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740683

Sigma-Aldrich

1,8-Dihydroxynaphthalene

95%

Synonym(s):

1,8-Naphthalenediol

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1 G
R$421.00

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1 G
R$421.00

About This Item

Empirical Formula (Hill Notation):
C10H8O2
CAS Number:
569-42-6
Molecular Weight:
160.17
Beilstein:
2044947
MDL number:
MFCD00042701
UNSPSC Code:
12352100
PubChem Substance ID:
329765431
NACRES:
NA.22

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Quality Level

100

Assay

95%

form

solid

mp

137-143 °C

storage temp.

2-8°C

SMILES string

Oc1cccc2cccc(O)c12

InChI

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

InChI key

OENHRRVNRZBNNS-UHFFFAOYSA-N

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Application

1,8-Dihydroxynaphthalene (DHN) can be used as:
  • An intermediate in the preparation of benzo analogs of spiromamakone A.[1]
  • A starting material to synthesize naphthopyran derivatives.[2]
  • An intermediate in the total synthesis of palmarumycin CP17 analogs.[3]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3985
MKCT1663
MKCS2303
MKCQ6385
MKCN3217

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E S Jacobson et al.
Infection and immunity, 63(12), 4944-4945 (1995-12-01)
1,8-Dihydroxynaphthalene melanin in Wangiella dermatitidis and Alternaria alternata was titrated in vivo with the oxidants permanganate, hypochlorite, and H2O2. Melanized strains neutralized more oxidant and withstood higher concentrations of permanganate and hypochlorite than albino strains did. H2O2 killing required 1,000-fold
E Thines et al.
The Journal of antibiotics, 51(4), 387-393 (1998-06-19)
From submerged cultures of Scytalidium sp. 36-93, ten metabolites were isolated due to their effects on dihydroxynaphthalene (DHN) or DOPA melanin biosynthesis. Four of the compounds, scytalols A (1a), B (1b), C (2) and D (3), are new secondary metabolites
Pigment biosynthesis and virulence.
A A Brakhage et al.
Contributions to microbiology, 2, 205-215 (1999-10-16)
Total synthesis and antifungal activity of palmarumycin CP17 and its methoxy analogues
Wang R, et al.
Molecules (Basel), 21, 600-600 (2016)
Hong Jiang et al.
Gene, 602, 8-15 (2016-11-16)
A PKS1 gene responsible for the melanin biosynthesis and a NPG1 gene in Aureobasidium melanogenum XJ5-1 were cloned and characterized. An ORF of the PKS1 gene encoding a protein with 2165 amino acids contained 6495bp while an ORF of the
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