Chelidonic acid

Chelidonic acid Property

Melting point:

265 °C (dec.) (lit.)

Boiling point:

238.02°C (rough estimate)

Density 

1.4880 (rough estimate)

refractive index 

1.5600 (estimate)

storage temp. 

2-8°C

solubility 

DMSO: 1 mg/ml; DMSO:PBS (pH 7.2) (1:6): 0.14 mg/ml

form 

Solid

pka

1.26±0.40(Predicted)

color 

Gray to brown

Water Solubility 

14.3g/L(25 ºC)

Merck 

13,2060

BRN 

163607

InChIKey

PBAYDYUZOSNJGU-UHFFFAOYSA-N

LogP

-0.746 (est)

CAS DataBase Reference

99-32-1(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UP7350000

HS Code 

29329990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Chelidonic acid Chemical Properties,Usage,Production

Configuration Method

Chelidonic acid is supplied as a crystalline solid. A stock solution may be made by dissolving thechelidonic acid in the solvent of choice, which should be purged with an inert gas. Chelidonic acid is soluble in the organic solvent DMSO at approximately 1 mg/ml concentration. Chelidonic acid is sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers,chelidonic acid should first be dissolved in DMSO and then diluted with the aqueous buffer of choice. Chelidonic acid has a solubility of approximately 0.14 mg/ml in a 1:6 solution of DMSO: PBS(pH 7.2) using this method. We do not recommend storing the aqueous solution for more than one day.

Uses

Chelidonic acid is suitable for use a in homogeneous preparation of native dihydrodipicolinate synthase from pea. It may be used as endocyclic oxygen-containing ligand in the synthesis of aqua[bis(2-pyridylmethyl)amine][chelidonato(1.5-)]-copper(II) chelidonate(0.5-) monohydrate.

Definition

ChEBI: Chelidonic acid is a carbonyl compound and a member of pyrans.

General Description

Chelidonic acid (CA) is a γ-pyrone. It is reported as constituent of the rhizome of Chelidonium majus L. It has many pharmacological effects, such as mild analgesic and antimicrobial effects. Therapeutic potential of CA for the treatment of intestinal inflammation has been investigated. CA is reported as inhibitor of the rat brain glutamate decarboxylase. Biosynthesis of CA in cell suspension cultures of Leucojum aestivum has been studied.

Synthesis

A modified literature method was used to synthesize betulinic acid from diethyl oxalate and acetone. The steps were as follows: in a typical experiment, sodium ethoxide (69.4 g, 1.02 mol) was suspended in ethanol (300 mL). After stirring at 60 °C for 45 min, a mixed solution of anhydrous acetone (29 g, 38 mL, 0.5 mol) and diethyl oxalate (155 g, 144 mL, 1.06 mol) was slowly added dropwise. After the dropwise addition, the reaction temperature was maintained at 60 °C and the reaction continued to be stirred for 14 hours. Subsequently, 37% aqueous hydrochloric acid solution (230 mL) and water (100 mL) were added to the reaction mixture and the reaction was stirred for 24 h. After 24 h, about half of the aqueous ethanol was evaporated under reduced pressure, and water (300 mL) and 37% aqueous hydrochloric acid solution (60 mL) were then added to the remaining mixture, and the stirring was continued at 50 °C for 20 h. The reaction was completed by filtration and the mixture was collected. Upon completion of the reaction, the resulting solid was collected by filtration and washed sequentially with water and acetone. The resulting solid was recrystallized using activated carbon in boiling water. The filtrate was allowed to stand at room temperature until crystals precipitated. The white crystals were collected and dried under vacuum to give the final target product leucocholic acid (42.3 g, 46% yield).

in vivo

IC 50

NF-κB; Caspase-1; Glutamate decarboxylase: 1.2 μM (Ki)

Purification Methods

The acid crystallises from aqueous EtOH. Dry it first at 100o/2hours, then at 160o to constant weight to remove water of crystallisation. It decarboxylates at 220-230o in a vacuum. [Riegel & Zwilgmeyer Org Synth Coll Vol II 126 1943, Beilstein 18 H 490, 18/8 V 646.]

References

[1] Synthetic Communications, 1999, vol. 29, # 21, p. 3719 - 3731
[2] European Journal of Inorganic Chemistry, 2013, # 19, p. 3323 - 3333
[3] Tetrahedron, 2015, vol. 71, # 33, p. 5321 - 5336
[4] Dalton Transactions, 2017, vol. 46, # 16, p. 5229 - 5239
[5] Journal of Organic Chemistry, 1952, vol. 17, p. 1492