Phosphoethanolamine (also known as Phosphorylethanolamine, Monoaminoethyl phosphate; NSC 254167; O-Phosphoethanolamine) is used to construct glycerophospholipid and sphingomyelin or sphingophospholipid. Phosphorylethanolamine is a polyprotic acid with potential anticancer activities.

Physicochemical Properties

Molecular Formula	C2H8NO4P
Molecular Weight	141.0630
Exact Mass	141.019
CAS #	1071-23-4
Related CAS #	1071-23-4;10389-08-9 (calcium);
PubChem CID	1015
Appearance	White to off-white solid powder
Density	1.554g/cm3
Boiling Point	335.8ºC at 760mmHg
Melting Point	241-243 °C(lit.)
Flash Point	156.9ºC
Vapour Pressure	2.2E-05mmHg at 25°C
LogP	-4.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	8
Complexity	98.2
Defined Atom Stereocenter Count	0
SMILES	P(=O)(O[H])(O[H])OC([H])([H])C([H])([H])N([H])[H]
InChi Key	SUHOOTKUPISOBE-UHFFFAOYSA-N
InChi Code	InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
Chemical Name	2-Aminoethyl dihydrogen phosphate
Synonyms	Monoaminoethyl phosphate; NSC 254167; NSC254167; NSC-254167; O-Phosphoethanolamine; 2-Aminoethyl dihydrogen phosphate; Colamine phosphate; Ethanolamine O-phosphate; Ethanolamine phosphate; PE 104; Phosphoethanolamine; Phosphonoethanolamine; Phosphoryethanolamine
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

References

Biochimie. 2016 Nov;130:81-90.

Additional Infomation

O-phosphoethanolamine is the ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimer's disease brain. It has a role as a human metabolite, an algal metabolite and a mouse metabolite. It is a phosphoethanolamine and a primary amino compound. It is a conjugate acid of an O-phosphonatoethanaminium(1-). O-Phosphoethanolamine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). 2-Aminoethyl dihydrogen phosphate has been reported in Drosophila melanogaster, Psychotria punctata, and other organisms with data available. Phosphorylethanolamine is a monophosphate ethanolamine ester that is an intermediate in the biosynthesis of sphingomyelins.

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	7.0892 mL	35.4459 mL	70.8918 mL
	5 mM	1.4178 mL	7.0892 mL	14.1784 mL
	10 mM	0.7089 mL	3.5446 mL	7.0892 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.