3-hydroxy-DL-Kynurenine

Modify Date: 2025-09-17 22:37:24

3-hydroxy-DL-Kynurenine Structure
3-hydroxy-DL-Kynurenine structure
Common Name 3-hydroxy-DL-Kynurenine
CAS Number 484-78-6 Molecular Weight 224.21300
Density 1.461g/cm3 Boiling Point 519.3ºC at 760mmHg
Molecular Formula C10H12N2O4 Melting Point N/A
MSDS N/A Flash Point 267.9ºC

 Use of 3-hydroxy-DL-Kynurenine


3-Hydroxykynurenine, a metabolite of tryptophan, is a potential endogenous neurotoxin whose increased levels have been described in several neurodegenerative disorders. 3-Hydroxykynurenine induces neuronal apoptosis[1].

 Names

Name 3-hydroxykynurenine
Synonym More Synonyms

 3-hydroxy-DL-Kynurenine Biological Activity

Description 3-Hydroxykynurenine, a metabolite of tryptophan, is a potential endogenous neurotoxin whose increased levels have been described in several neurodegenerative disorders. 3-Hydroxykynurenine induces neuronal apoptosis[1].
Related Catalog
Target

Human Endogenous Metabolite

In Vitro 3-Hydroxykynurenine-induced neuronal cell death shows several features of apoptosis[1].  3-Hydroxykynurenine is a metabolic intermediate of the kynurenine pathway, the major metabolic pathway of tryptophan (Trp)[1]. 3-Hydroxykynurenine acts as an endogenous neurotoxin in the brain under pathological conditions[1]. 3-Hydroxykynurenine (20-100 μM) significantly inhibits CD4+ T-cell proliferation in a dose-dependent manner with IC50 of approximately 70 μM[2]. 3-Hydroxykynurenine (20-100 μM) induces significant CD4+ T-cell-mediated cell death in a dose-dependent manner[2]. Cell Proliferation Assay[2] Cell Line: CD3/CD28 bead-stimulated CD4+ T cells Concentration: 0, 20, 40, 60, 80, and 100 μM Incubation Time: 72 hours Result: Significantly inhibited CD4+ T-cell proliferation in a dose-dependent manner with an IC50 of approximately 70 μM.
In Vivo 3-Hydroxykynurenine administration (560 mg/kg IP on a daily basis on days 1 to 7, days 7 to 14, or days 1 to 14) results in significant prolongation of graft survival whether administered between days 1 to 7, days 7 to 14, or days 1 to 14[2]. Animal Model: BALB/c (H2d) mice[2] Dosage: 560 mg/kg Administration: IP injection Result: There was significant prolongation of graft survival in all treatment groups in comparison to the controls.
References

[1]. S Okuda, et al. 3-Hydroxykynurenine, an endogenous oxidative stress generator, causes neuronal cell death with apoptotic features and region selectivity. J Neurochem. 1998 Jan;70(1):299-307.

[2]. Sarah S Zaher,et al. 3-hydroxykynurenine suppresses CD4+ T-cell proliferation, induces T-regulatory-cell development, and prolongs corneal allograft survival. Invest Ophthalmol Vis Sci. 2011 Apr 22;52(5):2640-8.

 Chemical & Physical Properties

Density 1.461g/cm3
Boiling Point 519.3ºC at 760mmHg
Molecular Formula C10H12N2O4
Molecular Weight 224.21300
Flash Point 267.9ºC
Exact Mass 224.08000
PSA 126.64000
LogP 1.24060
Vapour Pressure 1.49E-12mmHg at 25°C
Index of Refraction 1.635
InChIKey VCKPUUFAIGNJHC-UHFFFAOYSA-N
SMILES Nc1c(O)cccc1C(=O)CC(N)C(=O)O
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AY6475000
CHEMICAL NAME :
Alanine, 3-(3-hydroxyanthraniloyl)-
CAS REGISTRY NUMBER :
484-78-6
LAST UPDATED :
198910
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C10-H12-N2-O4
MOLECULAR WEIGHT :
224.24
WISWESSER LINE NOTATION :
ZR BQ FV1YZVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - tumors

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
10 mg/L
REFERENCE :
NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 222,484,1969 *** REVIEWS *** TOXICOLOGY REVIEW AEHLAU Archives of Environmental Health. (Heldref Pub., 4000 Albemarle St., NW, Washington, DC 20016) V.1- 1960- Volume(issue)/page/year: 23,6,1971

 Safety Information

HS Code 2922509090

 Customs

HS Code 2922509090
Summary 2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Synonyms

rac 3-Hydroxy Kynurenine
Benzenebutanoic acid, a,2-diamino-3-hydroxy-g-oxo-
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