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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

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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)
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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