Quick Search
Ethyl 3,4-Dihydroxybenzoate is an analogue of 2-oxoglutarate and thus a competitive inhibitor of prolyl hydroxylase domain enzymes (PHDs).
Ethyl 3,4-Dihydroxybenzoate is known as protocatechuic acid and is present in plant foods such as olives, roselle, du-zhong, and white grape wine.
Ethyl 3,4-Dihydroxybenzoate have antioxidant, cardioprotective, neuroprotective, antimicrobial, anti-inflammatory and myoprotective activity, as well as anti-ulcer activity.
CAS Number: 3943-89-3
Molecular Formula: C9H10O4
Molecular Weight: 182.17
EINECS Number: 223-529-0
Synonyms: Ethyl 3,4-dihydroxybenzoate, 3943-89-3, Ethyl protocatechuate, 3,4-Dihydroxybenzoic Acid Ethyl Ester, Ethyl-3,4-dihydroxybenzoate, Protocatechuic acid ethyl ester, 4YGJ96WTBG, DTXSID2057732, NSC-86130, DTXCID3031521, CHEBI:132364, 223-529-0, RefChem:138647, MFCD00002199, Benzoic acid, 3,4-dihydroxy-, ethyl ester, CHEMBL486216, EDHB, UNII-4YGJ96WTBG, 3,4-Dihydroxybenzoic Acid Ethyl Ester, Protocatechuic Acid Ethyl Ester, Ethyl Protocatechuate, NSC 619681, NSC 86130, EINECS 223-529-0, NSC 86130, EC 223-529-0, 3,4-DHBEEOP, SCHEMBL39791, Ethyl-3,4-dihydroxy-benzoate, orb1301586, Protocatechuic acid, ethyl ester, SCHEMBL29625511, Ethyl 3,4-dihydroxybenzoate (Protocatechuic acid ethyl ester), HMS6018C11, BCP26356, NSC86130, Tox21_113836, BDBM50428394, NSC619681, SBB063061, AKOS015856218, Protocatechuic acid ethyl ester, 97%, AC-9614, CS-W017125, FD02005, FD16015, HY-W016409, NSC-619681, PS-4053, 3,4-Dihydroxy-benzoic acid ethyl ester, 3,4-Dihydroxy-benzoic acid, ethyl ester, Benzoic acid,4-dihydroxy-, ethyl ester, NCGC00253717-01, SY017737, CAS-3943-89-3, DB-013234, D0571, NS00006102, ST50825182, SR-01000944711, Q3277971, SR-01000944711-1, F0001-1109, Ethyl 3,4-dihydroxybenzoate, Protocatechuic acid ethyl ester, Ethyl 3,4-dihydroxybenzoate (Discontinued, See C4X-1069119), InChI=1/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H, 3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER, ETHYL 3,4-DIHYDROXYBENZOATE, ETHYL PROTOCATECHUATE, RARECHEM AL BI 0069, PROTOCATECHUIC ACID ETHYL ESTER, 3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER 97%, 3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER 98+%, ETHYL 3,4-DIHYDROXYBENZOATE (PROTOCATECHUIC ACID ETHYL ESTER)
Ethyl 3,4-Dihydroxybenzoate is the anti-oxidative component of peanut seed testa.
Ethyl 3,4-Dihydroxybenzoate is a phenolic compound.
An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol.
Ethyl 3,4-Dihydroxybenzoate can be found in the peanut seed testa.
Ethyl 3,4-Dihydroxybenzoate is also present in wine.
Ethyl 3,4-Dihydroxybenzoate is the ethylic ester of protocatechuic acid.
Ethyl 3,4-Dihydroxybenzoate is a prolyl 4-hydroxylase inhibitor and can be used to protect the myocardium.
Ethyl 3,4-Dihydroxybenzoate is an orally effective, blood-brain barrier-permeable, competitive prolyl hydroxylase (PHD) inhibitor that inhibits the hydroxylation modification of hypoxia-inducible factor (HIF) by PHD. Ethyl 3,4-dihydroxybenzoate stabilizes HIF-1α by inhibiting PHD, activates downstream pathways to induce autophagy and apoptosis of tumor cells, and regulates inflammatory responses, inhibits the NF-κB pathway, improves vascular permeability, and promotes osteoblast differentiation.
Ethyl 3,4-Dihydroxybenzoate has anti-tumor, anti-hypoxic injury, and bone metabolism regulation effects.
It can also be used in the research of cardiovascular protection (such as reducing myocardial ischemic damage), bone tissue engineering (promoting osteogenesis/inhibiting osteoclast differentiation), and prevention and treatment of high-altitude cerebral edema.
Ethyl 3,4-Dihydroxybenzoate, also known as Ethyl Protocatechuate or Protocatechuic Acid Ethyl Ester, is a naturally occurring or synthetically produced ester of protocatechuic acid, which belongs to the class of hydroxybenzoic acids.
Ethyl 3,4-Dihydroxybenzoate consists of a benzoic acid core substituted with hydroxyl groups at the 3 and 4 positions on the aromatic ring, and an ethyl ester group attached to the carboxyl functional group, giving it the molecular formula C₉H₁₀O₄.
This structure allows it to exhibit strong antioxidant properties, as the hydroxyl groups on the aromatic ring can readily donate hydrogen atoms to neutralize free radicals and reactive oxygen species.
Ethyl 3,4-Dihydroxybenzoate is frequently studied and used in pharmaceutical, nutraceutical, and cosmetic applications, because its antioxidant and anti-inflammatory activities help protect cells from oxidative stress, lipid peroxidation, and DNA damage, which are associated with aging, chronic diseases, and degenerative conditions.
In addition, Ethyl 3,4-Dihydroxybenzoate has demonstrated potential cardioprotective, neuroprotective, and antimicrobial effects, making it a compound of interest in experimental therapies and dietary supplements.
Ethyl 3,4-Dihydroxybenzoate, also known as EDHB or ethyl protocatechuate, belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters.
These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.
An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. ethyl 3,4-dihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Ethyl 3,4-Dihydroxybenzoate has been identified in human blood as reported by (PMID: 31557052 ).
Ethyl 3,4-Dihydroxybenzoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives.
Technically Ethyl 3,4-dihydroxybenzoate is part of the human exposome.
The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health.
An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Ethyl 3,4-Dihydroxybenzoate is a high-purity compound suitable for various research applications.
Also known as ethyl protocatechuate, Ethyl 3,4-Dihydroxybenzoate is commonly utilized in biochemical and pharmaceutical studies
Due to its esterified form, Ethyl 3,4-Dihydroxybenzoate is more lipophilic than protocatechuic acid itself, which enhances its absorption, bioavailability, and membrane permeability in biological systems, allowing it to act more effectively in certain formulations or delivery systems.
In research and industrial contexts, it is often incorporated into antioxidant-enriched foods, cosmetic products, or polymer additives, where it can serve both as a functional active ingredient and a stabilizer to prevent oxidative degradation.
Melting point: 132-134 °C (lit.)
Boiling point: 275.56 °C (rough estimate)
Density: 1.2481 (rough estimate)
Vapor pressure: 0-9.4 Pa at 20-120℃
Refractive index: 1.4500 (estimate)
Storage temp.: Sealed in dry, Room Temperature
Solubility: DMSO (Slightly), Methanol (Slightly)
Form: Crystalline Powder
pKa: 8.19 ± 0.18 (Predicted)
Color: Pale yellow to beige
Odor: at 100.00% phenolic
Water Solubility: Insoluble in water. Soluble in ethanol.
BRN: 2097435
InChIKey: KBPUBCVJHFXPOC-UHFFFAOYSA-N
LogP: 1.4 at 35℃ and pH 6.6
Surface tension: 74.7 mN/m at 1 g/L and 20℃
Ethyl 3,4-Dihydroxybenzoate contains reducible polyphenol hydroxyl groups and exhibits antioxidant activity.
Recent studies have shown that Ethyl 3,4-Dihydroxybenzoate acts as an analog of the substrate α-ketoglutarate and competes for prolyl-hydroxylase activity, thus acting as an inhibitor and effectively inhibiting collagen synthesis and breast cancer metastasis.
In addition, in vitro and animal studies in a cerebral ischemic rat model have revealed that EDHB shows increased protective effects and improves rat behavior by inhibiting free radical damage.
Ethyl 3,4-Dihydroxybenzoate, an antioxidant, is a prolyl-hydroxylase inhibitor found in the testa of peanut seeds.
Ethyl 3,4-Dihydroxybenzoate is a highly versatile phenolic ester that combines the structural features of protocatechuic acid with the chemical properties conferred by ethyl esterification, which allows it to maintain strong antioxidant and radical-scavenging capabilities while improving its solubility in organic solvents and lipophilic environments.
The presence of the two hydroxyl groups at positions 3 and 4 on the aromatic ring makes the molecule capable of chelating metal ions, neutralizing reactive oxygen species, and stabilizing free radicals, which collectively reduce oxidative stress in biological systems or prevent oxidative degradation in chemical formulations.
In addition to its antioxidant function, Ethyl 3,4-Dihydroxybenzoate exhibits anti-inflammatory, antimicrobial, and anti-carcinogenic properties, as demonstrated in various in vitro and in vivo studies, making it a compound of interest for pharmaceutical research, functional foods, dietary supplements, and cosmetic formulations aimed at protecting cells, tissues, and biomolecules from oxidative and inflammatory damage.
Its esterified form enhances cellular uptake and bioavailability, meaning that when administered orally or topically, it can more efficiently reach target tissues and exert protective effects compared to its free acid counterpart.
Ethyl 3,4-Dihydroxybenzoate is also used in chemical and material sciences as a stabilizer or additive, where it functions to prevent oxidation of polymers, oils, and sensitive organic compounds, thereby extending the shelf life and performance of industrial or consumer products.
Its ability to interact with radical species without undergoing rapid degradation allows it to act as a long-lasting antioxidant in formulations, making it valuable in cosmetics, skincare products, and nutraceuticals where maintaining product integrity is critical.
Because of its chemical stability, mild acidity, and multifunctional reactivity, Ethyl 3,4-Dihydroxybenzoate can be incorporated into emulsions, gels, polymer matrices, and other complex systems, where it contributes both functional benefits and structural compatibility.
Researchers also explore its use in drug delivery systems, where its antioxidant properties can protect labile therapeutic agents from oxidative damage, or in bioactive coatings and surface treatments to provide long-term protective effects against environmental stressors.
Uses Of Ethyl 3,4-Dihydroxybenzoate:
An antioxidant compound found in Sicilian virgin olive oils and red wines.
Ethyl 3,4-Dihydroxybenzoate is a prolyl 4-hydroxylase inhibitor and can be used to protect the myocardium.
Ethyl 3,4-Dihydroxybenzoate is primarily used in pharmaceutical and nutraceutical applications as an antioxidant and anti-inflammatory agent, where its ability to scavenge free radicals, inhibit lipid peroxidation, and reduce oxidative stress makes it valuable in formulations aimed at protecting cells and tissues from oxidative damage associated with aging, chronic diseases, and degenerative conditions.
In research and experimental medicine, it has been studied for its cardioprotective, neuroprotective, and hepatoprotective effects, and it is sometimes included in dietary supplements or functional foods to enhance systemic antioxidant defenses and support overall health.
In the cosmetic and personal care industries, Ethyl 3,4-Dihydroxybenzoate is incorporated into anti-aging creams, lotions, serums, and sunscreen formulations, where it acts to prevent oxidative damage to skin cells, reduce inflammation, and stabilize sensitive ingredients in the formulation, thereby extending product shelf life while delivering bioactive benefits to the skin.
Its lipophilic ethyl ester structure allows it to penetrate the skin more effectively than the free acid form, increasing its efficacy in topical applications.
The compound is also used in industrial and chemical applications as a stabilizer or additive for polymers, oils, and sensitive organic compounds, where its antioxidant properties help prevent degradation caused by oxygen, light, or heat, thus enhancing the durability, performance, and shelf life of coatings, plastics, and other products susceptible to oxidative damage.
In experimental material science, it has been explored for bioactive coatings, protective films, and composite materials, where it can provide long-term oxidative stability and contribute to the functional performance of the final product.
Additionally, in laboratory research and experimental formulations, Ethyl 3,4-Dihydroxybenzoate is often employed as a model antioxidant or phenolic ester, used to study cellular oxidative stress, enzyme inhibition, and radical-scavenging mechanisms, as well as to evaluate the protective effects of bioactive compounds in both in vitro and in vivo models.
Its combination of chemical stability, antioxidant activity, and biocompatibility makes it a highly versatile compound for applications spanning healthcare, cosmetics, industrial chemistry, and experimental research.
Ethyl 3,4-Dihydroxybenzoate is widely employed in pharmaceutical formulations and nutraceutical products due to its strong antioxidant, anti-inflammatory, and radical-scavenging properties, which enable it to protect biological molecules such as lipids, proteins, and DNA from oxidative damage and cellular stress, making it a promising compound in preventive healthcare and disease management, particularly for conditions linked to chronic inflammation, cardiovascular disorders, and neurodegenerative diseases.
Researchers often incorporate it into functional food products, dietary supplements, and herbal formulations to enhance systemic antioxidant defenses, improve metabolic health, and potentially reduce the risk of age-related degenerative conditions by mitigating oxidative stress and modulating inflammatory pathways.
In the cosmetics and personal care industry, Ethyl 3,4-Dihydroxybenzoate is formulated into anti-aging creams, serums, sunscreens, and moisturizers, where it functions not only as a bioactive ingredient to protect skin cells from oxidative stress caused by UV radiation and environmental pollutants, but also as a stabilizer to preserve the integrity of other sensitive ingredients, thus extending product shelf life while delivering functional benefits such as improved skin elasticity, reduced erythema, and delayed appearance of wrinkles.
Its ethyl ester structure enhances lipophilicity and skin penetration, allowing it to reach deeper layers of the epidermis and exert more effective biological activity than the non-esterified form.
In industrial and material science applications, Ethyl 3,4-Dihydroxybenzoate is used as a stabilizer or additive in polymers, oils, coatings, and other sensitive organic compounds, where it prevents oxidative degradation, discoloration, or loss of mechanical performance under conditions of heat, light, or prolonged storage, thereby improving the durability, chemical resistance, and longevity of the final products.
Ethyl 3,4-Dihydroxybenzoate has also been investigated for use in bioactive or functional coatings, where the compound can provide antioxidant protection and extend the functional lifespan of surfaces in contact with reactive environments.
Furthermore, in biomedical and experimental research, Ethyl 3,4-Dihydroxybenzoate serves as a model phenolic ester and antioxidant probe, enabling scientists to study mechanisms of radical scavenging, oxidative stress mitigation, enzyme inhibition, and cytoprotective effects, while also acting as a reference compound for evaluating the efficacy of other antioxidant molecules.
Its chemical stability, multifunctional bioactivity, and compatibility with diverse formulations make it a highly versatile compound that bridges applications in healthcare, cosmetic science, food technology, polymer chemistry, and experimental research, where both its protective and functional roles can be fully utilized.
Safety Profile Of Ethyl 3,4-Dihydroxybenzoate:
Ethyl 3,4-Dihydroxybenzoate can cause mild to moderate skin irritation upon direct contact, manifesting as redness, itching, or dryness, particularly in individuals with sensitive skin or with prolonged exposure.
Accidental contact with the eyes may result in temporary irritation, watering, and discomfort, which highlights the importance of wearing protective gloves, long sleeves, and safety goggles when handling the compound in laboratory, industrial, or formulation environments.
While Ethyl 3,4-Dihydroxybenzoate is not highly volatile under normal conditions, inhalation of dust, powder, or aerosols generated during handling can irritate the respiratory tract, leading to coughing, throat discomfort, or mild breathing difficulty.
Adequate ventilation, fume hoods, or respirators should be used when working with the powder form or in processes that may aerosolize the compound.
Prolonged or repeated exposure to Ethyl 3,4-Dihydroxybenzoate may cause skin sensitization in susceptible individuals, resulting in allergic dermatitis or heightened sensitivity upon subsequent contact.
Ethyl 3,4-Dihydroxybenzoate is therefore critical to minimize direct skin contact and follow strict hygiene practices, such as washing hands thoroughly after handling and avoiding ingestion or prolonged skin exposure.
