4H-Pyran-2,6-dicarboxylic acid, 4-oxo-
chelidonic acid
CAS: 99-32-1
Molecular Formula: C7H4O6
4H-Pyran-2,6-dicarboxylic acid, 4-oxo- - Names and Identifiers
| Name | chelidonic acid |
| Synonyms | compoundxi* chelidonic acid Greater Calandine Herb 4-Pyranone-2,6-dicarboxylic acid 4-Oxopyran-2,6-dicarboxylic acid 4-ketopyran-2,6-dicarboxylic acid 4-oxo-4H-pyran-2,6-dicarboxylic acid 4H-Pyran-2,6-dicarboxylic acid, 4-oxo- Chelidonic acid,4-Oxo-4H-pyran-2,6-dicarboxylic acid |
| CAS | 99-32-1 |
| EINECS | 202-749-0 |
| InChI | InChI=1/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12) |
| InChIKey | PBAYDYUZOSNJGU-UHFFFAOYSA-N |
4H-Pyran-2,6-dicarboxylic acid, 4-oxo- - Physico-chemical Properties
| Molecular Formula | C7H4O6 |
| Molar Mass | 184.1 |
| Density | 1.4880 (rough estimate) |
| Melting Point | 265 °C (dec.) (lit.) |
| Boling Point | 238.02°C (rough estimate) |
| Water Solubility | 14.3g/L(25 ºC) |
| Solubility | DMSO |
| Appearance | Beige to Yellow to Brown Powder |
| Merck | 13,2060 |
| BRN | 163607 |
| pKa | 1.26±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5600 (estimate) |
| MDL | MFCD00006577 |
| Physical and Chemical Properties | White crystalline powder. 257 degrees C decomposition. 1g of the product can be dissolved in 65ml water, 26ml boiling water, difficult to dissolve in alcohol. |
| In vitro study | Chelidonic acid dose-dependently decreases IL-6 production at 0.1-10 μM, inhibits expression of IL-6 mRNA at 1-10 μM. Chelidonic acid (0.1-10 μM) decreases caspase-1 activation, nuclear NF-κB activation, and increases cytosol NF-κB activation. Chelidonic acid is a glutamate decarboxylase inhibitor, with a K i of 1.2 μM. Chelidonic acid does not promote formation of apoenzyme or react with free pyridoxal-P. |
| In vivo study | Chelidonic acid (0.2, 2 mg/kg p.o.) attenuates allergic reaction induced by ovalbumin in mice. |
4H-Pyran-2,6-dicarboxylic acid, 4-oxo- - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 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 |
4H-Pyran-2,6-dicarboxylic acid, 4-oxo- - Reference Information
| biological activity | cheliedonic acid (Jerva acid, Jervaic acid, γ-Pyrone-2,6-dicarboxylic acid) it is a secondary metabolite found in several plants and has therapeutic potential for allergic diseases in experimental animals. Celiac acid inhibited production by HMC-1 by blocking NF-κB and caspase-1 in IL-6 cells. Chillidonic acid is also an inhibitor of glutamate decarb oxylase with a Ki value of 1.2 μm. |
| Target | Value |
| Use | for organic synthesis. |
| production method | is obtained from the reaction of diethyl oxalate and acetone. |
Last Update：2024-04-09 02:00:11
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View History
4H-Pyran-2,6-dicarboxylic acid, 4-oxo-
1-BENZYL-2-(METHYLSULFANYL)-1H-IMIDAZOLE-5-CARBOXYLIC ACID
(2E)-N-(3,5-dichlorophenyl)-3-(furan-2-yl)prop-2-enamide
3-(sec-butoxymethyl)-4-iodo-1-(3,3,3-trifluoropropyl)-1H-pyrazole
1174019-00-1
3-[(5-Bromopyridin-2-yl)oxy]benzaldehyde
N-(4-Chloro-2-nitrophenyl)acetamide
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
1-methyl-1H,4H,6H,7H-pyrano[4,3-c]pyrazole-3-carboxylic acid
1171125-38-4
1-BENZYL-2-(METHYLSULFANYL)-1H-IMIDAZOLE-5-CARBOXYLIC ACID
(2E)-N-(3,5-dichlorophenyl)-3-(furan-2-yl)prop-2-enamide
3-(sec-butoxymethyl)-4-iodo-1-(3,3,3-trifluoropropyl)-1H-pyrazole
1174019-00-1
3-[(5-Bromopyridin-2-yl)oxy]benzaldehyde
N-(4-Chloro-2-nitrophenyl)acetamide
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
1-methyl-1H,4H,6H,7H-pyrano[4,3-c]pyrazole-3-carboxylic acid
1171125-38-4