Chemistry:Phytosphingosine

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Phytosphingosine
Chemical structure of phytosphingosine
Names
Preferred IUPAC name
(2S,3S,4R)-2-Aminooctadecane-1,3,4-triol
Other names
  • Hydroxysphinganine
  • D-ribo-Phytosphingosine
  • (4R)-Hydroxysphinganine
Identifiers
3D model (JSmol)
1725301
ChEBI
ChEMBL
ChemSpider
EC Number
  • 439-210-6
KEGG
UNII
Properties
C18H39NO3
Molar mass 317.514 g·mol−1
Melting point 102–103 °C (216–217 °F; 375–376 K)
Hazards
GHS pictograms GHS05: CorrosiveGHS09: Environmental hazard
GHS Signal word Danger
H318, H410
P273, P280, P305+351+338, P310, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phytosphingosine is a sphingoid base, a fundamental building block of more complex sphingolipids. It is abundant in plants and fungi and present in animals.[1] Phytosphingosine has also been found to have interesting T-cell related anti-inflammatory properties in models of inflammatory bowel disease.[2]

References

  1. Park, Moon-Taek; Kang, Jung A.; Choi, Jung-A.; Kang, Chang-Mo; Kim, Tae-Hwan; Bae, Sangwoo; Kang, Seongman; Kim, Sujong et al. (February 2003). "Phytosphingosine induces apoptotic cell death via caspase 8 activation and Bax translocation in human cancer cells". Clinical Cancer Research 9 (2): 878–885. ISSN 1078-0432. PMID 12576463. 
  2. Montenegro-Burke, J. Rafael; Kok, Bernard P.; Guijas, Carlos; Domingo-Almenara, Xavier; Moon, Clara; Galmozzi, Andrea; Kitamura, Seiya; Eckmann, Lars et al. (2021-09-28). "Metabolomics activity screening of T cell–induced colitis reveals anti-inflammatory metabolites" (in en). Science Signaling 14 (702): eabf6584. doi:10.1126/scisignal.abf6584. ISSN 1945-0877. PMID 34582249. PMC 8757460. https://www.science.org/doi/10.1126/scisignal.abf6584.