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MedKoo Cat#: 466164 | Name: 2ccPA sodium

Description:

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

2ccPA sodium is a lipid mediator, regulates neuronal apoptosis in traumatic brain injury (TBI).

Chemical Structure

2ccPA sodium
2ccPA sodium
CAS#927880-40-8 (sodium)

Theoretical Analysis

MedKoo Cat#: 466164

Name: 2ccPA sodium

CAS#: 927880-40-8 (sodium)

Chemical Formula: C22H40NaO5P

Exact Mass: 438.2511

Molecular Weight: 438.52

Elemental Analysis: C, 60.26; H, 9.19; Na, 5.24; O, 18.24; P, 7.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
633278-53-2 (free acid) 927880-40-8 (sodium)
Synonym
2ccPA sodium; 2-ccPA sodium; 2 ccPA sodium; 2ccPA; 2 ccPA; 2-ccPA; 2-Carba-cyclic phosphatidic acid sodium salt;
IUPAC/Chemical Name
sodium 4-((oleoyloxy)methyl)-1,2-oxaphospholan-2-olate 2-oxide
InChi Key
DNUYQLMNIMYOBI-KVVVOXFISA-M
InChi Code
InChI=1S/C22H41O5P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(23)26-18-21-19-27-28(24,25)20-21;/h9-10,21H,2-8,11-20H2,1H3,(H,24,25);/q;+1/p-1/b10-9-;
SMILES Code
[O-]P1(OCC(COC(CCCCCCC/C=C\CCCCCCCC)=O)C1)=O.[Na+]
Appearance
Solid powder
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 438.52 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: Nakashima M, Gotoh M, Hashimoto K, Endo M, Murakami-Murofushi K, Ikeshima- Kataoka H, Miyamoto Y. The neuroprotective function of 2-carba-cyclic phosphatidic acid: Implications for tenascin-C via astrocytes in traumatic brain injury. J Neuroimmunol. 2021 Dec 15;361:577749. doi: 10.1016/j.jneuroim.2021.577749. Epub 2021 Oct 9. PMID: 34688067. 2: Fukasawa K, Gotoh M, Uwamizu A, Hirokawa T, Ishikawa M, Shimizu Y, Yamamoto S, Iwasa K, Yoshikawa K, Aoki J, Murakami-Murofushi K. 2-Carba-lysophosphatidic acid is a novel β-lysophosphatidic acid analogue with high potential for lysophosphatidic acid receptor activation and autotaxin inhibition. Sci Rep. 2021 Aug 30;11(1):17360. doi: 10.1038/s41598-021-96931-2. PMID: 34462512; PMCID: PMC8405639. 3: Tsukahara T, Sahara Y, Ribeiro N, Tsukahara R, Gotoh M, Sakamoto S, Handa H, Murakami-Murofushi K. Adenine nucleotide translocase 2, a putative target protein for 2-carba cyclic phosphatidic acid in microglial cells. Cell Signal. 2021 Jun;82:109951. doi: 10.1016/j.cellsig.2021.109951. Epub 2021 Feb 13. PMID: 33592249. 4: Shimizu Y, Fukasawa K, Yamamoto S, Shibaike Y, Tsukahara R, Ishikawa M, Iwasa K, Yoshikawa K, Gotoh M, Murakami-Murofushi K. Evaluation of the pharmacokinetics of 2-carba-cyclic phosphatidic acid by liquid chromatography- triple quadrupole mass spectrometry. Prostaglandins Other Lipid Mediat. 2020 Oct;150:106450. doi: 10.1016/j.prostaglandins.2020.106450. Epub 2020 Apr 13. PMID: 32298781. 5: Shibaike Y, Gotoh M, Ogawa C, Nakajima S, Yoshikawa K, Kobayashi T, Murakami- Murofushi K. 2-Carba cyclic phosphatidic acid inhibits lipopolysaccharide- induced prostaglandin E2 production in a human macrophage cell line. Biochem Biophys Rep. 2019 Jul 19;19:100668. doi: 10.1016/j.bbrep.2019.100668. PMID: 31367683; PMCID: PMC6651843. 6: Higuchi T, Takagi K, Tochimoto A, Ichimura Y, Norose T, Katsumata Y, Masuda I, Yamanaka H, Morohoshi T, Kawaguchi Y. Antifibrotic effects of 2-carba cyclic phosphatidic acid (2ccPA) in systemic sclerosis: contribution to the novel treatment. Arthritis Res Ther. 2019 Apr 18;21(1):103. doi: 10.1186/s13075-019-1881-3. PMID: 30999934; PMCID: PMC6472078. 7: Hashimoto K, Nakashima M, Hamano A, Gotoh M, Ikeshima-Kataoka H, Murakami- Murofushi K, Miyamoto Y. 2-carba cyclic phosphatidic acid suppresses inflammation via regulation of microglial polarisation in the stab-wounded mouse cerebral cortex. Sci Rep. 2018 Jun 26;8(1):9715. doi: 10.1038/s41598-018-27990-1. PMID: 29946114; PMCID: PMC6018705. 8: Nakajima S, Gotoh M, Fukasawa K, Murofushi H, Murakami-Murofushi K. 2-O-Carba-oleoyl cyclic phosphatidic acid induces glial proliferation through the activation of lysophosphatidic acid receptor. Brain Res. 2018 Feb 15;1681:44-51. doi: 10.1016/j.brainres.2017.12.031. Epub 2017 Dec 24. PMID: 29278716. 9: Yamamoto S, Yamashina K, Ishikawa M, Gotoh M, Yagishita S, Iwasa K, Maruyama K, Murakami-Murofushi K, Yoshikawa K. Protective and therapeutic role of 2-carba-cyclic phosphatidic acid in demyelinating disease. J Neuroinflammation. 2017 Jul 21;14(1):142. doi: 10.1186/s12974-017-0923-5. Erratum in: J Neuroinflammation. 2018 Mar 5;15(1):67. PMID: 28732510; PMCID: PMC5521126. 10: Tsukahara T, Haniu H, Matsuda Y, Murakmi-Murofushi K. Short-term treatment with a 2-carba analog of cyclic phosphatidic acid induces lowering of plasma cholesterol levels in ApoE-deficient mice. Biochem Biophys Res Commun. 2016 Apr 22;473(1):107-113. doi: 10.1016/j.bbrc.2016.03.060. Epub 2016 Mar 21. PMID: 27012212. 11: Gotoh M, Nagano A, Tsukahara R, Murofushi H, Morohoshi T, Otsuka K, Murakami-Murofushi K. Cyclic phosphatidic acid relieves osteoarthritis symptoms. Mol Pain. 2014 Aug 14;10:52. doi: 10.1186/1744-8069-10-52. PMID: 25123228; PMCID: PMC4141741. 12: Kakiuchi Y, Nagai J, Gotoh M, Hotta H, Murofushi H, Ogawa T, Ueda H, Murakami-Murofushi K. Antinociceptive effect of cyclic phosphatidic acid and its derivative on animal models of acute and chronic pain. Mol Pain. 2011 May 14;7:33. doi: 10.1186/1744-8069-7-33. PMID: 21569544; PMCID: PMC3113318. 13: Nozaki E, Gotoh M, Hotta H, Hanazawa S, Kobayashi S, Murakami-Murofushi K. Synthesis of enantiopure 2-carba-cyclic phosphatidic acid and effects of its chirality on biological functions. Biochim Biophys Acta. 2011 Apr;1811(4):271-7. doi: 10.1016/j.bbalip.2011.01.003. Epub 2011 Jan 28. PMID: 21277386. 14: Gotoh M, Hotta H, Murakami-Murofushi K. Effects of cyclic phosphatidic acid on delayed neuronal death following transient ischemia in rat hippocampal CA1. Eur J Pharmacol. 2010 Dec 15;649(1-3):206-9. doi: 10.1016/j.ejphar.2010.09.052. Epub 2010 Sep 22. PMID: 20868671.

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