ContaminantDB: 4,6-Dinitro-o-cresol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:05 UTC

Update Date

2016-11-09 01:08:09 UTC

Accession Number

CHEM000093

Identification

Common Name

4,6-Dinitro-o-cresol

Class

Small Molecule

Description

4,6-Dinitro-o-cresol is the most commercially important of the 18 different dinitrocresols, a class of manufactured chemicals. 4,6-Dinitro-o-cresol (DNOC) is used primarily for insect control and crop protection. It may be sold under different trade names, including Antinonnin, Detal, and Dinitrol. DNOC was used in diet pills in the 1930s, but has since been banned for this use. (1)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Nitrite
Organic Compound
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,4-Dinitro-6-methylphenol	ChEBI
3,5-Dinitro-2-hydroxytoluene	ChEBI
6-Methyl-2,4-dinitrophenol	ChEBI
Antinonnin	ChEBI
DNOC	ChEBI
4,6-Dinitro-ortho-cresol	HMDB
Hedolit, ammonium salt	HMDB
Hedolit, barium salt	HMDB
Hedolit, lead salt	HMDB
DNOC CPD	HMDB
Flavin	HMDB
Hedolit, sodium salt	HMDB
2,4-Dinitro-O-cresol	HMDB
4,6-Dinitro-2-cresol	HMDB
4,6-Dinitro-O-cresol, lead salt	HMDB
4,6-Dinitro-O-cresol, lead(2+) salt	HMDB
Hedolit	HMDB
Hedolit, lead(2+) salt	HMDB
Hedolit, potassium salt	HMDB
4,6-Dinitro-O-cresol, barium salt	HMDB
4,6-Dinitro-O-cresol, potassium salt	HMDB
4,6-Dinitro-O-cresol, sodium salt	HMDB

Chemical Formula

C₇H₆N₂O₅

Average Molecular Mass

198.133 g/mol

Monoisotopic Mass

198.028 g/mol

CAS Registry Number

534-52-1

IUPAC Name

2-methyl-4,6-dinitrophenol

Traditional Name

dinitro

SMILES

CC1=CC(=CC(=C1O)[N+]([O-])=O)[N+]([O-])=O

InChI Identifier

InChI=1S/C7H6N2O5/c1-4-2-5(8(11)12)3-6(7(4)10)9(13)14/h2-3,10H,1H3

InChI Key

ZXVONLUNISGICL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dinitrophenols. These are organic aromatic compounds containing a benzene that carries a single phenol group and exactly two nitro groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Dinitrophenol
Dinitrotoluene
Nitrobenzene
Nitrotoluene
Nitroaromatic compound
O-cresol
Toluene
Monocyclic benzene moiety
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nitrotoluene (CHEBI:39349 )
hydroxytoluene (CHEBI:39349 )
dinitrophenol acaricide (CHEBI:39349 )
Nitrophenol herbicides (C18653 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

fungicide

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Yellow solid.

Experimental Properties

Property	Value
Melting Point	86.6°C
Boiling Point	Not Available
Solubility	0.198 mg/mL at 20 °C [SCHWARZENBACH,RP et al.(1988)]

Predicted Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	2.09	ALOGPS
logP	2.06	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.87 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.73 m³·mol⁻¹	ChemAxon
Polarizability	16.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uea-5900000000-addfeb5f588413c4b49c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0900000000-ef71bd0f4a52fb5512f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0002-0900000000-b95fb32e9e2211a53407	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0012-0900000000-01b99ab001927e982bea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0a5i-0900000000-274d829ba9ea4ed3734d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0a4i-1900000000-091a1f48cba20f4c4067	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4i-3900000000-708fd4e0598e94a078db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0pcc-0900000000-b8fd7d7437b5e88d5b63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0596-1900000000-7376fa305e57bacc91ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0900000000-5213e778a3b234c508ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0002-0900000000-5bfd8345420b89a7de64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-000b-0900000000-961457d0d3fad0fb5a91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-053j-0900000000-47979f204578ed692f6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-d59ff0bd014c543ab4e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-0900000000-db05405efe84b782857a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-007p-1900000000-3dabca56b7217ac455e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-8cc0e9707a165de70cde	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-ebd2c5a73e30a5a6253d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002s-0900000000-23028b68fd69670c19c3	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udj-9500000000-93be374bf50b7c0c8646	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (1) ; inhalation (1) ; dermal (1)

Mechanism of Toxicity

4,6-Dinitro-o-cresol is an uncoupler of oxidative phosphorylation. It is believed to cause an acceleration of metabolic processes that are part of the tricarboxylic acid (TCA) cycle. DNOC produces its accelerative effect by increasing the permeability of the inner mitochondrial membrane to Ca+, altering the proton electrochemical gradient and thus interrupting the phosphate transfer to adenosine diphosphate (ADP) to form ATP. Uncoupling allows electron transport to proceed unchecked even when ATP synthesis is inhibited. As a consequence, more ADP and inorganic phosphate are available to drive the TCA cycle, and most of the energy produced from catabolism of glucose is not stored in high energy phosphate bonds as ATP but is given off as heat. This results in the elevated body temperature and related effects characteristic of DNOC toxicity. (1)

Metabolism

4,6-Dinitro-o-cresol is absorbed via oral, inhalation, and dermal routes, then binds to albumin and is distributed to most tissues, including the lungs, heart, liver, kidney, brain, spleen, and muscle. Although small quantities of DNOC may be conjugated, most of it appears to be reduced to less toxic mono amino derivatives, such as 6-amino-4-nitro-o-cresol and 6-acetamido-4-nitro-o-cresol, and then subsequently conjugated. DNOC and its metabolites are eliminated primarily via the urine. (1)

Toxicity Values

LD50: 200 mg/kg (Dermal, Rat) (3) LD50: 21 mg/kg (Oral, Mouse) (3) LD50: 19 mg/kg (Intraperitoneal, Mouse) (3) LD50: 25 600 ug/kg (Subcutaneous, Rat) (2)

Lethal Dose

29 mg/kg (oral) or 1 mg/m3 (inhaled) for an adult human. (4)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

4,6-Dinitro-o-cresol is used primarily for insect control and crop protection. (1)

Minimum Risk Level

Not Available

Health Effects

Exposure to DNOC may cause mild damage to the stomach, kidneys, and liver. Ingesting DNOC for long periods may cause cataracts and skin rashes. (1)

Symptoms

Exposure to high levels of DNOC for short periods may cause convulsions, unconsciousness, and death. Exposure to low levels of DNOC may result in an increased basal metabolic rate, increased sweating, weight loss, and increased heart rate, breathing rate, and body temperature. Other effects from DNOC exposure may include difficulty in breathing, headache, drowsiness, dizziness, and a yellowing of skin and the whites of the eyes. (1)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0245221

FooDB ID

Not Available

Phenol Explorer ID