Protocatechuic Acid

HCID 72CAS 99-50-3

Basic information

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 acid99-50-34-Carboxy-1,2-dihydroxybenzeneProtocatehuic acid4,5-Dihydroxybenzoic acidDTXSID402121236R5QJ8L4BNSC-16631DTXCID601212FEMA NO. 4430CHEBI: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-3,4-DihydroxybenzoicacidMFCD000025093,4-Dihydroxy Benzoic Acidprotocatechuicacid

Database identifiers

CAS
99-50-3
PubChem CID
72
DTXSID
DTXSID4021212
ChEMBL
CHEMBL37537
ChEBI
CHEBI:36062
UNII
36R5QJ8L4B
EC Number
202-760-0
Nikkaji
J11.618A

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

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Plant Oils and Extracts
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.86
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 3 items

18.2 mg/mL at 14 °C

Soluble

Soluble (in ethanol)

Physicochemical properties

Melting point
197 · 197-200 °C (dec.) (lit.)
Boiling point
237.46 °C · 237.46°C (rough estimate)
Density
1.54 · 1.54
refractive index
1.64 · 1.6400 (estimate)
FEMA
4430 · 4430 | 3,4-DIHYDROXYBENZOIC ACID
FLAVIS Number
8.133 · 08.133 | 3,4-Dihydroxybenzoic acid

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

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

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 · 2 items

Present in wheat grains and many other plants; [Merck Index]

Synthetic Polymer MALDI Matrix Compounds

Use Classification · 2 items

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Applications · 5 items

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.

Uses3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).

General DescriptionProtocatechuic acid belongs to the class of polyphenolic compounds, which can be generally isolated from the dried flower of roselle. It can serve as a potential candidate possessing anticancer property, which can be involved in suppressing the growth of human promyelocytic leukemia HL-60 cells.

Preparation methods · 1 item

Preparation1.Preparation of piperonic acidAdd 12 g piperonal and 300 ml water into a 1000 ml three-necked flask, heat it to 70~80℃, and under vigorous stirring, add 5% potassium permanganate aqueous solution (18 g potassium permanganate plus 360 ml Water), the dripping time is about 30 minutes, after the addition, continue to stir until the purple fades, filter while hot, and wash the filter cake. The mother liquor is acidified and filtered to obtain piperonic acid. The finished product is naturally dried 12.4 g, the yield is 94%, and the melting point is 228~231℃.2. Preparation of protocatechuic acidAdd 4 g of aluminum trichloride to 150 ml of nitrobenzene, stir to dissolve, add 10 g of piperonic acid in batches, stir at room temperature for 3 to 5 h, pour the reaction solution into 100 ml of water, separate the water layer, Sulfur dioxide was introduced into the aqueous solution, and protocatechuic acid was precipitated. The dry weight is 7.5g, the melting point is 200~201℃, and the yield is 81%.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.

Related reactions

58 records

Linked notes

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