Protocatechuic Acid
Basic information
- CAS
99-50-3- Standard SMILES
O=C(O)c1ccc(O)c(O)c1- InChIKey
YQUVCSBJEUQKSH-UHFFFAOYSA-N- Molecular formula
- C7H6O4
- Average molar mass
- 154.12 g/mol
- Monoisotopic mass
- 154.02660867
Overview
3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor, an antineoplastic agent, a plant metabolite, a human xenobiotic metabolite and an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor. It is a dihydroxybenzoic acid and a member of catechols. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate.
Names & identifiers
- Preferred name
- Protocatechuic Acid
- IUPAC
- 3,4-dihydroxybenzoic acid
- English name
- Protocatechuic acid
- Molecular formula
- C7H6O4
- Molecular weight
- 154.12
Names & synonyms
3,4-DIHYDROXYBENZOIC ACIDprotocatechuic acid99-50-3Protocatehuic acid4-Carboxy-1,2-dihydroxybenzene4,5-Dihydroxybenzoic acidDTXSID402121236R5QJ8L4BFEMA NO. 4430NSC-16631DTXCID601212CHEBI:36062
Show more names
Protocatechoic AcidHypogallic acid3,4-DihydroxybenzoicPROTOCATECHUIC ACID(P)Protocatechuic aci3,4-Dihydroxybenzoic acid,97%Pyrocatechol-p-carboxylic acid
RefChem:25857202-760-0protocatechuateBenzoic acid, 3,4-dihydroxy-MFCD000025093,4-Dihydroxy Benzoic AcidCarbohydroquinonic acid1ykp
Database identifiers
- CAS
99-50-3- PubChem CID
- 72
- DTXSID
DTXSID4021212- ChEMBL
CHEMBL37537
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 157
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Oils and Extracts
DrugsPharmaceuticals -> Listed in ZINC15
LogP
0.86
0.99
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
18.2 mg/mL at 14 °C
Soluble
Soluble (in ethanol)
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point221 °C
Vapor Pressure0.0000021 [mmHg]
Physical Description
White to brownish solid; Discolored by air; [Merck Index]
Solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 140 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzoic acid, 3,4-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses other liver changes and multiple enzyme effects in 28-day intermittent oral studies of rats; Intraperitoneal LD50 (mouse) > 800 mg/kg; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- UL0560000
- hs_code
- 29182990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
Chemistry & industry
Pharmacology
Metabolism/MetabolitesProtocatehuic acid is a known human metabolite of 3,4-dihydroxyphenylacetic acid.
MeSH Pharmacological ClassificationAgents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Tissue LocationsFibroblasts
Uses & manufacturing
Uses
Present in wheat grains and many other plants; [Merck Index]
Synthetic Polymer MALDI Matrix Compounds
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
DescriptionProtocatechuic acid (3,4-dihydroxybenzoic acid, PCA) is a simple phenolic acid. It is found in a large variety of edible plants and possesses various pharmacological activities.Protocatechuic acid has an antibacterial effect, and has different degrees of antibacterial effect on Pseudomonas aeruginosa, Escherichia coli, Typhoid bacillus, Shigella, Alcaligenes, Bacillus subtilis and Staphylococcus aureus in vitro. It also has expectorant and anti-asthmatic effects. It is clinically used to treat chronic bronchitis.
UsesA phenolic acid antioxidant and chemopreventive agent
Uses3,4-Dihydroxybenzoic acid is a metabolite of polyphenols such as phloretin and quercetin. It is also a phenolic acid antioxidant present in fruits, vegetables and nuts. Further, it is found to be an efficacious chemopreventive agent in several carcinogenesis models. In addition to this, it acts as an anti-inflammatory agent.
3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).
Related reactions
58 records
Compound notes
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