Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H39NO2 |
| Molecular Weight | 301.5078 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO
InChI
InChIKey=OTKJDMGTUTTYMP-ZWKOTPCHSA-N
InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1
Sphinganine is a naturally occurring, skin-identical sphingoid base, a representative of the class of amino alcohols, or long chain bases (LCBs). Sphinganine is a blocker postlysosomal cholesterol transport by inhibition of low-density lipoprotein-induced esterification of cholesterol and cause unesterified cholesterol to accumulate in perinuclear vesicles. It has been suggested the possibility that endogenous sphinganine may inhibit cholesterol transport in Niemann-Pick Type C (NPC) disease. Sphinganine is a potent inhibitor of 5-α-reductase type I that prevents the conversion of testosterone to dihydrotestosterone, a key factor of androgenetic male baldness. As a cosmetic ingredient, sphinganine is well suited as a topical alternative for the improvement of scalp health and hair quality and anti-hair loss application. Sphinganine promotes differentiation and ceramide production in keratinocytes. Free sphinganine may serve as a dermatological and cosmetic agent by enhancing formation and maintenance of an intact epidermal lipid barrier, with beneficial effects for skin and hair care applications.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Quantification of sphingosine and sphinganine from crude lipid extracts by HPLC electrospray ionization tandem mass spectrometry. | 2003-11 |
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| Two mammalian longevity assurance gene (LAG1) family members, trh1 and trh4, regulate dihydroceramide synthesis using different fatty acyl-CoA donors. | 2003-10-31 |
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| Role of human sphingosine-1-phosphate phosphatase 1 in the regulation of intra- and extracellular sphingosine-1-phosphate levels and cell viability. | 2003-09-05 |
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| Metabolism of the unnatural anticancer lipid safingol, L-threo-dihydrosphingosine, in cultured cells. | 2003-09 |
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| Ligand-dependent inhibition of B16 melanoma cell migration and invasion via endogenous S1P2 G protein-coupled receptor. Requirement of inhibition of cellular RAC activity. | 2003-08-29 |
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| Cloning and characterization of a mouse endoplasmic reticulum alkaline ceramidase: an enzyme that preferentially regulates metabolism of very long chain ceramides. | 2003-08-15 |
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| Synthesis and potent antileukemic activities of N-lactylsphingosine and N-lactyldihydrosphingosine. | 2003-07-31 |
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| Sphinganine to sphingosine ratio and predictive biochemical markers of fumonisin B1 exposure in ducks. | 2003-07-25 |
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| Synthesis of 4-hydroxysphinganine and characterization of sphinganine hydroxylase activity in corn. | 2003-07-15 |
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| Glucosylceramide and glucosylsphingosine modulate calcium mobilization from brain microsomes via different mechanisms. | 2003-06-27 |
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| Sphingosine 1-phosphate is a novel inhibitor of T-cell proliferation. | 2003-06-15 |
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| Transmembrane topology of sphingoid long-chain base-1-phosphate phosphatase, Lcb3p. | 2003-06 |
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| Fumonisin-induced blockade of ceramide synthase in sphingolipid biosynthetic pathway alters aortic input impedance spectrum of pigs. | 2003-06 |
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| Elevation of de novo ceramide synthesis in tumor masses and the role of microsomal dihydroceramide synthase. | 2003-05-20 |
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| Using lowess to remove systematic trends over time in predictor variables prior to logistic regression with quantile categories. | 2003-05-15 |
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| Sphingoid bases and their phosphates: transient activation and delayed repression of protein kinase C isoforms and their possible involvement in fumonisin B1 cytotoxicity. | 2003-05-03 |
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| Membrane dynamics and cell polarity: the role of sphingolipids. | 2003-05 |
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| [The changes in the sphingenine/sphinganine ratio in sphingolipids of transplantable rat tumors depends on a transplantation organ]. | 2003-04-24 |
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| Sphingoid bases as possible diagnostic parameters. | 2003-04 |
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| Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63. | 2003-04 |
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| Ceramide 1-phosphate increases intracellular free calcium concentrations in thyroid FRTL-5 cells: evidence for an effect mediated by inositol 1,4,5-trisphosphate and intracellular sphingosine 1-phosphate. | 2003-02-15 |
|
| A novel role for sphingolipid intermediates in activation-induced cell death in T cells. | 2003-02 |
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| Enhanced phagocytosis through inhibition of de novo ceramide synthesis. | 2003-01-10 |
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| Identification and characterization of a novel human sphingosine-1-phosphate phosphohydrolase, hSPP2. | 2003-01-10 |
|
| Deletion of IFN-gamma reduces fumonisin-induced hepatotoxicity in mice via alterations in inflammatory cytokines and apoptotic factors. | 2003-01 |
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| Alveolar sphingolipids generated in response to TNF-alpha modifies surfactant biophysical activity. | 2003-01 |
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| Fumonisins and fumonisin analogs as inhibitors of ceramide synthase and inducers of apoptosis. | 2002-12-30 |
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| Sphingolipids are required for the stable membrane association of glycosylphosphatidylinositol-anchored proteins in yeast. | 2002-12-20 |
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| Paradoxical role of tumor necrosis factor alpha in fumonisin-induced hepatotoxicity in mice. | 2002-12-02 |
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| Prolonged activation of Ca2+-activated K+ current contributes to the long-lasting refractory period of Aplysia bag cell neurons. | 2002-12-01 |
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| Signalling mechanisms in sphingosine 1-phosphate-promoted mesangial cell proliferation. | 2002-12 |
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| Comparative study of naphthalene-2,3-dicarboxaldehyde and o-phthalaldehyde fluorogenic reagents for chromatographic detection of sphingoid bases. | 2002-11-15 |
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| Liquid chromatography/electrospray ionisation-mass spectrometry method for the quantification of sphingosine and sphinganine in cell cultures exposed to fumonisins. | 2002-11-15 |
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| The plant disease resistance gene Asc-1 prevents disruption of sphingolipid metabolism during AAL-toxin-induced programmed cell death. | 2002-11 |
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| A new class of lipid desaturase central to sphingolipid biosynthesis and signalling. | 2002-11 |
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| Sphingosine 1-phosphate is a ligand of the human gpr3, gpr6 and gpr12 family of constitutively active G protein-coupled receptors. | 2002-11 |
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| Increase of ceramide in adriamycin-induced HL-60 cell apoptosis: detection by a novel anti-ceramide antibody. | 2002-10-10 |
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| D-erythro-N,N-dimethylsphingosine inhibits bFGF-induced proliferation of cerebral, aortic and coronary smooth muscle cells. | 2002-10 |
|
| The Saccharomyces cerevisiae YBR159w gene encodes the 3-ketoreductase of the microsomal fatty acid elongase. | 2002-09-20 |
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| A role for the de novo sphingolipids in apoptosis of photosensitized cells. | 2002-09-10 |
|
| Effect of acute exercise on the content of free sphinganine and sphingosine in different skeletal muscle types of the rat. | 2002-09 |
|
| Identification and characterization of a Saccharomyces cerevisiae gene, RSB1, involved in sphingoid long-chain base release. | 2002-08-16 |
|
| Enhanced de novo ceramide generation through activation of serine palmitoyltransferase by the P-glycoprotein antagonist SDZ PSC 833 in breast cancer cells. | 2002-07 |
|
| Sphingolipid functions in Saccharomyces cerevisiae. | 2002-06-13 |
|
| Persistence and reversibility of the elevation in free sphingoid bases induced by fumonisin inhibition of ceramide synthase. | 2002-06 |
|
| Pharmacological antagonism of fumonisin B1 cytotoxicity in porcine renal epithelial cells (LLC-PK1): a model for reducing fumonisin-induced nephrotoxicity in vivo. | 2002-05 |
|
| Sphingoid bases and ceramide induce apoptosis in HT-29 and HCT-116 human colon cancer cells. | 2002-05 |
|
| Mutant analysis reveals complex regulation of sphingolipid long chain base phosphates and long chain bases during heat stress in yeast. | 2002-05 |
|
| In vitro activity of phytosphingosines against Malassezia furfur and Candida albicans. | 2002 |
|
| Carcinogenicity and mechanism of action of fumonisin B1: a mycotoxin produced by Fusarium moniliforme (= F. verticillioides). | 2002 |
Patents
Sample Use Guides
Two identical studies using randomized, placebo-controlled,and double-blind designs with a 16-week treatment period wereconducted. The first pilot study was carried out on 32 healthytest subjects of both sexes (male/female and verum/placebo,ratio 1:1) testing a concentration of 0.2% sphinganine. Inaddition, a follow-up study was done on a total of 80 male testsubjects divided into three treatment groups (sphinganine concentrationsof 0.1%, 0.2%, and 0.5%) and one control group.
Route of Administration:
Topical
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57817
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91486
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YT0ZSD64HM
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1947371
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DTXSID501016568
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Sphinganine
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YT0ZSD64HM
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SUBSTANCE RECORD
