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740683

Sigma-Aldrich

1,8-Dihydroxynaphthalene

95%

Synonym(s):

1,8-Naphthalenediol

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About This Item

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

Quality Level

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.
  • A starting material to synthesize naphthopyran derivatives.
  • An intermediate in the total synthesis of palmarumycin CP17 analogs.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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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
Pigment biosynthesis and virulence.
A A Brakhage et al.
Contributions to microbiology, 2, 205-215 (1999-10-16)
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
N A Yurlova et al.
Studies in mycology, 61, 39-49 (2008-01-01)
Dothideaceous black yeast-like fungi (BYF) are known to synthesise DHN-melanin that is inhibited by the systemic fungicide tricyclazole. The final step of the DHN melanin pathway is the conjoining of 1,8-DHN molecules to form the melanin polymer. There are several
H F Tsai et al.
Journal of bacteriology, 180(12), 3031-3038 (1998-06-11)
Aspergillus fumigatus, an important opportunistic pathogen which commonly affects neutropenic patients, produces conidia with a bluish-green color. We identified a gene, alb1, which is required for conidial pigmentation. The alb1 gene encodes a putative polyketide synthase, and disruption of alb1

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