A racemic mixture of 10(R)-hydroxy-12(Z)-octadecenoic acid and 10(S)-hydroxy-12(Z)-octadecenoic acid
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Labeled Version(s)
37282(±)-10-hydroxy-12(Z)-Octadecenoic Acid-d5
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(±)-10-hydroxy-12(Z)-Octadecenoic Acid

Item No. 37281

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
10-hydroxy-12Z-octadecenoic acid
CAS Number
34932-12-2
Synonyms
  • 12(Z)-10-HOME
  • 10-hydroxy-cis-12-Octadecenoic Acid
Molecular Formula
C18H34O3
Formula Weight
298.5
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: 1 mg/ml
SMILES
OC(C/C=C\CCCCC)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-
InChi Key
WVYIZGMCLSGZGG-FLIBITNWSA-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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    500 µg

    $33

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    1 mg

    $63

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    5 mg

    $278

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    Product Description

    (±)-10-hydroxy-12(Z)-Octadecenoic acid is a racemic mixture of 10(R)-hydroxy-12(Z)-octadecenoic acid and 10(S)-hydroxy-12(Z)-octadecenoic acid. 10(S)-hydroxy-12(Z)-Octadecenoic acid, also known as HYA™, is a gut microbiome metabolite of linoleic acid (Item Nos. 90150 | 90150.1 | 21909) that is formed by conjugated linoleic acid hydrase (CLA-HY) as an intermediate in CLA biosynthesis.1,2 10(S)-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.3 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.4 10(S)-hydroxy-12(Z)-Octadecenoic acid (100 µM) decreases LPS-induced maturation of the dendritic cell population within isolated mouse bone marrow cells. It induces calcium mobilization in HEK293 cells expressing the human free fatty acid receptor GPR40 or GPR120 (EC50s = 7.51 and 8.1 µM, respectively).5 In vivo, 10(S)-hydroxy-12(Z)-octadecenoic acid (1 g/kg) increases GLP-1 release and reduces body weight in a mouse model of high-fat diet-induced obesity.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takeuchi, M., Kishino, S., Hirata, A., et al. Characterization of the linoleic acid Δ9 hydratase catalyzing the first step of polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a. J. Biosci. Bioeng. 119(6), 636-641 (2015).

    2. 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).

    3. 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).

    4. 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).

    5. Miyamoto, J., Igarashi, M., Watanabe, K., et al. Gut microbiota confers host resistance to obesity by metabolizing dietary polyunsaturated fatty acids. Nat. Commun. 10(1), 4007 (2019).