Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

D131

Sigma-Aldrich

3,5-Dinitrocatechol

solid

Synonym(s):

3,5-Dinitro-1,2-benzenediol, OR-486

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C6H4N2O6
CAS Number:
7659-29-2
Molecular Weight:
200.11
MDL number:
MFCD00069263
UNSPSC Code:
12352202
PubChem Substance ID:
24278158
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (HPLC)

form

solid

color

yellow

mp

168-170  °C

solubility

H2O: slightly soluble 0.17 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 2.8 mg/mL
0.1 M HCl: slightly soluble
DMSO: soluble
aqueous buffer pH > 5: soluble
ethanol: soluble

storage temp.

2-8°C

SMILES string

Oc1cc(cc(c1O)[N+]([O-])=O)[N+]([O-])=O

InChI

1S/C6H4N2O6/c9-5-2-3(7(11)12)1-4(6(5)10)8(13)14/h1-2,9-10H

InChI key

VDCDWNDTNSWDFJ-UHFFFAOYSA-N

Gene Information

human ... COMT(1312)

Application

3,5-Dinitrocatechol (3,5-DNC) has been used in the preparation of the molybdenum (VI)-(3,5-DNC) complex. It has also been used as a catechol-O-methyltransferase (COMT) inhibitor and as a positive control for screening human COMT inhibition.
Chelating reagent used in a sensitive (μM) assay for vanadium.

Biochem/physiol Actions

Selective inhibitor of catechol O-methyl transferase (COMT); penetrates the blood brain barrier and is useful both orally and parenteraly in experiments where inhibition of COMT in the central nervous system is required.

Quality

Solutions may be stored for several days at 4 °C.

Caution

Photosensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000287895
SLCP5279
SLCF6118
SLBT2326
SLBP3194V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Microplate screening assay to identify inhibitors of human catechol-O-methyltransferase.
Mika Kurkela et al.
Analytical biochemistry, 331(1), 198-200 (2004-07-13)
E Nissinen et al.
European journal of pharmacology, 153(2-3), 263-269 (1988-08-24)
Catechol-O-methyltransferase (COMT) has an important role in the extraneuronal inactivation of catecholamine neurotransmitters and drugs with a catechol structure. Two novel COMT inhibitors, OR-462 and OR-486, were highly effective (IC50 = 18 and 12 nM, respectively) and selective in inhibiting
Raghvendra K Dubey et al.
The Journal of clinical endocrinology and metabolism, 89(8), 3922-3931 (2004-08-05)
Sequential conversion of estradiol to catecholestradiols and methoxyestradiols by cytochrome-P(450) (CYP450) and catechol-O-methyltransferase (COMT), respectively, contributes to the antimitogenic effects of estradiol on vascular smooth muscle cell (SMC) growth via estrogen receptor-independent mechanisms. Because catecholamines are also substrates for COMT
V W Couling et al.
Biophysical journal, 75(2), 1097-1106 (1998-07-24)
This paper presents a study of the use of ultraviolet resonance Raman (UVRR) spectroscopic methods as a means of elucidating aspects of drug-protein interactions. Some of the RR vibrational bands of the aromatic amino acids tyrosine and tryptophan are sensitive
A K Pani et al.
General pharmacology, 31(1), 67-73 (1998-05-22)
1. The efficacies of various agents that affect monoamine synthesis, oxidation and methylation were evaluated in the scallop, Placopecten magellanicus, through the use of high performance liquid chromatography with electrochemical detection. 2. Central ganglia, labial palps and feet from animals
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service