An agonist of BLT2
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12(S)-HHTrE

Item No. 34590

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12S-hydroxy-5Z,8E,10E-heptadecatrienoic acid
CAS Number
54397-84-1
Synonyms
  • 12(S)-HHT
Molecular Formula
C17H28O3
Formula Weight
280.4
Purity
≥95%
Formulation (Request formulation change)
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
232 nm
SMILES
CCCCC[C@H](O)/C=C/C=C/C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1
InChi Key
KUKJHGXXZWHSBG-WBGSEQOASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $134

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    50 µg

    $253

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    100 µg

    $477

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    250 µg

    $1,058

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    Product Description

    12(S)-HHTrE is a product of the cyclooxygenase (COX) pathway and one of the primary arachidonic acid metabolites of human platelets.1 It is biosynthesized by thromboxane (TXA2) synthase from prostaglandin H2 (PGH2) concurrently with TXA2. 12(S)-HHTrE is a natural lipid agonist of the leukotriene B2 receptor BLT2 in vivo that induces chemotaxis of mast cells and accelerates wound closure.2,3 12(S)-HHTrE is avidly oxidized to 12-oxoHTrE by porcine 15-hydroxy PGDH.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Diczfalusy, U., Falardeau, P., and Hammarström, S. Conversion of prostaglandin endoperoxides to C17-hydroxy acids catalyzed by human platelet thromboxane synthase. FEBS Lett. 84, 271-274 (1977).

    2. Okuno, T., Iizuka, Y., Okazaki, H., et al. 12(S)-hydroxyheptadeca-5Z, 8E, 10E-trienoic acid is a natural ligand for leukotriene B4 receptor 2. J. Exp. Med. 205(4), 759-766 (2008).

    3. Liu, M., Saeki, K., Matsunobu, T., et al. 12-hydroxyheptadecatrienoic acid promotes epidermal wound healing by accelerating keratinocyte migration via the BLT2 receptor. J. Exp. Med. 211(6), 1063-1078 (2014).

    4. Liu, Y., Yoden, K., Shen, R.F., et al. 12-L-Hydroxy-5,8,10-heptadecatrienoic acid (HHT) is an excellent substrate for NAD+-dependent 15-hydroxyprostaglandin dehydrogenase. Biochem. Biophys. Res. Commun. 129, 268-274 (1985).

    Product Citations

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. The FASEB Journal 35(6), e21666 (2021).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Okuno, T., and Yokomizo, T. Biological functions of 12(S)-hydroxyheptadecatrienoic acid as a ligand of leukotriene B4 receptor 2. Inflamm. Regen. 38, 29 (2018).

    Sarper, M., Allen, M.D., Gomm, J., et al. Loss of MMP-8 in ductal carcinoma in situ (DCIS)-associated myoepithelial cells contributes to tumour promotion through altered adhesive and proteolytic function. Breast Cancer Res. 19(1), 33 (2017).