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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:
Molecular Weight:
204.18
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

mp

220 °C (dec.) (lit.)

functional group

carboxylic acid

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

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

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

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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
Yung-Fu Wang et al.
Biotechnology and bioengineering, 101(3), 579-586 (2008-05-06)
The end-product profile of the glucose fermentation by Propionibacterium freudenreichii ET-3 changed on an electrochemical treatment, in which the culture vessel was filled with a carbon felt anode. Acetate and propionate were produced as final end products in a molar
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
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
V Sharma et al.
Gene, 168(1), 43-48 (1996-02-02)
In Escherichia coli, the biosynthesis of the electron carrier menaquinone (vitamin K2) involves at least seven identified enzymatic activities, five of which are encoded in the men cluster. One of these, the conversion of o-succinylbenzoic acid to 1,4-dihydroxy-2-naphthoic acid, requires

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