A bioactive sphingolipid
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Isomer(s)
28602C22 Ceramide (d18:1(14Z)/22:0)
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C22 Ceramide (d18:1/22:0)

Item No. 22533

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-docosanamide
CAS Number
27888-44-4
Synonyms
  • C22 Ceramide
  • Cer(d18:1/22:0)
  • Ceramide (d18:1/22:0)
Molecular Formula
C40H79NO3
Formula Weight
622.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.1 mg/ml
SMILES
OC[C@H](NC(CCCCCCCCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C40H79NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-40(44)41-38(37-42)39(43)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h33,35,38-39,42-43H,3-32,34,36-37H2,1-2H3,(H,41,44)/b35-33+/t38-,39+/m0/s1
InChi Key
KEPQASGDXIEOIL-GLQCRSEXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    5 mg

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    10 mg

    $268

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    Product Description

    C22 ceramide is an endogenous bioactive sphingolipid. Ceramides are involved in permeabilization of the mitochondrial outer membrane during apoptosis via the intrinsic pathway.1 C22 ceramide forms small channels in liposomes, whereas C16 ceramide (Item No. 10681) forms channels that can grow in size, suggesting that acyl chain length of ceramides is important in mitochondrial-mediated apoptosis. In addition, the mitochondrial-to-cytosolic stress response (MCSR) in C. elegans fed C22 ceramide decreases following inhibition of Hsp6 (mortalin/Grp75/mtHsp70) using RNAi.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stiban, J., and Perera, M. Very long chain ceramides interfere with C16-ceramide-induced channel formation: A plausible mechanism for regulating the initiation of intrinsic apoptosis. Biochim. Biophys. Acta 1848(2), 561-567 (2015).

    2. Kim, H.E., Grant, A.R., Simic, M.S., et al. Lipid biosynthesis coordinates a mitochondrial-to-cytosolic stress response. Cell 166(6), 1539-1552 (2016).