An essential ceramide for prevention of epidermal water loss
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Product Categories

Product Type

Biochemicals
Lipids
Sphingolipids

Research Area

Lipid Biochemistry
Sphingolipids

EOS (d18:1/30:0/18:2)

Item No. 24394

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
30-[[2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]amino]-30-oxotriacontyl ester, 9,12-octadecadienoic acid
CAS Number
97040-38-5
Synonyms
  • N-(30-linoleoyloxy-triacontanoyl)-Sphingosine
  • C48:2 EOS (d18:1/30:0w18:2 (9Z,12Z))
Molecular Formula
C66H125NO5
Formula Weight
1012.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleDMF: solubleMethanol: soluble
SMILES
OCC(NC(CCCCCCCCCCCCCCCCCCCCCCCCCCCCCOC(CCCCCCC/C=C\C/C=C\CCCCC)=O)=O)C(O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C66H125NO5/c1-3-5-7-9-11-13-15-17-31-36-40-44-48-52-56-60-66(71)72-61-57-53-49-45-41-37-33-30-28-26-24-22-20-18-19-21-23-25-27-29-32-35-39-43-47-51-55-59-65(70)67-63(62-68)64(69)58-54-50-46-42-38-34-16-14-12-10-8-6-4-2/h11,13,17,31,54,58,63-64,68-69H,3-10,12,14-16,18-30,32-53,55-57,59-62H2,1-2H3,(H,67,70)/b13-11-,31-17-,58-54+
InChi Key
CJKGLEVYDCRGBX-UUHZUQCYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $602

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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. EOS (d18:1/30:0/18:2) is a sphingolipid that has been found in intact and desquamated human stratum corneum as well as porcine epidermis.2,3 [Matreya, LLC. Catalog No. 2084]

    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).

    2. Long, S.A., Wertz, P.W., Strauss, J.S., et al. Human stratum corneum polar lipids and desquamation. Arch. Dermatol. Res. 277(4), 284-287 (1985).

    3. Wertz, P.W., Abraham, W., Cho, E.S., et al. Linoleate-rich O-acylsphingolipids of mammalian epidermis: Structures and effects of essential fatty acid deficiency. Prog. Lipid Res. 25, 383-389 (1986).

    Product Citations

    Nobumoto, W., Naganuma, T., Nozaka, N., et al. Acid ceramidase ASAH1 is a key regulator of epidermal ceramide levels and composition. The Journal of Biological Chemisty 302(3), 111178 (2026).