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490-79-9

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490-79-9 Usage

Description

Different sources of media describe the Description of 490-79-9 differently. You can refer to the following data:
1. Gentisic acid is a dihydroxy benzoic acid. It is a derivative of benzoic acid and a minor (1 %) product of the metabolic break down of aspirin, excreted by the kidneys. It is also found in the African tree Alchornea cordifolia and in wine.
2. Gentisic acid is a benzoic acid that has been found in Gentiana and an active metabolite of aspirin with diverse biological activities. It decreases radiation-induced production of thiobarbituric acid reactive substances (TBARS), hydrogen peroxide, and protein carbonyls, increases superoxide dismutase activity, and prevents hemolysis in isolated human erythrocytes when used at concentrations ranging from 5 to 100 μM. Gentisic acid (1-10 μM) inhibits LDL oxidation and formation of cholesterol ester hydroperoxides in isolated human plasma. It induces relaxation of isolated guinea pig trachea (EC50 = 20 μM), an effect that is reduced by the large-conductance calcium-activated potassium channel blocker charybdotoxin . Gentisic acid (10 and 100 mg/kg) reduces cardiac hypertrophy and fibrosis and pulmonary remodeling, suppresses the renin-angiotensin-aldosterone system, and inhibits cardiac dysfunction in a mouse model of transverse aortic constriction-induced cardiac hypertrophy. It also prevents cardiovascular collapse and lactic acidemia in a canine model of P. aeruginosa-induced septic shock.

Chemical Properties

white to light beige crystalline powder

Uses

Different sources of media describe the Uses of 490-79-9 differently. You can refer to the following data:
1. Medicine, as sodium gentisate (analgesic).
2. 2,5-dihydroxybenzoic acid are?used as intermediates for pharmaceuticals (especially for antipyetic anlgesic, antirheumatism) and other organic synthesis. They are used as matrix for ionization of peptides, proteins and carbohydrates. In industrial field, they are?used as intermediates for the production of other organic chemicals, resins, polyesters, plasticizers, dyestuffs, preservatives, and rubber chemicals.

Definition

ChEBI: A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.

Production Methods

Gentisic acid is produced by carboxylation of hydroquinone. C6H4(OH)2 + CO2 → C6H3(CO2H)(OH)2 This conversion is an example of a Kolbe–Schmitt reaction.

Application

As a hydroquinone , gentisic acid is readily oxidized and is used as an antioxidant excipient in some pharmaceutical preparations. In the laboratory, it is used as a sample matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry , and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI .

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 3292, 1950 DOI: 10.1021/ja01163a521

General Description

Aspirin metabolite.

Safety Profile

Poison bp intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise gentisic acid from hot water or *benzene/acetone. Dry it in a vacuum desiccator over silica gel. [Beilstein 10 H 384, 10 IV 1441.]

Check Digit Verification of cas no

The CAS Registry Mumber 490-79-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 0 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 490-79:
(5*4)+(4*9)+(3*0)+(2*7)+(1*9)=79
79 % 10 = 9
So 490-79-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)/p-1

490-79-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D0569)  2,5-Dihydroxybenzoic Acid  >98.0%(HPLC)(T)

  • 490-79-9

  • 25g

  • 350.00CNY

  • Detail
  • TCI America

  • (D0569)  2,5-Dihydroxybenzoic Acid  >98.0%(HPLC)(T)

  • 490-79-9

  • 500g

  • 3,450.00CNY

  • Detail
  • Alfa Aesar

  • (A11459)  2,5-Dihydroxybenzoic acid, 99%   

  • 490-79-9

  • 25g

  • 291.0CNY

  • Detail
  • Alfa Aesar

  • (A11459)  2,5-Dihydroxybenzoic acid, 99%   

  • 490-79-9

  • 100g

  • 1092.0CNY

  • Detail
  • Sigma-Aldrich

  • (39319)  2,5-Dihydroxybenzoicacid  matrix substance for MALDI-MS, ≥99.5% (HPLC), Ultra pure

  • 490-79-9

  • 39319-10X10MG-F

  • 2,556.45CNY

  • Detail
  • Sigma

  • (85707)  2,5-Dihydroxybenzoicacid  matrix substance for MALDI-MS, >99.0% (HPLC)

  • 490-79-9

  • 85707-10MG-F

  • 153.27CNY

  • Detail
  • Sigma

  • (85707)  2,5-Dihydroxybenzoicacid  matrix substance for MALDI-MS, >99.0% (HPLC)

  • 490-79-9

  • 85707-250MG-F

  • 2,058.03CNY

  • Detail
  • Sigma

  • (85707)  2,5-Dihydroxybenzoicacid  matrix substance for MALDI-MS, >99.0% (HPLC)

  • 490-79-9

  • 85707-1G-F

  • 6,698.25CNY

  • Detail

490-79-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,5-dihydroxybenzoic acid

1.2 Other means of identification

Product number -
Other names Benzoic acid,2,5-dihydroxy

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:490-79-9 SDS

490-79-9Synthetic route

2,5-bis-methoxymethoxy-benzoic acid methoxymethyl ester

2,5-bis-methoxymethoxy-benzoic acid methoxymethyl ester

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With methanol; iodine at 20℃; for 48h;96%
5-Allyloxy-2-hydroxy-benzoic acid benzyl ester

5-Allyloxy-2-hydroxy-benzoic acid benzyl ester

A

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

B

3,4-dihydro-5,8-dihydroxy-3-methylisocoumarin
84213-08-1

3,4-dihydro-5,8-dihydroxy-3-methylisocoumarin

C

5-Hydroxy-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid

5-Hydroxy-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid

Conditions
ConditionsYield
In trifluoroacetic acid for 17h; Heating;A 25%
B 31%
C 8.5%
benzoic acid
65-85-0

benzoic acid

A

2,3-Dihydroxybenzoic acid
303-38-8

2,3-Dihydroxybenzoic acid

B

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

C

3-Carboxyphenol
99-06-9

3-Carboxyphenol

D

salicylic acid
69-72-7

salicylic acid

E

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With oxygen; iron(II) sulfate In water at 40℃; for 3h; Product distribution; pH 6.8 buffer;A 9%
B 5%
C 14%
D 4%
E 9%
benzoic acid
65-85-0

benzoic acid

A

2,3-Dihydroxybenzoic acid
303-38-8

2,3-Dihydroxybenzoic acid

B

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

C

3-Carboxyphenol
99-06-9

3-Carboxyphenol

D

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With oxygen; iron(II) sulfate In water at 40℃; for 3h; Further byproducts given;A 9%
B 5%
C 14%
D 9%
2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With potassium hydroxide durch Schmelzen;
2,5-diacetoxytoluene
717-27-1

2,5-diacetoxytoluene

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With permanganate(VII) ion; magnesium sulfate at 85℃; folgende Verseifung mit Salzsaeure;
5-Aminosalicylic Acid
89-57-6

5-Aminosalicylic Acid

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
Diazotization.Kochen der erhaltenen Diazoverbindung mit Wasser;
2-hydroxy-5-iodobenzoic acid
119-30-2

2-hydroxy-5-iodobenzoic acid

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With potassium hydroxide
2,5-dimethoxybenzoic acid
2785-98-0

2,5-dimethoxybenzoic acid

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With hydrogen bromide
5-bromosalicyclic acid
89-55-4

5-bromosalicyclic acid

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With sodium hydroxide; copper
With sodium hydroxide
5-methoxysalicylic acid
2612-02-4

5-methoxysalicylic acid

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With hydrogen bromide
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With sodium hydroxide; water
2-carboxy-4-hydroxy-benzenediazonium-betaine

2-carboxy-4-hydroxy-benzenediazonium-betaine

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With sulfuric acid
methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

hydroquinone
123-31-9

hydroquinone

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With potassium carbonate at 140 - 210℃;
hydroquinone
123-31-9

hydroquinone

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With potassium sulfite; water; potassium hydrogencarbonate at 130℃;
With potassium hydrogencarbonate; glycerol at 180℃;
Multi-step reaction with 2 steps
1: NaOH-solution
2: potassium hydroxide / durch Schmelzen
View Scheme
With tetrachloromethane; sodium hydroxide; copper
salicylic acid
69-72-7

salicylic acid

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With phosphate buffer; oxygen; rose bengal Rate constant; Mechanism; Irradiation; other singlet oxygen generating systems; effect of inhibitors;
With potassium peroxomonosulphate Kochen des Reaktionsproduktes mit verd. Salzsaeure;
With dipotassium peroxodisulfate
salicylic acid
69-72-7

salicylic acid

A

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

B

2,3,5-trihydroxybenzoic acid
33580-60-8

2,3,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; ammonium peroxydisulfate
carbon dioxide
124-38-9

carbon dioxide

p-Isopropoxyphenyl methyl ether
20744-02-9

p-Isopropoxyphenyl methyl ether

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
Multistep reaction;
2,5-dihydroxybenzoic acid benzyl ester
21782-87-6

2,5-dihydroxybenzoic acid benzyl ester

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With potassium hydroxide In ethanol Yield given;
salicylic acid
69-72-7

salicylic acid

A

2,3-Dihydroxybenzoic acid
303-38-8

2,3-Dihydroxybenzoic acid

B

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With iron(III)-acetylacetonate; dihydrogen peroxide; methylene blue at 25℃; for 4h; Product distribution; Mechanism; Irradiation; other salicylic derivatives, hydroxylation;
With oxygen; potassium oxalate; iron(III) chloride In water at 25℃; Product distribution; Irradiation; role of hydrogen peroxide in dyoxygen induced hydroxylation of title compound; photochemicall and thermal (pH 7.1) hydroxylation;
With dihydrogen peroxide In water at 20℃; for 0.5h; Mechanism; Product distribution; Quantum yield; Irradiation; various pH value and reaction time, HClO4 or K2CO3 presence;
methylene blue

methylene blue

salicylic acid
69-72-7

salicylic acid

A

2,3-Dihydroxybenzoic acid
303-38-8

2,3-Dihydroxybenzoic acid

B

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With Fe(III)(sal)3(3-); dihydrogen peroxide In water at 25℃; for 1h; Product distribution; Thermodynamic data; Irradiation; other times; presence of O2;
5-(β-D-glucopyranosyloxy)-2-hydroxybenzoic acid
1820-89-9

5-(β-D-glucopyranosyloxy)-2-hydroxybenzoic acid

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With β-glucosidase for 168h; Ambient temperature; enzymatic hydrolysis;

A

2,3-Dihydroxybenzoic acid
303-38-8

2,3-Dihydroxybenzoic acid

B

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With dihydrogen peroxide; potassium carbonate In water at 20℃; for 0.5h; Mechanism; Product distribution; Quantum yield; Irradiation; various pH value and reaction time;
salicylic acid
69-72-7

salicylic acid

A

4-hydroxysalicylic acid
89-86-1

4-hydroxysalicylic acid

B

2,3-Dihydroxybenzoic acid
303-38-8

2,3-Dihydroxybenzoic acid

C

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

D

2,6-Dihydroxybenzoic acid
303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; iron(II) sulfate In water at 37℃; for 0.0833333h; hydroxylation; Further byproducts given. Title compound not separated from byproducts;
2,5-dihydroxybenzoic acid 2-O-β-4C1-glucopyranoside
98102-34-2

2,5-dihydroxybenzoic acid 2-O-β-4C1-glucopyranoside

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 3h; Hydrolysis;
anthracene
120-12-7

anthracene

A

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
In water Oxidation; Formation of xenobiotics; simulated solar irradiation;
hydrogenchloride
7647-01-0

hydrogenchloride

4,7-dihydroxyisoindole-1,3-dione
51674-11-4

4,7-dihydroxyisoindole-1,3-dione

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

6-hydroxy-2,3-dimethyl-chromen-4-one
103988-07-4

6-hydroxy-2,3-dimethyl-chromen-4-one

diluted NaOH-solution

diluted NaOH-solution

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

gentisin
437-50-3

gentisin

potash

potash

A

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

B

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

C

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
Beim Schmelzen;
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

sulfuric acid
7664-93-9

sulfuric acid

lead (IV)-oxide-anode

lead (IV)-oxide-anode

A

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

B

oxalic acid
144-62-7

oxalic acid

C

propionic acid
802294-64-0

propionic acid

D

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
Electrolysis;
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

meloxicam
71125-38-7

meloxicam

meloxicam gentisic acid
1174325-98-4

meloxicam gentisic acid

Conditions
ConditionsYield
for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

agomelatine
138112-76-2

agomelatine

agomelatine gentisic acid
1419379-42-2

agomelatine gentisic acid

Conditions
ConditionsYield
In toluene for 0.75h;100%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

methyl iodide
74-88-4

methyl iodide

Methyl 2,5-dihydroxybenzoate
2150-46-1

Methyl 2,5-dihydroxybenzoate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃;99%
Stage #1: 2,5-dihydroxybenzoic acid. With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone for 0.166667h;
Stage #2: methyl iodide In acetone at 20℃; for 4h;
92%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

allyl bromide
106-95-6

allyl bromide

allyl 2,5-bis(allyloxy)benzoate
95731-73-0

allyl 2,5-bis(allyloxy)benzoate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;99%
Stage #1: 2,5-dihydroxybenzoic acid. With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.05h;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 48h;
78%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

pomalidomide
19171-19-8

pomalidomide

(R,S)-4-amino-2-(2,6-dioxo-3-piperidinyl)isoindol-1,3-dione gentisicate

(R,S)-4-amino-2-(2,6-dioxo-3-piperidinyl)isoindol-1,3-dione gentisicate

Conditions
ConditionsYield
In acetonitrile at 20℃; Solvent; Temperature;99%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

ethyl 2,5-dihydroxybenzoate
3943-91-7

ethyl 2,5-dihydroxybenzoate

Conditions
ConditionsYield
at 120℃; for 4h;99%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

2,5-dihydroxy-benzoic acid 4-bromobenzyl ester

2,5-dihydroxy-benzoic acid 4-bromobenzyl ester

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium hydrogencarbonate In N,N-dimethyl acetamide at 70℃; for 24h; Inert atmosphere;98.4%
With potassium hydrogencarbonate In N,N-dimethyl acetamide at 65℃; for 24h; Inert atmosphere;98.4%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 70℃; for 24h; Inert atmosphere;78%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

benzyl chloride
100-44-7

benzyl chloride

2,5-dihydroxybenzoic acid benzyl ester
21782-87-6

2,5-dihydroxybenzoic acid benzyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone at 70℃; for 12h;98%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

benzyl bromide
100-39-0

benzyl bromide

2,5-dihydroxybenzoic acid benzyl ester
21782-87-6

2,5-dihydroxybenzoic acid benzyl ester

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl acetamide at 65℃; for 24h; Inert atmosphere;98%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 18h;93%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃;91%
methanol
67-56-1

methanol

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

Methyl 2,5-dihydroxybenzoate
2150-46-1

Methyl 2,5-dihydroxybenzoate

Conditions
ConditionsYield
With sulfuric acid for 48h; Reflux;97%
With sulfuric acid at 25℃; for 12h; Reflux; Inert atmosphere;97%
With 95percent H2SO4 Heating;96%
1-methyl-3-ethyl-4,5-bis(N-methylcarbamoyl)imidazolium benzenesulfonate

1-methyl-3-ethyl-4,5-bis(N-methylcarbamoyl)imidazolium benzenesulfonate

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

1-methyl-3-ethyl-4,5-bis(N-methylcarbamoyl)-imidazolium 2,5-dihydroxybenzoate

1-methyl-3-ethyl-4,5-bis(N-methylcarbamoyl)-imidazolium 2,5-dihydroxybenzoate

Conditions
ConditionsYield
With Amberlite IRA-410 10 (OH(1-)form) In water97%
Mirodenafil

Mirodenafil

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

5-ethyl-2-{5-[4-(2-hydroxy-ethyl)-piperazin-1-ylsulfonyl]-2-n-propoxy-phenyl}-7-n-propyl-3,5-dihydro-pyrrolo[3,2-d]pyrimidin-4-one gentisate

5-ethyl-2-{5-[4-(2-hydroxy-ethyl)-piperazin-1-ylsulfonyl]-2-n-propoxy-phenyl}-7-n-propyl-3,5-dihydro-pyrrolo[3,2-d]pyrimidin-4-one gentisate

Conditions
ConditionsYield
In water; acetone at 20℃; for 1h; Product distribution / selectivity;96.5%
In water; acetone at 20℃; Product distribution / selectivity;96.5%
In acetone at 20℃; for 1h; Product distribution / selectivity;77.1%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

allyl bromide
106-95-6

allyl bromide

allyl 5-allyloxy-2-hydroxybenzoate
84213-07-0

allyl 5-allyloxy-2-hydroxybenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone96%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

methyl iodide
74-88-4

methyl iodide

methyl 2,5-dimethoxybenzoate
2150-40-5

methyl 2,5-dimethoxybenzoate

Conditions
ConditionsYield
Stage #1: 2,5-dihydroxybenzoic acid. With sodium hydride In N,N-dimethyl-formamide; mineral oil for 1h; Cooling with ice;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h; Cooling with ice;
96%
With potassium carbonate
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

aniline
62-53-3

aniline

2,5-dihydroxy-N-phenylbenzamide
52405-79-5

2,5-dihydroxy-N-phenylbenzamide

Conditions
ConditionsYield
With triphenylphosphine In toluene for 3h; Heating;96%
With phosphorus trichloride In chlorobenzene at 135℃; for 0.333333h; Microwave irradiation;58%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

bosentan
147536-97-8

bosentan

N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide gentisic acid cocrystal
1450829-49-8

N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide gentisic acid cocrystal

Conditions
ConditionsYield
In n-heptane; acetone at 55℃; for 2.33333h; Concentration; Solvent; Temperature; Time; Sonication;96%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

(S)-3-(1-((1-acryloylpyrrolidin-3-yl)oxy)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-one

(S)-3-(1-((1-acryloylpyrrolidin-3-yl)oxy)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-one

(S)-3-(1-((1-acryloylpyrrolidin-3-yl)oxy)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-one gentisic acid cocrystal

(S)-3-(1-((1-acryloylpyrrolidin-3-yl)oxy)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-one gentisic acid cocrystal

Conditions
ConditionsYield
With air In acetonitrile at 10 - 35℃; for 120h; Sealed tube;96%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

1-ethyl-7-[[(1S)-1-[4-[(4-prop-2-enoylpiperazin-1-yl)methyl]phenyl]ethyl]amino]-4H-pyrimido[4,5-d][1,3]oxazin-2-one

1-ethyl-7-[[(1S)-1-[4-[(4-prop-2-enoylpiperazin-1-yl)methyl]phenyl]ethyl]amino]-4H-pyrimido[4,5-d][1,3]oxazin-2-one

1-ethyl-7-[[(1S)-1-[4-[(4-prop-2-enoylpiperazin-1-yl)methyl]phenyl]ethyl]amino]-4H-pyrimido[4,5-d][1,3]oxazin-2-one bis(2,5-dihydroxybenzoic acid) salt

1-ethyl-7-[[(1S)-1-[4-[(4-prop-2-enoylpiperazin-1-yl)methyl]phenyl]ethyl]amino]-4H-pyrimido[4,5-d][1,3]oxazin-2-one bis(2,5-dihydroxybenzoic acid) salt

Conditions
ConditionsYield
In ethanol at 48℃;95.62%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

allyl bromide
106-95-6

allyl bromide

allyl 2,5-dihydroxybenzoate
133416-39-4

allyl 2,5-dihydroxybenzoate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 70℃;95%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl 5-methoxy-2-hydroxybenzoate
2905-82-0

methyl 5-methoxy-2-hydroxybenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃; for 30h;94%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

C11H12O4

C11H12O4

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 70℃;94%
ethanol
64-17-5

ethanol

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

ethyl 2,5-dihydroxybenzoate
3943-91-7

ethyl 2,5-dihydroxybenzoate

Conditions
ConditionsYield
With sulfuric acid for 144h; Heating;93%
With thionyl chloride at 0℃; Reflux; Inert atmosphere;60%
With sulfuric acid
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

benzyl chloride
100-44-7

benzyl chloride

benzyl 2,5-bis(benzyloxy)benzoate
78283-37-1

benzyl 2,5-bis(benzyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 20h;93%
With potassium carbonate In butanone for 16h; Heating;
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

hexan-1-ol
111-27-3

hexan-1-ol

n-hexyl 2,5-dihydroxybenzoate
37622-50-7

n-hexyl 2,5-dihydroxybenzoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 9.5h; Heating;93%
With toluene-4-sulfonic acid In toluene at 120℃; for 8h;81.1%
With sulfuric acid Fischer-Speier Esterification;
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

3-benzoyl-5-hydroxy-2-phenylbenzofuran-4-carboxylic acid

3-benzoyl-5-hydroxy-2-phenylbenzofuran-4-carboxylic acid

Conditions
ConditionsYield
With sodium acetate In water; acetonitrile Electrochemical reaction;93%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

allyl bromide
106-95-6

allyl bromide

5-allyloxy-2-hydroxybenzoic acid
84213-04-7

5-allyloxy-2-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: 2,5-dihydroxybenzoic acid. With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h;
Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h;
92.9%
Stage #1: 2,5-dihydroxybenzoic acid. With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide pH=3;
75%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

dimethyl sulfate
77-78-1

dimethyl sulfate

Methyl 2,5-dihydroxybenzoate
2150-46-1

Methyl 2,5-dihydroxybenzoate

Conditions
ConditionsYield
With sodium hydrogencarbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 40℃; for 0.333333h;92%
(S)-(-)-amlodipine-hemi-dibenzoyl-D-tartrate

(S)-(-)-amlodipine-hemi-dibenzoyl-D-tartrate

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

S-amlodipine gentisate
856256-16-1

S-amlodipine gentisate

Conditions
ConditionsYield
Stage #1: (S)-(-)-amlodipine-hemi-dibenzoyl-D-tartrate With sodium hydroxide In dichloromethane; water for 0.5h;
Stage #2: 2,5-dihydroxybenzoic acid. In dichloromethane; acetone at 20℃; for 2h;
92%
(S)-(-)-amlodipine-hemi-dibenzoyl-D-tartrate

(S)-(-)-amlodipine-hemi-dibenzoyl-D-tartrate

2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

S-amlodipine gentisate
856256-16-1

S-amlodipine gentisate

Conditions
ConditionsYield
Stage #1: (S)-(-)-amlodipine-hemi-dibenzoyl-D-tartrate With sodium hydroxide In dichloromethane; water for 0.5h;
Stage #2: 2,5-dihydroxybenzoic acid. In dichloromethane; acetone at 20℃; for 2h;
92%

490-79-9Relevant articles and documents

Starovoitov et al.

, (1975)

-

Senhofer,Sarlay

, p. 448 (1881)

-

Formation of oxygen radicals in solutions of different 7,8- dihydropterins: Quantitative structure-activity relationships

Oettl, Karl,Pfleiderer, Wolfgang,Reibnegger, Gilbert

, p. 954 - 965 (2000)

Under certain conditions, 7,8-dihydroneopterin in aqueous solution promotes hydroxyl-radical formation. Thus, we investigated the stimulation of hydroxyl-radical formation by ten different 7,8-dihydropterins (=2-amino-7,8- dihydropteridin-4(1H)-one), i.e., 6-(1'-hydroxy) derivatives 1 and 2, methyl derivatives 3-7, and 6-(1'-oxo) derivatives 8-10. All but the 6-(1'-oxo) derivatives produced hydroxyl radicals, as measured by the amount of salicylic acid hydroxylation products. This amount was dependent on the stability of the dihydropterin used. In the presence of chelated iron ions, hydroxylation was increased in every case; even 6-(1'-oxo) derivatives showed a low hydroxylation of salicylic acid. The degree of increase, however, strongly depended on the side chain of the dihydropterin. The 7,8- dihydroneopterin (2) was investigated in more detail. Iron ions influenced both, the stability of 2 and hydroxyl-radical formation. While iron ions determined the kinetics of the reaction, the amount of 2 was responsible for the amount of hydroxyl radicals formed. Our data establish that promotion of hydroxyl-radical formation by 7,8-dihydropterins depends on the oxidizability of the dihydropterins and on their iron-chelating properties.

Black TiO2 nanotube arrays decorated with Ag nanoparticles for enhanced visible-light photocatalytic oxidation of salicylic acid

Plodinec, Milivoj,Gr?i?, Ivana,Willinger, Marc G.,Hammud, Adnan,Huang, Xing,Pan?i?, Ivana,Gajovi?, Andreja

, p. 883 - 896 (2018/11/10)

Novel forms of black TiO2 nanotubes-based photocatalysts for water purification were prepared. Two features were combined: decoration of TiO2 nanotube arrays with Ag nanoparticles (sample TiO2-NT's@Ag) and further hydrogenation of this material (TiO2-NT's@Ag-HA). Obtained photocatalysts show high efficiency for degradation of salicylic acid, a typical water-borne pollutant. The photocatalysts considerably exceed the photocatalytic properties of TiO2 nanotubes and commercial TiO2 P25 taken as a reference for modeling of the photocatalytic process. The comparison of photocatalytic activities between novel photocatalyst was based on a numerical approach supported by the complex kinetic model. This model allowed a separate study of different contributions on overall degradation rate. The contributions include: salicylic acid photolysis, photocatalysis in UVB, UVA and in the visible part of applied simulated solar irradiation. The superior photocatalytic performance of the photocatalyst TiO2-NT's@Ag-HA, particularly under visible irradiation, was explained by the combined effect of a local surface plasmon resonance (LSPR) due to Ag nanoparticles and creation of additional energy levels in band-gap of TiO2 due to Ti3+ states at nanotube surfaces. The presence of Ag also positively influence charge separation of created electron-holes pairs. The synergy of several effects was quantified by a complex kinetic model through the factor of synergy, fSyn. Stability testing indicated that the catalysts were stable for at least 20 h. The novel design of catalysts, attached on Ti foils, presents a solid base for the development of more efficient photocatalytic reactors for large-scale with a long-term activity.

Evidence for the electrochemical production of persulfate at TiO2 nanotubes decorated with PbO2

Santos, José Eudes L.,Antonio Quiroz, Marco,Cerro-Lopez, Monica,De Moura, Dayanne Chianca,Martínez-Huitle, Carlos A.

, p. 5523 - 5531 (2018/04/02)

It is well known that PbO2-based electrodes are considered to be non-active anodes, producing higher concentrations of hydroxyl radicals in aqueous solutions, and consequently, favouring the electrochemical degradation of organic pollutants. However, no evidence has been reported on the production of persulfates using this kind of electrode in sulphate aqueous solutions. For this reason, the aim of this work is to prepare (by an electrochemical procedure (anodization and electrodeposition)) and characterize (by X-ray diffraction, scanning electron microscopy, and potentiodynamic measurements) Ti/TiO2-nanotubes/PbO2 disk electrodes (with a geometrical area of 65 cm2) in order to evaluate the electrochemical production of persulfate using Na2SO4 solution as the support electrolyte and applying current densities of 7.5 and 60 mA cm-2, as well as the influence of the electrosynthesis of hydroxyl radicals, in concomitance. The results clearly showed that significant production of hydroxyl radicals and persulfate is achieved at the Ti/TiO2-nanotubes/PbO2 surface, but this depends on the current density. The production of OH at the Ti/TiO2-nanotubes/PbO2 surface in Na2SO4 solution was confirmed by a RNO spin trapping reaction. The results were compared with those of a Ti/Pt electrode in order to understand the effect when a lower amount of OH is produced at the active anode surface. Based on the results, the Ti/TiO2-nanotubes/PbO2 anode could exhibit good electrocatalytic properties for environmental applications involving persulfate oxidants.

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