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740683

Sigma-Aldrich

1,8-Dihydroxynaphthalene

95%

Synonym(s):

1,8-Naphthalenediol

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1 G
€49.00

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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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
Bo Wang et al.
BMC genomics, 18(1), 729-729 (2017-09-17)
Ectophytic fungi occupy the waxy plant surface, an extreme environment characterized by prolonged desiccation, nutrient limitation, and exposure to solar radiation. The nature of mechanisms that facilitate adaptation to this environment remains unclear. In this study, we sequenced the complete
Synthesis of spiromamakone a benzo analogues via double oxa-michael addition of 1, 8-dihydroxynaphthalene
Tsukamoto H, et al.
Organic Letters, 18, 4848-4851 (2016)
R Romero-Martinez et al.
Infection and immunity, 68(6), 3696-3703 (2000-05-19)
Sporothrix schenckii is a human pathogen that causes sporotrichosis, an important cutaneous mycosis with a worldwide distribution. It produces dark-brown conidia, which infect the host. We found that S. schenckii synthesizes melanin via the 1,8-dihydroxynaphthalene pentaketide pathway. Melanin biosynthesis in
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