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860617P

Avanti

N-16:0 Phytosphingosine

Avanti Research™ - A Croda Brand 860617P, powder

Synonym(s):

N-palmitoyl-phytosphingosine (Saccharomyces Cerevisiae)

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About This Item

Empirical Formula (Hill Notation):
C34H69NO4
CAS Number:
111149-09-8
Molecular Weight:
555.92
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (860617P-10mg)
pkg of 1 × 5 mg (860617P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860617P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

O[C@]([H])(CCCCCCCCCCCCCC)[C@](O)([H])[C@@]([H])(NC(CCCCCCCCCCCCCCC)=O)CO

General description

Phytosphingosine is a biologically significant saturated long-chain sphingoid base, found in membranes of yeasts, fungi, plants and mammalian epidermis, including the stratum corneum.

Application

N-16:0 Phytosphingosine has been used as a lipid standard in electrospray ionization (ESI)-mass spectrometry (MS)-based lipidomic analysis.

Biochem/physiol Actions

Phytosphingosine plays a vital role in the defense mechanism of the skin by exhibiting anti-microbial and anti-inflammatory properties. It elicits keratinocyte differentiation and is therefore, used as an active ingredient in the cosmetic formulations. PHS helps in maintaining the structural integrity of the membranes. It also regulates cellular growth and mediates the heat stress response of yeast.

Packaging

5 mL Amber Glass Screw Cap Vial (860617P-10mg)
5 mL Amber Glass Screw Cap Vial (860617P-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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Antimicrobial Activity of Phytosphingosine Nanoemulsions against Bacteria and Yeasts
Bascpinar P, et al.
CBE Life Sciences Education, 14(2), 223-228 (2018)
Delineating the rules for structural adaptation of membrane-associated proteins to evolutionary changes in membrane lipidome
Makarova M, et al.
Current Biology (2020)
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
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