2,5-Dihydroxybenzoesäure

Bezeichnung:2,5-Dihydroxybenzoesäure

CAS-Nr490-79-9

Englisch Name:2,5-Dihydroxybenzoic acid

CBNumberCB5853669

SummenformelC7H6O4

Molgewicht154.12

MOL-Datei490-79-9.mol

Synonyma

Gentisinsure

2,5-Dihydroxybenzoesäure

2,5-Dihydroxybenzoesäure physikalisch-chemischer Eigenschaften

Schmelzpunkt	204-208 °C(lit.)
Siedepunkt	237.46°C (rough estimate)
Dichte	1.3725 (rough estimate)
Brechungsindex	1.6400 (estimate)
storage temp.	Store below +30°C.
Löslichkeit	It is soluble in alcohol and ether.
pka	2.97(at 25℃)
Aggregatzustand	Crystalline Powder
Farbe	White to light beige
PH	3.21(1 mM solution);2.56(10 mM solution);2.01(100 mM solution)
Wasserlöslichkeit	soluble
ε(Extinktionskoeffizient)	>2000 at 337nm
Merck	14,4398
BRN	2209119
Kosmetik-Inhaltsstoffe Funktionen	SKIN CONDITIONING
InChI	1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
InChIKey	WXTMDXOMEHJXQO-UHFFFAOYSA-N
SMILES	OC(=O)c1cc(O)ccc1O
LogP	1.740
CAS Datenbank	490-79-9(CAS DataBase Reference)
NIST chemische Informationen	2,5-Dihydroxybenzoic acid(490-79-9)
EPA chemische Informationen	Benzoic acid, 2,5-dihydroxy- (490-79-9)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	22-36/37/38
S-Sätze:	26-36-37/39
WGK Germany	3
RTECS-Nr.	LY3850000
Hazard Note	Harmful
TSCA	TSCA listed
HS Code	29182990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral

Gefahreninformationscode (GHS)

2,5-Dihydroxybenzoic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
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.
Beschreibung
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.
Chemische Eigenschaften
White to light beige crystalline powder. 2,5-Dihydroxybenzoic Acid [490-79-9] (gentisic acid, 2,5-DHBA), C7H6O4, Mr 154.1, mp 205 C, is soluble in water and alcohols but insoluble in benzene and chloroform. The acid is stable in boiling water and gives a deep blue color with iron(III) chloride. Here, the acid decomposes to form p-benzoquinone [106-51-4] and carbon dioxide. 2–5-Dihydroxybenzoic acid is used as an antirheumatic drug and, more recently, as a color developer for thermal paper.
Verwenden
2,5-dihydroxybenzoic acid areused 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 areused as intermediates for the production of other organic chemicals, resins, polyesters, plasticizers, dyestuffs, preservatives, and rubber chemicals.
Verwenden
Medicine, as sodium gentisate (analgesic).
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 .
Vorbereitung Methode
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.
Definition
ChEBI: 2,5-dihydroxybenzoic acid is a dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions. It has a role as a MALDI matrix material, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a human metabolite, a fungal metabolite and a mouse metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,5-dihydroxybenzoate.
Synthesis Reference(s)
Journal of the American Chemical Society, 72, p. 3292, 1950 DOI: 10.1021/ja01163a521
Allgemeine Beschreibung
Aspirin metabolite.
Sicherheitsprofil
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.
läuterung methode
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.]
Einzelnachweise
[1] RAVI JOSHI. Antioxidant activity and free radical scavenging reactions of gentisic acid: in-vitro and pulse radiolysis studies.[J]. Free Radical Research, 2012, 46 1: 11-20. DOI: 10.3109/10715762.2011.633518
[2] KEIKO ASHIDATE . Gentisic acid, an aspirin metabolite, inhibits oxidation of low-density lipoprotein and the formation of cholesterol ester hydroperoxides in human plasma[J]. European journal of pharmacology, 2005, 513 3: Pages 173-179. DOI: 10.1016/j.ejphar.2005.03.012
[3] J. F. CUNHA. The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors.[J]. Brazilian Journal of Medical and Biological Research, 2001, 4 1: 381-388. DOI: 10.1590/s0100-879x2001000300013
[4] SIMEI SUN. Gentisic acid prevents the transition from pressure overload-induced cardiac hypertrophy to heart failure.[J]. Scientific Reports, 2019: 3018. DOI: 10.1038/s41598-019-39423-8
[5] STEVEN MINK. Gentisic acid sodium salt, a phenolic compound, is superior to norepinephrine in reversing cardiovascular collapse, hepatic mitochondrial dysfunction and lactic acidemia in Pseudomonas aeruginosa septic shock in dogs.[J]. Intensive Care Medicine Experimental, 2016, 4 1: 24. DOI: 10.1186/s40635-016-0095-0

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