A 5-LO product derived from α-linolenic acid
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9(S)-HpOTrE

Item No. 45120

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9S-hydroperoxy-10E,12Z,15Z-octadecatrienoic acid
CAS Number
111004-08-1
Molecular Formula
C18H30O4
Formula Weight
310.4
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: >50 mg/ml (from 13(S)-HODE)DMSO: >50 mg/ml (from 13(S)-HODE)Ethanol: >50 mg/ml (from 13(S)-HODE)PBS pH 7.2: >1 mg/ml (from 13(S)-HODE)
λmax
236 nm
SMILES
CC/C=C\C/C=C\C=C\[C@@H](OO)CCCCCCCC(O)=O
InChi Code
InChI=1S/C18H30O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h3-4,6,8,11,14,17,21H,2,5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/b4-3-,8-6-,14-11+
InChi Key
RWKJTIHNYSIIHW-CUHSZNQNSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    100 µg

    $121

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    500 µg

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    1 mg

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    Product Description

    9(S)-HpOTrE is a monohydroperoxy polyunsaturated fatty acid produced by the action of 5-lipoxygenase (5-LO) on α-linolenic acid.1 It can be further metabolized to colnelenic acid by a divinyl ether synthase activity found in garlic and potato microsomal fractions.2,3 9(S)-HpOTrE also serves as a substrate for further oxidation by both soybean and potato LOs, resulting in the formation of 9,16-dihydroperoxy acid.4,5 The suicide inactivation of LOs when 9(S)-HpOTrE is used as a substrate is thought to occur via formation of an unstable epoxide.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Galliard, T., and Phillips, D.R. Lipoxygenase from potato tubers. Partial purification and properties of an enzyme that specifically oxygenates the 9-position of linoleic acid. Biochem. J. 124, 431-438 (1971).

    2. Crombie, L., Morgan, D.O., and Smith, E.H. An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: The origin of shorter chain aldehydes. J. Chem. Soc. Perkin 1 567-575 (1991).

    3. Grechkin, A.N., and Hamberg, M. Divinyl ether synthase from garlic (Allium sativum L.) bulbs: Sub-cellular localization and substrate regio- and stereospecificity. FEBS Lett. 388, 112-114 (1996).

    4. Sok, D.E., and Kim, M.R. Enzymatic formation of 9,16-dihydro(pero)xyoctadecatrienoic acid isomers from α-linolenic acid. Arch. Biochem. Biophys. 277, 86-93 (1990).

    5. Grechkin, A.N., Kuramshin, R.A., Safonova, E.Y., et al. Double hydroperoxidation of α-linolenic acid by potato tuber lipoxygenase. Biochim. Biophys. Acta 1081, 79-84 (1991).

    6. Sok, D.E., and Kim, M.R. The possible role of 9(S)-hydroperoxyoctadecatrienoic acid as a suicide substrate of soybean lipoxygenase. Biochem. Biophys. Res. Commun. 162, 1357-1362 (1989).

    7. Kim, M.R., Kim, S.H., and Sok, D.E. Inactivation of potato lipoxygenase by hydroperoxy acids as suicide substrates. Biochem. Biophys. Res. Commun. 164, 1384-1390 (1989).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).