 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C₂₂H₄₆NO₇P |
| Molecular Weight | 467.58 |
| Exact Mass | 467.301 |
| CAS # | 20559-16-4 |
| PubChem CID | 460604 |
| Appearance | White to light yellow solid powder |
| LogP | 4.869 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 22 |
| Heavy Atom Count | 31 |
| Complexity | 489 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O |
| InChi Key | VXUOFDJKYGDUJI-OAQYLSRUSA-N |
| InChi Code | InChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1 |
| Chemical Name | [(2R)-2-hydroxy-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl 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
| Targets |
Histamine receptor Acetylcholine receptor[1] |
| ln Vitro |
LysoPC(14:0/0:0) (myristoyl-LPC) exerts non-competitive antispasmodic effects on guinea pig ileum against spasms induced by histamine and acetylcholine. Pretreatment of the gut with the compound for 5 minutes is required to achieve the effect. As the concentration of LysoPC(14:0/0:0) for pretreatment increases, the slope of the cumulative dose-response curve of histamine or acetylcholine becomes gentler, the maximal contraction is significantly suppressed, and the curve shifts toward higher concentrations of the stimulants. Among synthetic LPCs with saturated fatty acid moieties, LysoPC(14:0/0:0) shows the second strongest antispasmodic effect, following palmitoyl-LPC[1] LysoPC(14:0/0:0) exhibits a relaxing effect on perfused rabbit ear vessel preparations, with the activity order consistent with its antispasmodic effect on guinea pig ileum[1] |
| ln Vivo | The highest antispasmodic activity against acetylcholine- or histamine-induced guinea pig ileum contraction is shown by palmitoyl-LPC among the saturated fatty acid-containing L-α-lysolecithins (LPC); the other potencies are as follows: myristoyl- > stearoyl-, lauroyl- > decanoyl-LPC (LysoPC(14:0 /0:0)). When a cis-double bond was added to LPC's C18 fatty acid chain, the antispasmodic efficacy was somewhat reduced[1]. |
| Cell Assay |
Guinea pig ileum tissue preparations were pretreated with LysoPC(14:0/0:0) for 5 minutes, followed by cumulative addition of histamine or acetylcholine as spasmogens. The contraction responses of the ileum were recorded to analyze the changes in the dose-response curve, including slope, maximal contraction amplitude, and curve shift[1] Rabbit ear vessel preparations were perfused, and the relaxing effect of LysoPC(14:0/0:0) on the vessels was observed and evaluated[1] |
| References |
[1]. Comparison of antispasmodic effect of synthetic lysolecithins with various fatty acid moieties on guinea pig ileum.J Pharmacobiodyn. 1984 Jun;7(6):400-6. |
| Additional Infomation |
1-myristoyl-sn-glycero-3-phosphocholine is a lysophosphatidylcholine 14:0 in which the acyl group specified is myristoyl. The major species at pH 7.3. It is a lysophosphatidylcholine 14:0, a 1-O-acyl-sn-glycero-3-phosphocholine and a tetradecanoate ester. 1-Myristoyl-sn-glycero-3-phosphocholine has been reported in Homo sapiens with data available. PC(14:0/0:0) is a metabolite found in or produced by Saccharomyces cerevisiae. LysoPC(14:0/0:0) is a synthetic L-alpha-lysolecithin (1-O-acyl-2-lyso-sn-glycero-3-phosphocholine) with a myristoyl fatty acid moiety[1] The antispasmodic activity of LysoPC(14:0/0:0) is influenced by the structure of the fatty acid moiety; incorporation of a cis-double bond into the C18 fatty acid chain of LPC leads to a slight decrease in antispasmodic effect[1] |
Solubility Data
| Solubility (In Vitro) | Ethanol : ~50 mg/mL (~106.93 mM) |
| 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 | 2.1387 mL | 10.6934 mL | 21.3867 mL | |
| 5 mM | 0.4277 mL | 2.1387 mL | 4.2773 mL | |
| 10 mM | 0.2139 mL | 1.0693 mL | 2.1387 mL |