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9(S),12(S),13(S)-TriHOME

(Synonyms: (–)-Pinellic Acid, 9S,12S,13S-Pinellic Acid) 目录号 : GC46753

An oxylipin

9(S),12(S),13(S)-TriHOME Chemical Structure

Cas No.:97134-11-7

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100 μg
¥5,396.00
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产品描述

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

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 acidPlant 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 branJ. Korean Soc. Appl. Biol. Chem.5569-74(2012) 3.Kim, C.S., Kwon, O.W., Kim, S.Y., et al.Five new oxylipins from Chaenomeles sinensisLipids49(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 acidsTetrahedron62(40)9483-9496(2006) 5.Fuchs, D., Tang, X., Johnsson, A.-K., et al.Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent processBiochim. Biophys. Acta Mol. Cell Biol. Lipids1865(4)158611(2020)

Chemical Properties

Cas No. 97134-11-7 SDF
别名 (–)-Pinellic Acid, 9S,12S,13S-Pinellic Acid
Canonical SMILES CCCCC[C@H](O)[C@@H](O)/C=C/[C@@H](O)CCCCCCCC(O)=O
分子式 C18H34O5 分子量 330.5
溶解度 Ethanol: soluble 储存条件 Store at -20°C
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10 mM 0.3026 mL 1.5129 mL 3.0257 mL
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