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
Show more names
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
- Formal charge
- 0
- Complexity
- 157
Experimental & physicochemical properties
Solubility
18.2 mg/mL at 14 °C
Soluble
Soluble (in ethanol)
Physical Description
White to brownish solid; Discolored by air; [Merck Index]
Solid
Light brown solid
Collision Cross Section
122.3 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
122.9 Ų [M-H]-
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
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 20 g/l · 20g/l
- pka
- 4.48 · 4.48(at 25℃)
- form
- Fine Crystalline Powder
- color
- Beige to brown
- PH
- 3.78 · 3.78(1 mM solution);3.25(10 mM solution);2.74(100 mM solution)
- Odor
- 100 % · at 100.00 %. mild phenolic balsamic
- Odor Type
- phenolic
- Water Solubility
- Soluble in hot alcohol and ether. Slightly soluble in water.
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,7894
- JECFA Number
- 2278 · 2278
- BRN
- 1448841 · 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
- 1.16 · 1.16
- CAS DataBase Reference
- 99 · 99-50-3(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 3 · 3,4-DIHYDROXYBENZOIC ACID
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 36 R5QJ8L4B · 36R5QJ8L4B
- EPA Substance Registry System
- Protocatechuic acid (99-50-3)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- RTECS
- 560000 · UL0560000
- HS Code
- 29182990 · 29182990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
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
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
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
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.
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
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%.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.
Related reactions
Linked notes
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