A bioactive sphingolipid
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C24 (2’(R)-hydroxy) Phytoceramide (t18:0/24:0)

Item No. 28933

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-2-hydroxy-tetracosanamide
CAS Number
154801-30-6
Synonyms
  • N-(R)-alpha-Hydroxytetracosanoyl-Phytosphingosine
  • C24(2'OH)Phy
  • 2′-(R)-hydroxy-C24 Phytoceramide
  • N-24:0(2R-OH) Phytosphingosine
  • N-(R)-α-C24 Phytosphingosine (t18:0/24:0)
Molecular Formula
C42H85NO5
Formula Weight
684.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (4:1): solubleEthanol: warmed
SMILES
OC[C@H](NC([C@H](O)CCCCCCCCCCCCCCCCCCCCCC)=O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
InChi Code
InChI=1S/C42H85NO5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-40(46)42(48)43-38(37-44)41(47)39(45)35-33-31-29-27-25-16-14-12-10-8-6-4-2/h38-41,44-47H,3-37H2,1-2H3,(H,43,48)/t38-,39+,40+,41-/m0/s1
InChi Key
ZFUXWVVVWGWGPQ-QLLOZFISSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $369

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    Product Description

    C24 (2’(R)-hydroxy) Phytoceramide is a naturally occurring sphingolipid that has been found in adlay seed hull.1 It inhibits LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages (IC50 = 19 μg/ml), as well as increases in COX-2 and inducible nitric oxide synthase (iNOS) levels. It increases production of chemokine (C-X-C motif) ligand 8 (CXCL8), CXCL1, chemokine (C-C motif) ligand 2 (CCL2), and CCL20 in human umbilical vein endothelial cells (HUVECs) in a concentration-dependent manner.2 C24 (2’(R)-hydroxy) Phytoceramide is a hydroxylated form of C24 phytoceramide (Item No. 22827). [Matreya, LLC. Catalog No. 2094]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huang, D.-W., Chung, C.-P., Kuo, Y.-H., et al. Identification of compounds in adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) seed hull extracts that inhibit lipopolysaccharide-induced inflammation in RAW 264.7 macrophages. J. Agric. Food Chem. 57(22), 10651-10657 (2009).

    2. Sekiya, M., Ueda, K., Okazaki, K., et al. A phytoceramide analog stimulates the production of chemokines through CREB activation in human endothelial cells. Int. Immunopharmacol. 11(10), 1497-1503 (2011).