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281255

Sigma-Aldrich

1,4-Dihydroxy-2-naphthoic acid

97%

Synonym(s):

1,4-Dihydroxy-2-carboxy naphthoic acid, 1,4-Dihydroxy-2-naphthalenecarboxylic acid, 1,4-Dihydroxy-2-naphthoate

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About This Item

Linear Formula:
(HO)2C10H5CO2H
CAS Number:
31519-22-9
Molecular Weight:
204.18
EC Number:
250-674-7
MDL number:
MFCD00010370
UNSPSC Code:
12352100
PubChem Substance ID:
24856853
NACRES:
NA.22

assay

97%

mp

220 °C (dec.) (lit.)

SMILES string

OC(=O)c1cc(O)c2ccccc2c1O

InChI

1S/C11H8O4/c12-9-5-8(11(14)15)10(13)7-4-2-1-3-6(7)9/h1-5,12-13H,(H,14,15)

InChI key

VOJUXHHACRXLTD-UHFFFAOYSA-N

Related Categories

General description

1,4-Dihydroxy-2-naphthoic acid from Propionibacterium freudenreichii is known to promote the proliferation of Bifidobacterium. It has potential therapeutic application for psoriasis treatment.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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D J Shaw et al.
Journal of bacteriology, 152(3), 1132-1137 (1982-12-01)
Four independent menaquinone (vitamin K(2))-deficient mutants of Escherichia coli, blocked in the conversion of o-succinylbenzoate (OSB) to 1,4-dihydroxy-2-naphthoate (DHNA), were found to represent two distinct classes. Enzymatic complementation was observed when a cell-free extract of one mutant was mixed with
M Matsubara et al.
Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA, 21(8), 1437-1447 (2009-10-09)
The main component of the metabolic by-products of fermentation by Propionibacterium freudenreichii ET-3 is 1,4-dihydroxy-2-naphthoic acid (DHNA), which has a naphthoquinone skeleton, as in vitamin K2. This study showed that DHNA improved bone mass reduction with osteoporosis model mice caused
Alexey P Kostikov et al.
The Journal of organic chemistry, 72(24), 9190-9194 (2007-10-26)
Irradiation of alcohols, phenols, and carboxylic acids "caged" with the 2,5-dihydroxybenzyl group or its naphthalene analogue results in the efficient release of the substrate. The initial byproduct of the photoreaction, 4-hydroxyquinone-2-methide, undergoes rapid tautomerization into methyl p-quinone. The UV spectrum
K Suvarna et al.
Journal of bacteriology, 180(10), 2782-2787 (1998-06-06)
A key reaction in the biosynthesis of menaquinone involves the conversion of the soluble bicyclic naphthalenoid compound 1, 4-dihydroxy-2-naphthoic acid (DHNA) to the membrane-bound demethylmenaquinone. The enzyme catalyzing this reaction, DHNA-octaprenyltransferase, attaches a 40-carbon side chain to DHNA. The menA
Junichi Sakai et al.
Bioorganic & medicinal chemistry, 16(9), 4854-4859 (2008-04-05)
Ac-DNLD-CHO is a novel caspase-3 specific peptide inhibitor that was rationally designed by our computational strategy. The specificity was shown to be due to the specific interaction of NLD moiety with the active site of caspase-3 on the basis of
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