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N6250

Sigma-Aldrich

1,3-Dihydroxynaphthalene

≥99% purity , crystalline

Synonym(s):

1,3-Naphthalenediol, Naphthoresorcinol

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About This Item

Linear Formula:
C10H6(OH)2
CAS Number:
132-86-5
Molecular Weight:
160.17
Beilstein:
2044002
EC Number:
205-079-7
MDL number:
MFCD00003965
UNSPSC Code:
12171500
PubChem Substance ID:
24897775
NACRES:
NA.47

product name

1,3-Dihydroxynaphthalene, ≥99%, crystalline

Assay

≥99%

form

crystalline

color

white to tan

mp

123-125 °C (lit.)
124-125 °C

solubility

ethanol: 50 mg/mL

λmax

288 nm (298 nm (ethanol))

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Oc1cc(O)c2ccccc2c1

InChI

1S/C10H8O2/c11-8-5-7-3-1-2-4-9(7)10(12)6-8/h1-6,11-12H

InChI key

XOOMNEFVDUTJPP-UHFFFAOYSA-N

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General description

1,3-Dihydroxynaphthalene is a dye intermediate forming stable colors when applied with particular mordants and in mixtures with other oxidizing dyes. This specific reagent is intended for the quantitative colorimetric determination of alduronic acids, such as glucuronic acid from urine. The mutagenicity of ozonation derivatives of 1,3-dihydroxynaphthalene against several Salmonella typhimurium strains has been studied.

Application

1,3-Dihydroxynaphthalene is utilized in carbohydrate chromatography, sometimes in conjunction with resorcinol. It has been used incorporated into a thin-layer electrophoretic method for the analysis of biomass degradation products which contain comprising mono-, oligo- and polysaccharides, and their derivatives, in addition to phenolic compounds.

Preparation Note

1,3-Dihydroxynaphthalene is soluble in ethanol (50 mg/ml), with heat as needed, yielding a clear to slightly hazy, colorless to orange-brown solution. It is also soluble in water and ether.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H341

Hazard Classifications

Muta. 2

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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Karen A Nolan et al.
Bioorganic & medicinal chemistry letters, 20(24), 7331-7336 (2010-11-16)
The NCI chemical database has been screened using in silico docking to identify novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Compounds identified from the screen exhibit a diverse range of scaffolds and inhibitory potencies are generally in the micromolar range.
Y Sayato et al.
Mutation research, 189(3), 217-222 (1987-11-01)
The mutagenicity of products formed by ozonation of naphthoresorcinol in aqueous solution was assayed with Salmonella typhimurium strains TA97, TA98, TA100, TA102 and TA104 in the presence and absence of S9 mix from phenobarbital- and 5,6-benzoflavone-induced rat liver. Ozonated naphthoresorcinol
Wilson Terán et al.
The Journal of biological chemistry, 281(11), 7102-7109 (2006-01-13)
The RND family transporter TtgABC and its cognate repressor TtgR from Pseudomonas putida DOT-T1E were both shown to possess multidrug recognition properties. Structurally unrelated molecules such as chloramphenicol, butyl paraben, 1,3-dihydroxynaphthalene, and several flavonoids are substrates of TtgABC and activate
Determination of glycolaldehyde in the presence of hydroxypyruvate and tartronate semialdehyde.
F E de Windt et al.
Analytical biochemistry, 106(2), 342-343 (1980-08-01)
Amy L Kieran et al.
Chemical communications (Cambridge, England), (14)(14), 1842-1844 (2005-03-30)
New macrocycles incorporating a porphyrin and a [small pi] electron-rich aromatic were prepared from a dynamic disulfide library. The outcome could be influenced by use of templates.
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