Stereochemistry | ACHIRAL |
Molecular Formula | C11H14O3 |
Molecular Weight | 194.2271 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(CCC(C)=O)=CC=C1O
InChI
InChIKey=OJYLAHXKWMRDGS-UHFFFAOYSA-N
InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3
Molecular Formula | C11H14O3 |
Molecular Weight | 194.2271 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Zingerone is one of the active phenolic components isolated from Zingiber officinale. Zingerone is primarily present in dry ginger, but cooking or drying also converts gingerol into zingerone by a retroaldol reaction. Chemically synthesized zingerone is vanillyl acetone, which is a member of the phenolic alkanone group, and its varied pharmacological properties include antioxidant, anti-inflammatory, and anticancer activities. Thus, zingeroneshowed strong anti-angiogenic activity via the inhibition of MMP-2 and MMP-9 during tumor progression. Zingerone was likely to be broad-spectrum anti-inflammatory agents in most organs that suppressed the activation of NF-κB, the production of IL-1β, and the infiltration of inflammatory cells in mice. Zingerone effectively inhibits 1,2-dimethylhydrazine-induced colon carcinogenesis in male Wistar rats. Zingerone possess radioprotective effects in laboratory animals and in cultured cells in vitro. Zingerone produced marked improvement in stress induced irritable bowel disorder, which could be attributed to the powerful antioxidant nature, direct effect on the intestinal smooth muscle and adaptogenic nature. Analysis of the qualities that constituted zingerone irritation found that the sensations produced are predominantly burning and warmth, making it qualitatively similar to capsaicin.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
To investigate whether zingerone regulates the activities of MMPs, gelatin-based zymography using conditioned media from Renca cells was performed. The gelatinase activities of MMP-2 and MMP-9 were increased under hypoxic conditions, but zingerone (1 and 2 mM) treatment decreased these activities. 1 or 2 mM of zingerone significantly decreased expression of MMP-2 in Renca cells.