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99-50-3

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  • High quality 3,4-Dihydroxybenzoic acid CAS 99-50-3 99% with best price

    Cas No: 99-50-3

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99-50-3 Usage

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

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

Different sources of media describe the Uses of 99-50-3 differently. You can refer to the following data:
1. 3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).
2. A phenolic acid antioxidant and chemopreventive agent
3. 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.

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

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.

Check Digit Verification of cas no

The CAS Registry Mumber 99-50-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 99-50:
(4*9)+(3*9)+(2*5)+(1*0)=73
73 % 10 = 3
So 99-50-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)/p-1

99-50-3 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (B24016)  3,4-Dihydroxybenzoic acid, 97%   

  • 99-50-3

  • 25g

  • 444.0CNY

  • Detail
  • Alfa Aesar

  • (B24016)  3,4-Dihydroxybenzoic acid, 97%   

  • 99-50-3

  • 100g

  • 1402.0CNY

  • Detail
  • Alfa Aesar

  • (B24016)  3,4-Dihydroxybenzoic acid, 97%   

  • 99-50-3

  • 500g

  • 5594.0CNY

  • Detail
  • Sigma-Aldrich

  • (08992)  3,4-Dihydroxybenzoicacid  analytical standard

  • 99-50-3

  • 08992-50MG

  • 1,088.10CNY

  • Detail
  • Sigma-Aldrich

  • (03930590)  Protocatechuicacid  primary pharmaceutical reference standard

  • 99-50-3

  • 03930590-50MG

  • 1,930.50CNY

  • Detail
  • USP

  • (1579310)  Protocatechuicacid  United States Pharmacopeia (USP) Reference Standard

  • 99-50-3

  • 1579310-25MG

  • 4,662.45CNY

  • Detail

99-50-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,4-dihydroxybenzoic acid

1.2 Other means of identification

Product number -
Other names 4-Carboxy-1,2-dihydroxybenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:99-50-3 SDS

99-50-3Synthetic route

3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;100%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;100%
With 1,4-dithio-D,L-threitol; phosphite dehydrogenase; phosphite ion; iron(II) sulfate; NADH In dimethyl sulfoxide at 30℃; for 7h; pH=7.5; Catalytic behavior; Reagent/catalyst; Solvent; Enzymatic reaction;77%
vanillin
121-33-5

vanillin

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 260℃; for 0.75h;94%
With potassium carbonate durch Schmelzen;
With potassium hydroxide durch Schmelzen;
With potassium hydroxide at 250℃;
3-hydroxy-4-methoxybenzoate
6702-50-7

3-hydroxy-4-methoxybenzoate

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;89%
4-oxocyclohexanecarboxylic acid
874-61-3

4-oxocyclohexanecarboxylic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h;84%
4-hydroxy-3-methoxybenzoic acid methyl ester
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

3,4-dihydroxybenzoic acid methyl ester
2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With aluminium(III) iodide; ethyl acetate; diisopropyl-carbodiimide In acetonitrile at 80℃; for 5h; Temperature;A 14%
B 72%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 40℃; for 18h; Temperature; Overall yield = 89 %; Overall yield = 0.684 g;A 64%
B 31%
4-formyl-3-hydroxybenzoic acid
619-12-5

4-formyl-3-hydroxybenzoic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 35℃; for 12h; Dakin Phenol Oxidation;71%
acetic anhydride
108-24-7

acetic anhydride

3',4'-dihydroxy-7-dimethoxyflavylium chloride
89475-36-5

3',4'-dihydroxy-7-dimethoxyflavylium chloride

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

4-methoxysalicylic acid
2237-36-7

4-methoxysalicylic acid

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate 1) 5 h, room temp., pyridine; 2) acetic ester, water, 20 min : decomposition reaction;A 70%
B 67%
3-hydroxy-4-methoxybenzoate
6702-50-7

3-hydroxy-4-methoxybenzoate

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

3,4-dihydroxybenzoic acid methyl ester
2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 40℃; for 18h;A 64%
B 31%
3-oxo-cyclohexanecarboxylic acid
16205-98-4

3-oxo-cyclohexanecarboxylic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h; regioselective reaction;63%
(-)-3-dehydroshikimic acid
2922-42-1

(-)-3-dehydroshikimic acid

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With copper diacetate In water; acetic acid at 40℃; for 36h; Oxidation; aromatization;A 0.7%
B 62%
With copper diacetate; oxygen; zinc(II) oxide In acetic acid at 50℃; under 760.051 Torr; for 14h; Kinetics; Product distribution; Further Variations:; Reagents; Oxidation; aromatization;
3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium bromate; hydrogenchloride; potassium bromide In water for 12h; Time;55%
With potassium carbonate durch Schmelzen;
With potassium hydroxide at 150 - 190℃; Ausschluss von Sauerstoff;
methanol
67-56-1

methanol

3-dehydroquinic acid
10534-44-8

3-dehydroquinic acid

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate
84806-48-4

methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate

C

methyl 3-dehydroquinate
57764-14-4

methyl 3-dehydroquinate

Conditions
ConditionsYield
With Amberlite IR 120 for 1.5h; Heating;A 30%
B 20%
C 50%
cyanidin 3-O-glucopyranoside chloride

cyanidin 3-O-glucopyranoside chloride

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

glucopyranosyl 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylacetate

glucopyranosyl 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylacetate

C14H16O10

C14H16O10

Conditions
ConditionsYield
With 2,2'-azobis-(2,4-dimethylvaleronitrile) In water; acetonitrile at 60℃; for 6h;A 34%
B 13.6%
C 15%
quercetol
117-39-5

quercetol

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃; for 18h;17%
With potassium carbonate beim Schmelzen;
With potassium carbonate
With potassium hydroxide
With potassium hydroxide Heating;
(-)-3-dehydroshikimic acid
2922-42-1

(-)-3-dehydroshikimic acid

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

tricarallylic acid
99-14-9

tricarallylic acid

C

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

D

dihydrogallic acid
184105-29-1

dihydrogallic acid

E

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
With air; Na1.5H1.5PO4 at 40℃; for 50h; Rate constant; Mechanism; other oxidant, var. time;A 12 % Spectr.
B 14 % Spectr.
C 13%
D n/a
E 3 % Spectr.
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With peroxygenase; dihydrogen peroxide In acetonitrile at 20℃; for 0.5h; pH=5; pH-value; Enzymatic reaction;12.4%
With Aspergillus carbonarius peroxygenase gene; dihydrogen peroxide; ascorbic acid In aq. phosphate buffer; acetonitrile at 20℃; for 0.25h; pH=6; Catalytic behavior; Enzymatic reaction;1%
With potassium peroxomonosulphate Kochen des Reaktionsproduktes mit verd. Salzsaeure;
Multi-step reaction with 2 steps
1: bromine
2: concentrated KOH-solution
View Scheme
methanol
67-56-1

methanol

caffeic acid
331-39-5

caffeic acid

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

C

(E)-2-hydroxy-2-(3,4-dihydroxyphenyl)ethanaloxime

(E)-2-hydroxy-2-(3,4-dihydroxyphenyl)ethanaloxime

D

(E)-2-(3,4-dihydroxyphenyl)-2-methoxyethanaloxime

(E)-2-(3,4-dihydroxyphenyl)-2-methoxyethanaloxime

Conditions
ConditionsYield
With acetate buffer; sodium nitrite at 20℃; for 4h; pH=4; Further byproducts.;A 6%
B 9%
C 10%
D 5%
cyanidin-3-O-glucoside

cyanidin-3-O-glucoside

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

C21H22O13

C21H22O13

C

jaboticabin acid (2-O-(3,4-dihydroxybenzoyl)-2,4,6-dihydroxyphenyl)acetic acid

jaboticabin acid (2-O-(3,4-dihydroxybenzoyl)-2,4,6-dihydroxyphenyl)acetic acid

Conditions
ConditionsYield
With water; dihydrogen peroxide In acetonitrile at 40℃; for 8h; Mechanism; Reagent/catalyst; Solvent; Time;A 9%
B n/a
C n/a
D-erythrose
583-50-6

D-erythrose

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

C

1-(3,4-dihydroxyphenyl)ethan-1-one
1197-09-7

1-(3,4-dihydroxyphenyl)ethan-1-one

D

1-[5-(hydroxymethyl)furan-2-yl]ethan-1-one
55087-82-6

1-[5-(hydroxymethyl)furan-2-yl]ethan-1-one

E

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

F

3-methylbenzene-1,2-diol
488-17-5

3-methylbenzene-1,2-diol

Conditions
ConditionsYield
With acetate buffer for 45h; Product distribution; Heating;A 0.04%
B 0.03%
C 0.01%
D 0.15%
E 0.01%
F 0.03%
piperonal
120-57-0

piperonal

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With tetrachloromethane; chlorine Einwirkung im Sonnenlicht und Verseifen des entstandenen Chlorids mit Wasser;
oxalyl dichloride
79-37-8

oxalyl dichloride

1,2-dimethoxybenzene
91-16-7

1,2-dimethoxybenzene

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

4-allylguaiacol
97-53-0

4-allylguaiacol

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
bei der Kalischmelze;
Multi-step reaction with 3 steps
1: KOH; water
2: K2cr2O7; glacial acetic acid / 100 °C
3: hydriodic acid / 120 - 130 °C / im geschlossenen Rohr
View Scheme
3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
bei der Kalischmelze;
Piperonylic acid
94-53-1

Piperonylic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With hydrogenchloride at 170℃; im geschlossenen Rohr;
With water at 210℃; im geschlossenen Rohr;
With aluminium trichloride; chlorobenzene
2-oxo-benzo[1,3]dioxole-5-carboxylic acid
861605-32-5

2-oxo-benzo[1,3]dioxole-5-carboxylic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With water
With salt solution
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

3-bromo-4-hydroxybenzylaldehyde
2973-78-6

3-bromo-4-hydroxybenzylaldehyde

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

C

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

D

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
at 160℃;
at 190℃;
(2,4‐dihydroxyphenyl)(3,4,5‐trihydroxyphenyl)methanone
10425-09-9

(2,4‐dihydroxyphenyl)(3,4,5‐trihydroxyphenyl)methanone

A

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

B

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With sulfuric acid at 120℃;
With potassium hydroxide
(2,4‐dihydroxyphenyl)(3,4,5‐trihydroxyphenyl)methanone
10425-09-9

(2,4‐dihydroxyphenyl)(3,4,5‐trihydroxyphenyl)methanone

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide
With sulfuric acid at 120℃;
With hydrogenchloride at 120℃;
2-methoxy-4-(2-propenyl)phenoxyacetic acid
6331-61-9

2-methoxy-4-(2-propenyl)phenoxyacetic acid

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
bei der Kalischmelze;
4-ethoxy-3-hydroxybenzaldehyde
2539-53-9

4-ethoxy-3-hydroxybenzaldehyde

4-ethoxy-3-methoxybenzoic acid
3535-30-6

4-ethoxy-3-methoxybenzoic acid

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

4-ethoxy-3-hydroxy-benzoic acid
90536-50-8

4-ethoxy-3-hydroxy-benzoic acid

Conditions
ConditionsYield
With hydrogen bromide Reaktion ueber mehrere Stufen;
methanol
67-56-1

methanol

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

3,4-dihydroxybenzoic acid methyl ester
2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride Heating;100%
With sulfuric acid for 8h; Reflux;100%
With sulfuric acid under 760.051 Torr; Reflux;100%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

para-tert-butoxycarbonyloxybenzaldehyde
87188-50-9

para-tert-butoxycarbonyloxybenzaldehyde

C34H40N2O8

C34H40N2O8

Conditions
ConditionsYield
Stage #1: 4-methoxy-benzylamine; para-tert-butoxycarbonyloxybenzaldehyde In ethanol; 2,2,2-trifluoroethanol for 4h; Inert atmosphere;
Stage #2: 3,4-Dihydroxybenzoic acid; Cyclohexyl isocyanide In ethanol; 2,2,2-trifluoroethanol for 48h; Inert atmosphere;
100%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

ethanol
64-17-5

ethanol

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With sulfuric acid Heating;99%
With sulfuric acid at 50℃; for 3h;98%
With sulfuric acid98%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

5,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole

5,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole

7,10-dichloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

7,10-dichloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;99%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

benzyl chloride
100-44-7

benzyl chloride

3,4-(bisbenzyloxy)benzoic acid benzyl ester
882427-72-7

3,4-(bisbenzyloxy)benzoic acid benzyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;98%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;98%
With sodium carbonate In N,N-dimethyl-formamide for 48h; Reflux;85%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 85℃; for 12h; Inert atmosphere;
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3,4‐bis(tert‐butyldimethylsilyloxy)benzoic acid
154083-18-8

3,4‐bis(tert‐butyldimethylsilyloxy)benzoic acid

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h;98%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;76.7%
With 1H-imidazole In N,N-dimethyl-formamide for 66h; Inert atmosphere;75%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

6,8-difluoro-2,3,4,9-tetrahydro-1H-carbazole

6,8-difluoro-2,3,4,9-tetrahydro-1H-carbazole

7,9-difluoro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

7,9-difluoro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;96%
6-(trifluoromethyl)-2,3,4,9,-tetrahydro-1H-carbazole
2805-84-7

6-(trifluoromethyl)-2,3,4,9,-tetrahydro-1H-carbazole

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

C20H16F3NO4

C20H16F3NO4

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;96%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

8‐methyl‐2‐tosyl‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole

8‐methyl‐2‐tosyl‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole

9-methyl-13-tosyl-6H-5a,10b-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

9-methyl-13-tosyl-6H-5a,10b-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;96%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione
1418195-30-8

1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione

Conditions
ConditionsYield
In aq. phosphate buffer at 20℃; pH=7; Electrochemical reaction;95.5%
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction;
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-L-Arg-OH
91000-69-0

Fmoc-L-Arg-OH

protocatechuic-RA-NH2

protocatechuic-RA-NH2

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one for 3h;
Stage #2: With piperidine In 1-methyl-pyrrolidin-2-one
Stage #3: 3,4-Dihydroxybenzoic acid; Fmoc-L-Arg-OH Further stages;
95.215%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

acetic anhydride
108-24-7

acetic anhydride

3,4-Diacetoxy-benzoesaeure
58534-64-8

3,4-Diacetoxy-benzoesaeure

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Inert atmosphere;95%
With sulfuric acid at 70℃;86.5%
for 2h; Heating;84%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

1-Tetradecanol
112-72-1

1-Tetradecanol

tetradecanyl 3,4-dihydroxybenzoate

tetradecanyl 3,4-dihydroxybenzoate

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 45 - 65℃; for 120 - 240h; Darkness; Molecular sieve;95%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;36%
With dicyclohexyl-carbodiimide In tetrahydrofuran
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5℃; for 48h;
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

tert-butyl alcohol
75-65-0

tert-butyl alcohol

3,4-dihydroxy-benzoic acid tert-butyl ester
760947-24-8

3,4-dihydroxy-benzoic acid tert-butyl ester

Conditions
ConditionsYield
With dmap at 20℃; for 72h;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

6,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole
101349-10-4

6,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole

C19H15Cl2NO4

C19H15Cl2NO4

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In acetonitrile for 0.0833333h; Cooling with ice;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

8-chloro-2,3,4,9-tetrahydro-1H-carbazole
53475-34-6

8-chloro-2,3,4,9-tetrahydro-1H-carbazole

C19H16ClNO4

C19H16ClNO4

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In acetonitrile for 0.0833333h; Cooling with ice;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

8‐methyl‐2‐tosyl‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole

8‐methyl‐2‐tosyl‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole

C26H24N2O6S

C26H24N2O6S

Conditions
ConditionsYield
With methanesulfonic acid; di-tert-butyl peroxide; iron phthalocyanine; acetic acid In acetonitrile for 0.0833333h; Cooling with ice;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

ethyl 1,3,4,9‐tetrahydro‐2H‐pyrido[3,4‐b]indole‐2‐carboxylate
89424-03-3

ethyl 1,3,4,9‐tetrahydro‐2H‐pyrido[3,4‐b]indole‐2‐carboxylate

C21H20N2O6

C21H20N2O6

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In acetonitrile for 0.0833333h; Cooling with ice;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

2‐(phenylsulfonyl)‐2,3,4,9‐tetrahydro‐1H‐pyrido[3,4‐b]indole

2‐(phenylsulfonyl)‐2,3,4,9‐tetrahydro‐1H‐pyrido[3,4‐b]indole

C24H20N2O6S

C24H20N2O6S

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In acetonitrile for 0.25h; Cooling with ice;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

6,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole
101349-10-4

6,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole

7,9-dichloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

7,9-dichloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

8-chloro-2,3,4,9-tetrahydro-1H-carbazole
53475-34-6

8-chloro-2,3,4,9-tetrahydro-1H-carbazole

7-chloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

7-chloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

2‐(phenylsulfonyl)‐2,3,4,9‐tetrahydro‐1H‐pyrido[3,4‐b]indole

2‐(phenylsulfonyl)‐2,3,4,9‐tetrahydro‐1H‐pyrido[3,4‐b]indole

14-(phenylsulfonyl)-6H-10b,5a-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

14-(phenylsulfonyl)-6H-10b,5a-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.25h;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

ethyl 1,3,4,9‐tetrahydro‐2H‐pyrido[3,4‐b]indole‐2‐carboxylate
89424-03-3

ethyl 1,3,4,9‐tetrahydro‐2H‐pyrido[3,4‐b]indole‐2‐carboxylate

14-(ethoxycarbonyl)-6H-10b,5a-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

14-(ethoxycarbonyl)-6H-10b,5a-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;95%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

3,4-dihydroxybenzoic acid dodecyl ester

3,4-dihydroxybenzoic acid dodecyl ester

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 45 - 65℃; for 120 - 240h; Darkness; Molecular sieve;94%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 20h;81%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;33%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5℃; for 48h;
With sulfuric acid Fischer-Speier Esterification;
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

benzyl bromide
100-39-0

benzyl bromide

3,4-(bisbenzyloxy)benzoic acid benzyl ester
882427-72-7

3,4-(bisbenzyloxy)benzoic acid benzyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere;94%
With potassium carbonate In N,N-dimethyl-formamide for 20h; Inert atmosphere;92%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;91%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

difluoroethanol
359-13-7

difluoroethanol

C9H8F2O4

C9H8F2O4

Conditions
ConditionsYield
With thionyl chloride Inert atmosphere; Reflux;94%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

chloro-methylsulfanyl-methane
2373-51-5

chloro-methylsulfanyl-methane

C9H10O4S

C9H10O4S

Conditions
ConditionsYield
With triethylamine In acetonitrile Reflux;93.4%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

butan-1-ol
71-36-3

butan-1-ol

protocatechuic acid n-butyl ester
37622-53-0

protocatechuic acid n-butyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5℃; for 48h;93%
With sulfuric acid In tetrahydrofuran at 45 - 65℃; for 120 - 240h; Darkness; Molecular sieve;82%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;64%

99-50-3Relevant articles and documents

Quercetin inhibits advanced glycation end product formation via chelating metal ions, trapping methylglyoxal, and trapping reactive oxygen species

Bhuiyan, Mohammad Nazrul Islam,Mitsuhashi, Shinya,Sigetomi, Kengo,Ubukata, Makoto

, p. 882 - 890 (2017)

Physiological concentration of Mg2+, Cu2+, and Zn2+ accelerated AGE formation only in glucosemediated conditions, which was effectively inhibited by chelating ligands. Only quercetin (10) inhibited MGO-mediated AGE formation as well as glucoseand ribose-mediated AGE formation among 10 polyphenols (1-10) tested. We performed an additional structure-activity relationship (SAR) study on flavanols (10, 11, 12, 13, and 14). Morin (12) and kaempherol (14) showed inhibitory activity against MGO-mediated AGE formation, whereas rutin (11) and fisetin (13) did not. These observations indicate that 3,5,7,4'-tetrahydroxy and 4-keto groups of 10 are important to yield newly revised mono-MGO adducts (16 and 17) and di-MGO adduct (18) having cyclic hemiacetals, while 3'-hydroxy group is not essential. We propose here a comprehensive inhibitory mechanism of 10 against AGE formation including chelation effect, trapping of MGO, and trapping of reactive oxygen species (ROS), which leads to oxidative degradation of 18 to 3,4-dihydroxybenzoic acid (15) and other fragments.

Phenolic compounds from Urtica urens growing in Georgia

Kavtaradze

, p. 314 - 314 (2003)

-

Multi-Enzymatic Cascade Reactions for the Synthesis of cis,cis-Muconic Acid

Di Nardo, Giovanna,Gazzola, Silvia,Gilardi, Gianfranco,Pollegioni, Loredano,Rosini, Elena,Valetti, Francesca,Vignali, Elisa

, p. 114 - 123 (2021/10/07)

Lignin valorization allows the generation of a number of value-added products such as cis,cis-muconic acid (ccMA), which is widely used for the synthesis of chemicals for the production of biodegradable plastic materials. In the present work, we reported the first multi-enzymatic, one-pot bioconversion process of vanillin into ccMA. In details, we used four sequential reactions catalyzed by xanthine oxidase, O-demethylase LigM (and the tetrahydrofolate-regeneration enzyme methyl transferase MetE), decarboxylase AroY (based on the use of E. coli transformed cells) and catechol 1,2-dioxygenase CatA. The optimized lab-scale procedure allowed to reach, for the first time, the conversion of 5 mM vanillin into ccMA in ~30 h with a 90% yield: this achievement represents an improvement in terms of yields and time when compared to the use of a whole-cell system. This multi-enzymatic system represents a sustainable alternative for the production of a high value added product from a renewable resource. (Figure presented.).

Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives

Grimm, Christopher,Kroutil, Wolfgang,Pompei, Simona,Schiller, Christine,Schober, Lukas

supporting information, p. 16906 - 16910 (2021/07/02)

Demethylating methyl phenyl ethers is challenging, especially when the products are catechol derivatives prone to follow-up reactions. For biocatalytic demethylation, monooxygenases have previously been described requiring molecular oxygen which may cause oxidative side reactions. Here we show that such compounds can be demethylated anaerobically by using cobalamin-dependent methyltransferases exploiting thiols like ethyl 3-mercaptopropionate as a methyl trap. Using just two equivalents of this reagent, a broad spectrum of substituted guaiacol derivatives were demethylated, with conversions mostly above 90 %. This strategy was used to prepare the highly valuable antioxidant hydroxytyrosol on a one-gram scale in 97 % isolated yield.

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Bhardwaj, Nivedita,Goel, Bharat,Indra, Arindam,Jain, Shreyans K.,Singh, Ajit Kumar,Tripathi, Nancy

, p. 14177 - 14183 (2021/08/16)

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.

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