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P0503

Sigma-Aldrich

O-Phosphorylethanolamine

Synonym(s):

2-Aminoethyl dihydrogen phosphate, O-Phosphocolamine, O-Phosphoethanolamine, Colaminephosphoric acid

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About This Item

Linear Formula:
NH2CH2CH2OPO3H2
CAS Number:
1071-23-4
Molecular Weight:
141.06
Beilstein:
1758916
EC Number:
213-988-5
MDL number:
MFCD00008178
UNSPSC Code:
12161700
PubChem Substance ID:
24898109
NACRES:
NA.25
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form

powder

storage temp.

−20°C

SMILES string

NCCOP(O)(O)=O

InChI

1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)

InChI key

SUHOOTKUPISOBE-UHFFFAOYSA-N

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Application

O-Phosphorylethanolamine has been used:
  • in LHC-8 medium as a supplement in culturing the transformed human liver epithelial (THLE)-2 and THLE-3 cells[1]
  • in C-reactive protein (CRP) binding sucrose flotation experiment[2]
  • to incubate phosphomonoesters with anion-exchange chromatography (AEC) fractions for the detection of phosphatase activity[3]
  • to add in the washed beads for the preparation of phosphorylethanolamine (Pet) -conjugated sepharose column for chromatographic purification of mutant CRP[4]

Biochem/physiol Actions

Phosphorylethanolamine participates in phospholipid metabolism. Its release can be stimulated occasionally by depolarizing stimuli. Reduction of phosphorylethanolamine levels has been observed in Alzheimer′s and Huntington′s disease.[5]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0267
BCCM0292
BCCF3299
BCCK6213
BCCK2170

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Phosphoethanolamine-complexed C-reactive protein: a pharmacological-like macromolecule that binds to native low-density lipoprotein in human serum
Singh SK, et al.
Clinica Chimica Acta; International Journal of Clinical Chemistry, 394(1-2), 94-98 (2008)
The phosphocholine-binding pocket on C-reactive protein is necessary for initial protection of mice against pneumococcal infection
Gang TB, et al.
Test, jbc-M112 (2012)
Phosphoethanolamine and ethanolamine are decreased in Alzheimer's disease and Huntington's disease
Ellison David W, et al.
Brain Research, 417(2), 389-392 (1987)
Lin Zhu et al.
ACS nano, 6(4), 3491-3498 (2012-03-14)
A novel "smart" multifunctional drug delivery system was successfully developed to respond to the up-regulated matrix metalloprotease 2 (MMP2) in the tumor microenvironment and improve cancer cell-specific delivery of loaded drugs. The system represents a surface-functionalized liposomal nanocarrier, for which
Margaret N Holme et al.
Nature nanotechnology, 7(8), 536-543 (2012-06-12)
Atherosclerosis results in the narrowing of arterial blood vessels and this causes significant changes in the endogenous shear stress between healthy and constricted arteries. Nanocontainers that can release drugs locally with such rheological changes can be very useful. Here, we
View All Related Papers

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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