Chelidonic acid - 10mM in DMSO , CAS No.99-32-1

CAS: 99-32-1 Cat. No.: C427222 Molecular Weight: 184.1 Beilstein Registry Number: 163607 EC Number: 202-749-0

GRADE & PURITY 10mM in DMSO

Synonyms

Chelidonic acid, analytical standard | UNII-T33U4W5K6O | 4-Oxo-1,6-dicarboxylic acid | 4-oxo-pyran-2,6-dicarboxylic acid | BBL037230 | chelidonsaure | HLD | s5579 | 2,6-dicarboxy-4-pyrone | 4H-Pyran-2,6-dicarboxylic acid, 4-oxo- | Chelidonic acid (not val

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

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.

Biological activity

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. Chelidonic acid is a glutamate decarboxylase inhibitor, with a Ki of 1.2 μM。

Specifications

Synonyms

Chelidonic acid, analytical standard | UNII-T33U4W5K6O | 4-Oxo-1, 6-dicarboxylic acid | 4-oxo-pyran-2, 6-dicarboxylic acid | BBL037230 | chelidonsaure | HLD | s5579 | 2, 6-dicarboxy-4-pyrone | 4H-Pyran-2, 6-dicarboxylic acid, 4-oxo- | Chelidonic acid (not val

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: C1=C(OC(=CC1=O)C(=O)O)C(=O)O
• IUPAC Name: 4-oxopyran-2,6-dicarboxylic acid
• InChIKey: PBAYDYUZOSNJGU-UHFFFAOYSA-N
• INCHI: 1S/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12)
• Isomeric SMILES: C1=C(OC(=CC1=O)C(=O)O)C(=O)O
• WGK Germany: 3
• RTECS: UP7350000
• Molecular Weight: 184.1
• Beilstein: 163607
• Reaxy-Rn: 163607
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=163607&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrans
      • Subclass Pyranones and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrans
• Subclass: Pyranones and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyranones and derivatives
• Alternative Parents: Dicarboxylic acids and derivatives Heteroaromatic compounds Cyclic ketones Oxacyclic compounds Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyranone - Dicarboxylic acid or derivatives - Heteroaromatic compound - Cyclic ketone - Oxacycle - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyranones and derivatives. These are compounds containing a pyran ring which bears a ketone.
• External Descriptors: Monocyclic gamma-pyrones

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Melt Point(°C): 265 °C
• Molecular Weight: 184.100 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 184.001 Da
• Monoisotopic Mass: 184.001 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 316.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhiming Mi, Lintao Liao, Lingjun Meng, Yuhang Zhao, Mingli Yin, Guangqiu Lei, Haoye Xiong, Gao Hu, Qianqian Xu, Zhixiao Liu.  (2024)  Chelidonic acid-regulated synthesis of asymmetric polyamide nanofiltration membrane: Mechanisms and separation performance.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2024.131031]