Phytosphingosine

Phytosphingosine
Names
	Preferred IUPAC name (2S,3S,4R)-2-Aminooctadecane-1,3,4-triol
	Other names Hydroxysphinganine; D-ribo-Phytosphingosine; (4R)-Hydroxysphinganine;
Identifiers
CAS Number	554-62-1;
3D model (JSmol)	Interactive image;
Beilstein Reference	1725301
ChEBI	CHEBI:46961;
ChEMBL	ChEMBL236036;
ChemSpider	108921;
ECHA InfoCard	100.103.588
EC Number	439-210-6;
KEGG	C12144;
PubChem CID	122121;
UNII	GIN46U9Q2Q;
CompTox Dashboard (EPA)	DTXSID80203951 ;
	InChI InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1 Key: AERBNCYCJBRYDG-KSZLIROESA-N;
	SMILES CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O;
Properties
Chemical formula	C18H39NO3
Molar mass	317.514 g·mol−1
Melting point	102–103 °C (216–217 °F; 375–376 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318, H410
Precautionary statements	P273, P280, P305+P351+P338, 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

^ Park, Moon-Taek; Kang, Jung A.; Choi, Jung-A.; Kang, Chang-Mo; Kim, Tae-Hwan; Bae, Sangwoo; Kang, Seongman; Kim, Sujong; Choi, Weon-Ik (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.
^ Montenegro-Burke, J. Rafael; Kok, Bernard P.; Guijas, Carlos; Domingo-Almenara, Xavier; Moon, Clara; Galmozzi, Andrea; Kitamura, Seiya; Eckmann, Lars; Saez, Enrique; Siuzdak, Gary E.; Wolan, Dennis W. (2021-09-28). "Metabolomics activity screening of T cell–induced colitis reveals anti-inflammatory metabolites". Science Signaling. 14 (702): eabf6584. doi:10.1126/scisignal.abf6584. ISSN 1945-0877. PMC 8757460. PMID 34582249.

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[1] Park, Moon-Taek; Kang, Jung A.; Choi, Jung-A.; Kang, Chang-Mo; Kim, Tae-Hwan; Bae, Sangwoo; Kang, Seongman; Kim, Sujong; Choi, Weon-Ik (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; Saez, Enrique; Siuzdak, Gary E.; Wolan, Dennis W. (2021-09-28). "Metabolomics activity screening of T cell–induced colitis reveals anti-inflammatory metabolites". Science Signaling. 14 (702): eabf6584. doi:10.1126/scisignal.abf6584. ISSN 1945-0877. PMC 8757460. PMID 34582249.

[1]

[2]

Names

Preferred IUPAC name (2S,3S,4R)-2-Aminooctadecane-1,3,4-triol
Other names Hydroxysphinganine D-ribo-Phytosphingosine (4R)-Hydroxysphinganine
Identifiers
CAS Number	554-62-1
3D model (JSmol)	Interactive image
Beilstein Reference	1725301
ChEBI	CHEBI:46961
ChEMBL	ChEMBL236036
ChemSpider	108921
ECHA InfoCard	100.103.588
EC Number	439-210-6
KEGG	C12144
PubChem CID	122121
UNII	GIN46U9Q2Q
CompTox Dashboard (EPA)	DTXSID80203951
InChI InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1 Key: AERBNCYCJBRYDG-KSZLIROESA-N
SMILES CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O
Properties
Chemical formula	C₁₈H₃₉NO₃
Molar mass	317.514 g·mol⁻¹
Melting point	102–103 °C (216–217 °F; 375–376 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318, H410
Precautionary statements	P273, P280, P305+P351+P338, 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