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Sigma-Aldrich

3,4-Dihydroxy-benzoesäure

≥97.0% (T)

Synonym(e):

Protocatechusäure

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About This Item

Lineare Formel:
(HO)2C6H3CO2H
CAS-Nummer:
99-50-3
Molekulargewicht:
154.12
Beilstein:
1448841
EG-Nummer:
202-760-0
MDL-Nummer:
MFCD00002509
UNSPSC-Code:
12352100
PubChem Substanz-ID:
57649743
NACRES:
NA.22

Assay

≥97.0% (T)

mp (Schmelzpunkt)

197-200 °C (dec.) (lit.)

SMILES String

OC(=O)c1ccc(O)c(O)c1

InChI

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

InChIKey

YQUVCSBJEUQKSH-UHFFFAOYSA-N

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Allgemeine Beschreibung

3,4-Dihydroxybenzoic acid is reported as dietery polyphenol. Antiviral activity of 3,4-dihydroxybenzoic acid (protocatechuic acid, PCA) against a virulent H9N2 strain in a mouse model is reported. Cytotoxic effects of PCA on 3 non-small cell lung cancer (NSCLC) cell lines, A549, H3255, and Calu-6 cell lines is reported. PCA is reported to prevent the carcinogenesis or antitumor growth in vivo. Signaling pathway involved in PCA-induced apoptosis in human gastric adenocarcinoma (AGS) cells is reported. The oxidation of 3,4-dihydroxybenzoic acid by H2O2 in aqueous/goethite slurry at varying operating conditions (catalyst load, temperature, pH, substrate and hydrogen peroxide starting concentration) is investigated.

Anwendung

3,4-Dihydroxybenzoic acid is suitable for use in a study to investigate the effect of 4-coumaric and 3,4-dihydroxybenzoic acid on the basal oxidative DNA damage of rat colonic mucosa in vivo. It may be used in the derivatization of chitosan resin.

Biochem./physiol. Wirkung

Chemopräventiv bei der Krebsentstehung in verschiedenen Tiermodellen. Hemmt die Zellproliferation in der Post-Initiationsphase.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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Hui-Hsuan Lin et al.
International journal of cancer, 120(11), 2306-2316 (2007-02-17)
3,4-Dihydroxybenzoic acid (protocatechuic acid, PCA) is discussed to represent antioxidative food components in a human diet rich in fruits and vegetables, and has been shown to prevent carcinogenesis or antitumor growth in vivo. However, the molecular mechanisms involved in chemopreventive
Akhmad Sabarudin et al.
Analytica chimica acta, 581(2), 214-220 (2007-03-28)
A chitosan resin derivatized with 3,4-dihydroxybenzoic acid moiety (CCTS-DHBA resin) was newly synthesized for the collection/concentration of trace uranium by using cross-linked chitosan (CCTS) as base material, and the adsorption behavior of uranium as well as 60 elements on the
Roberto Andreozzi et al.
Water research, 36(11), 2761-2768 (2002-07-31)
The oxidation by H2O2 of 3,4-dihydroxybenzoic acid (3,4-DHB) in aqueous/goethite slurry at varying operating conditions (catalyst load, temperature, pH, substrate and hydrogen peroxide starting concentration) is investigated. At adopted catalyst loads the observed kinetic developments are consistent with a non-radicalic
Shih-ming Tsao et al.
Nutrition and cancer, 66(8), 1331-1341 (2014-10-31)
Cytotoxic effects of protocatechuic acid (PCA) upon 3 nonsmall cell lung cancer (NSCLC) cell lines, A549, H3255, and Calu-6 cell lines, were examined. PCA at 1, 2, 4, and 8 μM was used to treat these cells. Results showed that
Francesco Guglielmi et al.
The British journal of nutrition, 89(5), 581-587 (2003-05-02)
The effect of 4-coumaric and 3,4-dihydroxybenzoic (protocatechuic) acid on the basal oxidative DNA damage of rat colonic mucosa in vivo was studied, relative to vitamin E. F344 rats were treated with 4-coumaric or protocatechuic acid mixed in the diet (25
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