2,5-Dihydroxybenzoesäure
2,5-Dihydroxybenzoic acid
Grundinformationen
- CAS
490-79-9- Standard-SMILES
O=C(O)c1cc(O)ccc1O- InChIKey
WXTMDXOMEHJXQO-UHFFFAOYSA-N- Summenformel
- C7H6O4
- Durchschnittliche Molmasse
- 154,12 g/mol
- Monoisotopische Masse
- 154,02660867
Überblick
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 mouse metabolite, a fungal metabolite and a human metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,5-dihydroxybenzoate.
Namen und Bezeichner
- Bevorzugter Name
- 2,5-Dihydroxybenzoic acid
- IUPAC
- 2,5-dihydroxybenzoic acid
- Lokaler Name
- 2,5-Dihydroxybenzoesäure
- Englischer Name
- 2,5-Dihydroxybenzoic acid
- Summenformel
- C7H6O4
- Molmasse
- 154.12
Namen und Synonyme
2,5-DIHYDROXYBENZOIC ACIDgentisic acid490-79-9Benzoic acid, 2,5-dihydroxy-5-Hydroxysalicylic acidHydroquinonecarboxylic acidGensigenGensigon2,5-Dhba2,5-Dioxybenzoic acidSalicylic acid, 5-hydroxy-Kyselina gentisinova
Weitere Namen anzeigen
DHBGentisateGentisicPhloretate2,5-dihydroxybenzoic2,5-Dihydroxybenzoes?ureKyselina 2,5-dihydroxybenzoova
Acido gentisicoAcide gentisiqueAcidum gentisicumVP36V95O3TNSC-27224DTXSID4060078CHEBI:17189RefChem:639843
Datenbank-Bezeichner
- CAS
490-79-9- PubChem CID
- 3469
- DTXSID
DTXSID4060078- ChEMBL
CHEMBL1461
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,6
- Polarare Oberfläche (TPSA)
- 77,8 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 157
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Other Aromatic Compounds
DrugsPharmaceuticals -> Metabolite of Acetylsalicylic acid
LogP
1.74
1.12
Solubility5.0 mg/mL at 5 °C
Melting Point199.5 °C
Vapor Pressure0.0000021 [mmHg]
Physical Description
Solid; [Merck Index] Light yellow crystals; [Aldrich MSDS]
Solid
Collision Cross Section
122.67 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
125 Ų [M-H]-
Physikochemische Eigenschaften
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 1.5% (1 of 67) of reports.
Warning
H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]
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.
Gefahrenhinweise
Regulatory Information
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
Hazards SummaryCauses convulsions in intravenous lethal-dose studies of mice; [RTECS] A skin and strong eye irritant; Harmful by ingestion and skin absorption; Evidence of reproductive toxicity in experimental animals; [Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (94%)
Toxikologische Informationen
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29182990
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites5-hydroxylation is a known human metabolite of salicylic acid.
Cellular LocationsCytoplasm
Verwendung und Herstellung
Uses
Excreted in urine of dogs following ingestion of salicylates; Used therapeutically (analgesic and anti-inflammatory); [Merck Index] An oxidative product of saligenin; [ChemIDplus] Used as an analgesic medicine; [Hawley]
Synthetic Polymer MALDI Matrix Compounds
Household ProductsInformation on 1 consumer products that contain Gentisic acid in the following categories is provided:
General Manufacturing InformationBenzoic acid, 2,5-dihydroxy-: ACTIVE
Anwendungen
BeschreibungGentisic 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.
Verwenden2,5-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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
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