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MedKoo Cat#: 463106 | Name: Chelidonic Acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Chelidonic acid is a pyran that has been found in C. majus and has diverse biological activities. It inhibits rat brain glutamate decarboxylase. Chelidonic acid reduces serum IL-6 and TNF-α levels, colonic COX-2 and prostaglandin E2 levels, and the disease activity index score in a mouse model of ulcerative colitis induced by dextran sulfate sodium. It inhibits ovalbumin challenge-induced decreases in spleen IFN-γ levels and increases in serum, spleen, and nasal mucosa IgE levels, spleen IL-4 levels, and nasal mucosa eosinophil and mast cell infiltration in a mouse model of ovalbumin-sensitized allergic rhinitis when administered at a dose of 2 mg/kg.

Chemical Structure

Chelidonic Acid
Chelidonic Acid
CAS#99-32-1

Theoretical Analysis

MedKoo Cat#: 463106

Name: Chelidonic Acid

CAS#: 99-32-1

Chemical Formula: C7H4O6

Exact Mass: 184.0008

Molecular Weight: 184.10

Elemental Analysis: C, 45.67; H, 2.19; O, 52.14

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Chelidonic Acid; NSC 3979; NSC3979; NSC-3979;
IUPAC/Chemical Name
4-oxo-4H-pyran-2,6-dicarboxylic acid
InChi Key
PBAYDYUZOSNJGU-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C1C=C(OC(C(O)=O)=C1)C(O)=O
Appearance
To be determined
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 184.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kopp T, Abdel-Tawab M, Khoeiklang M, Mizaikoff B. Development of a Selective Adsorbing Material for Binding of Pyrrolizidine Alkaloids in Herbal Extracts, Based on Molecular Group Imprinting. Planta Med. 2019 Sep;85(13):1107-1113. doi: 10.1055/a-0961-2658. Epub 2019 Aug 5. PMID: 31382302. 2: Malaganvi SS, Tonannavar Yenagi J, Tonannavar J. Experimental, DFT dimeric modeling and AIM study of H-bond-mediated composite vibrational structure of Chelidonic acid. Heliyon. 2019 May 14;5(5):e01586. doi: 10.1016/j.heliyon.2019.e01586. PMID: 31193235; PMCID: PMC6522660. 3: Avdeeva E, Shults E, Rybalova T, Reshetov Y, Porokhova E, Sukhodolo I, Litvinova L, Shupletsova V, Khaziakhmatova O, Khlusov I, Guryev A, Belousov M. Chelidonic Acid and Its Derivatives from Saussurea Controversa: Isolation, Structural Elucidation and Influence on the Osteogenic Differentiation of Multipotent Mesenchymal Stromal Cells In Vitro. Biomolecules. 2019 May 16;9(5):189. doi: 10.3390/biom9050189. PMID: 31100934; PMCID: PMC6572306. 4: Singh DK, Gulati K, Ray A. Effects of chelidonic acid, a secondary plant metabolite, on mast cell degranulation and adaptive immunity in rats. Int Immunopharmacol. 2016 Nov;40:229-234. doi: 10.1016/j.intimp.2016.08.009. Epub 2016 Sep 9. PMID: 27620504. 5: Jeong HJ, Yang SY, Kim HY, Kim NR, Jang JB, Kim HM. Chelidonic acid evokes antidepressant-like effect through the up-regulation of BDNF in forced swimming test. Exp Biol Med (Maywood). 2016 Aug;241(14):1559-67. doi: 10.1177/1535370216642044. Epub 2016 Mar 31. PMID: 27037280; PMCID: PMC4994898. 6: Zarei A, Changizi-Ashtiyani S, Taheri S, Ramezani M. A quick overview on some aspects of endocrinological and therapeutic effects of Berberis vulgaris L. Avicenna J Phytomed. 2015 Nov-Dec;5(6):485-97. PMID: 26693406; PMCID: PMC4678494. 7: Liu H, Zheng YF, Li CY, Zheng YY, Wang DQ, Wu Z, Huang L, Wang YG, Li PB, Peng W, Su WW. Discovery of Anti-inflammatory Ingredients in Chinese Herbal Formula Kouyanqing Granule based on Relevance Analysis between Chemical Characters and Biological Effects. Sci Rep. 2015 Dec 10;5:18080. doi: 10.1038/srep18080. PMID: 26657159; PMCID: PMC4674803. 8: Hamada Y, Suzuki K, Nakanishi T, Sarma D, Ohta H, Yamaguchi R, Yamasaki M, Hidaka K, Ishiura S, Kiso Y. Structure-activity relationship study of BACE1 inhibitors possessing a chelidonic or 2,6-pyridinedicarboxylic scaffold at the P(2) position. Bioorg Med Chem Lett. 2014 Jan 15;24(2):618-23. doi: 10.1016/j.bmcl.2013.12.007. Epub 2013 Dec 8. PMID: 24360554. 9: Kim DS, Kim SJ, Kim MC, Jeon YD, Um JY, Hong SH. The therapeutic effect of chelidonic acid on ulcerative colitis. Biol Pharm Bull. 2012;35(5):666-71. doi: 10.1248/bpb.35.666. PMID: 22687399. 10: Ghadermazi M, Olmstead MM, Attar Gharamaleki J, Rostami S. Statistically disordered short hydrogen bonds in (pipzH2)(cdoH)2 and a comparison with (pipzH2)(cdo)·H2O (pipz is piperazine and cdoH2 is chelidonic acid). Acta Crystallogr C. 2011 Apr;67(Pt 4):o134-8. doi: 10.1107/S0108270111008110. Epub 2011 Mar 11. PMID: 21467620. 11: Shin HJ, Kim HL, Kim SJ, Chung WS, Kim SS, Um JY. 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. doi: 10.3109/08923973.2011.552508. Epub 2011 Feb 15. PMID: 21320026. 12: Oh HA, Kim HM, Jeong HJ. Beneficial effects of chelidonic acid on a model of allergic rhinitis. Int Immunopharmacol. 2011 Jan;11(1):39-45. doi: 10.1016/j.intimp.2010.10.002. Epub 2010 Oct 23. PMID: 20974310. 13: Yasodha V, Govindarajan S, Low JN, Glidewell C. Cationic, neutral and anionic metal(II) complexes derived from 4-oxo-4H-pyran-2,6-dicarboxylic acid (chelidonic acid). Acta Crystallogr C. 2007 May;63(Pt 5):m207-15. doi: 10.1107/S010827010701459X. Epub 2007 Apr 21. PMID: 17478903. 14: Shen Z-W, Fisinger U, Poulev A, Eisenreich W, Werner I, Pleiner E, Bacher A, Zenk MH. Tracer studies with 13C-labeled carbohydrates in cultured plant cells. Retrobiosynthetic analysis of chelidonic acid biosynthesis. Phytochemistry. 2001 May;57(1):33-42. doi: 10.1016/s0031-9422(00)00496-9. PMID: 11336258. 15: Gude M, Hausen BM, Heitsch H, König WA. An investigation of the irritant and allergenic properties of daffodils (Narcissus pseudonarcissus L., Amaryllidaceae). A review of daffodil dermatitis. Contact Dermatitis. 1988 Jul;19(1):1-10. doi: 10.1111/j.1600-0536.1988.tb02860.x. PMID: 2972509. 16: Porter TG, Martin DL. Chelidonic acid and other conformationally restricted substrate analogues as inhibitors of rat brain glutamate decarboxylase. Biochem Pharmacol. 1985 Dec 1;34(23):4145-50. doi: 10.1016/0006-2952(85)90207-2. PMID: 4062982. 17: Eiden F, Beuttenmüller M. Notiz über die Reaktion von Chelidonsäure mit o-Phenylendiamin [Reaction of chelidonic acid with o-phenylenediamine]. Arch Pharm Ber Dtsch Pharm Ges. 1971 Jun;304(6):442-5. German. doi: 10.1002/ardp.19713040611. PMID: 5282738. 18: Malcolm MJ, Gear JR. The biosynthesis of chelidonic acid. Can J Biochem. 1971 Apr;49(4):412-6. doi: 10.1139/o71-060. PMID: 5102735. 19: Bohm BA. Biosynthesis of chelidonic acid. I. Preliminary observation on the precursors of chelidonic acid in Convallaria majalis L. Arch Biochem Biophys. 1966 Jul;115(1):181-6. doi: 10.1016/s0003-9861(66)81054-8. PMID: 6007597. 20: Eiden F, Peter P. Reaktionen mit Chelidonsäure. 3. Uber Umsetzungen von Pyranyliden-carbonsäurederivaten mit Diaminen. 10. Untersuchungen an gamma- Pyronen [Reactions with chelidonic acid. 3. On re-arrangements of pyranylidene- carbonic acid derivatives with diamines. 10. Studies on gamma-pyrones]. Arch Pharm Ber Dtsch Pharm Ges. 1966 Feb;299(2):139-46. German. doi: 10.1002/ardp.19662990207. PMID: 5223107.