Protocatechuic Acid
3,4-DIHYDROXYBENZOIC ACID · protocatechuate · Protocatechoic Acid · Hypogallic acid · 3,4-Dihydroxybenzoic · PROTOCATECHUIC ACID(P) · Protocatechuic aci · 3,4-Dihydroxybenzoic acid,97%
Identifiers & Physical Properties
| CAS No. | 99-50-3 |
|---|---|
| Molecular formula | C7H6O4 |
| Average molar mass | 154.12 g/mol |
| Monoisotopic mass | 154.02660867 g/mol |
| SMILES | O=C(O)c1ccc(O)c(O)c1 |
| InChIKey | YQUVCSBJEUQKSH-UHFFFAOYSA-N |
| PubChem CID | 72 |
| ChEMBL | CHEMBL37537 |
| ChEBI | CHEBI:36062 |
| EC No. | 202-760-0 |
| DTXSID | DTXSID4021212 |
Chemical & Physical Properties
| XLogP | 1.1 |
|---|---|
| Topological polar surface area | 77.8 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 1 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 157 |
| Chemical classes | Biological Agents -> Plant Oils and Extracts |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| LogP (partition coefficient) | 0.86 |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Flavoring agents | EU Flavoring substances |
| Solubility | 18.2 mg/mL at 14 °CSolubleSoluble (in ethanol)20g/lSoluble in hot alcohol and ether. Slightly soluble in water. |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Melting point | 221 °C197-200 °C (dec.) (lit.) |
| Vapor pressure | 0.0000021 [mmHg] |
| Physical Description | White to brownish solidDiscolored by air[Merck Index]Light brown solid |
| Dissociation Constants | 4.26 (at 25 °C) |
| Collision Cross Section | 122.3 Ų [M+H-H2O]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]122.9 Ų [M-H]- |
| Boiling point | 237.46°C (rough estimate) |
| Density | 1.54 |
| Refractive index | 1.6400 (estimate) |
| FEMA | 4430 | 3,4-DIHYDROXYBENZOIC ACID |
| FLAVIS Number | 08.133 | 3,4-Dihydroxybenzoic acid |
| Storage conditions | Store below +30°C. |
| pKa (acidity coefficient) | 4.48(at 25℃) |
| Physical state | Fine Crystalline Powder |
| Color | Beige to brown |
| pH | 3.78(1 mM solution)3.25(10 mM solution)2.74(100 mM solution) |
| Odor | at 100.00 %. mild phenolic balsamic |
| Odor type | phenolic |
| Sensitivity | Air Sensitive |
| Merck | 14,7894 |
| JECFA Number | 2278 |
| BRN | 1448841 |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
| Cosmetics Ingredients Functions | SKIN PROTECTING |
| 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 | OC(=O)c1ccc(O)c(O)c1 |
| LogP (partition coefficient) | 1.16 |
| CAS DataBase Reference | 99-50-3(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | 3,4-DIHYDROXYBENZOIC ACID |
| EWG's Food Scores | 1 |
| FDA UNII | 36R5QJ8L4B |
| EPA Substance Registry System | Protocatechuic acid (99-50-3) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36-37/39 |
| Water hazard class (WGK) | 3 |
| RTECS number | UL0560000 |
| Customs code | 29182990 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Safety & Regulations
| GHS classification | WarningH315 (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. |
|---|---|
| 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 summary | Causes other liver changes and multiple enzyme effects in 28-day intermittent oral studies of ratsIntraperitoneal LD50 (mouse) > 800 mg/kg[RTECS] A skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| RTECS number | UL0560000 |
| Customs code | 29182990 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36-37/39 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335 |
Applications & Uses
Description
Protocatechuic 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.
Uses
A phenolic acid antioxidant and chemopreventive agent
Uses
3,4-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.
Uses
3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).
General Description
Protocatechuic 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 & Synthesis
Preparation
1.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%.