| Identification | More | [Name]
Chelidonic acid | [CAS]
99-32-1 | [Synonyms]
4-OXO-4H-PYRAN-2,6-DICARBOXYLIC ACID
AKOS AUF02028
CHELIDONIC ACID
GAMMA-PYRONE-2,6-DICARBOXYLIC ACID
G-PYRONE-2,6-DICARBOXYLIC ACID
JERVA ACID
JERVASIC ACID
TIMTEC-BB SBB000242
4-oxo-1,4-pyran-2,6-dicarboxylicacid
4-oxo-4h-pyran-6-dicarboxylicacid
6-dicarboxylicacid,4-oxo-4H-Pyran-2
compoundxi*
jervaicacid
-Pyrone-2,6-dicarboxylicacid
CHELIDONIC ACID, ANHYDROUS
AI3-19253
CHELIDONIC ACID(RG)
PYRAN-2,6-DICARBOXYLICACID,4-OXO-
4-Oxopyran-2,6-dicarboxylic acid
4-Pyranone-2,6-dicarboxylic acid | [EINECS(EC#)]
202-749-0 | [Molecular Formula]
C7H4O6 | [MDL Number]
MFCD00006577 | [Molecular Weight]
184.1 | [MOL File]
99-32-1.mol |
| Chemical Properties | Back Directory | [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. ]
Sealed in dry,2-8°C | [solubility ]
DMSO: 1 mg/ml; DMSO:PBS (pH 7.2) (1:6): 0.14 mg/ml | [form ]
neat | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
UP7350000
| [HS Code ]
29329990 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Diethyl oxalate-->Sodium ethoxide-->DIETHYL TRIOXOPIMELATE-->Hydrochloric acid-->Acetone-->Diethyl 1,3-acetonedicarboxylate | [Preparation Products]
2,6-Bis(bromomethyl)-4-bromopyridine-->4-Hydroxypyridine-2,6-dicarboxylic acid-->Methyl 4,6-dichloropyridine-2-carboxylate-->Dimethyl 4-oxo-1,4-dihydropyridine-2,6-dicarboxylate-->4,6-Dichloro-2-pyridinecarboxylic acid-->Diethyl 4-bromopyridine-2,6-dicarboxylate-->2,4,6-trioxoheptanedioic acid |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [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]
Chelidonic acid (0.2, 2 mg/kg p.o.) attenuates allergic reaction induced by ovalbumin in mice[3]. | [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 |
|
|