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126209

Sigma-Aldrich

2,3-Dihydroxybenzoic acid

99%

Sinónimos:

Hypogallic acid, Pyrocatechuic acid

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About This Item

Fórmula lineal:
(HO)2C6H3CO2H
Número de CAS:
303-38-8
Peso molecular:
154.12
Beilstein/REAXYS Number:
2209117
EC Number:
206-139-5
MDL number:
MFCD00002446
UNSPSC Code:
12352100
PubChem Substance ID:
24847707
NACRES:
NA.22

assay

99%

mp

204-206 °C (lit.)

solubility

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

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)

InChI key

GLDQAMYCGOIJDV-UHFFFAOYSA-N

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Application

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 Actions

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.

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 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

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3,4-Dihydroxybenzoic acid analytical standard

Supelco

08992

3,4-Dihydroxybenzoic acid

François Le Mauff et al.
The Journal of biological chemistry, 294(28), 10760-10772 (2019-06-07)
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
Anna Nilsson et al.
Scientific reports, 7(1), 6352-6352 (2017-07-27)
Knowledge about the region-specific absorption profiles from the gastrointestinal tract of orally administered drugs is a critical factor guiding dosage form selection in drug development. We have used a novel approach to study three well-characterized permeability and absorption marker drugs
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
Axel B Janssen et al.
mSphere, 5(2) (2020-03-13)
Infections by multidrug-resistant Gram-negative bacteria are increasingly common, prompting the renewed interest in the use of colistin. Colistin specifically targets Gram-negative bacteria by interacting with the anionic lipid A moieties of lipopolysaccharides, leading to membrane destabilization and cell death. Here
Bryan H Bellaire et al.
Infection and immunity, 71(4), 1794-1803 (2003-03-26)
Brucella abortus reportedly produces the monocatechol siderophore 2,3-dihydroxybenzoic acid (2,3-DHBA) in response to iron limitation. Nucleotide sequence analysis of the cloned DHBA biosynthesis locus from virulent B. abortus 2308 and genetic complementation of defined Escherichia coli mutants were used to
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