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126209

Sigma-Aldrich

2,3-Dihydroxybenzoic acid

99%

Synonym(s):

Hypogallic acid, Pyrocatechuic acid

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About This Item

Linear Formula:
(HO)2C6H3CO2H
CAS Number:
303-38-8
Molecular Weight:
154.12
Beilstein:
2209117
EC Number:
206-139-5
MDL number:
MFCD00002446
UNSPSC Code:
12352100
PubChem Substance ID:
24847707
NACRES:
NA.22

Quality Level

200

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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
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
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
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