8-Shogaol

8-Shogaol is a phenol that has been found in Z. officinale and has diverse biological activities. It is an inhibitor of TGF-beta-activated kinase 1 (TAK1, IC50 = 5.027 nM). 8-Shogaol is also an inhibitor of COX-2 (IC50 = 32 µM). It reduces IL-17-induced secretion of IL-8 from SW 982 synovial sarcoma cells and Tnf-alpha from RAW 264.7 macrophages when used at a concentration of 10 µM. 8-Shogaol (5 or 10 µM) decreases TNF-alpha-induced secretion of IL-6, IL-8, and chemokine (C-C motif) ligand 2 (CCL2) by, and reduces IL-17-induced migration and invasion of, primary human rheumatoid arthritis fibroblast-like synoviocytes. It inhibits migration and invasion induced by phorbol 12-myristate 13-acetate (PMA, Cay-10008014) in MDA-MB-231 breast cancer cells when used at a concentration of 10 µM. In vivo, 8-shogaol (30 mg/kg every three days) reduces paw thickness, as well as adjuvant-induced increases in joint space, synovial tissue proliferation, and cartilage damage, and improves gait without reducing body weight in a rat model of adjuvant-induced arthritis (AIA).Formal Name: 1-(4-hydroxy-3-methoxyphenyl)-4-dodecen-3-one. CAS Number: 36700-45-5. Molecular Formula: C19H28O3. Formula Weight: 304.4. Purity: >98%. Formulation: (Request formulation change), A solution in ethanol. Solubility: Ethanol: Soluble, Methanol: Soluble. SMILES: O=C(CCC1=CC=C(C(OC)=C1)O)C=CCCCCCCC. InChi Code: InChI=1S/C19H28O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-10,12,14-15,21H,3-8,11,13H2,1-2H3. InChi Key: LGZSMXJRMTYABD-UHFFFAOYSA-N. Origin: Plant/Zingiberis Rhizoma Recens.