Ononetin
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MedKoo CAT#: 563139

CAS#: 487-49-0

Description: Ononetin is a TRPM3 channel blocker.


Chemical Structure

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Ononetin
CAS# 487-49-0

Theoretical Analysis

MedKoo Cat#: 563139
Name: Ononetin
CAS#: 487-49-0
Chemical Formula: C15H14O4
Exact Mass: 258.09
Molecular Weight: 258.273
Elemental Analysis: C, 69.76; H, 5.46; O, 24.78

Price and Availability

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250mg USD 310
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Synonym: Ononetin;

IUPAC/Chemical Name: 1-(2,4-Dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone

InChi Key: XHBZOAYMBBUURD-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H14O4/c1-19-12-5-2-10(3-6-12)8-14(17)13-7-4-11(16)9-15(13)18/h2-7,9,16,18H,8H2,1H3

SMILES Code: COC1=CC=C(CC(C2=CC=C(O)C=C2O)=O)C=C1

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: 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: 2934.99.03.00

More Info:

Product Data:
Biological target: Ononetin, a natural deoxybenzoin, is a potent and selective TRPM3 channel blocker with an IC50 of 0.3 μM.
In vitro activity: TBD
In vivo activity: Intraplantar injections of EP2 or BK2 agonists inhibited both the nocifensive response evoked by TRPM3 agonists, and the heat hypersensitivity produced by Freund's Complete Adjuvant (FCA). Furthermore, FCA-induced heat hypersensitivity was completely reversed by the selective TRPM3 antagonist ononetin in WT mice and did not develop in Trpm3-/- mice. These results demonstrate that TRPM3 is subject to promiscuous inhibition by Gβγ protein in heterologous expression systems, primary neurons and in vivo, and suggest a critical role for this ion channel in inflammatory heat hypersensitivity. Reference: J Neurosci. 2019 Oct 2;39(40):7840-7852. https://pubmed.ncbi.nlm.nih.gov/31451581/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 12.0 46.46
DMSO 45.9 177.89
Ethanol 18.9 73.24
PBS (pH 7.2) 0.3 0.97

Preparing Stock Solutions

The following data is based on the product molecular weight 258.27 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
Formulation protocol: Alkhatib O, da Costa R, Gentry C, Quallo T, Bevan S, Andersson DA. Promiscuous G-Protein-Coupled Receptor Inhibition of Transient Receptor Potential Melastatin 3 Ion Channels by Gβγ Subunits. J Neurosci. 2019 Oct 2;39(40):7840-7852. doi: 10.1523/JNEUROSCI.0882-19.2019. Epub 2019 Aug 26. Erratum in: J Neurosci. 2020 Sep 30;40(40):7778. PMID: 31451581; PMCID: PMC6774412.
In vitro protocol: TBD
In vivo protocol: Alkhatib O, da Costa R, Gentry C, Quallo T, Bevan S, Andersson DA. Promiscuous G-Protein-Coupled Receptor Inhibition of Transient Receptor Potential Melastatin 3 Ion Channels by Gβγ Subunits. J Neurosci. 2019 Oct 2;39(40):7840-7852. doi: 10.1523/JNEUROSCI.0882-19.2019. Epub 2019 Aug 26. Erratum in: J Neurosci. 2020 Sep 30;40(40):7778. PMID: 31451581; PMCID: PMC6774412.

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1: Son GY, Yang YM, Park WS, Chang I, Shin DM. Hypotonic stress induces RANKL via transient receptor potential melastatin 3 (TRPM3) and vaniloid 4 (TRPV4) in human PDL cells. J Dent Res. 2015 Mar;94(3):473-81. doi: 10.1177/0022034514567196. Epub 2015 Jan 16. PubMed PMID: 25595364; PubMed Central PMCID: PMC4814022.

2: Straub I, Krügel U, Mohr F, Teichert J, Rizun O, Konrad M, Oberwinkler J, Schaefer M. Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo. Mol Pharmacol. 2013 Nov;84(5):736-50. doi: 10.1124/mol.113.086843. Epub 2013 Sep 4. PubMed PMID: 24006495.

3: Straub I, Mohr F, Stab J, Konrad M, Philipp SE, Oberwinkler J, Schaefer M. Citrus fruit and fabacea secondary metabolites potently and selectively block TRPM3. Br J Pharmacol. 2013 Apr;168(8):1835-50. doi: 10.1111/bph.12076. PubMed PMID: 23190005; PubMed Central PMCID: PMC3623054.