An internal standard for the quantification of EOS
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Unlabeled Version(s)
22442EOS (d18:1/32:1/18:2)
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EOS-d9 (d18:1-d9/32:0/18:2)

Item No. 24423

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(9Z,12Z)-9,12-octadecadienoic acid, 32-[[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl-14,14,15,15,16,16,17,17,17-d9]amino]-32-oxodotriacontyl ester
CAS Number
2692624-26-1
Synonyms
  • N-(32-linoleoyloxy-dotriacontanoyl)-Sphingosine-d9
Molecular Formula
C68H120D9NO5
Formula Weight
1049.8
Purity
≥99% deuterated forms (d1-d9)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleDMF: solubleMethanol: soluble
SMILES
OC[C@H](NC(CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOC(CCCCCCC/C=C\C/C=C\CCCCC)=O)=O)[C@H](O)/C=C/CCCCCCCCCC([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H]
InChi Code
InChI=1S/C68H129NO5/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/h11,13,17,33,56,60,65-66,70-71H,3-10,12,14-16,18-32,34-55,57-59,61-64H2,1-2H3,(H,69,72)/b13-11-,33-17-,60-56+/t65-,66+/m0/s1/i2D3,4D2,6D2,8D2
InChi Key
NKZDGPMKCOVGRH-SIBFFXIQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $736

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    Product Description

    EOS-d9 (d18:1-d9/32:0/18:2) is intended for use as an internal standard for the quantification of EOS (Item No. 22442) by GC- or LC-MS. 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 fatty acid (C28-36) esterified to the essential fatty acid linoleic acid (Item No. 90150) and glucosylated to sphingosine. 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. [Matreya, LLC. Catalog No. 2208]

    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).

    Product Citations

    Tagi, H., Qiu, C., Zeng, Y., et al. Serine supplementation suppresses hypoxia-induced pathological retinal angiogenesis. Theranostics 15(1), 5087-5105 (2025).