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860624P

Avanti

C18:1 Dihydroceramide (d18:0/18:1(9Z))

Avanti Research™ - A Croda Brand 860624P, powder

Synonym(s):

N-oleoyl-D-erythro-sphinganine

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About This Item

Empirical Formula (Hill Notation):
C36H71NO3
CAS Number:
34227-83-3
Molecular Weight:
565.95
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860624P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860624P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@]([H])(NC(CCCCCCC/C=C\CCCCCCCC)=O)[C@]([H])(O)CCCCCCCCCCCCCCC

InChI

1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,34-35,38-39H,3-16,19-33H2,1-2H3,(H,37,40)/b18-17-/t34-,35+/m0/s1

InChI key

MJQIARGPQMNBGT-WWUCIAQXSA-N

General description

C18:1 Dihydroceramide (d18:0/18:1(9Z)) is a synthetic lipid. Dihydroceramide belongs to the ceramide family. It contains sphinganine, which is devoid of the 4,5-trans-double bond in the sphingoid base backbone.

Application

C18:1 Dihydroceramide (d18:0/18:1(9Z)) has been used as an internal standard to quantify the levels of serum and skeletal muscle lipids extracted from muscle tissue by liquid chromatography-mass spectrometry (MS) analysis. It has also been used as an standard to study its structural characterization by positive-ionization mode 193 nm ultraviolet photodissociation (UVPD)-mass spectrometry/MS.

Biochem/physiol Actions

Dihydroceramide is synthesized by the N-acylation of dihydrosphingosine. It functions as an inactive precursor for ceramide in de-novo sphingolipid synthesis. (Dihydro)-ceramide desaturase catalyzes the conversion of dihydroceramide to ceramide by the addition of C4–5 trans-double bond in the sphingoid backbone. Dihydroceramide has an ability to induce autophagy.

Packaging

5 mL Amber Glass Screw Cap Vial (860624P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

also commonly purchased with this product

Product No.
Description
Pricing

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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Skeletal muscle ceramides and relationship with insulin sensitivity after 2 weeks of simulated sedentary behaviour and recovery in healthy older adults
Reidy PT, et al.
The Journal of Physiology, 596(21), 5217-5236 (2018)
B K Gillard et al.
Glycobiology, 8(9), 885-890 (1998-07-24)
There are several pathways for the incorporation of sugars into glycosphingolipids (GSL). Sugars can be added to ceramide that contains sphinganine (dihydrosphingosine) synthesized de novo (pathway 1), to ceramide synthesized from sphingoid bases produced by hydrolysis of sphingolipids (pathway 2)
Eileen Ryan et al.
Journal of the American Society for Mass Spectrometry, 28(7), 1406-1419 (2017-04-30)
Sphingolipids serve not only as components of cellular membranes but also as bioactive mediators of numerous cellular functions. As the biological activities of these lipids are dependent on their structures, and due to the limitations of conventional ion activation methods
Variations among cell lines in the synthesis of sphingolipids in de novo and recycling pathways
Gillard BK, et al.
Glycobiology, 8(9), 885-890 (1998)
Chiara Mencarelli et al.
Cellular and molecular life sciences : CMLS, 70(2), 181-203 (2012-06-26)
Ceramide, the precursor of all complex sphingolipids, is a potent signaling molecule that mediates key events of cellular pathophysiology. In the nervous system, the sphingolipid metabolism has an important impact. Neurons are polarized cells and their normal functions, such as
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