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D131

Sigma-Aldrich

3,5-Dinitrocatechol

solid

Synonym(s):

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

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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Microplate screening assay to identify inhibitors of human catechol-O-methyltransferase.
Mika Kurkela et al.
Analytical biochemistry, 331(1), 198-200 (2004-07-13)
Kirila Stojnova et al.
Acta chimica Slovenica, 65(1), 213-220 (2018-03-22)
The equilibria of the chelate formation and ion-association in the liquid-liquid extraction system Mo(VI)‒3,5-DNC‒INT‒H2O‒CHCl3 were studied by spectrophotometry. The optimum conditions for the chelate formation and extraction of the ion-associated complex formed between the anionic chelate of Mo(VI)‒3,5-dinitrocatechol (3,5-DNC) and
Reda Saber Ibrahim Ahmed et al.
Journal of cellular biochemistry, 117(10), 2357-2369 (2016-03-08)
Uterine fibroids (leiomyomas) are very common benign tumors grown on the smooth muscle layer of the uterus, present in up to 75% of reproductive-age women and causing significant morbidity in a subset of this population. Although the etiology and biology
Raghvendra K Dubey et al.
Hypertension (Dallas, Tex. : 1979), 42(3), 349-355 (2003-08-13)
Local sequential conversion of estradiol to hydroxyestradiols and methoxyestradiols by CYP450 and catechol-O-methyltransferase, respectively, contributes to the antimitogenic effects of estradiol on glomerular mesangial cell growth via estrogen receptor-independent mechanisms. Catecholamines are also substrates for catechol-O-methyltransferase and therefore, might abrogate
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
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