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73914

Sigma-Aldrich

Sphingosine 1-phosphate

≥98.0% (TLC)

Synonym(s):

(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-phosphate, D-erythro-Sphingosine 1-phosphate

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About This Item

Empirical Formula (Hill Notation):
C18H38NO5P
CAS Number:
Molecular Weight:
379.47
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.85

Assay

≥98.0% (TLC)

form

powder

composition

carbon content, 56.97%
hydrogen content, 10.09%
nitrogen content, 3.69%

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O

InChI

1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1

InChI key

DUYSYHSSBDVJSM-KRWOKUGFSA-N

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Application

Repurposing Siponimod for osteoporosis: A study highlighted the potential of Siponimod, an S1P receptor modulator originally developed for multiple sclerosis, to treat osteoporosis by influencing Sphingosine 1-phosphate pathways (Hu et al., 2024).

Sphingosine-1-phosphate in ocular health: Research demonstrated that a selective agonist for Sphingosine-1-phosphate receptor 1/5 could mitigate ocular vascular pathologies, suggesting therapeutic potentials in eye disease management, it is also responsible for regulating various intracellular processes, including cell survival, differentiation, and proliferation (Nakamura et al., 2024).

Targeting diabetic kidney disease: The study investigated how Plantaginis Semen, through the sphingosine kinase 1/Sphingosine-1-phosphate pathway, could ameliorate diabetic kidney disease, underscoring the pathways role in metabolic health (Lan et al., 2024).

Advancements in neurodegenerative disease treatments: A review focused on the development of small-molecule modulators targeting Sphingosine-1-phosphate receptors, presenting new directions in treating neurodegenerative diseases (Sankar Kar et al., 2024).

Biochem/physiol Actions

A lipid second messenger that binds to S1P1 and S1P3 receptors. Mobilizes intracellular Ca2+ stores and decreases cellular cAMP. Activates phospholipase D. S1P stimulates the migration of endothelial cells but inhibits the migration of other cell types. Induces angiogenesis.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Craig T Wallington-Beddoe et al.
British journal of haematology, 161(5), 623-638 (2013-03-26)
The sphingosine kinases (SphKs) have relatively recently been implicated in contributing to malignant cellular processes with particular interest in the oncogenic properties of SPHK1. Whilst SPHK1 has received considerable attention as a putative oncoprotein, SPHK2 has been much more difficult
Tal I Arnon et al.
Current topics in microbiology and immunology, 378, 107-128 (2014-04-15)
The spleen, the largest secondary lymphoid organ, has long been known to play important roles in immunity against blood-borne invaders. Yet how cells migrate within the spleen to ensure fast and effective responses is only now coming to light. Chemokines
Gregory T Kunkel et al.
Nature reviews. Drug discovery, 12(9), 688-702 (2013-08-21)
The bioactive lipid sphingosine-1-phosphate (S1P) is involved in multiple cellular signalling systems and has a pivotal role in the control of immune cell trafficking. As such, S1P has been implicated in disorders such as cancer and inflammatory diseases. This Review
Roland Martin et al.
Current topics in microbiology and immunology, 378, 149-170 (2014-04-15)
The development of fingolimod, an unselective functional antagonist of the interactions between sphingosine 1 phosphate (S1P) and sphingosine 1 phosphate receptors (S1PRs), as the first oral therapy for multiple sclerosis (MS) has been a milestone. The parallel intensive research on
Tsuyoshi Nishi et al.
Biochimica et biophysica acta, 1841(5), 759-765 (2013-08-08)
Sphingosine 1-phosphate (S1P) is a lipid mediator that plays important roles in diverse cellular functions such as cell proliferation, differentiation and migration. S1P is synthesized inside the cells and subsequently released to the extracellular space, where it binds to specific

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