An internal standard for the quantification of (±)-10-hydroxy-12(Z)-octadecenoic acid
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Unlabeled Version(s)
37281(±)-10-hydroxy-12(Z)-Octadecenoic Acid
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(±)-10-hydroxy-12(Z)-Octadecenoic Acid-d5

Item No. 37282

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
10-hydroxyoctadec-12Z-enoic-17,17,18,18,18-d5 acid
Synonyms
  • 10-hydroxy-cis-12-Octadecenoic Acid-d5
Molecular Formula
C18H29D5O3
Formula Weight
303.5
Purity
≥95%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: 1 mg/mL
SMILES
OC(C/C=C\CCCC([2H])([2H])C([2H])([2H])[2H])CCCCCCCCC(O)=O
InChi Code
InChI=1S/C18H34O3/c1-2-3-4-5-8-11-14-17(19)15-12-9-6-7-10-13-16-18(20)21/h8,11,17,19H,2-7,9-10,12-16H2,1H3,(H,20,21)/b11-8-/i1D3,2D2
InChi Key
WVYIZGMCLSGZGG-PJKSMEJXSA-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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    25 µg

    $174

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    50 µg

    $329

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    100 µg

    $589

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    Product Description

    (±)-10-hydroxy-12(Z)-Octadecenoic acid-d5 is intended for use as an internal standard for the quantification of (±)-10-hydroxy-12(Z)-octadecenoic acid (Item No. 37281) by GC- or LC-MS. (±)-10-hydroxy-12(Z)-Octadecenoic acid is an oxylipin and a metabolite of linoleic acid (Item Nos. 90150 | 90150.1 | 21909).1 It is formed from linoleic acid by conjugated linoleic acid-hydrase (CLA-HY) as an intermediate in CLA biosynthesis and can also be produced from linoleic acid by gut microbiota. (±)-10-hydroxy-12(Z)-Octadecenoic acid (30 µM) inhibits LPS-induced nitric oxide (NO) production, ERK phosphorylation, and increases in inducible NO synthase (iNOS) levels in BV-2 microglia cells.2 It reduces TNF-α, NO2, and IL-10 levels in LPS-stimulated and -unstimulated isolated dendritic bone marrow cells when used at a concentration of 100 µM.3 (±)-10-hydroxy-12(Z)-Octadecenoic acid (100 µM) decreases LPS-induced maturation of dendritic cells in isolated mouse bone marrow cells.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kishino, S., Takeuchi, M., Park, S.-B., et al. Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition. Proc. Natl. Acad. Sci. USA 110(44), 17808-17813 (2013).

    2. Ikeguchi, S., Izumi, Y., Kitamura, N., et al. Inhibitory effect of the gut microbial linoleic acid metabolites, 10-oxo-trans-11-octadecenoic acid and 10-hydroxy-cis-12-octadecenoic acid, on BV-2 microglial cell activation. J. Pharmacol. Sci. 138(1), 9-15 (2018).

    3. Bergamo, P., Luongo, D., Miyamoto, J., et al. Immunomodulatory activity of a gut microbial metabolite of dietary linoleic acid, 10-hydroxy-cis-12-octadecenoic acid, associated with improved antioxidant/detoxifying defences. J. Funct. Foods 11, 192-202 (2014).