Chelidonic acid

Modify Date: 2025-08-25 11:16:52

Chelidonic acid structure	Common Name	Chelidonic acid
	CAS Number	99-32-1	Molecular Weight	184.10
	Density	1.821 g/cm3	Boiling Point	471.3ºC at 760 mmHg
	Molecular Formula	C₇H₄O₆	Melting Point	265 °C (dec.)(lit.)
	MSDS	Chinese USA	Flash Point	204.1ºC
	Symbol	GHS07	Signal Word	Warning

Use of Chelidonic acid

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].

Name	Chelidonic Acid
Synonym	More Synonyms

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.

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

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

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

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Precursor 5
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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%

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...

4-oxopyran-2,6-dicarboxylic acid

EINECS 202-749-0

MFCD00006577

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