An oxylipin, inhibitor of 5-LO, and active metabolite of γ-linolenic acid
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13(S)-HOTrE(γ)

Item No. 39610

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13S-hydroxy-6Z,9Z,11E-octadecatrienoic acid
CAS Number
74784-20-6
Synonyms
  • FA 18:3;O
  • 13(S)-hydroxy-cis-6,9-trans-11-γ-Octadecatrienoic Acid
  • 13(S)-hydroxy-γ-Octadecatrienoic Acid
  • 13(S)-hydroxy-γ-Linolenic Acid
  • 13(S)-hydroxy-6(Z),9(Z),11(E)-OTrE(γ)
Molecular Formula
C18H30O3
Formula Weight
294.4
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
236 nm
SMILES
CCCCC[C@@H](O)/C=C/C=C\C/C=C\CCCCC(O)=O
InChi Code
InChI=1S/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h4,6-7,9,12,15,17,19H,2-3,5,8,10-11,13-14,16H2,1H3,(H,20,21)/b6-4-,9-7-,15-12+/t17-/m0/s1
InChi Key
HNBLUNXZQNJFRB-KYLWABQHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

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    500 µg

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    1 mg

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    Product Description

    13(S)-HOTrE(γ) is an oxylipin, inhibitor of 5-lipoxygenase (5-LO; IC50 = 29 µM for the rat enzyme), and an active metabolite of the ω-6 fatty acid γ-linolenic acid (GLA; Item No. 90220).1,2,3 It is formed from GLA by 12-LO and 15-LO-2. Vitreous levels of 13(S)-HOTrE(γ) are decreased in patients with proliferative diabetic retinopathy.4 Levels of 13(S)-HOTrE(γ) are also decreased in the amniotic fluid of patients with clinical chorioamnionitis at term following spontaneous labor and in the plasma of patients with pulmonary hypertension.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Haviv, F., Ratajczyk, J.D., DeNet, R.W., et al. Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogues. J. Med. Chem. 30(2), 254-263 (1987).

    2. Hamberg, M. ω6-Oxygenation of 6,9,12-octadecatrienoic acid in human platelets. Biochem. Biophys. Res. Commun. 117, 593-600 (1983).

    3. Joshi, N., Hoobler, E.K., Perry, S., et al. Kinetic and structural investigations into the allosteric and pH effect on the substrate specificity of human epithelial 15-lipoxygenase-2. Biochemistry 52(45), 8026-8035 (2013).

    4. Zhao, T., Wang, Y., Guo, X., et al. Altered oxylipin levels in human vitreous indicate imbalance in pro-/anti-inflammatory homeostasis in proliferative diabetic retinopathy. Exp. Eye Res. 214, 108799 (2022).

    5. Maddipati, K.R., Romero, R., Chaiworapongsa, T., et al. Lipidomic analysis of patients with microbial invasion of the amniotic cavity reveals up-regulation of leukotriene B4. The FASEB Journal (2016).

    6. McNeill, J.N., Roshandelpoor, A., Alotaibi, M., et al. The association of eicosanoids and eicosanoid-related metabolites with pulmonary hypertension. Eur. Respir .J. 62(4), 2300561 (2023).

    Product Citations

    Delaplace, P., Fauconnier, M.-L., Sergeant, K., et al. Potato (Solanum tuberosum L.) tuber ageing induces changes in the proteome and antioxidants associated with the sprouting pattern. J. Exp. Bot. 604), 1273-1288 (2009).