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860668P

Avanti

4E,11Z-Sphingadiene

(2S,3R,4E,11Z)-2-aminooctadec-4,11-diene-1,3-diol, powder

Empirical Formula (Hill Notation):
C18H35NO2
Molecular Weight:
297.48
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 1 mg (860668P-1mg)

manufacturer/tradename

Avanti Polar Lipids 860668P

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCC/C=C\CCCCCC

General description

4E,11Z-Sphingadiene is a unique sphingoid base containing trans double bond at C4 and cis double bond at C11 positions along the sphingoid base alkyl chain. Sphingadienes are found in insects, marine organisms, legumes including soybeans and soy products.

Application

4E,11Z-Sphingadiene has been used as a standard in 193 nm ultraviolet photodissociation (UVPD)-ultra high resolution tandem mass spectrometry for its detailed structural characterization.

Biochem/physiol Actions

Sphingadienes are growth-inhibitory sphingoid bases, involved in apoptosis and cell signaling. It inhibits Akt/Wnt signaling that might contribute to their chemopreventive properties in colon cancer.

Packaging

5 mL Amber Glass Screw Cap Vial (860668P-1mg)

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

Certificate of Analysis

Certificate of Origin

Detailed structural characterization of sphingolipids via 193 nm ultraviolet photodissociation and ultrahigh resolution tandem mass spectrometry
Ryan E, et al.
Journal of the American Society For Mass Spectrometry, 28(7), 1406-1419 (2017)
Occurrence, structure elucidation, biosynthesis, functions and synthesis of sphingadienes
U Abeytunga T
Mini-Reviews in Organic Chemistry, 12(3), 282-292 (2015)
Ashok Kumar et al.
Carcinogenesis, 33(9), 1726-1735 (2012-05-15)
Sphingadienes (SDs) derived from soy and other natural sphingolipids are cytotoxic to colon cancer cells via an Akt-dependent mechanism and reduce adenoma formation in Apc(Min/+) mice. Wnt signaling is fundamental to colon carcinogenesis and is the basis for spontaneous tumorigenesis

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