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860609P

Avanti

N-08:0 Phytosphingosine

Avanti Research™ - A Croda Brand 860609P, powder

Synonym(s):

N-octanoyl 4-hydroxysphinganine (Saccharomyces Cerevisiae)

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About This Item

Empirical Formula (Hill Notation):
C26H53NO4
CAS Number:
475995-74-5
Molecular Weight:
443.70
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860609P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860609P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C26H53NO4/c1-3-5-7-9-10-11-12-13-14-15-17-18-20-24(29)26(31)23(22-28)27-25(30)21-19-16-8-6-4-2/h23-24,26,28-29,31H,3-22H2,1-2H3,(H,27,30)/t23-,24+,26-/m0/s1

InChI key

XQNJLWJVISBYSS-GSLIJJQTSA-N

General description

D-ribo-phytosphingosine or phytosphingosine is a phospholipid found naturally in the stratum corneum. It is found both in its free form and as a fragment of the major fraction of ceramides.

Biochem/physiol Actions

Phytosphingosine exhibits cutaneous anti-microbial barrier function. It acts as a natural anti-inflammatory agent. PHS stimulates keratinocyte differentiation. Thus, it is used as an active component in the cosmetic formulations. PHS is implicated in maintaining the structural integrity of the membranes. In addition, it also controls cellular growth and mediates the heat stress response of yeast.

Packaging

5 mL Amber Glass Screw Cap Vial (860609P-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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Anti-microbial and-inflammatory activity and efficacy of phytosphingosine: an in vitro and in vivo study addressing acne vulgaris
Pavicic T, et al.
International Journal of Cosmetic Science, 29(3), 181-190 (2007)
T Pavicic et al.
International journal of cosmetic science, 29(3), 181-190 (2008-05-21)
Lipids are important constituents of the human epidermis. Either free and organized into broad lipid bilayers in the intercorneocytes spaces, or covalently bound to the corneocyte envelope, they play a crucial role in permeability barrier function and are major contributors
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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