An internal standard for the quantification of 2-hydroxy oleic acid
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Unlabeled Version(s)
360442-hydroxy Oleic Acid
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2-hydroxy Oleic Acid-d17

Item No. 9004307

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(Z)-2-hydroxyoctadec-9-enoic-11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-d17 acid
CAS Number
1346606-40-3
Synonyms
  • FA 18:1;O-d17
  • 2-HOME-d17
  • 2-hydroxy-cis-9-Octadecenoic Acid-d17
  • α-hydroxy-cis-9-Octadecenoic Acid-d17
  • 2-hydroxy-9(Z)-OME-d-d17
  • 2-Hydroxyoctadecenoic Acid-d17
  • 2-OHOA-d17
Molecular Formula
C18H17D17O3
Formula Weight
315.6
Purity
≥99% deuterated forms (d1-d17)
Formulation
A solution in methyl acetate
Solubility(Learn about Variance in Solubility)
Chloroform: Soluble
SMILES
OC(C(O)=O)CCCCCCC=CC([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])(C([2H])([2H])[2H])[2H]
InChi Code
InChI=1S/C18H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h9-10,17,19H,2-8,11-16H2,1H3,(H,20,21)/i1D3,2D2,3D2,4D2,5D2,6D2,7D2,8D2
InChi Key
JBSOOFITVPOOSY-OISRNESJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    2-hydroxy Oleic acid-d17 is intended for use as an internal standard for the quantification of 2-hydroxy oleic acid (Item No. 36044) by GC- or LC-MS. 2-hydroxy Oleic acid is a synthetic monounsaturated hydroxylated fatty acid.1 It decreases the lamellar-to-hexagonal transition temperature of bovine liver phosphatidylethanolamine (PE) membranes by approximately 12.5°C when included at a 20:1 molar ratio of PE:2-hydroxy oleic acid. 2-hydroxy Oleic acid increases levels of protein kinase C α (PKCα) in and decreases proliferation of A549 non-small cell lung cancer (NSCLC) cells in a concentration-dependent manner. It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 75 and 200 mg/kg. 2-hydroxy Oleic acid has been used in the generation of liposomes.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Martínez, J., Vögler, O., Casas, J., et al. Membrane structure modulation, protein kinase Cα activation, and anticancer activity of minerval. Mol. Pharmacol. 67(2), 531-540 (2004).

    2. Olechowska, K., Mach, M., Hąc-Wydro, K., et al. Studies on the interactions of 2‑hydroxyoleic acid with monolayers and bilayers containing cationic lipid: Searching for the formulations for more efficient drug delivery to cancer cells. Langmuir 35(27), 9084-9092 (2019).