Farnesyl pyrophosphate (Farnesyl diphosphate) is a 15-carbon isoprenoid and a metabolic intermediate in the mevalonate (MVA) pathway. Farnesyl pyrophosphate is a TRPM2 (TRP Channel) agonist that activates TRPM2 to open, allowing ions to flow into cells. Farnesyl pyrophosphate is a key branch substrate for cholesterol synthesis, ubiquinone synthesis, protein farnesylation modification, and geranyl-geranyl pyrophosphate (GGPP) synthesis.

Physicochemical Properties

Molecular Formula	C15H28O7P2
Molecular Weight	382.33
Exact Mass	433.21
CAS #	13058-04-3
Related CAS #	Farnesyl Pyrophosphate ammonium
PubChem CID	445713
Appearance	Typically exists as solid at room temperature
Flash Point	16 °C - closed cup (lit.)
LogP	5.603
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	11
Heavy Atom Count	24
Complexity	568
Defined Atom Stereocenter Count	0
SMILES	C/C(=C/CC/C(=C/CC/C(=C/COP(OP(=O)(O)O)(O)=O)/C)/C)/C
InChi Key	VWFJDQUYCIWHTN-YFVJMOTDSA-N
InChi Code	InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
Chemical Name	phosphono [(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] hydrogen phosphate
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In stroke, farnesyl pyrophosphate functions as a well-known danger signal that causes immediate cell death and subsequent loss of neurons. With its highly charged pyrophosphate head group and hydrophobic 15-carbon isoprenyl chain, farnesyl pyrophosphate causes abrupt cell death without affecting the cell's downstream metabolic pathways. Mechanistically, the cation channel transient receptor potential melastatin 2 (TRPM2) and extracellular calcium influx are key players in the cell death caused by farnesyl pyrophosphate. TRPM2 is activated by farnesyl pyrophosphate acid, which opens ion inflow [1].
ln Vivo	Farnesyl pyrophosphate builds up in the brain of a mouse model of middle cerebral artery occlusion (MCAO), suggesting a role for both Farnesyl pyrophosphate and the TRPM2 danger signal axis in ischemia damage. Important functions for the MVA pathway and the Farnesyl pyrophosphate/TRPM2 signaling axis are seen in brain ischemia and possible neurodegenerative disorders [1].
References	[1]. Farnesyl pyrophosphate is a new danger signal inducing acute cell death. PLoS Biol. 2021 Apr 26;19(4):e3001134.
Additional Infomation	2-trans,6-trans-farnesyl diphosphate is the trans,trans-stereoisomer of farnesyl diphosphate. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a conjugate acid of a 2-trans,6-trans-farnesyl diphosphate(3-). Farnesyl pyrophosphate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Farnesyl diphosphate has been reported in Tripterygium wilfordii, Myxococcus xanthus, and other organisms with data available. Farnesyl pyrophosphate is a metabolite found in or produced by Saccharomyces cerevisiae. 2-trans,6-trans-farnesyl diphosphate is a metabolite found in or produced by Saccharomyces cerevisiae.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6155 mL	13.0777 mL	26.1554 mL
	5 mM	0.5231 mL	2.6155 mL	5.2311 mL
	10 mM	0.2616 mL	1.3078 mL	2.6155 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.