WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H329598
CAS#: 1071-23-4 (free base)
Description: Phosphoethanolamine is an ethanolamine derivative that is used to construct two different categories of phospholipids. One category termed a glycerophospholipid and the other a sphingomyelin, or more specifically within the sphingomyelin class, a sphingophospholipid. Phosphorylethanolamine is a polyprotic acid with two pKa values at 5.61 and 10.39. On April 14, 2016, a law was passed in Brazil allowing the use of synthetic phosphoethanolamine for cancer treatment, despite opposition from the Brazilian Medical Association, the Brazilian Society of Clinical Oncology, and the regulatory agency ANVISA. However, shortly after, the country's Supreme Court suspended the law.
Hodoodo Cat#: H329598
Name: Phosphoethanolamine
CAS#: 1071-23-4 (free base)
Chemical Formula: C2H8NO4P
Exact Mass: 141.02
Molecular Weight: 141.063
Elemental Analysis: C, 17.03; H, 5.72; N, 9.93; O, 45.37; P, 21.96
Related CAS #: 1071-23-4 (free base),10389-08-9 (calcium).
Synonym: Phosphoethanolamine; Ethanolamine O-phosphate; Ethanolamine phosphate; NSC 254167; O-Phosphoethanolamine; O-Phosphorylethanolamine; PE 104.
IUPAC/Chemical Name: Phosphoethanolamine
InChi Key: SUHOOTKUPISOBE-UHFFFAOYSA-N
InChi Code: InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
SMILES Code: OP(O)(OCCN)=O
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: >2 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: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 141.06 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.
| 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Hullin-Matsuda F, Makino A, Murate M, Kobayashi T. Probing phosphoethanolamine-containing lipids in membranes with duramycin/cinnamycin and aegerolysin proteins. Biochimie. 2016 Nov;130:81-90. doi: 10.1016/j.biochi.2016.09.020. Review. PubMed PMID: 27693589.
2: Bobenchik AM, Augagneur Y, Hao B, Hoch JC, Ben Mamoun C. Phosphoethanolamine methyltransferases in phosphocholine biosynthesis: functions and potential for antiparasite therapy. FEMS Microbiol Rev. 2011 Jul;35(4):609-19. doi: 10.1111/j.1574-6976.2011.00267.x. Review. PubMed PMID: 21303393; PubMed Central PMCID: PMC4107886.
3: Guo L, Davies SS. Bioactive aldehyde-modified phosphatidylethanolamines. Biochimie. 2013 Jan;95(1):74-8. doi: 10.1016/j.biochi.2012.07.010. Review. PubMed PMID: 22819995.
4: Bakovic M, Fullerton MD, Michel V. Metabolic and molecular aspects of ethanolamine phospholipid biosynthesis: the role of CTP:phosphoethanolamine cytidylyltransferase (Pcyt2). Biochem Cell Biol. 2007 Jun;85(3):283-300. Review. PubMed PMID: 17612623.
5: Yamaji-Hasegawa A, Hullin-Matsuda F, Greimel P, Kobayashi T. Pore-forming toxins: Properties, diversity, and uses as tools to image sphingomyelin and ceramide phosphoethanolamine. Biochim Biophys Acta. 2016 Mar;1858(3):576-92. doi: 10.1016/j.bbamem.2015.10.012. Review. PubMed PMID: 26498396.
6: Che J, Okeke CI, Hu ZB, Xu J. DSPE-PEG: a distinctive component in drug delivery system. Curr Pharm Des. 2015;21(12):1598-605. Review. PubMed PMID: 25594410.
7: Salomon RG, Bi W. Isolevuglandin adducts in disease. Antioxid Redox Signal. 2015 Jun 20;22(18):1703-18. doi: 10.1089/ars.2014.6154. Review. PubMed PMID: 25557218; PubMed Central PMCID: PMC4484713.
8: Sullivan SM, Doukas J, Hartikka J, Smith L, Rolland A. Vaxfectin: a versatile adjuvant for plasmid DNA- and protein-based vaccines. Expert Opin Drug Deliv. 2010 Dec;7(12):1433-46. doi: 10.1517/17425247.2010.538047. Review. PubMed PMID: 21118032.
9: Aktas M, Narberhaus F. Unconventional membrane lipid biosynthesis in Xanthomonas campestris. Environ Microbiol. 2015 Sep;17(9):3116-24. doi: 10.1111/1462-2920.12956. Review. PubMed PMID: 26119594.
10: Phoenix DA, Harris F, Mura M, Dennison SR. The increasing role of phosphatidylethanolamine as a lipid receptor in the action of host defence peptides. Prog Lipid Res. 2015 Jul;59:26-37. doi: 10.1016/j.plipres.2015.02.003. Review. PubMed PMID: 25936689.
11: O'Donnell VB, Murphy RC. New families of bioactive oxidized phospholipids generated by immune cells: identification and signaling actions. Blood. 2012 Sep 6;120(10):1985-92. doi: 10.1182/blood-2012-04-402826. Review. PubMed PMID: 22802337; PubMed Central PMCID: PMC3437593.
12: Frampton JE. Mifamurtide: a review of its use in the treatment of osteosarcoma. Paediatr Drugs. 2010 Jun;12(3):141-53. doi: 10.2165/11204910-000000000-00000. Review. PubMed PMID: 20481644.
13: Tanida I, Ueno T, Kominami E. In vitro assays of lipidation of Mammalian Atg8 homologs. Curr Protoc Cell Biol. 2014 Sep 2;64:11.20.1-13. doi: 10.1002/0471143030.cb1120s64. Review. PubMed PMID: 25181299.
14: Rahman IA, Tsuboi K, Uyama T, Ueda N. New players in the fatty acyl ethanolamide metabolism. Pharmacol Res. 2014 Aug;86:1-10. doi: 10.1016/j.phrs.2014.04.001. Review. PubMed PMID: 24747663.
15: Bogdanov M, Dowhan W, Vitrac H. Lipids and topological rules governing membrane protein assembly. Biochim Biophys Acta. 2014 Aug;1843(8):1475-88. doi: 10.1016/j.bbamcr.2013.12.007. Review. PubMed PMID: 24341994; PubMed Central PMCID: PMC4057987.
16: Meyers PA, Chou AJ. Muramyl tripeptide-phosphatidyl ethanolamine encapsulated in liposomes (L-MTP-PE) in the treatment of osteosarcoma. Adv Exp Med Biol. 2014;804:307-21. doi: 10.1007/978-3-319-04843-7_17. Review. PubMed PMID: 24924182.
17: Tsuboi K, Uyama T, Ueda N. [Metabolism of N-acylphosphatidylethanolamine, a phospholipid molecule with three acyl chains, in animal tissues]. Seikagaku. 2011 Jun;83(6):485-94. Review. Japanese. PubMed PMID: 21800679.
18: Sugi T. Kininogen-dependent antiphosphatidylethanolamine antibodies and autoantibodies to factor XII in patients with recurrent pregnancy losses. J Obstet Gynaecol Res. 2013 Jul;39(7):1223-9. doi: 10.1111/jog.12110. Review. PubMed PMID: 23803004.
19: Ando K, Mori K, Corradini N, Redini F, Heymann D. Mifamurtide for the treatment of nonmetastatic osteosarcoma. Expert Opin Pharmacother. 2011 Feb;12(2):285-92. doi: 10.1517/14656566.2011.543129. Review. PubMed PMID: 21226638; PubMed Central PMCID: PMC3413631.
20: Shaikh SR, Wassall SR, Brown DA, Kosaraju R. N-3 Polyunsaturated Fatty Acids, Lipid Microclusters, and Vitamin E. Curr Top Membr. 2015;75:209-31. doi: 10.1016/bs.ctm.2015.03.003. Review. PubMed PMID: 26015284.
