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Protocatechuic acid

CAS No.
99-50-3
Chemical Name:
Protocatechuic acid
Synonyms
3,4-DIHYDROXYBENZOIC ACID;protocatechuate;3,4-Dihydroxybenzoic;Protocatechuic aci;Protocatechoic Acid;PROTOCATECHUIC ACID(P);3,4-Dihydroxybenzoic acid,97%;Pyrocatechol-p-carboxylic acid;3,4- twohydroxybenzoic acid/protocatechuicacid;3,4-Dihydroxybenzoic acid Vetec(TM) reagent grade, 97%
CBNumber:
CB3305861
Molecular Formula:
C7H6O4
Molecular Weight:
154.12
MDL Number:
MFCD00002509
MOL File:
99-50-3.mol
MSDS File:
SDS
Last updated:2023-11-21 16:03:41

Protocatechuic acid Properties

Melting point 197-200 °C (dec.) (lit.)
Boiling point 237.46°C (rough estimate)
Density 1.54
refractive index 1.6400 (estimate)
FEMA 4430 | 3,4-DIHYDROXYBENZOIC ACID
storage temp. Store below +30°C.
solubility 20g/l
pka 4.48(at 25℃)
form 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
Water Solubility Soluble in hot alcohol and ether. Slightly soluble in water.
Sensitive Air Sensitive
Merck 14,7894
BRN 1448841
Stability Stable. Incompatible with strong oxidizing agents, strong bases.
InChIKey YQUVCSBJEUQKSH-UHFFFAOYSA-N
LogP 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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-37/39
WGK Germany  3
RTECS  UL0560000
HS Code  29182990
NFPA 704
1
2 0

Protocatechuic acid price More Price(49)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHL89766 Protocatechuic acid phyproof? Reference Substance 99-50-3 100MG $262 2024-03-01 Buy
Sigma-Aldrich 37580 3,4-Dihydroxybenzoic acid ≥97.0% (T) 99-50-3 25g $117 2024-03-01 Buy
Sigma-Aldrich 37580 3,4-Dihydroxybenzoic acid ≥97.0% (T) 99-50-3 100g $221 2024-03-01 Buy
Sigma-Aldrich 08992 3,4-Dihydroxybenzoic acid analytical standard 99-50-3 50mg $136 2024-03-01 Buy
Sigma-Aldrich 03930590 Protocatechuic acid primary reference standard 99-50-3 50mg $234 2024-03-01 Buy
Product number Packaging Price Buy
PHL89766 100MG $262 Buy
37580 25g $117 Buy
37580 100g $221 Buy
08992 50mg $136 Buy
03930590 50mg $234 Buy

Protocatechuic acid Chemical Properties,Uses,Production

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.

Physical properties

Protocatechuic acid has a density of 1.54g/cm3 and a melting point of about 200°C. It is soluble in ethanol, ether, acetone, ethyl acetate, soluble in hot water, slightly soluble in cold water, and insoluble in benzene and chloroform. Decomposes in boiling water and emits carbon dioxide. Its aqueous solution is green when it meets ferric chloride, and red when it meets sodium bicarbonate. It is a white to brown crystalline powder that will change color in the air.

Pharmaceutical Applications

Protocatechuic acid is a metabolite of complex polyphenols, such as anthocyanins and proanthocyanidins. They are high in plants and fruits and can be absorbed by animals and humans. It is estimated that people’s daily intake of anthocyanins is higher than other anthocyanins. Polyphenols are higher, so the nutritional value of protocatechuic acid is increasingly recognized. A large number of experiments have proved that protocatechuic acid has a variety of biological activities against different molecular targets. It has antibacterial, antioxidant, anti-inflammatory, anti-hyperglycemic and neuroprotective effects. In addition, protocatechin has potential chemical Protective effect, it can inhibit chemical carcinogens in vitro and produce pro-apoptosis and anti-proliferation effects in different aspects.

Preparation

99-50-3 synthesis
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%.

Chemical Properties

white to light yellow crystal powder

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

A phenolic acid antioxidant and chemopreventive agent

Uses

3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).

Definition

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

Biosynthesis

Protocatechuic acid is synthesized from the intermediates of the shikimate pathway. In this case, 3-dehydroshikimate is converted to protocatechuic acid as shown in Fig.11.2. Activity measurements from mung bean seedlings, on the other hand, indicate that 3-dehydroshikimate can be converted to protocatechuic acid (Widhalm and Dudareva 2015). Protocatechuic acid (11.12) upon hydroxylation produces gal- lic acid. The enzyme catalyzing this reaction is not well understood (Muir et al.2011).
Biosynthesis of Protocatechuic Acid
Biosynthesis of Protocatechuic Acid

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.

Biological Activity

Protocatechuic acid (PCA) is a dihydroxybenzoic acid phenolic compound found in many edible and medicinal plants. It is a major metabolite of antioxidant polyphenols found in green tea and demonstrates free radical scavenging capability in a 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity assay (IC50 = 16.3 μM). It is thought to possess anti-inflammatory, antihyperglycemic, neuroprotective, and anticancer activities. Dietary administration of PCA dose dependently inhibits in vitro chemical carcinogenesis and exerts pro-apoptotic and anti-proliferative effects in different tissues. In studies of tumor cell migration and invasion using mouse melanoma B16/F10 cells, PCA at 0.1-2 mM down-regulated the Ras/Akt/NF-κB pathway by targeting RhoB activation, leading to a reduction of MMP-mediated activity.

Biochem/physiol Actions

Chemopreventive in several animal models of carcinogenesis. Blocks cell proliferation in the post-initiation phase.

Source

Protocatechuic acid, in free or bound form, is found in the leaves, fruits, wood, barks, flowers of many angiosperms. Free protocatechuic acid is found in the scales of onion (Allium cepa L.), star anise fruits (Illicium L.) and leaves of grapevines (Vitis L.). It is part of the tannins from leaves of apple trees, bark of oak, bark and flowers of acacia (Acacia L). The 3,4-dimethyl ether of protocatechuic acid, the socalled veratric acid, is widely distributed.

121-34-6
99-50-3
Synthesis of Protocatechuic acid from Vanillic acid
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View Lastest Price from Protocatechuic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
3,4-Dihydroxybenzoic acid pictures 2024-03-19 3,4-Dihydroxybenzoic acid
99-50-3
US $0.00 / Kg/Drum 1KG 99% 200mt/year Jinan Finer Chemical Co., Ltd
3,4-Dihydroxybenzoic acid pictures 2024-01-08 3,4-Dihydroxybenzoic acid
99-50-3
US $110.00 / KG 10KG 99.50% 100kg Wuhan Boyuan Import & Export Co., LTD
protocatechuic acid pictures 2024-01-08 protocatechuic acid
99-50-3
US $0.00-0.00 / KG 1KG 99% 5000Tons Wuhan Boyuan Import & Export Co., LTD
3,4-Dihydroxybenzoic acid >=97.0% (T) Carbohydroquinonic acid Hypogallic acid 3,4-Dihydroxybenzoic acid, >=99% Benzoic acid, 3,4-dihydroxy- PROTOCATECHUIC ACID(RG) 3,4-DIHYDROXYBENZOIC ACID / PROTOCATECHUIC ACID 4-Carboxy-1,2-dihydroxybenzene Protocatechuic acid ,99% 4-Carboxypyrocatechol Catechol-p-carboxylic acid Protocatechuic acid / 3,4-Dihydroxybenzoic acid Protocatechuic Acid (25 mg) (3,4-dihydroxybenzoic acid) 3,4-Dihydroxybenzoic acid, 97% 25GR 4,5-dihydroxybenzoicacid 3,4-DihydroxybenzoicAcid98% 1,2-Dihydroxybenzene-4-carboxylic Acid NSC 16631 Catechol-4-carboxylic Acid Protocatechuic Acid Pyrocatechol-4-carboxylic Acid CATECHOL-4-CARBOXYLIC ACID 3,4-DIHYDROXYBENZOIC ACID N-HYDRATE 3,4-DIHYDROBENZOIC ACID AKOS 220-70 RARECHEM AL BO 0347 PROTOCATECHUIC ACID N-HYDRATE PROTOCATECHUIC ACID PYROCATECHOL-4-CARBOXYLIC ACID 3,4-dihydroxy-benzoicaci 3,4-Dihydroxybenzoic acid in stock Factory 3,4-Dihydroxybenzoic acid 99-50-3 Protocatechuic acid, 99%, for synthesis Protocatechuic acid@100 μg/mL in AcCN 3,4-Dihydroxybenzoic acid USP/EP/BP Protocatechuic acid CAS 99-50-3 with best price Protocatechuic acidQ: What is Protocatechuic acid Q: What is the CAS Number of Protocatechuic acid Q: What is the storage condition of Protocatechuic acid Q: What are the applications of Protocatechuic acid Protocatechuic aci Protocatechuic acid, 4-Carboxybenzene-1,2-diol, 4-Carboxycatechol 3,4- twohydroxybenzoic acid/protocatechuicacid 3,4-Dihydroxybenzoic acid Vetec(TM) reagent grade, 97% PROTOCATECHUIC ACID(P) Pyrocatechol-p-carboxylic acid protocatechuate 3,4-Dihydroxybenzoic acid,97% 3,4-Dihydroxybenzoic Protocatechoic Acid 3,4-DIHYDROXYBENZOIC ACID Protocatechuic acid (8CI) 99-50-3 99-50-4 C7H6O4xH2O C7H7O6 Chemopreventive Agents C7 Cancer Research Carbonyl Compounds Carboxylic Acids Building Blocks Anti-proliferative Agents