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860665P

Avanti

4E,14Z-Sphingadiene

Avanti Research™ - A Croda Brand 860665P, powder

Synonym(s):

(2S,3R,4E,14Z)-2-aminooctadec-4,14-diene-1,3-diol

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About This Item

Empirical Formula (Hill Notation):
C18H35NO2
CAS Number:
25696-03-1
Molecular Weight:
297.48
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 1 mg (860665P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860665P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCC/C=C\CCC

InChI

1S/C18H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h4-5,14-15,17-18,20-21H,2-3,6-13,16,19H2,1H3/b5-4-,15-14+

InChI key

KWDXKYNWAKMLKK-YQMRQDNGSA-N

General description

4E,14Z-Sphingadiene is a unique sphingoid base containing C18 chain, with trans double bond at C-4 and cis double bond between C14 and C15 with a bent structure. It is found in the plasma, lymph, brain, kidney and lungs of humans and mice. 4E,14Z-Sphingadiene or d-erythro-1,3-dihydroxy-2-amino-4-trans-14-cis-octadecadiene is the second largest long-chain base of human plasma sphingomyelins.

Biochem/physiol Actions

Sphingadiene, a vital component of sphingolipids facilitates numerous processes such as apoptosis and cell signaling. It inhibits Akt/Wnt signaling and acts as an anticancer agent in colon cancer.

Packaging

5 mL Amber Glass Screw Cap Vial (860665P-1mg)

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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Biosynthesis of the anti-lipid-microdomain sphingoid base 4, 14-sphingadiene by the ceramide desaturase FADS3
Jojima K, et al.
Faseb Journal (2020)
Structure of plasma sphingadienine
Renkonen O and Hirvisalo EL
Journal of Lipid Research, 10(6), 687-693 (1969)
O Renkonen et al.
Journal of lipid research, 10(6), 687-693 (1969-11-01)
The dienic long-chain base (sphingadienine) of human plasma sphingomyelins has been identified as d-erythro-1,3-dihydroxy-2-amino-4-trans-14-cis-octadecadiene. A similar sphingosine was also detected in plasma sphingomyelins of rat, rabbit, and cat. The key reaction in the structural studies was partial reduction of sphingadienine
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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