SMILES
O=C(O)Cc1ccc(O)c(O)c1- InChIKey
CFFZDZCDUFSOFZ-UHFFFAOYSA-N- Molecular formula
- C8H8O4
- Average molar mass
- 168.15 g/mol
- Monoisotopic mass
- 168.04225874
Overview
(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.
Names & identifiers
- Preferred name
- Dopac
- IUPAC
- 2-(3,4-dihydroxyphenyl)acetic acid
- English name
- 3,4-Dihydroxyphenylacetic acid
- Molecular formula
- C8H8O4
- Molecular weight
- 168.15
Names & synonyms
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
Show more names
N,N-DIMETHYL-P-PHENYLENEDIAMINE SULFATE3,4-DihydroxyphenyLba2773dopaceticacid
HMDB013363,4 Dihydroxyphenylacetic AcidRefChem:486240DTXCID3032676203-024-13,4-Dihydroxybenzeneacetic acidDihydroxyphenylacetic acid(3,4-DIHYDROXYPHENYL)ACETIC ACID
Database identifiers
- CAS
102-32-9- PubChem CID
- 547
- DTXSID
DTXSID9074430- ChEMBL
CHEMBL1284- ChEBI
CHEBI:41941- UNII
- KEX5N0R4N5
- EC Number
- 203-024-1
- Nikkaji
- J804D
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 168
Experimental & physicochemical properties
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]-
Physicochemical properties
- Melting point
- 127 · 127-130 °C (lit.)
- Boiling point
- 257.07 °C · 257.07°C (rough estimate)
- Density
- 1.3037 · 1.3037 (rough estimate)
- refractive index
- 1.509 · 1.5090 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 50 mg/mL, · water: soluble50mg/mL, clear, almost colorless
- pka
- 4.42 · 4.42±0.10(Predicted)
- form
- Powder, Crystals or Lumps
- color
- White to off-white
- Water Solubility
- 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 DataBase Reference
- 102 · 102-32-9(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-4
- FDA UNII
- 5 N0R4N5 · KEX5N0R4N5
- NIST Chemistry Reference
- Acetic acid, (3,4-dihydroxyphenyl)-,(102-32-9)
- EPA Substance Registry System
- 3 · 3,4-Dihydroxyphenylacetic acid (102-32-9)
- UNSPSC Code
- 77101502 · 77101502
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- RTECS
- 590000 · AH0590000
- F
- 10 · 10-23
- HS Code
- 29182900 · 29182900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2
Safety & regulation
GHS classification
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.
Hazard information
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 10-23
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- AH0590000
- hs_code
- 29182900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
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
Uses & manufacturing
UsesA deaminated metabolite of LEVODOPA. [ChemIDplus]
Applications
Description3,4-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
Uses3,4-Dihydroxyphenylacetic Acid is a metabolite of Dopamine (D533782).
Uses3,4-Dihydroxyphenylacetic acid is an important metabolite when studying the behavior of the dopaminergic system.
General Description3,4-dihydroxyphenylacetic acid (DOPAC) is a normal constituent of rat brain tissue. A mass fragmentographic method for determination of DOPAC in rat brain tissue has been described. It is major metabolite of dopamine (DA). The voltammetric reduction of DOPAC has been studied at a glassy carbon electrode modified with single-wall carbon nanotubes (SWNTs). Semi-automatic fluorometric assay technique for DOPAC has been reported.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: (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 dihydroxyphenylacetic acid and a member of catechols. It is functionally related to a phenylacetic acid. It is a conjugate acid of a (3,4-dihydroxyphenyl)acetate.
Related reactions
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