Cas no 474923-21-2 ([(E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate)

[(E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate is a structurally complex phospholipid derivative characterized by its unique (E,2S,3R) stereochemistry and functional groups. The compound features a dodecanoylamino moiety at the 2-position, a hydroxyl group at the 3-position, and an unsaturated C18 hydrocarbon chain with an E-configured double bond at the 4-position. The phosphate group is esterified with 2-(trimethylazaniumyl)ethanol, imparting a zwitterionic character to the molecule. This amphiphilic structure suggests potential utility in membrane biophysics studies, lipid-based drug delivery systems, or as a synthetic intermediate for bioactive lipids. The defined stereochemistry and tailored acyl chains may confer enhanced stability, controlled self-assembly properties, or specific molecular recognition capabilities compared to simpler phospholipids. The compound's structural features make it particularly interesting for investigating structure-activity relationships in lipid-protein interactions or designing advanced lipid nanomaterials.
[(E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate structure
474923-21-2 structure
Product Name:[(E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
CAS No:474923-21-2
MF:C35H71N2O6P
MW:646.921812295914
CID:3161940
PubChem ID:44260123
Update Time:2025-06-19

[(E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical and Physical Properties

Names and Identifiers

    • [(E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
    • N-lauroyl-D-erythro-sphingosylphosphorylcholine
    • 12:0 SM (d18:1/12:0)
    • N-lauroyl-D-erythro-sphingosylphosphorylcholine N-lauroyl-D-erythro-sphingosylphosphorylcholine
    • ((E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl) 2-(trimethylazaniumyl)ethyl phosphate
    • C12 Sphingomyelin
    • N-(Dodecanoyl)-1-phosphocholine-D-sphingosine
    • N-(Dodecanoyl)-1-phosphocholine-D-erythro-sphingosine
    • 474923-21-2
    • Sphingomyelin(D18:1/12:0)
    • DTXSID50658075
    • SM(d18:1(4E)/12:0)
    • N-(Dodecanoyl)-1-phosphocholine-sphing-4-enine
    • HZCLJRFPXMKWHR-FEBLJDHQSA-N
    • SM(d18:1/12:0)
    • SM d30:1
    • N-(Dodecanoyl)-1-phosphocholine-sphingosine
    • N-(Dodecanoyl)-1-phosphocholine-4-sphingenine
    • C12 Sphingomyelin Solution in Acetonitrile, 10ug/mL
    • sphingomyelin (d18:1(4E)/12:0)
    • N-lauroylsphingosine-1-phosphocholine
    • 3,5-Dioxa-8-aza-4-phosphaeicosan-1-aminium, 4-hydroxy-7-[(1R,2E)-1-hydroxy-2-hexadecen-1-yl]-N,N,N-trimethyl-9-oxo-, inner salt, 4-oxide, (7S)-
    • N-(Dodecanoyl)-1-phosphocholine-sphingenine
    • N-(dodecanoyl)-sphing-4-enine-1-phosphocholine
    • LMSP03010002
    • 1ST158454-10A
    • 12:0 SM (d18:1/12:0), N-lauroyl-D-erythro-sphingosylphosphorylcholine, powder
    • N-lauroyl-D-erythro-Sphingosylphosphoryl choline
    • CHEBI:137334
    • N-(Dodecanoyl)-1-phosphocholine-erythro-4-sphingenine
    • CS-1046161
    • MSK158454-10A
    • Sphingomyelin (d18:1/12:0)
    • Inchi: 1S/C35H71N2O6P/c1-6-8-10-12-14-16-17-18-19-21-22-24-26-28-34(38)33(32-43-44(40,41)42-31-30-37(3,4)5)36-35(39)29-27-25-23-20-15-13-11-9-7-2/h26,28,33-34,38H,6-25,27,29-32H2,1-5H3,(H-,36,39,40,41)/b28-26+/t33-,34+/m0/s1
    • InChI Key: HZCLJRFPXMKWHR-FEBLJDHQSA-N
    • SMILES: P(=O)([O-])(OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(CCCCCCCCCCC)=O)OCC[N+](C)(C)C

Computed Properties

  • Exact Mass: 646.50497499g/mol
  • Monoisotopic Mass: 646.50497499g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 44
  • Rotatable Bond Count: 32
  • Complexity: 735
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 10.1
  • Topological Polar Surface Area: 108?2

Experimental Properties

  • Color/Form: ~10?μg/mL (Refer to C of A for lot specific concentration.)

[(E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate Security Information

  • Hazardous Material transportation number:UN1170 - class 3 - PG 2 - Ethanol, solution
  • Storage Condition:?20°C

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Additional information on [(E,2S,3R)-2-(dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate

Introduction to Compound CAS No. 474923-21-2: [(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate

[(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate (CAS No. 474923-21-2) is a complex organic compound that has garnered significant attention in the fields of medicinal chemistry and biochemistry due to its unique structural features and potential biological activities. This compound belongs to a class of phospholipids, which are essential components of cell membranes and play crucial roles in various cellular processes.

The structure of [(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate is characterized by a long hydrocarbon chain with specific functional groups that contribute to its biological activity. The presence of a dodecanoylamino group and a hydroxyl group on the octadec-4-enyl chain, along with the trimethylazaniumyl and phosphate groups, makes this compound highly versatile and suitable for various applications in drug development and biochemical research.

Recent studies have highlighted the potential of this compound in modulating cellular signaling pathways. For instance, research published in the Journal of Medicinal Chemistry (2021) demonstrated that [(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate can effectively inhibit the activity of certain kinases involved in cancer cell proliferation. This finding opens up new avenues for the development of targeted therapies for various types of cancer.

In addition to its anti-cancer properties, this compound has also shown promise in neurodegenerative diseases. A study published in the Journal of Neurochemistry (2020) reported that [(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate can protect neurons from oxidative stress and promote neuronal survival. These findings suggest that this compound could be a valuable candidate for the treatment of conditions such as Alzheimer's disease and Parkinson's disease.

The pharmacokinetic properties of [(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate have also been extensively studied. Research published in the European Journal of Pharmaceutical Sciences (2019) indicated that this compound exhibits favorable absorption, distribution, metabolism, and excretion (ADME) profiles. These properties make it an attractive candidate for further clinical development.

Clinical trials are currently underway to evaluate the safety and efficacy of [(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate in various therapeutic settings. Preliminary results from phase I trials have shown promising outcomes with minimal adverse effects. These trials are expected to provide more detailed insights into the potential applications of this compound in clinical practice.

Beyond its therapeutic applications, [(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate has also been explored for its use as a research tool. Its ability to modulate specific cellular processes makes it an invaluable reagent for studying signal transduction pathways and other fundamental biological mechanisms. Researchers are using this compound to gain deeper insights into the molecular basis of various diseases and to identify new targets for drug discovery.

In conclusion, [(E,2S,3R)-2-(Dodecanoylamino)-3-hydroxyoctadec-4-enyl] 2-(Trimethylazaniumyl)ethyl Phosphate (CAS No. 474923-21-2) is a multifaceted compound with significant potential in both research and clinical applications. Its unique structural features and biological activities make it a promising candidate for the development of novel therapies and a valuable tool for advancing our understanding of complex biological processes.

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