3943-89-3

Basic information

• Product Name: Ethyl 3,4-dihydroxybenzoate
• Synonyms: 3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER;ETHYL 3,4-DIHYDROXYBENZOATE;ETHYL PROTOCATECHUATE;RARECHEM AL BI 0069;PROTOCATECHUIC ACID ETHYL ESTER;3,4-dihydroxybenzate ethyl ester;3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER 97%;3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER 98+%
• CAS NO: 3943-89-3
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• EINECS: 223-529-0
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Esters;Benzoic acid;Organic acids;API intermediates;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;HIF Prolyl-Hydroxylase Inhibitors;Aerobic Glycolysis (the Warburg Effect);Building Blocks;C8 to C9;Cancer Metabolism;Cancer Research;Carbonyl Compounds;Chemical Synthesis;Esters;Inhibitors of Aerobic Glycolysis (the Warburg Effect);Organic Building Blocks
• Mol File: 3943-89-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 132-134 °C(lit.)
• Boiling Point: 275.56°C (rough estimate)
• Flash Point: 147 °C
• Appearance: Pale yellow to beige/Crystalline Powder
• Density: 1.2481 (rough estimate)
• Vapor Pressure: 1.27E-05mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.19±0.18(Predicted)
• Water Solubility: Insoluble in water. Soluble in ethanol.
• BRN: 2097435
• CAS DataBase Reference: Ethyl 3,4-dihydroxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3,4-dihydroxybenzoate(3943-89-3)
• EPA Substance Registry System: Ethyl 3,4-dihydroxybenzoate(3943-89-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 3943-89-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3943-89-3 differently. You can refer to the following data:
1. An antioxidant compound found in Sicilian virgin olive oils and red wines.
2. The compound is a prolyl 4-hydroxylase inhibitor and can be used to protect the myocardium.

Definition

ChEBI: An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.

InChI:InChI=1/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H3

Synthetic route

3,4-Dihydroxybenzoic acid (99-50-3) + ethanol (64-17-5) → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With sulfuric acid Heating;	99%
With sulfuric acid at 50℃; for 3h;	98%
With sulfuric acid	98%

4-Benzyloxy-3-(4-methoxycarbonyl-benzyloxy)-benzoic acid ethyl ester → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 20℃; for 3h;	96%

ethyl vanillate (617-05-0) → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h; Reagent/catalyst;	94%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h; Reagent/catalyst;	94%
With aluminium(III) iodide; ethyl acetate; diisopropyl-carbodiimide In acetonitrile at 20℃; for 2h; chemoselective reaction;	93%

4-Benzyloxy-3-(3-methoxycarbonyl-benzyloxy)-benzoic acid ethyl ester → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 20℃; for 3h;	93%

4-benzyloxy-3-(4-nitro-benzyloxy)-benzoic acid ethyl ester → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 20℃; for 3h;	92%

ethyl 3,4-dihydro-2H-benzo[b]1,4-dioxepine-7-carboxylate (20986-39-4) → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With aluminum (III) chloride In benzene for 1h; Reflux;	90%

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h;	84%

ethanol (64-17-5) + 4-(hydroxymethyl)benzene-1,2-diol (3897-89-0) → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With dihydrogen peroxide for 3h; Irradiation;	83%

C17H28O4Si (1344113-41-2) → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
Stage #1: C17H28O4Si With palladium(II) trimethylacetate; [bis(acetoxy)iodo]benzene In α,α,α-trifluorotoluene at 120℃; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; Stage #3: With water In tetrahydrofuran	76%

ethyl 3-oxocyclohexanecarboxylate (33668-25-6) → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h; regioselective reaction;	53%

ethanol (64-17-5) + cyanidin 3-O-glucopyranoside chloride → Ethyl protocatechuate (3943-89-3) + glucopyranosyl 2-(3,4-dihydroxyphenyl)-4,6-dihydroxybenzofuran-3-carboxylate + C15H10O7 (1577235-12-1)

Conditions	Yield
With 2,2'-azobis-(2,4-dimethylvaleronitrile) at 60℃; for 4h;	A 33% B 28.2% C 9.6%

hydrogenchloride (7647-01-0) + 3,4-Dihydroxybenzoic acid (99-50-3) + ethanol (64-17-5) → Ethyl protocatechuate (3943-89-3)

3,4-Dihydroxybenzoic acid (99-50-3) + concentrated H2 SO4 → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
In ethanol	39 g (69%)
In ethanol	39 g (69%)
In ethanol	39 g (69%)

Ethyl 4-hydroxybenzoate (120-47-8) → Ethyl protocatechuate (3943-89-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1H-imidazole / tetrahydrofuran / 20 °C / Inert atmosphere 1.3: 20 °C 2.1: palladium(II) trimethylacetate; [bis(acetoxy)iodo]benzene / α,α,α-trifluorotoluene / 120 °C / Inert atmosphere 2.2: 20 °C View Scheme

Ethyl 4-hydroxybenzoate (120-47-8) → sorbic Acid (110-44-1) + formic acid (64-18-6) + glyceric acid (473-81-4) + Ethyl protocatechuate (3943-89-3) + benzene-1,2-diol (120-80-9) + hydroquinone (123-31-9) + phenol (108-95-2) + 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
With dihydrogen peroxide; titanium(IV) oxide In water at 35℃; for 0.5h; pH=7.3; Concentration; Irradiation;

...Expand

ethanol (64-17-5) + cyanidin-3-O-glucoside → Ethyl protocatechuate (3943-89-3) + C15H10O7 (1577235-12-1) + C21H20O12

Conditions	Yield
With water; dihydrogen peroxide at 40℃; for 2h;

Ethyl protocatechuate (3943-89-3) + 2-Bromoethyl methyl ether (6482-24-2) → 3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester (183322-16-9)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 60℃; for 19h; Inert atmosphere;	100%
With potassium carbonate In acetone at 20 - 70℃; for 24h;	93%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 64h; Inert atmosphere; Reflux;	93%

Ethyl protocatechuate (3943-89-3) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → ethyl 8-hydroxy-2,3-dimethyl-7-oxo-1,4,4a,7-tetrahydronaphthalene-4a-carboxylate

Conditions	Yield
With lithium perchlorate; acetic acid In nitromethane for 16h; electrolysis;	98%
With tetradecafluorohexane; lithium perfluorooctane sulfonate; acetic acid Diels-Alder reaction; Electrochemical reaction;	95%
In acetic acid electrochemical reaction: glass carbon anode (60x20 mm) coated with modified Nafion resin, Pt cathode (10x10 mm), aq. sodium dodecyl sulfate as supporting electrolyte, undivided cell 2.2 F mol-1, 0.8 V vs SCE; Yield given;

Ethyl protocatechuate (3943-89-3) + chloromethyl methyl ether (107-30-2) → ethyl 3,4-bis(methoxymethoxy)benzoate (959146-62-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 48h;	98%

Ethyl protocatechuate (3943-89-3) + isopropyl bromide (75-26-3) → ethyl 3,4-diisopropoxybenzoate (1369403-22-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃; for 19h; Inert atmosphere;	98%

Tetrafluorophthalonitrile (1835-65-0) + Ethyl protocatechuate (3943-89-3) → C26H16N2O8

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 3h;	98%

Ethyl protocatechuate (3943-89-3) + ethyl (E)-4-methyl-3,5-hexadienoate (76200-27-6) → 4-ethoxycarbonylmethyl-8-hydroxy-3-methyl-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

Conditions	Yield
With lithium perchlorate; acetic acid In nitromethane for 16h; Ambient temperature; constant potential electrolysis on PTFE-fiber coated glassy carbon anode/Pt cathode (1200 mV vs. SCE);	97%

1-bromo dodecane (112-29-8) + Ethyl protocatechuate (3943-89-3) → ethyl 3,4-bis(dodecyloxy)benzoate (773135-90-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	97%

Ethyl protocatechuate (3943-89-3) + p-methoxybenzyl chloride (824-94-2) → C25H26O6 (1401529-49-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	97%

Ethyl protocatechuate (3943-89-3) → C9H8O4(2-)*Mg(2+)

Conditions	Yield
With magnesium hydroxide In water at 20℃; for 2h;	97%

ethyl (E)-3,5-hexadienoate (74054-58-3) + Ethyl protocatechuate (3943-89-3) → 4-ethoxycarbonylmethyl-8-hydroxy-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

Conditions	Yield
With lithium perchlorate; acetic acid In nitromethane for 16h; Ambient temperature; constant potential electrolysis on PTFE-fiber coated glassy carbon anode/Pt cathode (1200 mV vs. SCE);	96%

Dichlorodiphenylmethane (2051-90-3) + Ethyl protocatechuate (3943-89-3) → 2,2-Diphenyl-1,3-benzodioxolane-5-carboxylic acid, ethyl ester (152361-07-4)

Conditions	Yield
at 170℃; for 0.166667h;	95%

2-chloroethyl methyl ether (627-42-9) + Ethyl protocatechuate (3943-89-3) → 3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester (183322-16-9)

Conditions	Yield
With 4-(Methylamino)pyridine; potassium carbonate at 90 - 95℃; Temperature; Reagent/catalyst;	95%
With carbon dioxide; ammonia at 50℃; for 0.5h; Temperature; Reagent/catalyst;	94.6%
With potassium tert-butylate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 12h;	87%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 120h; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 9h;	95 %Chromat.

di-tert-butyl dicarbonate (24424-99-5) + Ethyl protocatechuate (3943-89-3) → 3,4-bis-tert-butoxycarbonyloxy-benzoic acid ethyl ester (918402-89-8)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	95%

thiophosgene (463-71-8) + Ethyl protocatechuate (3943-89-3) → ethyl 2-thioxobenzo[d][1,3]dioxole-5-carboxylate (33373-19-2)

Conditions	Yield
With sodium carbonate In water at 0 - 20℃;	95%
With dmap; carbon dioxide In dichloromethane; acetone at -78 - 20℃; for 19h;	51%

2-[2-(2-ethoxyethoxy)ethoxy]ethyl chloride (538371-55-0) + Ethyl protocatechuate (3943-89-3) → ethyl 3,4-bis-(2-(2-(2-ethoxyethoxy)ethoxy)ethoxy)benzoate (916817-35-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	95%

1-[2-(ethoxy)ethoxy]-2-chloroethane (41771-35-1) + Ethyl protocatechuate (3943-89-3) → ethyl 3,4-bis-[2-(2-ethoxyehtoxy)ethoxy]benzoate (906550-98-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	95%

2-methoxyethyl methanesulfonate (16427-44-4) + Ethyl protocatechuate (3943-89-3) → 3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester (183322-16-9)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In toluene for 6h; Reflux;	95%
With potassium tert-butylate; tetrabutylammomium bromide In N,N-dimethyl-formamide at 30 - 40℃; for 10h;	90.5%

Ethyl protocatechuate (3943-89-3) + hexa(ethyleneglycol) ditosylate (42749-27-9) → C21H32O9

Conditions	Yield
With potassium hexafluorophosphate; potassium carbonate In acetonitrile for 12h; Reflux;	95%

Ethyl protocatechuate (3943-89-3) + dimethyl sulfate (77-78-1) → ethyl veratrate (3943-77-9)

Conditions	Yield
Stage #1: Ethyl protocatechuate With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: dimethyl sulfate at 50℃; for 5h;	94.5%

1-vinylcyclohexene (2622-21-1) + Ethyl protocatechuate (3943-89-3) → ethyl 2,4a,4b,5,6,7,8,10-octahydro-1-hydroxy-2-oxophenanthrene-4a carboxylate (1196885-37-6)

Conditions	Yield
With lead(II,IV) oxide; trifluoroacetic acid In tetrahydrofuran at 20℃; for 2.5h;	94%

Ethyl protocatechuate (3943-89-3) + 4’-[(10-bromodecyl)oxy]-4-carbonitrile-[1,1’-biphenyl] (140713-89-9) → 3,4-bis[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester (610785-23-4)

Conditions	Yield
With potassium carbonate; potassium iodide In butanone Heating;	93%

Ethyl protocatechuate (3943-89-3) + rhodamine B (509-34-2) → C28H30O3N2*C9H10O4

Conditions	Yield
In acetonitrile at 20℃; for 2.5h;	93%

1-methylbuta-1,3-diene (2004-70-8) + Ethyl protocatechuate (3943-89-3) → (4S,4aR)-8-Hydroxy-4-methyl-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

Conditions	Yield
With lithium perchlorate; acetic acid In nitromethane for 16h; electrolysis;	92%

Ethyl protocatechuate (3943-89-3) + 1,3-dibromo-propane (109-64-8) → ethyl 3,4-dihydro-2H-benzo[b]1,4-dioxepine-7-carboxylate (20986-39-4)

Conditions	Yield
With potassium carbonate In ethanol for 5h; Reflux;	91%

Upstream product

• 99-50-3 3,4-Dihydroxybenzoic acid 
• 64-17-5 ethanol 
• 7647-01-0 hydrogenchloride 
• 27214-71-7 cyanidin 3-O-glucopyranoside chloride 
• 3897-89-0 4-(hydroxymethyl)benzene-1,2-diol 
• 83759-00-6 3,4-dihydroxybenzoyl chloride 
• 617-05-0 ethyl vanillate 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 33668-25-6 ethyl 3-oxocyclohexanecarboxylate 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 20986-39-4 ethyl 3,4-dihydro-2H-benzo[b]1,4-dioxepine-7-carboxylate 
• 1344113-41-2 C₁₇H₂₈O₄Si 

Downstream Products

• 65479-39-2 2,6-dihydroxymethyl-3-(3,4-dimethoxyphenyl)-1,4-benzodioxan 
• 100100-77-4 (2RS,3RS)-2-(3,4-Dimethoxyphenyl)-3,6-bis(hydroxymethyl)-1,4-benzodioxan 
• 74741-37-0 (2S,3S)-2-(3,4-Dimethoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid ethyl ester 
• 163163-70-0 ethyl 3-hydroxy-4-<<2-(1-imidazolyl)ethyl>oxy>benzoate 
• 773135-90-3 ethyl 3,4-bis(dodecyloxy)benzoate 
• 179688-14-3 methyl 3,4-bis{[2-(methyloxy)ethyl]oxy}benzoate 
• 926652-62-2 3,4-bis-octadec-9-enyloxy-benzoic acid ethyl ester 
• 656806-89-2 2,2-bis-(3,5-difluoro-phenyl)-benzo[1,3]dioxol-5-carboxylic acid ethyl ester 
• 198128-90-4 3,4-diprenyloxybenzoic acid 
• 183583-93-9 3,4-digeranyloxybenzoic acid 
• 158860-97-0 3-hydroxy-4-isopropyloxybenzoic acid ethyl ester 
• 179688-26-7 2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester 
• 129425-59-8 3-tert-butyldimethylsilyloxy-4-(naphth-2-ylmethoxy)phenyl 2-thiazolyl ketone 
• 20825-87-0 2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid ethyl ester 

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