Chelidonic acid

Names

[ CAS No. ]:
99-32-1

[ Name ]:
Chelidonic acid

[Synonym ]:
4-oxopyran-2,6-dicarboxylic acid
EINECS 202-749-0
MFCD00006577

Biological Activity

[Description]:

Chelidonic acid is a component of Chelidonium majus L., used as a mild analgesic, an antimicrobial, an acentral nervous system sedative. Chelidonic acid also shows anti-inflammatory activity. Chelidonic acid has potential to inhibit IL-6 production by blocking NF-κB and caspase-1[1]. Chelidonic acid is a glutamate decarboxylase inhibitor, with a Ki of 1.2 μM[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Caspase

Research Areas >> Inflammation/Immunology

[Target]

NF-κB

Caspase-1

Glutamate decarboxylase:1.2 μM (Ki)

[In Vitro]

Chelidonic acid dose-dependently decreases IL-6 production at 0.1-10 μM, inhibits expression of IL-6 mRNA at 1-10 μM[1]. Chelidonic acid (0.1-10 μM) decreases caspase-1 activation, nuclear NF-κB activation, and increases cytosol NF-κB activation[1]. Chelidonic acid is a glutamate decarboxylase inhibitor, with a Ki of 1.2 μM. Chelidonic acid does not promote formation of apoenzyme or react with free pyridoxal-P[2].

[In Vivo]

Chelidonic acid (0.2, 2 mg/kg p.o.) attenuates allergic reaction induced by ovalbumin in mice[3].

[References]

[1]. Shin HJ, et al. Inhibitory effects of chelidonic acid on IL-6 production by blocking NF-κB and caspase-1 in HMC-1 cells. Immunopharmacol Immunotoxicol. 2011 Dec;33(4):614-9.

[2]. Porter TG, et al. Chelidonic acid and other conformationally restricted substrate analogues as inhibitors of rat brain glutamate decarboxylase. Biochem Pharmacol. 1985 Dec 1;34(23):4145-50.

[3]. Oh HA, et al. Beneficial effects of chelidonic acid on a model of allergic rhinitis. Send to Int Immunopharmacol. 2011 Jan;11(1):39-45.

Chemical & Physical Properties

[ Density]:
1.821 g/cm3

[ Boiling Point ]:
471.3ºC at 760 mmHg

[ Melting Point ]:
265 °C (dec.)(lit.)

[ Molecular Formula ]:
C₇H₄O₆

[ Molecular Weight ]:
184.10

[ Flash Point ]:
204.1ºC

[ Exact Mass ]:
184.00100

[ PSA ]:
104.81000

[ LogP ]:
0.03620

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UP7350000

CHEMICAL NAME :: 4H-Pyran-2,6-dicarboxylic acid, 4-oxo-

CAS REGISTRY NUMBER :: 99-32-1

BEILSTEIN REFERENCE NO. :: 0163607

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C7-H4-O6

MOLECULAR WEIGHT :: 184.11

WISWESSER LINE NOTATION :: T6O DVJ BVQ FVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CBCCT* "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. (National Academy of Science Library, 2101 Constitution Ave., NW, Washington, DC 20418) Volume(issue)/page/year: 6,54,1954

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UP7350000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Chelidonic acid and other conformationally restricted substrate analogues as inhibitors of rat brain glutamate decarboxylase.

Biochem. Pharmacol. 34 , 4145-4150, (1985)

Twenty conformationally restricted analogues of glutamate including benzoic acids, hydroxy-benzoic acids, pyridine dicarboxylic acids, and pyran dicarboxylic acids were tested as inhibitors of glutama...

Purification and characterization of dihydrodipicolinate synthase from pea.

Plant Physiol. 98(3) , 813-821., (1992)

Dihydrodipicolinate synthase (EC 4.2.1.52), the first enzyme unique to lysine biosynthesis in bacteria and higher plants, has been purified to homogeneity from etiolated pea (Pisum sativum) seedlings ...

Tracer studies with 13C-labeled carbohydrates in cultured plant cells. Retrobiosynthetic analysis of chelidonic acid biosynthesis.

Phytochemistry 57(1) , 33-42, (2001)

The biosynthesis of chelidonic acid was studied in cell suspension cultures of Leucojum aestivum. Cell cultures were supplied with [U-13C]glucose, [l-13C]glucose or [U-13Cs]ribose/ribulose in standard...