An essential ceramide for prevention of epidermal water loss
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Labeled Version(s)
24423EOS-d9 (d18:1-d9/32:0/18:2)
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EOS (d18:1/32:1/18:2)

Item No. 22442

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9Z,12Z-octadecadienoic acid, (10Z)-32-[[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]amino]-32-oxo-10-dotriaconten-1-yl ester
CAS Number
1318771-31-1
Synonyms
  • C52:3 EOS (18:1/32:1(22 Z)w18:2(9Z,12Z)
  • Esterified ω-hydroxyacyl Sphingosine
Molecular Formula
C68H127NO5
Formula Weight
1038.8
Purity
≥95%
Formulation (Request formulation change)
A 1 mg/ml solution in dichloromethane
Solubility(Learn about Variance in Solubility)
DMF: 0.15 mg/ml
SMILES
OC[C@H](NC(CCCCCCCCCCCCCCCCCCCC/C=C\CCCCCCCCCOC(CCCCCCC/C=C\C/C=C\CCCCC)=O)=O)[C@H](O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C68H127NO5/c1-3-5-7-9-11-13-15-17-33-38-42-46-50-54-58-62-68(73)74-63-59-55-51-47-43-39-35-32-30-28-26-24-22-20-18-19-21-23-25-27-29-31-34-37-41-45-49-53-57-61-67(72)69-65(64-70)66(71)60-56-52-48-44-40-36-16-14-12-10-8-6-4-2/h11,13,17,28,30,33,56,60,65-66,70-71H,3-10,12,14-16,18-27,29,31-32,34-55,57-59,61-64H2,1-2H3,(H,69,72)/b13-11-,30-28-,33-17-,60-56+/t65-,66+/m0/s1
InChi Key
RPCGMGJNWKWWGU-AXIQRGFZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    100 µg

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    Product Description

    EOS is a ceramide found in the outer layer of the epidermis in mammals.1 It is comprised of an ω-hydroxy very long-chain ceramide (C28-36) esterified to the essential fatty acid linoleic acid (Item No. 90150). The consecutive regio- and stereospecific oxygenation of the linoleate portion of EOS by 12(R)-lipoxygenase (12(R)-LO) and eLOX3 is essential for the maintenance of the epidermal barrier to prevent water loss. Following oxygenation, the oxidized linoleate is hydrolyzed, leaving the ω-hydroxy end of the very long-chain fatty acid to covalently bind the protein layer, forming the corneocyte lipid envelope and sealing the gap between the extracellular lipid lamellae and the cornified cell envelope of the corneocyte.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zheng, Y., Yun, H., Boeglin, W.E., et al. Lipoxygenases mediate the effect of essential fatty acid in skin barrier formation: A proposed role in releasing omega-hydroxyceramide for construction of the corneocyte lipid envelope. The Journal of Biological Chemisty 286(27), 24046-24056 (2011).