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2,5-Dihydroxybenzoesäure
GENTISIC ACID · DHB · Gentisate · Gentisic · 2,5-Dhba · Phloretate · Gensigen · 2,5-dihydroxybenzoic
Identifikatoren & physikalische Daten
| CAS No. | 490-79-9 |
|---|---|
| Summenformel | C7H6O4 |
| Durchschnittliche Molmasse | 154,12 g/mol |
| Monoisotopische Masse | 154,02660867 g/mol |
| SMILES | O=C(O)c1cc(O)ccc1O |
| InChIKey | WXTMDXOMEHJXQO-UHFFFAOYSA-N |
| PubChem CID | 3469 |
| ChEMBL | CHEMBL1461 |
| ChEBI | CHEBI:17189 |
| EC No. | 207-718-5 |
| DTXSID | DTXSID4060078 |
| Lokaler Name | 2,5-Dihydroxybenzoesäure |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 77,8 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 157 |
| LogP (Verteilungskoeffizient) | 1.74 |
| Löslichkeit | 5.0 mg/mL at 5 °CIt is soluble in alcohol and ether. |
| Schmelzpunkt | 199.5 °C204-208 °C(lit.) |
| Dampfdruck | 0.0000021 [mmHg] |
| Physical Description | Solid[Merck Index] Light yellow crystals[Aldrich MSDS] |
| Collision Cross Section | 122.67 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]125 Ų [M-H]- |
| Siedepunkt | 237.46°C (rough estimate) |
| Dichte | 1.3725 (rough estimate) |
| Brechungsindex | 1.6400 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 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) |
| 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 (Verteilungskoeffizient) | 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 & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.5% (1 of 67) of reports.WarningH302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (94%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (94%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (92.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 67 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 67 reports by companies.There are 10 notifications provided by 66 of 67 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Benzoic acid, 2,5-dihydroxy-Benzoic acid, 2,5-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Causes convulsions in intravenous lethal-dose studies of mice[RTECS] A skin and strong eye irritantHarmful by ingestion and skin absorptionEvidence of reproductive toxicity in experimental animals[Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (94%)Skin Irrit. 2 (94%)Eye Irrit. 2 (94%)STOT SE 3 (92.5%) |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29182990 |
| RTECS-Nr. | LY3850000 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Harmful |
| Sicherheitshinweise (S) | 26-36-37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
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.
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.