Suzuki, Masahiro, Haruka Uematsu, and Kenji Hanabusa. Tetrahedron Letters 57.25 (2016): 2807-2810.
Phytosphingosine, a bioactive sphingolipid, has been successfully utilized as a molecular scaffold for the synthesis of novel organogelators. These gelators demonstrate superior gelation properties in a range of solvents, including alkanes, aromatic solvents, mineral oils, vegetable oils, and silicone oils. Notably, the urea-based derivatives exhibit remarkable thermal stability and rigidity, making them promising candidates for advanced material applications.
The synthesis of urea-type phytosphingosine-based gelators involves the reaction of phytosphingosine with an isocyanate in dry tetrahydrofuran (THF), leading to the formation of highly stable urea linkages. Subsequent purification via recrystallization yields the final products. Similarly, amide-type derivatives are synthesized using a selective amidation strategy employing 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as a coupling agent. This approach ensures the selective formation of carboxamide linkages, preventing side reactions involving the multiple hydroxyl groups of phytosphingosine.
The resulting organogels exhibit outstanding mechanical strength and high thermal resistance, highlighting their potential in various industrial applications, including cosmetics, pharmaceuticals, and advanced materials. The strategic use of phytosphingosine as a gelator backbone underscores its versatility in molecular self-assembly and functional material development. These findings pave the way for further exploration of phytosphingosine-based materials in next-generation gelation technologies.
Sun, Chunxiao, et al. Ecotoxicology and Environmental Safety 256 (2023): 114840.
Phytosphingosine (PHS) has demonstrated significant cytotoxic effects in various human cell lines, with nasopharyngeal carcinoma CNE2 cells exhibiting the highest sensitivity. The half-maximal inhibitory concentration (IC50) of PHS in CNE2 cells was determined to be 14.77 µM, indicating its potent anti-proliferative activity.
Exposure of CNE2 cells to PHS (0-25 µM) for 24 hours resulted in abnormal nuclear morphology, micronuclei formation, and DNA damage, suggesting that PHS induces genotoxic stress. Furthermore, PHS treatment led to a dose-dependent inhibition of cell proliferation. At concentrations ranging from 2 to 8 µM, the number of viable cells significantly decreased, with the highest dose reducing cell growth to nearly 10% of the control group. This inhibition was further amplified over time, with prolonged exposure (12-72 hours) exacerbating the anti-proliferative effects.
Mechanistically, PHS arrested the cell cycle at the S phase, preventing DNA replication and halting cell division. This regulatory effect on cell cycle progression highlights the potential of PHS as a therapeutic candidate for nasopharyngeal carcinoma. The observed cytotoxicity and proliferation inhibition underscore its promise for further investigation in cancer treatment strategies, particularly in targeting highly sensitive tumor cell lines such as CNE2.
Sankar, Arumugam, I-Cheng Chen, and Shun-Yuan Luo. Carbohydrate Research 463 (2018): 1-5.
Phytosphingosine has emerged as an efficient and economical starting material for the synthesis of sphingosine, a crucial bioactive lipid with significant roles in cellular signaling and membrane integrity. Two synthetic pathways have been developed to achieve this transformation, differing in their approach to amino group protection and subsequent functionalization steps.
In the first strategy, phthalic anhydride was used to protect the amino group of phytosphingosine, followed by regioselective benzylidene ring formation between the C1 and C3 hydroxyl groups, ensuring stability and selectivity. Subsequent functionalization, including leaving group insertion and elimination, led to the formation of sphingosine after a final one-pot deprotection step.
An alternative route involved the conversion of phytosphingosine into an azido intermediate via reaction with trifluoromethanesulfonyl azide in the presence of copper sulfate and potassium carbonate. This intermediate underwent benzylidene protection and further transformations, including tosylation, elimination, and Staudinger reduction, ultimately yielding sphingosine.
These synthetic strategies demonstrate the versatility of phytosphingosine as a precursor in sphingosine synthesis, providing streamlined routes with high regioselectivity and controlled functionalization. The findings offer valuable insights for the efficient production of sphingosine and its derivatives, which are widely utilized in pharmaceutical and biomedical research.
What is the CAS number for Phytosphingosine?
The CAS number for Phytosphingosine is 554-62-1.
What is the molecular formula of Phytosphingosine?
The molecular formula of Phytosphingosine is C18H39NO3.
What is the IUPAC name of Phytosphingosine?
The IUPAC name of Phytosphingosine is (2S,3S,4R)-2-aminooctadecane-1,3,4-triol.
What is the boiling point and melting point of Phytosphingosine?
The boiling point is predicted to be 483.7±40.0 °C and the melting point is 102°C.
What is the purity of Phytosphingosine?
The purity of Phytosphingosine is 98%.
What is the appearance of Phytosphingosine?
Phytosphingosine appears as a white solid.
What is the typical application of Phytosphingosine?
The typical applications of Phytosphingosine include use as an emulsifying agent, dispersing agent, lubricant, and intermediate in organic synthesis.
What is the storage recommendation for Phytosphingosine?
The storage recommendation for Phytosphingosine is in the freezer.
What is the physical state of Phytosphingosine?
Phytosphingosine is in a solid physical state.
What percentage of actives does Phytosphingosine contain?
Phytosphingosine contains 95% of actives.
CONNECT WITH US
Interested in our Services & Products ?
Need detailed information?
Terms & Conditions
Privacy Policy | Cookie Policy | Copyright © 2025 Alfa Chemistry. All rights reserved.
