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L-THREO-DIHYDROSPHINGOSINE

CAS No.
15639-50-6
Chemical Name:
L-THREO-DIHYDROSPHINGOSINE
Synonyms
SAFINGOL;L-threo-dihydrospingosine;L-THREO-DIHYDROSPHINGOSINE;L-THREO-SPHINGANINE, C18 CHAIN;L-threo-dihydrosphingosine (d18:0);L-threo-Dihydrosphingosine (Safingol);Safingol - CAS 15639-50-6 - Calbiochem;1,3-Octadecanediol, 2-amino-, (2S,3S)-;L-THREO-DIHYDROSPHINGOSINE (D18:0);SAFINGOL
CBNumber:
CB1192274
Molecular Formula:
C18H39NO2
Molecular Weight:
301.51
MDL Number:
MFCD00792847
MOL File:
15639-50-6.mol
MSDS File:
SDS
Last updated:2023-05-18 11:31:17

L-THREO-DIHYDROSPHINGOSINE Properties

Melting point 126-128 °C
Boiling point 446.2±25.0 °C(Predicted)
Density 0.927±0.06 g/cm3(Predicted)
Flash point 110 °C
storage temp. -20°C
solubility ≤0.25mg/ml in ethanol
pka 12.57±0.45(Predicted)
form White solid
FDA UNII OWA98U788S
NCI Dictionary of Cancer Terms L-threo-dihydrosphingosine; safingol
NCI Drug Dictionary safingol

SAFETY

Risk and Safety Statements

WGK Germany  3

L-THREO-DIHYDROSPHINGOSINE price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D4681 L-threo-Dihydrosphingosine ≥95% (TLC) 15639-50-6 1mg $239 2024-03-01 Buy
Sigma-Aldrich 559300 Safingol A cell-permeable and reversible 15639-50-6 1mg $209 2023-01-07 Buy
Cayman Chemical 18624 Safingol ≥98% 15639-50-6 1mg $79 2024-03-01 Buy
Cayman Chemical 18624 Safingol ≥98% 15639-50-6 5mg $292 2024-03-01 Buy
Cayman Chemical 18624 Safingol ≥98% 15639-50-6 25mg $881 2024-03-01 Buy
Product number Packaging Price Buy
D4681 1mg $239 Buy
559300 1mg $209 Buy
18624 1mg $79 Buy
18624 5mg $292 Buy
18624 25mg $881 Buy

L-THREO-DIHYDROSPHINGOSINE Chemical Properties,Uses,Production

Uses

L-threo-Dihydrosphingosine is a lyso-sphingolipid protein kinase C inhibitor. It suppresses the growth of human oral squamous cell carcinoma (SCC) cells.

Uses

Safingol has been used as a substituent of dihydrosphingosine (dhSph) to increase the cytotoxic response in N-(4-hydroxyphenyl)retinamide (4-HPR)-resistant cells.

Uses

Safingol is the L-threo diastereomer of D-erythro-sphinganine Both forms of sphinganine inhibit PKC by binding at the regulatory phorbol-binding domain (IC50s = 7 and 24 μM for erythro-sphinganine and safingol, respectively). Safingol also inhibits sphingosine kinases (Ki = 3-5 μM). Safingol, alone or in combination with chemotherapeutic agents, is cytotoxic against cancer cell lines.

Definition

ChEBI: Safingol ( L-threo-sphinganine) is an amino alcohol.

General Description

A cell-permeable and reversible lyso-sphingolipid protein kinase C (PKC) inhibitor that competitively interacts at the regulatory phorbol binding domain of PKC. Inhibits enzymatic activity and 3H-phorbol dibutyrate binding of purified rat brain PKC (IC50 = 37.5 μM and 31 μM, respectively). Inhibits human PKCα, the major overexpressed isoenzyme in MCF-7 DOXR cells (IC50 = 40 μM). Enhances the cytotoxic effect of the chemotherapeutic agent Mitomycin C (MMC; Cat. Nos. 47589 and 475820) in gastric cancer cells by promoting drug-induced apoptosis.

Biological Activity

ki: sphk with a ki of about 5 μmol/lsafingol is a sphingosine and pkc kinases inhibitor.sphingosine 1-phosphate, a product of sphingosine kinases (sphk), mediates various biological processes including cell proliferation, differentiation, motility, and apoptosis. protein kinase c (pkc), is a family of protein kinase enzymes involved in controlling the function of other proteins through the phosphorylation of hydroxyl groups of serine and threonine amino acid residues.

Biochem/physiol Actions

Sphingosine kinase inhibitor; protein kinase C alpha (PKCα) -specific inhibitor; Sphingosine analog; potentiates the effect of doxorubicin (DOX) in tumor-bearing animals.

in vitro

safingol was identified as a potent competitive inhibitor of sphk and had significant in-vitro anticancer activity. safingol could increase the in-vitro antitumor effect of various chemotherapeutic agents including cisplatin, doxorubicin, and mitomycin c via enhancing chemotherapy induced apoptosis. it was also found that safingol alone induced cell death by autophagy. safingol was also extensively studied as an inhibitor of pkc, although the ki was higher than that for sphk [1].

in vivo

previous studies found that although safingol showed limited single-agent activity in vivo, xenograft experiments had indicated that safingol could increase the antitumor activity of cisplatin without increasing toxicity [1].

References

[1] dickson ma, carvajal rd, merrill ah jr, gonen m, cane lm, schwartz gk. a phase i

L-THREO-DIHYDROSPHINGOSINE Preparation Products And Raw materials

Raw materials

Preparation Products

L-THREO-DIHYDROSPHINGOSINE Suppliers

Global( 68)Suppliers
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Career Henan Chemica Co
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Aladdin Scientific
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Alfa Chemistry 1-516-6625404 support@alfa-chemistry.com United States 9171 60
Codow Chemical Co.,Ltd. 18620099427 amy@howeipharm.com China 17698 55
SAFINGOL L-THREO-SPHINGANINE, C18 CHAIN L-THREO-DIHYDROSPHINGOSINE L-threo-dihydrospingosine L-THREO-DIHYDROSPHINGOSINE (D18:0);SAFINGOL L-threo-dihydrosphingosine (d18:0) 1,3-Octadecanediol, 2-amino-, (2S,3S)- Safingol - CAS 15639-50-6 - Calbiochem L-threo-Dihydrosphingosine (Safingol) 15639-50-6 Biochemicals and Reagents BioChemical Lipids Sphingolipids Sphinganines Sphingoid bases