An oxylipin
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Isomer(s)
267689(S),10(S),13(S)-TriHOME
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9(S),12(S),13(S)-TriHOME

Item No. 10005143

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9S,12S,13S-trihydroxy-10E-octadecenoic acid
CAS Number
97134-11-7
Synonyms
  • (–)-Pinellic Acid
  • 9S,12S,13S-Pinellic Acid
Molecular Formula
C18H34O5
Formula Weight
330.5
Purity
≥98%
Formulation (Request formulation change)
A 200 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: soluble
SMILES
CCCCC[C@H](O)[C@@H](O)/C=C/[C@@H](O)CCCCCCCC(O)=O
InChi Code
InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1
InChi Key
MDIUMSLCYIJBQC-MVFSOIOZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

    $423

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    Product Description

    9(S),12(S),13(S)-TriHOME is a linoleic acid-derived oxylipin that has diverse biological activities.1,2,3,4 It has been found in various plants and is produced in human eosinophils in a 15-lipoxygenase-dependent, soluble epoxide hydrolase-independent manner.1,5 9(S),12(S)13(S)-TriHOME inhibits antigen-induced β-hexosaminidase release from RBL-2H3 mast cells (IC50 = 28.7 µg/ml).2 It inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia (IC50 = 40.95 µM).3 In vivo, 9(S),12(S),13(S)-TriHOME (1 g/animal) enhances the antiviral IgA and IgG antibody responses induced by a nasal influenza hemagglutinin (HA) vaccine by 5.2- and 2-fold, respectively, in mice.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamberg, M., and Hamberg, G. Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds: Sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid. Plant Physiol. 110(3), 807-815 (1996).

    2. Hong, S.S., and Oh, J.S. Inhibitors of antigen-induced degranulation of RBL-2H3 cells isolated from wheat bran. J. Korean Soc. Appl. Biol. Chem. 55, 69-74 (2012).

    3. Kim, C.S., Kwon, O.W., Kim, S.Y., et al. Five new oxylipins from Chaenomeles sinensis. Lipids 49(11), 1151-1159 (2014).

    4. Shirahata, T., Sunazuka, T., Yoshida, K., et al. Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids. Tetrahedron 62(40), 9483-9496 (2006).

    5. Fuchs, D., Tang, X., Johnsson, A.-K., et al. Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent process. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1865(4), 158611 (2020).