PHYTOSPHINGOSINE

Details

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

SHOW SMILES / InChI

Structure Search

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

Molecular Formula	C18H39NO3
Molecular Weight	317.5072
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723652 | https://www.truthinaging.com/ingredients/phytosphingosine | https://www.ncbi.nlm.nih.gov/pubmed/28390782 | https://www.ncbi.nlm.nih.gov/pubmed/18489348 | https://www.ncbi.nlm.nih.gov/pubmed/20179727 | https://www.ncbi.nlm.nih.gov/pubmed/14522966

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

Targets

Primary Target	Pharmacology	Condition	Potency
MITF signaling pathway 3 Target ID: MITF signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28390782	Modulator 846
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14522966 \| https://www.ncbi.nlm.nih.gov/pubmed/15723652	Activator 1447
apoptotic DNA fragmentation 5 Target ID: GO:0006309 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723652	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Metabolic syndrome 34 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20179727	Primary	Phase II 1147	Unknown Approved Use Unknown
Acne vulgaris 34 Sources: https://www.truthinaging.com/ingredients/phytosphingosine https://www.ncbi.nlm.nih.gov/pubmed/18489348	Primary	Phase II 1147	Unknown Approved Use Unknown
Hyperpigmentation 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28390782	Primary	Basic research	Unknown Approved Use Unknown
Skin Care 16 Sources: https://www.drugs.com/otc/130001/white-petrolatum.html	Inactive ingredient	Approved 8583	CheryLee MD TrueLipids Relieve and Protect Ointment Approved Use Uses: helps relieve, prevent and temporarily protect chafed, chapped, cracked or windburned skin and lips temporarily protects minor: cuts scrapes burns helps protect from the drying effects of wind and cold weather

PubMed

Title	Date	PubMed
Comparative analysis of glycosylinositol phosphorylceramides from fungi by electrospray tandem mass spectrometry with low-energy collision-induced dissociation of Li(+) adduct ions.	2001	11746891
Natural zeolite clinoptilolite increases the concentrations of sphingoid bases in the yeast Yarrowia lipolytica.	2001	11314249
Characterization of novel structures of mannosylinositolphosphorylceramides from the yeast forms of Sporothrix schenckii.	2001 Aug	11488918
Constituents of ophiuroidea. 1. Isolation and structure of three ganglioside molecular species from the brittle star Ophiocoma scolopendrina.	2001 Dec	11767069
Sphingoid base signaling via Pkh kinases is required for endocytosis in yeast.	2001 Dec 3	11726514
Phytosphingosine as a specific inhibitor of growth and nutrient import in Saccharomyces cerevisiae.	2001 Sep 21	11468289
Dependence of the sphingoid bases concentration on growth phase and temperature in the yeast Yarrowia lipolytica.	2002	11925759
Simultaneous quantitative analysis of sphingoid base 1-phosphates in biological samples by o-phthalaldehyde precolumn derivatization after dephosphorylation with alkaline phosphatase.	2002 Apr 15	11950216
Sphingosine kinase, sphingosine-1-phosphate, and apoptosis.	2002 Dec 30	12531554
Sphingolipid functions in Saccharomyces cerevisiae.	2002 Jun 13	12069845
Mutant analysis reveals complex regulation of sphingolipid long chain base phosphates and long chain bases during heat stress in yeast.	2002 May	11967828
Identification of target tissue glycosphingolipid receptors for uropathogenic, F1C-fimbriated Escherichia coli and its role in mucosal inflammation.	2002 May 17	11877427
Isolation and structure of monomethylated GM3-type ganglioside molecular species from the starfish Luidia maculata.	2002 Oct	12372870
Analysis of ceramides in cosmetics by reversed-phase liquid chromatography/electrospray ionization mass spectrometry with collision-induced dissociation.	2003	12478556
A facile synthesis of phytosphingosine from diisopropylidene-D-mannofuranose.	2003 Jul 11	12839486
Sphingophosphonolipid molecular species from edible mollusks and a jellyfish.	2003 Sep	12941637
Isolation and structure of a GD3-Type ganglioside molecular species possessing neuritogenic activity from the starfish Luidia maculata.	2004 Aug	15305002
Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine.	2004 Aug 20	15307742
Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine.	2004 Aug 27	15190065
Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon.	2004 Aug 6	15287793
Potentiation of UVB-induced apoptosis by novel phytosphingosine derivative, tetraacetyl phytosphingosine in HaCaT cell and mouse skin.	2004 Jul	15192327
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	15155728
Acylceramide head group architecture affects lipid organization in synthetic ceramide mixtures.	2004 Nov	15482479
Effects of lipid chain lengths in alpha-galactosylceramides on cytokine release by natural killer T cells.	2004 Oct 27	15493902
Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.	2004 Oct 28	15496103
Molecular species of ceramides from the ascomycete truffle Tuber indicum.	2004 Sep	15351272
Anti-ulcer actions of phytosphingosine hydrochloride in different experimental rat ulcer models.	2005	16149714
A novel coaxial electrospray ionization method for characterizing hexacosanoylceramides by Fourier transform ion cyclotron resonance mass spectrometry.	2005	15838927
Influence of phytosphingosine-type ceramides on the structure of DMPC membrane.	2005 Dec	16202987
Lipid mixtures prepared with well-defined synthetic ceramides closely mimic the unique stratum corneum lipid phase behavior.	2005 Dec	16150830
Phytosphingosine induced mitochondria-involved apoptosis.	2005 Feb	15723652
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	15695468
Arabidopsis sphingosine kinase and the effects of phytosphingosine-1-phosphate on stomatal aperture.	2005 Feb	15665242
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	15486061
Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(alpha-hydroxyoctadecanoyl)-phytosphingosine.	2005 Jan	15589229
The sphingoid long chain base phytosphingosine activates AGC-type protein kinases in Saccharomyces cerevisiae including Ypk1, Ypk2, and Sch9.	2005 Jun 17	15840588
FTIR spectroscopic studies of lipid dynamics in phytosphingosine ceramide models of the stratum corneum lipid matrix.	2005 Mar	15752463
Design of a phytosphingosine-containing, positively-charged nanoemulsion as a colloidal carrier system for dermal application of ceramides.	2005 May	15848061
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	15560753
Candida albicans serotype B strains synthesize a serotype-specific phospholipomannan overexpressing a beta-1,2-linked mannotriose.	2005 Nov	16262785
Signalling functions for sphingolipid long-chain bases in Saccharomyces cerevisiae.	2005 Nov	16246074
Regulation of the sphingoid long-chain base kinase Lcb4p by ergosterol and heme: studies in phytosphingosine-resistant mutants.	2005 Nov 4	16141212
APP1 transcription is regulated by inositol-phosphorylceramide synthase 1-diacylglycerol pathway and is controlled by ATF2 transcription factor in Cryptococcus neoformans.	2005 Oct 28	16129666
Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids.	2006 Dec	17070498
An efficient synthesis of the natural tetrahydrofuran pachastrissamine starting from D-ribo-phytosphingosine.	2006 Jan 20	16409007
Long chain base tolerance in Saccharomyces cerevisiae is induced by retrograde signals from the mitochondria.	2006 Mar 10	16407254
A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs.	2006 Mar 21	16525559
Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes.	2006 Sep 29	16904073
Combination treatment with arsenic trioxide and phytosphingosine enhances apoptotic cell death in arsenic trioxide-resistant cancer cells.	2007 Jan	17237268
Phytosphingosine in combination with TRAIL sensitizes cancer cells to TRAIL through synergistic up-regulation of DR4 and DR5.	2007 Jan	17143496

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:03:27 GMT 2025` Edited by `admin` on `Mon Mar 31 20:03:27 GMT 2025`
Record UNII	GIN46U9Q2Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHYTOSPHINGOSINE

Official Name

English

BIOMIDE PS

Preferred 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

SPHINGANINE, 4-D-HYDROXY

Common Name

English

Phytosphingosine [WHO-DD]

Common Name

English

4-D-HYDROXYSPHINGANINE

Common Name

English

Code System Code Type Description

DRUG BANK

DB14119