Crotonyl-CoA tetrasodium 

Crotonyl-CoA tetrasodium, a high-energy acyl donor, is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan. Crotonyl-CoA tetrasodium is important in the metabolism of fatty acids and amino acids. Crotonyl-CoA tetrasodium acts as a substrate for p300’s histone crotonyltransferase activity, competing with acetyl-CoA for p300-mediated histone acylation reactions. Crotonyl-CoA tetrasodium regulates global and gene-specific histone crotonylation levels in cells, with cellular concentration changes altering histone crotonylation at regulatory elements of activated genes. Crotonyl-CoA tetrasodium serves as the substrate for crotonyl-CoA reductase/carboxylase (CCRC)-catalyzed NADPH-mediated reduction and carbon dioxide trapping to form unusual alkylmalonyl-CoA polyketide synthase extender units. Crotonyl-CoA tetrasodium can be used for the research of LPS-induced inflammatory response^[1][2].

Crotonyl-CoA tetrasodium directly stimulates transcription in a cell-free system more potently than acetylation, with a 1.66-fold greater transcript production^[1].
Crotonyl-CoA tetrasodium, when cellular concentrations are increased via 2.5 mM, 5 mM, 10 mM sodium crotonate treatment (12 h), led to dose-dependent increases in global H3K18Cr levels in HeLa S3 cells^[1].
Crotonyl-CoA tetrasodium, when cellular concentrations are increased via 0 mM, 2.5 mM, 5 mM, 10 mM sodium crotonate pretreatment (6 h prior to 2 h LPS stimulation), enhanced H3K18Cr at de novo-activated gene promoters and increased their expression upon LPS stimulation in RAW 264.7 cells^[1].
Crotonyl-CoA tetrasodium, when its cellular levels are reduced via ACSS2 knockdown (72 h prior to 2 h LPS stimulation), reduced H3K18Cr at de novo-activated gene promoters and attenuated their expression upon LPS stimulation in RAW 264.7 cells^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

923.54

C₂₅H₃₆N₇Na₄O₁₇P₃S

Solid

White to off-white

NC1=NC=NC2=C1N=CN2[C@H]3[C@H](O)[C@H](OP(O[Na])(O[Na])=O)[C@@H](COP(OP(OCC(C)(C)[C@@H](O)C(NCCC(NCCSC(/C=C/C)=O)=O)=O)(O[Na])=O)(O[Na])=O)O3

Room temperature in continental US; may vary elsewhere.

4°C, stored under nitrogen, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen, away from moisture)

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

• [1]. Sabari BR, et al. Intracellular crotonyl-CoA stimulates transcription through p300-catalyzed histone crotonylation. Mol Cell. 2015;58(2):203-215.  [Content Brief]

  [2]. Ray L, et al. A crotonyl-CoA reductase-carboxylase independent pathway for assembly of unusual alkylmalonyl-CoA polyketide synthase extender units. Nat Commun. 2016 Dec 21;7:13609.  [Content Brief]