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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

9(S)-HpOTrE Exclusive

Cayman Chemical Item Number 45120

(CAS 111004-08-1)

9(S)-HpOTrE (CAS 111004-08-1)

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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

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 Trans I 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., 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., 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. Inactivation of potato lipoxygenase by hydroperoxy acids as suicide substrates. Biochem Biophys Res Commun 164 1384-1390 (1989).

Formal Name 9S-​hydroperoxy-​10E,​12Z,​15Z-​octadecatrienoic acid
CAS Number 111004-08-1
Molecular Formula C18H30O4
Formula Weight 310.4
Formulation A solution in ethanol
Purity ≥98%
λmax 236 nm
ε 23
Stability 6 months
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CC/C=C\C/C=C\C=C/C(OO)​CCCCCCCC(=O)​O

Background Reading

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).

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).

Sok, D., 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).

Sok, D., 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).

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).

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 Trans I 567-575 (1991).

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

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9(S)-HpOTrE is available in the following screening library:

Size Price Quantity Subtotal
100 µg $42.00 $0.00
500 µg $189.00 $0.00
1 mg $336.00 $0.00
5 mg $1,470.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-11. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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5-Lipoxygenase (potato)
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9(S)-HOTrE
α-Linolenic Acid
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