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860627P

Avanti

C18 Dihydroceramide (d18:0/18:0)

Avanti Research™ - A Croda Brand 860627P, powder

Synonym(s):

N-stearoyl-D-erythro-sphinganine

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About This Item

Empirical Formula (Hill Notation):
C36H73NO3
CAS Number:
2304-80-5
Molecular Weight:
567.97
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 25 mg (860627P-25mg)
pkg of 1 × 5 mg (860627P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860627P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@]([H])(NC(CCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)CCCCCCCCCCCCCCC

InChI

1S/C36H73NO3/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/h34-35,38-39H,3-33H2,1-2H3,(H,37,40)/t34-,35+/m0/s1

InChI key

KZTJQXAANJHSCE-OIDHKYIRSA-N

General description

C18 Dihydroceramide (d18:0/18:0) or N-Stearoylsphinganine is a synthetic lipid. Acylation of sphinganine with stearoyl (FA-CoA with C18 acyl chain) by dihydro ceramide synthase 1, yields C18-dihydroceramide.

Application

C18 Dihydroceramide (d18:0/18:0) has been used as a standard for the quantitation of sphingolipid metabolites in adipose tissues by quadrupole time-of-flight (Q-TOF) mass spectrometry.

Biochem/physiol Actions

Dihydroceramides act as precursors for ceramides in the mammalian de-novo sphingolipid pathway. vitamin D supplementation increases plasma C18 dihydroceramide (C18-DHC) levels in type 2 diabetes mellitus (T2D) patients. Low serum concentration of C18-DHC has been observed in patients with history of graft rejection and ischemic type biliary lesions (ITBL). Therefore, it can be used as a predictor of graft rejection.

Packaging

5 mL Amber Glass Screw Cap Vial (860627P-25mg)
5 mL Amber Glass Screw Cap Vial (860627P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

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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Thomas D Mullen et al.
Journal of lipid research, 52(1), 68-77 (2010-10-14)
Mammalian ceramide synthases 1 to 6 (CerS1-6) generate Cer in an acyl-CoA-dependent manner, and expression of individual CerS has been shown to enhance the synthesis of ceramides with particular acyl chain lengths. However, the contribution of each CerS to steady-state
Chain length-specific properties of ceramides
Grosch S, et al.
Progress in Lipid Research, 51(1), 50-62 (2012)
Selective knockdown of ceramide synthases reveals complex interregulation of sphingolipid metabolism
Mullen TD, et al.
Journal of Lipid Research, 52(1), 68-77 (2011)
Sabine Grösch et al.
Progress in lipid research, 51(1), 50-62 (2011-12-03)
Ceramides are a class of sphingolipids that are abundant in cell membranes. They are important structural components of the membrane but can also act as second messengers in various signaling pathways. Until recently, ceramides and dihydroceramides were considered as a
Adipocyte Hypoxia-Inducible Factor 2alpha Suppresses Atherosclerosis by Promoting Adipose Ceramide Catabolism
Zhang X, et al.
Cell Metabolism, 30(5), 937-951 (2019)
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