860602P
Avanti
D-ribo-phytosphingosine (C17 base)
Avanti Research™ - A Croda Brand 860602P, powder
Synonym(s):
4-hydroxysphinganine (C17 base)
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About This Item
Empirical Formula (Hill Notation):
C17H37NO3
CAS Number:
Molecular Weight:
303.48
UNSPSC Code:
12352211
NACRES:
NA.25
Recommended Products
form
powder
packaging
pkg of 1 × 10 mg (860602P-10mg)
pkg of 1 × 5 mg (860602P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 860602P
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
O[C@]([H])(CCCCCCCCCCCCC)[C@](O)([H])[C@](N)([H])CO
General description
D-ribo-phytosphingosine (C17 base), also known as 4D-hydroxysphinganine or PHS, is widely found in membranes of fungi, plants, bacteria, marine organisms and mammalian tissues.
Application
D-ribo-phytosphingosine (C17 base) has been used as a standard for the quantification of total plant long-chain bases (LCB) by gas chromatography-mass spectrometry (GC-MS).
Biochem/physiol Actions
D-ribo-phytosphingosine helps in maintaining the structural integrity of membrane. It also controls cellular growth and mediates the heat stress response of yeast. In addition, PHS acts as a precursor for synthesis of various key lipid mediators including PHS 1-phosphate, inositol phosphorylceramide and KRN7000 (α-anomer of galactosylceramide). This phospholipid also has an ability to stimulate keratinocyte differentiation. Therefore, PHS is used as an active constituent in cosmetic formulations.
Packaging
5 mL Amber Glass Screw Cap Vial (860602P-10mg)
5 mL Amber Glass Screw Cap Vial (860602P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Certificates of Analysis (COA)
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Polar emollients in cosmetic formulations enhance the penetration and biological effects of Phytosphingosine on skin
Schiemann Y, et al.
Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 331(1-2), 103-107 (2008)
Asymmetric synthesis of d-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy) acetaldehyde
Liu Z, et al.
The Journal of Organic Chemistry, 75(13), 4356-4364 (2010)
Zheng Liu et al.
The Journal of organic chemistry, 75(13), 4356-4364 (2010-06-10)
An asymmetric synthesis of d-ribo-phytosphingosine (1) was achieved by utilizing the ProPhenol (12)-catalyzed alkynylation of unsaturated aldehyde 8 to afford allylic propargylic alcohol (S)-6 followed by asymmetric epoxidation and opening of propargylic epoxy alcohol anti-5 with NaN(3)/NH(4)Cl. Deprotection and reduction
Jean-Luc Cacas et al.
Analytical and bioanalytical chemistry, 403(9), 2745-2755 (2012-05-12)
In eukaryotic organisms, sphingolipids are major structural lipids of biological membranes and perform additional essential functions as signalling molecules. While long-chain bases (LCB), the common precursor to all sphingolipid classes, is represented by only one major molecular species in animals
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