Basic information
- CAS
59-00-7- Standard SMILES
O=C(O)c1cc(=O)c2cccc(O)c2[nH]1- InChIKey
FBZONXHGGPHHIY-UHFFFAOYSA-N- Molecular formula
- C10H7NO4
- Average molar mass
- 205.17 g/mol
- Monoisotopic mass
- 205.0375077
Overview
Xanthurenic acid is a quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8. It has a role as an iron chelator, a metabotropic glutamate receptor agonist, a vesicular glutamate transport inhibitor and an animal metabolite. It is a dihydroxyquinoline and a quinolinemonocarboxylic acid. It is a conjugate acid of a xanthurenate.
Names & identifiers
- Preferred name
- Xanthurenic Acid
- IUPAC
- 8-hydroxy-4-oxo-1H-quinoline-2-carboxylic acid
- English name
- Xanthurenic acid
- Molecular formula
- C10H7NO4
- Molecular weight
- 205.17
Names & synonyms
xanthurenic acid59-00-74,8-Dihydroxyquinoline-2-carboxylic acidXanthuric acid8-Hydroxykynurenic acid4,8-Dihydroxyquinaldic acid8-hydroxy-4-oxo-1H-quinoline-2-carboxylic acid58LAB1BG8JNSC-401570DTXSID90207728CHEBI:10072RefChem:902266
Show more names
NSC 401570JACS-59-00-7XENTHURENIC ACIDTIMTEC-BB SBB003498XANTHURENIC ACID(RG)Xanthurenic acid 96%
DTXCID40130219200-410-1Xanthurenate4,8-Dihydroxyquinaldinic acid2-Quinolinecarboxylic acid, 4,8-dihydroxy-4,8-Dihydroxy-2-quinolinecarboxylic acid8-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acidMFCD00006754
Database identifiers
- CAS
59-00-7- PubChem CID
- 5699
- DTXSID
DTXSID90207728- ChEMBL
CHEMBL312535- ChEBI
CHEBI:10072
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 86.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 336
Experimental & physicochemical properties
Melting Point289 °C
Physical DescriptionSolid
Collision Cross Section
137.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
132.51 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
140.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
134.6 Ų [M-H]-
Physicochemical properties
- Melting point
- 297 · 297-298 °C (dec.)(lit.)
- Boiling point
- 343.83 °C · 343.83°C (rough estimate)
- Density
- 1.3849 · 1.3849 (rough estimate)
- refractive index
- 1.56 · 1.5600 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- DMSO (Slightly, Heated), Water (Slightly, Heated)
- form
- Powder
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information2-Quinolinecarboxylic acid, 4,8-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- UZ9275000
- hs_code
- 29334900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Pharmacology
Metabolism/MetabolitesXanthurenic acid has known human metabolites that include Xanthurenic acid 8-O-sulfate.
MeSH Pharmacological ClassificationSubstances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Tissue LocationsEpidermis
Cellular LocationsMembrane
Metabolite PathwaysTryptophan metabolism
Applications
Usescaspase activator, guanylyl cyclase stimulant
UsesXanthurenic acid can be used as a substrate for the synthesis of: Silica-gel functionalized xanthurenic acid (4, 8-dihydroxyquinoline-2-carboxylic acid) as an adsorbent for metal ions.N, N′-bis-((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ethers as fluorescent sensors of magnesium in living cells via one-pot Mannich reaction.Poly-xanthurenic acid (poly-Xa) for biosensing applications.
UsesExcreted by pyridoxine-deficient animals after the ingestion of tryptophan.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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