| Identification | More | [Name]
2,5-Dihydroxybenzoic acid | [CAS]
490-79-9 | [Synonyms]
2,5-DIHYDROXYBENZOIC ACID
DHB
DIHYDROXYBENZOIC(2,5-) ACID
GENTISIC ACID
HYDROQUINONECARBOXYLIC ACID
RARECHEM AL BE 0043
2,5-Dhba
2,5-dihydroxy-benzoicaci
2,5-Dioxybenzoic acid
5-Hydroxysalicylic acid
5-hydroxy-salicylicaci
5-hydroxysalicylicacid
acido2,5-diidrossibenzoico
Benzoic acid, 2,5-dihydroxy-
Benzoicacid,2,5-dihydroxy-
Gensigen
Gensigon
Gentisate
Hydroguinonecarboxylicacid
Kyselina 2,5-dihydroxybenzoova | [EINECS(EC#)]
207-718-5 | [Molecular Formula]
C7H6O4 | [MDL Number]
MFCD00002460 | [Molecular Weight]
154.12 | [MOL File]
490-79-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light beige crystalline powder | [Melting point ]
204-208 °C(lit.)
| [Boiling point ]
237.46°C (rough estimate) | [density ]
1.3725 (rough estimate) | [refractive index ]
1.6400 (estimate) | [storage temp. ]
Store below +30°C. | [solubility ]
It is soluble in alcohol and ether. | [form ]
Crystalline Powder | [pka]
2.97(at 25℃) | [color ]
White to light beige | [PH]
3.21(1 mM solution);2.56(10 mM solution);2.01(100 mM solution) | [Water Solubility ]
soluble | [ε(extinction coefficient)]
>2000 at 337nm | [Merck ]
14,4398 | [BRN ]
2209119 | [InChIKey]
WXTMDXOMEHJXQO-UHFFFAOYSA-N | [LogP]
1.740 | [Uses]
Medicine, as sodium gentisate (analgesic). | [CAS DataBase Reference]
490-79-9(CAS DataBase Reference) | [NIST Chemistry Reference]
2,5-Dihydroxybenzoic acid(490-79-9) | [EPA Substance Registry System]
490-79-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
LY3850000
| [Hazard Note ]
Harmful | [TSCA ]
Yes | [HS Code ]
29182990 | [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. |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
white to light beige crystalline powder | [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 . | [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. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 72, p. 3292, 1950 DOI: 10.1021/ja01163a521 | [General Description]
Aspirin metabolite. | [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.] | [References]
[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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