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126535

Sigma-Aldrich

2,6-Dimethylnaphthalene

99%

Synonym(s):

2,6-Dimethylnaphthalene

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About This Item

Linear Formula:
C10H6(CH3)2
CAS Number:
581-42-0
Molecular Weight:
156.22
Beilstein:
1903544
EC Number:
209-464-0
MDL number:
MFCD00004120
UNSPSC Code:
12352100
PubChem Substance ID:
24847732
NACRES:
NA.22

Assay

99%

bp

262 °C (lit.)

mp

106-110 °C (lit.)

SMILES string

Cc1ccc2cc(C)ccc2c1

InChI

1S/C12H12/c1-9-3-5-12-8-10(2)4-6-11(12)7-9/h3-8H,1-2H3

InChI key

YGYNBBAUIYTWBF-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

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General description

2,6-dimethylnaphthalene is a polycyclic aromatic hydrocarbon available in the water bodies and can be determined by gas chromatography with flame-ionization.

Application

2,6-Dimethylnaphthalene hs been used as a substrate in intramolecular isotope effect experiments to compare substrate dynamics in CYP2E1 and CYP2A6.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

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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Aryl sulfate formation in sea urchins (Strongylocentrotus droebachiensis) ingesting marine algae (Fucus distichus) containing 2,6-dimethylnaphthalene.
D C Malins et al.
Environmental research, 27(2), 290-297 (1982-04-01)
Z A Shamsuddin et al.
Drug metabolism and disposition: the biological fate of chemicals, 14(6), 724-732 (1986-11-01)
Metabolism of the environmental contaminant 2,6-dimethylnaphthalene (2,6-DMN) by rat liver microsomes and an NADPH-regenerating system led to the formation of three ring oxidation metabolites--2,6-dimethyl-3-naphthol, 2,6-dimethyl-3,4-naphthoquinone, and 3,4-dihydro-3,4-dihydroxy-2,6-dimethylnaphthalene--and one side chain oxidation metabolite--2-hydroxymethyl-6-methylnaphthalene. In addition, one metabolite remained unidentified. Pretreatment of
E A Barnsley
Applied and environmental microbiology, 54(2), 428-433 (1988-02-01)
Flavobacteria that were able to grow on 2,6-dimethylnaphthalene (2,6-DMN) were isolated from soil. Most were able to oxidize a broad range of aromatic hydrocarbons after growth on 2,6-DMN at rates comparable to that of the oxidation of 2,6-DMN itself. One
M M Krahn et al.
Journal of chromatography, 236(2), 441-452 (1982-02-19)
An automated extractor-concentrator was used to extract metabolites of naphthalene, 2,6-dimethylnaphthalene, and benzo[a]pyrene from serum, bile and liver homogenate of rainbow trout (Salmo gairdneri). The extracts were analyzed by reversed-phase high-performance liquid chromatography (HPLC) with fluorescence detection. Recoveries of naphthalene
J V Schnell et al.
Xenobiotica; the fate of foreign compounds in biological systems, 10(3), 229-234 (1980-03-01)
1. Benzo[a]pyrene, 2,6-dimethylnaphthalene, and naphthalene were used as substrates for a coho salmon (Oncorhynchus kisutch) liver microsomal preparation. 2. The apparent Michaelis constants (Km) were as follows: benzo[a]pyrene, 2.1 microM; 2,6-dimethylnaphthalene, 15.3 microM; and naphthalene, 300 microM. 3. The results
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