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| Synonyms | AC-9617 | Carbohydroquinonic acid | DIHYDROXYBENZOIC ACID, 3,4- | Protocatechuic acid, primary pharmaceutical reference standard | NCGC00246757-01 | KUC104409N | Q418599 | STL163570 | 4fht | MLS000737807 | 1225528-47-1 | AM20060767 | EINECS 202-760-0 | SY |
|---|---|
| Specifications & Purity | ≥97% |
| Biochemical and Physiological Mechanisms | Chemopreventive in several animal models of carcinogenesis. Blocks cell proliferation in the post-initiation phase.Phenolic acid, major metabolite of antioxidant polyphenols. Anti-inflammatory, chemopreventive effects in vitro and in vivo. Orally active. |
| Storage Temp | Protected from light |
| Shipped In | Normal |
| Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
| Product Description |
Protocatechuic Acid is a phenolic acid antioxidant present in fruits, vegetables and nuts. Protocatechuic Acid has been found to be an efficacious chemopreventive agent in several carcinogenesis models. 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. A phenolic acid antioxidant and chemopreventive agent. 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. |
Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Hydroxybenzoic acid derivatives |
| Alternative Parents | Benzoic acids Catechols Benzoyl derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Monocarboxylic acids and derivatives Carboxylic acids Organooxygen compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Dihydroxybenzoic acid - Hydroxybenzoic acid - Benzoic acid - Benzoyl - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. |
| External Descriptors | catechols - dihydroxybenzoic acid |
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| Pubchem Sid | 488179485 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488179485 |
| IUPAC Name | 3,4-dihydroxybenzoic acid |
| INCHI | 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 |
| Smiles | C1=CC(=C(C=C1C(=O)O)O)O |
| Isomeric SMILES | C1=CC(=C(C=C1C(=O)O)O)O |
| WGK Germany | 3 |
| RTECS | UL0560000 |
| Molecular Weight | 154.12 |
| Beilstein | 1448841 |
| Reaxy-Rn | 1448841 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1448841&ln= |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
| Certificate of Analysis | Apr 29, 2025 | P104382 | |
| Certificate of Analysis | Jul 10, 2023 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Nov 28, 2022 | P104382 | |
| Certificate of Analysis | Jun 11, 2022 | P104382 | |
| Certificate of Analysis | Jun 11, 2022 | P104382 | |
| Certificate of Analysis | Jun 11, 2022 | P104382 | |
| Certificate of Analysis | Jun 11, 2022 | P104382 | |
| Certificate of Analysis | Jul 05, 2021 | P104382 |
| Solubility | Soluble in water (1:50), ethanol, and ether. |
|---|---|
| Sensitivity | Light sensitive. |
| Melt Point(°C) | 200°C |
| Molecular Weight | 154.120 g/mol |
| XLogP3 | 1.100 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Exact Mass | 154.027 Da |
| Monoisotopic Mass | 154.027 Da |
| Topological Polar Surface Area | 77.800 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 157.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
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