A polyphenol with diverse biological activities
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8-Shogaol

Item No. 40273

Technical Information
Formal Name
1-(4-hydroxy-3-methoxyphenyl)-4-dodecen-3-one
CAS Number
36700-45-5
Molecular Formula
C19H28O3
Formula Weight
Purity
≥98%
A 10 mg/ml solution in ethanol
Ethanol: SolubleMethanol: 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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    8-Shogaol is a phenol that has been found in Z. officinale and has diverse biological activities.1,2,3 It is an inhibitor of TGF-β-activated kinase 1 (TAK1; IC50 = 5.027 nM). 8-Shogaol is also an inhibitor of COX-2 (IC50 = 32 µM).2 It reduces IL-17-induced secretion of IL-8 from SW 982 synovial sarcoma cells and Tnf-α from RAW 264.7 macrophages when used at a concentration of 10 µM.1 8-Shogaol (5 or 10 µM) decreases TNF-α-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; Item No. 10008014) in MDA-MB-231 breast cancer cells when used at a concentration of 10 µM.3 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).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jo, S., Samarpita, S., Lee, J.S., et al8-Shogaol inhibits rheumatoid arthritis through targeting TAK1. Pharmacol. Res. 178, 106176 (2022).

    2. van Breemen, R.B., Tao, Y., and Li, W. Cyclooxygenase-2 inhibitors in ginger (Zingiber officinale). Fitoterapia 82(1), 38-43 (2011).

    3. Ling, H., Yang, H., Tan, S.H., et al6-Shogaol, an active constituent of ginger, inhibits breast cancer cell invasion by reducing matrix metalloproteinase-9 expression via blockade of nuclear factor-κB activation. Br. J. Pharmacol. 161(8), 1763-1777 (2010).