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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)
Occurrence, structure elucidation, biosynthesis, functions and synthesis of sphingadienes
U Abeytunga T
Mini-Reviews in Organic Chemistry, 12(3), 282-292 (2015)
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
Structure of plasma sphingadienine
Renkonen O and Hirvisalo EL
Journal of Lipid Research, 10(6), 687-693 (1969)
Keisuke Jojima et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(2), 3318-3335 (2020-01-10)
Sphingolipids are multifunctional lipids. Among the sphingolipid-component sphingoid bases, 4,14-sphingadiene (SPD) is unique such that it has a cis double bond with a bent structure. Although SPD was discovered half a century ago, its tissue distribution, biosynthesis, and degradation remain
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