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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H39NO3
Molecular Weight 317.5072
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHYTOSPHINGOSINE

SMILES

CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO

InChI

InChIKey=AERBNCYCJBRYDG-KSZLIROESA-N
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

HIDE SMILES / InChI

Description

Phytosphingosine is structural analog of sphingolipids and is classified as long-chain sphingoid base. Phytosphingosine significantly induced chromatin DNA fragmentation. Phytosphingosine caused strong induction of caspase-8 activity and caspase-independent Bax translocation to the mitochondria. It shows excellent clinical results in the context of skin care in acne, based on both anti-inflammatory and anti-microbial activity. Phytosphingosine is currently seen in a variety of products as a skin and hair conditioning agent. Phytosphingosine might serve as an effective melanogenesis inhibitor in melanocytes via the regulation of the MITF signaling pathways. Dietary supplementation of phytosphingosine decreases plasma cholesterol levels and enhances insulin sensitivity in men with the metabolic syndrome.

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
Primary
Inactive ingredient
CheryLee MD TrueLipids Relieve and Protect Ointment
PubMed

PubMed

TitleDatePubMed
Suppression of extracellular signal-related kinase and activation of p38 MAPK are two critical events leading to caspase-8- and mitochondria-mediated cell death in phytosphingosine-treated human cancer cells.
2003 Dec 12
Induction of apoptosis and expression of cell cycle regulatory proteins in response to a phytosphingosine derivative in HaCaT human keratinocyte cells.
2003 Dec 31
Tetraacetyl phytosphingosine-induced caspase activation and apoptosis occur through G2 arrest in human keratinocyte HaCaT cells.
2003 Nov
Differential regulation of cyclooxygenase-2 expression by phytosphingosine derivatives, NAPS and TAPS, and its role in the NAPS or TAPS-mediated apoptosis.
2003 Nov
Alteration of the 4-sphingenine scaffolds of ceramides in keratinocyte-specific Arnt-deficient mice affects skin barrier function.
2003 Nov
Cloning and functional characterization of the SUR2/SYR2 gene encoding sphinganine hydroxylase in Pichia ciferrii.
2004 Apr 15
Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine.
2004 Aug 20
Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine.
2004 Aug 27
Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon.
2004 Aug 6
Potentiation of UVB-induced apoptosis by novel phytosphingosine derivative, tetraacetyl phytosphingosine in HaCaT cell and mouse skin.
2004 Jul
Newly discovered neutral glycosphingolipids in aureobasidin A-resistant zygomycetes: Identification of a novel family of Gala-series glycolipids with core Gal alpha 1-6Gal beta 1-6Gal beta sequences.
2004 Jul 30
Structure and biological functions of fungal cerebrosides.
2004 Mar
Sphingolipids as bioactive regulators of thrombin generation.
2004 Mar 26
Acylceramide head group architecture affects lipid organization in synthetic ceramide mixtures.
2004 Nov
Effects of lipid chain lengths in alpha-galactosylceramides on cytokine release by natural killer T cells.
2004 Oct 27
Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.
2004 Oct 28
Molecular species of ceramides from the ascomycete truffle Tuber indicum.
2004 Sep
A novel coaxial electrospray ionization method for characterizing hexacosanoylceramides by Fourier transform ion cyclotron resonance mass spectrometry.
2005
Influence of phytosphingosine-type ceramides on the structure of DMPC membrane.
2005 Dec
Phytosphingosine induced mitochondria-involved apoptosis.
2005 Feb
Phosphorylation of sphingoid long-chain bases in Arabidopsis: functional characterization and expression of the first sphingoid long-chain base Kinase gene in plants.
2005 Feb
Arabidopsis sphingosine kinase and the effects of phytosphingosine-1-phosphate on stomatal aperture.
2005 Feb
Phytosphingosine in combination with ionizing radiation enhances apoptotic cell death in radiation-resistant cancer cells through ROS-dependent and -independent AIF release.
2005 Feb 15
Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(alpha-hydroxyoctadecanoyl)-phytosphingosine.
2005 Jan
The sphingoid long chain base phytosphingosine activates AGC-type protein kinases in Saccharomyces cerevisiae including Ypk1, Ypk2, and Sch9.
2005 Jun 17
Design of a phytosphingosine-containing, positively-charged nanoemulsion as a colloidal carrier system for dermal application of ceramides.
2005 May
Inositol phosphoceramide synthase is a regulator of intracellular levels of diacylglycerol and ceramide during the G1 to S transition in Saccharomyces cerevisiae.
2005 May 15
Candida albicans serotype B strains synthesize a serotype-specific phospholipomannan overexpressing a beta-1,2-linked mannotriose.
2005 Nov
Signalling functions for sphingolipid long-chain bases in Saccharomyces cerevisiae.
2005 Nov
Regulation of the sphingoid long-chain base kinase Lcb4p by ergosterol and heme: studies in phytosphingosine-resistant mutants.
2005 Nov 4
APP1 transcription is regulated by inositol-phosphorylceramide synthase 1-diacylglycerol pathway and is controlled by ATF2 transcription factor in Cryptococcus neoformans.
2005 Oct 28
Structure-activity relationships of dimethylsphingosine (DMS) derivatives and their effects on intracellular pH and Ca2+ in the U937 monocyte cell line.
2006 Aug
Identification of mouse sphingomyelin synthase 1 as a suppressor of Bax-mediated cell death in yeast.
2006 Aug
Rapid demonstration of diversity of sulfatide molecular species from biological materials by MALDI-TOF MS.
2006 Aug
Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids.
2006 Dec
Effect of lipid-containing, positively charged nanoemulsions on skin hydration, elasticity and erythema--an in vivo study.
2006 Jan 13
An efficient synthesis of the natural tetrahydrofuran pachastrissamine starting from D-ribo-phytosphingosine.
2006 Jan 20
Phytosphingosine stimulates the differentiation of human keratinocytes and inhibits TPA-induced inflammatory epidermal hyperplasia in hairless mouse skin.
2006 Jan-Mar
Constituents of Holothuroidea, 17. Isolation and structure of biologically active monosialo-gangliosides from the sea cucumber Cucumaria echinata.
2006 Jul
An efficient high-yield synthesis of D-ribo-phytosphingosine.
2006 Jul 20
Long chain base tolerance in Saccharomyces cerevisiae is induced by retrograde signals from the mitochondria.
2006 Mar 10
A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs.
2006 Mar 21
Structural organisation and phase behaviour of a stratum corneum lipid analogue: ceramide 3A.
2006 May 21
[New ceramides from sea sponge Oceanapia sp].
2006 May-Jun
Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate.
2006 Oct 27
Constituents of Holothuroidea, 18. Isolation and structure of biologically active disialo- and trisialo-gangliosides from the sea cucumber Cucumaria echinata.
2006 Sep
Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes.
2006 Sep 29
Combination treatment with arsenic trioxide and phytosphingosine enhances apoptotic cell death in arsenic trioxide-resistant cancer cells.
2007 Jan
Phytosphingosine in combination with TRAIL sensitizes cancer cells to TRAIL through synergistic up-regulation of DR4 and DR5.
2007 Jan
SVF1 regulates cell survival by affecting sphingolipid metabolism in Saccharomyces cerevisiae.
2007 Jan
Patents

Sample Use Guides

In Vivo Use Guide
500 mg twice daily for a 4 weeks
Route of Administration: Oral
In Vitro Use Guide
Jurkat and NCI-H460 cells were treated with 5 or 10 ug/ml phytosphingosine, respectively, for the 2, 5, 10, 30, 60, 120 min. phytosphingosine treatment led to a dramatic down-regulation of phosphorylated ERK1/2. The phosphorylated ERK started to diminish within 2 min of the phytosphingosine treatment.
Name Type Language
PHYTOSPHINGOSINE
INCI  
INCI  
Official Name English
D-RIBO-1,3,4-TRIHYDROXY-2-AMINOOCTADECANE
Common Name English
1,3,4-OCTADECANETRIOL, 2-AMINO-, (2S-(2R*,3R*,4S*))-
Common Name English
1,3,4-OCTADECANETRIOL, 2-AMINO-, D-RIBO-
Common Name English
D-RIBO-PHYTOSPHINGOSINE
Common Name English
DS-PHYTOSPHINGOSINE
Brand Name English
1,3,4-OCTADECANETRIOL, 2-AMINO-, (2S,3S,4R)-
Systematic Name English
(+)-D-RIBO-PHYTOSPHINGOSINE
Common Name English
C18-PHYTOSPHINGOSINE
Common Name English
CYTOMIDE PGS
Brand Name English
BIOMIDE PS
Brand Name English
SPHINGANINE, 4-D-HYDROXY
Common Name English
PHYTOSPHINGOSINE [INCI]
Common Name English
4-D-HYDROXYSPHINGANINE
Common Name English
PHYTOSPHINGOSINE [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
122121
Created by admin on Tue Oct 22 14:14:59 UTC 2019 , Edited by admin on Tue Oct 22 14:14:59 UTC 2019
PRIMARY
EPA CompTox
554-62-1
Created by admin on Tue Oct 22 14:14:59 UTC 2019 , Edited by admin on Tue Oct 22 14:14:59 UTC 2019
PRIMARY
RXCUI
1363444
Created by admin on Tue Oct 22 14:14:59 UTC 2019 , Edited by admin on Tue Oct 22 14:14:59 UTC 2019
PRIMARY RxNorm
CAS
554-62-1
Created by admin on Tue Oct 22 14:14:59 UTC 2019 , Edited by admin on Tue Oct 22 14:14:59 UTC 2019
PRIMARY
EVMPD
SUB35223
Created by admin on Tue Oct 22 14:14:59 UTC 2019 , Edited by admin on Tue Oct 22 14:14:59 UTC 2019
PRIMARY