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89822

Sigma-Aldrich

N-Arachidoyl-D-sphingosine

≥98.0% (TLC)

Synonym(s):

Cer(d18:1/20:0), (2S,3R,4E)-2-(Eicosanoylamino)-4-octadecene-1,3-diol, N-Arachidoyl-D-erythro-sphingosine, N-Eicosanoyl-D-sphingosine, N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]eicosanamide, C20 Ceramide (d18:1/20:0), C20-Ceramide

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About This Item

Empirical Formula (Hill Notation):
C38H75NO3
CAS Number:
7344-02-7
Molecular Weight:
594.01
Beilstein:
7316231
MDL number:
MFCD02259131
UNSPSC Code:
12352211
PubChem Substance ID:
329769547
NACRES:
NA.85

Assay

≥98.0% (TLC)

form

powder

composition

carbon content, 76.84%
hydrogen content, 12.73%
nitrogen content, 2.36%

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

OC[C@]([H])(NC(CCCCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

InChI

1S/C38H75NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-38(42)39-36(35-40)37(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h31,33,36-37,40-41H,3-30,32,34-35H2,1-2H3,(H,39,42)/b33-31+/t36-,37+/m0/s1

InChI key

XWBWIAOWSABHFI-NUKVNZTCSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Kumi Izawa et al.
Scientific reports, 7(1), 4298-4298 (2017-06-29)
Sepsis is a serious clinical problem. Negative regulation of innate immunity is associated with sepsis progression, but the underlying mechanisms remains unclear. Here we show that the receptor CD300f promotes disease progression in sepsis. CD300f
J Jiang et al.
Toxicology and applied pharmacology, 332, 100-108 (2017-07-25)
The mechanisms of idiosyncratic drug-induced hepatotoxicity remain largely unclear. It has demonstrated that the drug idiosyncrasy is potentiated in the context of inflammation and intracellular ceramides may play a role in this process. To study the mechanisms, HepG2 cells were
Thomas Morville et al.
Medicine and science in sports and exercise, 49(2), 308-316 (2016-09-30)
Fat metabolism and muscle adaptation was investigated in six older trained men (age, 61 ± 4 yr; V˙O2max, 48 ± 2 mL·kg·min) after repeated prolonged exercise). A distance of 2706 km (1681 miles) cycling was performed over 14 d, and
Wendi Teng et al.
Nutrients, 11(5) (2019-05-30)
Sulforaphane (SFA), a naturally active isothiocyanate compound from cruciferous vegetables used in clinical trials for cancer treatment, was found to possess potency to alleviate insulin resistance. But its underlying molecular mechanisms are still incompletely understood. In this study, we assessed
Baharan Fekry et al.
Nature communications, 9(1), 4149-4149 (2018-10-10)
Ceramides are important participants of signal transduction, regulating fundamental cellular processes. Here we report the mechanism for activation of p53 tumor suppressor by C16-ceramide. C16-ceramide tightly binds within the p53 DNA-binding domain (Kd ~ 60 nM), in close vicinity to the Box V

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