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860610P

Avanti

N-18:0 Phytosphingosine

Name: N-18:0 Phytosphingosine
Brand: AVANTI

Avanti Polar Lipids 860610P, powder

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Synonym(s):

N-stearoyl 4-hydroxysphinganine (Saccharomyces Cerevisiae)

Empirical Formula (Hill Notation):

C₃₆H₇₃NO₄

CAS Number:

475995-75-6

Molecular Weight:

583.97

NACRES:

NA.25

form

powder

packaging

pkg of 1 × 10 mg (860610P-10mg)
pkg of 1 × 5 mg (860610P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860610P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C36H73NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-35(40)37-33(32-38)36(41)34(39)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h33-34,36,38-39,41H,3-32H2,1-2H3,(H,37,40)/t33-,34+,36-/m0/s1

InChI key

IEZRNEGTKRQRFV-LFBNJJMOSA-N

General description

D-ribo-phytosphingosines or phytosphingosines (PHS) are biologically important long-chain bases present in various sphingolipids from yeasts, fungi, plants and mammals.

Application

N-18:0 Phytosphingosine has been used as a standard for the analysis of lipids from epidermis and stratum corneum in mice by mass spectrometry.

Biochem/physiol Actions

Phytosphingosine (PHS) exhibits bactericidal and anti-inflammatory activities. It prevents loss of moisture from the skin. In addition, PHS controls epidermal cell growth, differentiation and apoptosis.

Packaging

5 mL Amber Glass Screw Cap Vial (860610P-10mg)

5 mL Amber Glass Screw Cap Vial (860610P-5mg)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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The acyl-CoA binding protein is required for normal epidermal barrier function in mice

Bloksgaard M, et al.

Journal of Lipid Research, 53(10), 2162-2174 (2012)

The acyl-CoA binding protein is required for normal epidermal barrier function in mice.

Maria Bloksgaard et al.

Journal of lipid research, 53(10), 2162-2174 (2012-07-26)

The acyl-CoA binding protein (ACBP) is a 10 kDa intracellular protein expressed in all eukaryotic species. Mice with targeted disruption of Acbp (ACBP(-/-) mice) are viable and fertile but present a visible skin and fur phenotype characterized by greasy fur

Phytosphingosine derivatives ameliorate skin inflammation by inhibiting NF-κB and JAK/STAT signaling in keratinocytes and mice.

Byung-Hak Kim et al.

The Journal of investigative dermatology, 134(4), 1023-1032 (2013-11-02)

Phytosphingosine is abundant in plants and fungi and is found in mammalian epidermis, including the stratum corneum. Phytosphingosine and its derivatives N-acetyl phytosphingosine and tetraacetyl phytosphingosine are part of the natural defense system of the body. However, these molecules exhibit

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