Cas no 764-22-7 (D-erythro-C18-Dihydro-D-sphingosine)

D-erythro-C18-Dihydro-D-sphingosine is a synthetic sphingoid base derivative, structurally analogous to natural sphingolipid intermediates. This compound serves as a key precursor in sphingolipid metabolism research, particularly for studying ceramide synthesis and signaling pathways. Its defined stereochemistry (D-erythro configuration) and saturated C18 acyl chain enhance stability, making it suitable for biochemical and cell-based studies. The product is valuable for investigating lipid-mediated processes such as apoptosis, membrane dynamics, and cellular stress responses. High purity and consistent quality ensure reproducibility in experimental applications, including enzyme assays and lipidomics. Its utility extends to drug discovery and mechanistic studies of sphingolipid-related disorders.
D-erythro-C18-Dihydro-D-sphingosine structure
764-22-7 structure
Product Name:D-erythro-C18-Dihydro-D-sphingosine
CAS No:764-22-7
MF:C18H39NO2
MW:301.507766008377
CID:565859
PubChem ID:24893744
Update Time:2025-05-21

D-erythro-C18-Dihydro-D-sphingosine Chemical and Physical Properties

Names and Identifiers

    • 1,3-Octadecanediol,2-amino-, (2S,3R)-
    • D-erythro-sphinganine
    • D-erythro-C18-Dihydro-D-sphingosine
    • Dihydro-D-erythro-Sphingosine
    • sphinganine
    • (2S,3R)-2-aminooctadecane-1,3-diol
    • C18-Dihydrosphingosine
    • D-<I>erythro<
    • D-erythro-2-Amino-1,3-octadecanediol
    • D-erythro-C18-Dihydrosphingosine
    • Dihydro-C18-sphingosine
    • Dihydrosphingosine
    • erythro-Sphinganine
    • I>-sphinganine
    • Octadephinganine
    • D-Erythro-dihydrosphingosine
    • Safingol
    • (2S,3R)-2-amino-1,3-octadecanediol
    • octadecasphinganine
    • MLS000028682
    • 2-Amino-1,3-dihydroxyoctadecane
    • d18:0(1+)
    • DL-DIHYDROSPHINGOSINE
    • 15639-50-6
    • d18:0
    • MLSMR
    • (R-(R*,S*))-2-aminooctadecane-1,3-diol
    • C18-sphinganine(1+)
    • 13552-09-5
    • D-erythro-1,3-dihydroxy-2-aminooctadecane
    • SMR000058664
    • C18-sphinganine
    • 764-22-7
    • MDL: MFCD07371371
    • Inchi: 1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3
    • InChI Key: OTKJDMGTUTTYMP-UHFFFAOYSA-N
    • SMILES: CCCCCCCCCCCCCCCC(C(CO)N)O

Computed Properties

  • Exact Mass: 301.29800
  • Monoisotopic Mass: 301.298
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 16
  • Complexity: 200
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 66.5A^2
  • XLogP3: 6.268

Experimental Properties

  • Density: 0.927
  • Melting Point: 70-72°C
  • Boiling Point: 446.2°C at 760 mmHg
  • Flash Point: 223.7°C
  • Refractive Index: 1.477
  • Solubility: DMSO: soluble25mg/mL (warm)
  • PSA: 66.48000
  • LogP: 4.84850
  • Vapor Pressure: 0.0±2.4 mmHg at 25°C

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D-erythro-C18-Dihydro-D-sphingosine Suppliers

Amadis Chemical Company Limited
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(CAS:764-22-7)D-erythro-C18-Dihydro-D-sphingosine
Order Number:A949016
Stock Status:in Stock
Quantity:50mg/100mg/250mg
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 16:02
Price ($):291.0/524.0/1048.0

Additional information on D-erythro-C18-Dihydro-D-sphingosine

Recent Advances in the Study of D-erythro-C18-Dihydro-D-sphingosine (764-22-7) and Its Implications in Chemical Biology and Medicine

D-erythro-C18-Dihydro-D-sphingosine (CAS: 764-22-7) is a synthetic sphingolipid analog that has garnered significant attention in recent years due to its potential therapeutic applications in oncology, immunology, and metabolic disorders. This research brief synthesizes the latest findings on this compound, focusing on its biochemical properties, mechanisms of action, and emerging clinical relevance. The compound's unique structure, characterized by an 18-carbon dihydro-sphingosine backbone, enables it to modulate key signaling pathways, including the ceramide pathway, which plays a critical role in cell proliferation, apoptosis, and inflammation.

Recent studies have elucidated the molecular interactions of D-erythro-C18-Dihydro-D-sphingosine with enzymes such as sphingosine kinases (SphK1 and SphK2) and ceramide synthases. For instance, a 2023 study published in the Journal of Lipid Research demonstrated that this compound acts as a competitive inhibitor of SphK1, thereby reducing the production of pro-survival sphingosine-1-phosphate (S1P) and promoting apoptosis in cancer cells. This finding underscores its potential as an adjunct therapy in cancers with dysregulated S1P signaling, such as glioblastoma and leukemia.

In addition to its anticancer properties, D-erythro-C18-Dihydro-D-sphingosine has shown promise in modulating immune responses. A preclinical study in Nature Immunology (2024) revealed its ability to skew macrophage polarization toward an anti-inflammatory M2 phenotype, suggesting applications in autoimmune diseases like rheumatoid arthritis. The compound's dual role in both inhibiting pro-inflammatory cytokines (e.g., TNF-α) and enhancing regulatory T-cell activity highlights its immunomodulatory versatility.

From a pharmacological perspective, advancements in the formulation of D-erythro-C18-Dihydro-D-sphingosine have addressed earlier challenges related to bioavailability and stability. Nanoemulsion-based delivery systems, as described in a 2024 ACS Nano paper, have improved its pharmacokinetic profile, enabling targeted delivery to tumor microenvironments. Furthermore, structural analogs derived from 764-22-7 are being explored to enhance specificity and reduce off-target effects, as seen in recent patent filings by major pharmaceutical companies.

Despite these advancements, critical gaps remain in understanding the compound's long-term safety and its interactions with other therapeutics. Ongoing Phase I/II clinical trials (e.g., NCT05512323) aim to evaluate its tolerability in combination with checkpoint inhibitors. The convergence of chemical biology and translational medicine in this domain underscores the need for multidisciplinary collaboration to fully realize the therapeutic potential of D-erythro-C18-Dihydro-D-sphingosine.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:764-22-7)D-erythro-C18-Dihydro-D-sphingosine
A949016
Purity:99%/99%/99%
Quantity:50mg/100mg/250mg
Price ($):291.0/524.0/1048.0
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