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Merck

126209

Sigma-Aldrich

2,3-Dihydroxybenzoesäure

99%

Synonym(e):

Hypogallic acid, Pyrocatechuic acid

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About This Item

Lineare Formel:
(HO)2C6H3CO2H
CAS-Nummer:
Molekulargewicht:
154.12
Beilstein:
2209117
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

99%

mp (Schmelzpunkt)

204-206 °C (lit.)

Löslichkeit

methanol: soluble 50 mg/mL, clear to faintly hazy, orange

Funktionelle Gruppe

carboxylic acid

SMILES String

OC(=O)c1cccc(O)c1O

InChI

1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)

InChIKey

GLDQAMYCGOIJDV-UHFFFAOYSA-N

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Anwendung

2,3-Dihydroxybenzoic acid was used to study the complexes of manganese with aliphatic and aromatic polyhydroxy ligands in basic media by electrochemical, spectrophotometric and magnetic methods. It was used in isolation of new siderophore named vulnibactin from low iron cultures of Vibrio vulnificus, a human pathogen. It was used as cocrystal former to study the influence of position isomerism on the co-crystals formation and physicochemical properties of piracetam.

Biochem./physiol. Wirkung

2,3-Dihydroxybenzoic acid was found to be orally effective iron-chelating drug in hypertransfused rat model. It is monocatechol siderophore produced by Brucella abortus.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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The identification of 2, 3-dihydroxybenzoic acid as a potentially useful iron-chelating drug.
J H Graziano et al.
The Journal of pharmacology and experimental therapeutics, 190(3), 570-575 (1974-09-01)
N Okujo et al.
Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine, 7(2), 109-116 (1994-04-01)
A new siderophore named vulnibactin has been isolated from low iron cultures of Vibrio vulnificus, a human pathogen. The structure was established as N-[3-(2,3-dihydroxybenzamido)propyl]-1,3-bis[2-(2-hydroxy-phenyl)- trans-5 - methyl-2-oxazoline-4-carboxamido]propane by a combination of acid hydrolysis, nuclear magnetic resonance spectroscopy and positive fast
Xiangmin Liao et al.
Journal of pharmaceutical sciences, 99(1), 246-254 (2009-06-09)
The effect of position isomerism on the co-crystals formation and physicochemical properties was evaluated. Piracetam was used as the model compound. Six position isomers, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dihydroxybenzoic acid (DHBA), were used as the co-crystal formers. Co-crystals
Nao Yamakawa et al.
Nature communications, 9(1), 4647-4647 (2018-11-09)
The emergence of zebrafish Danio rerio as a versatile model organism provides the unique opportunity to monitor the functions of glycosylation throughout vertebrate embryogenesis, providing insights into human diseases caused by glycosylation defects. Using a combination of chemical modifications, enzymatic
François Le Mauff et al.
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During infection, the fungal pathogen Aspergillus fumigatus forms biofilms that enhance its resistance to antimicrobials and host defenses. An integral component of the biofilm matrix is galactosaminogalactan (GAG), a cationic polymer of α-1,4-linked galactose and partially deacetylated N-acetylgalactosamine (GalNAc). Recent

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