Chelidonic acid

Modify Date: 2024-01-02 18:44:47

Chelidonic acid Structure
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
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].

 Names

Name Chelidonic Acid
Synonym More Synonyms

 Chelidonic acid 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
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
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

~88%

Chelidonic acid Structure

Chelidonic acid

CAS#:99-32-1

Literature: Terazzi, Emmanuel; Zaim, Amir; Bocquet, Bernard; Varin, Johan; Guenee, Laure; Dutronc, Thibault; Lemonnier, Jean-Francois; Floquet, Sebastien; Cadot, Emmanuel; Heinrich, Benoit; Donnio, Bertrand; Piguet, Claude European Journal of Inorganic Chemistry, 2013 , # 19 p. 3323 - 3333

~84%

Chelidonic acid Structure

Chelidonic acid

CAS#:99-32-1

Literature: Gan, Xin-Min; Paine, Robert T.; Duesler, Eileen N.; Noeth, Heinrich Dalton Transactions, 2003 , # 1 p. 153 - 159

~%

Chelidonic acid Structure

Chelidonic acid

CAS#:99-32-1

Literature: Organic Letters, , vol. 13, # 12 p. 3194 - 3197

~%

Chelidonic acid Structure

Chelidonic acid

CAS#:99-32-1

Literature: Bulletin de la Societe Chimique de France, , vol. <4> 53, p. 565,569

 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%

 Articles9

More 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...

 Synonyms

4-oxopyran-2,6-dicarboxylic acid
EINECS 202-749-0
MFCD00006577
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