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Phytosphingosine

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Phytosphingosine Basic information
Product Name:Phytosphingosine
Synonyms:PHYTOSPHINGOSINE HYDROCHLORIDE;(2S, 3S, 4R)-2-AMINO-1,3,4-OCTADECANETRIOL 4-HYDROXYSPHINGANINE;4-HYDROXYSPHINGANINE;1,3,4-Octadecanetriol,2-amino-, (2S, 3S, 4R) -;(2S,3S,4R)-2-Amino-1,3,4-octadecanetriol;(4R)-4-Hydroxysphinganine;D-ribo-Phytosphingosine;D-threo-Phytosphingosine
CAS:554-62-1
MF:C18H39NO3
MW:317.51
EINECS:439-210-6
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Chiral Reagents;cosmestic;554-62-1
Mol File:554-62-1.mol
Phytosphingosine Structure
Phytosphingosine Chemical Properties
Melting point 102 °C
Boiling point 483.7±40.0 °C(Predicted)
density 0.983
vapor pressure 0.2Pa at 20℃
refractive index 9 ° (C=1, Pyridine)
storage temp. −20°C
solubility Soluble in Ethanol (up to 2 mg/ml).
form White to off-white solid.
pka11.91±0.45(Predicted)
color White
Water Solubility 2.6mg/L at 20℃
Stability:Stable for 1 year from date of purchase as supplied. Solutions in ethanol may be stored at -20°C for up to 1 month.
Cosmetics Ingredients FunctionsSKIN CONDITIONING
HAIR CONDITIONING
InChIInChI=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
InChIKeyAERBNCYCJBRYDG-KSZLIROESA-N
SMILESC(O)[C@H](N)[C@H](O)[C@H](O)CCCCCCCCCCCCCC
LogP6.2 at 22℃
Safety Information
WGK Germany 1
HS Code 29221990
Storage Class11 - Combustible Solids
MSDS Information
Phytosphingosine Usage And Synthesis
DescriptionPhytosphingosine is a sphingolipid with a hydroxyl group at the C4 position that is found mainly in fungi and plants but also in animals, including humans. It is metabolized to odd-numbered fatty acids with 2-hydroxy palmitic acid as an intermediate. Phytosphingosine dose-dependently induces cell death of CHO cells and inhibits carbachol-induced activation of phospholipase D (PLD) in CHO cells transfected with C. elegans muscarinic acetylcholine receptors. It is essential in the heat stress response in S. cerevisiae. [Matreya, LLC. Catalog No. 1330]
Chemical PropertiesOff-White Solid
Usesphytosphingosine is a sphingolipid that can improve the overall condition of skin and hair. Some sources site anti-microbial and anti-inflammatory properties. Research indicates similar activity to retinoic acid, in which case it may be particularly beneficial for aging and photo-aging skin.
UsesPhytosphingosine is a natural anti-microbial compound and it is involved in several cellular processes such as cell differentiation and anti-inflammation.
DefinitionChEBI: Phytosphingosine is a sphingoid, an amino alcohol and a triol. It has a role as a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is functionally related to a N-acyl-beta-D-galactosylphytosphingosine and a sphinganine. It is a conjugate base of a phytosphingosine(1+).
OriginIn 1884, chemist J.L.W coined the word phytosphingosine, which was taken from the term “sphingoid”, a major component in all biological membranes. There are four types of sphingoid bases and phytosphingosine is one of them. Phytosphingosine is a widely distributed natural sphingoid base and found in fungi, plants, and animals.
Flammability and ExplosibilityNot classified
Veterinary Drugs and TreatmentsPhytosphingosine is a unique topical antiseborrheic compound. It is in a class called ceramides which are waxy materials meant to meant to mimic the normal lipid composition of the stratum corneum. It may also have some antiinflammatory and antimicrobial properties.
References[1] CAROL L FISCHER. Antibacterial activity of sphingoid bases and fatty acids against Gram-positive and Gram-negative bacteria.[J]. Antimicrobial Agents and Chemotherapy, 2012: 1157-1161. DOI:10.1128/aac.05151-11
[2] C L FISCHER. Sphingoid bases are taken up by Escherichia coli and Staphylococcus aureus and induce ultrastructural damage.[J]. Skin Pharmacology and Physiology, 2013, 26 1: 36-44. DOI:10.1159/000343175
Phytosphingosine Preparation Products And Raw materials
Preparation ProductsN-hexacosanoylphytosphingosine-->N-tert-Butyloxycarbonyl-D-ribo-phytosphingosine-->salicyloyl phytosphingosine
Tag:Phytosphingosine(554-62-1) Related Product Information
HISTONE Lactobacillus plantarum beta-Sitosterol phytosphingosine Phytic acid Phytol Calcium phytate PHYTOSTEROLS TRILAURIN N-HEXANOYL-PHYTOSPHINGOSINE N-(6-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]CAPROYL)-PHYTOSPHINGOSINE N-ACETYL-PHYTOSPHINGOSINE N-TETRACOSANOYL-PHYTOSPHINGOSINE N-Stearoyl-phytosphingosine Phytosphingosine YEAST N-08:0 PHYTOSPHINGOSINE,N-OCTANOYL-PHYTOSPHINGOSINE (SACCHAROMYCES CEREVISIAE),N-OCTANOYL-PHYTOSPHINGOSINE alpha-Hydroxyoctadecanoyl-phytosphingosine Ceramides

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