223801-42-1

Basic information

• Product Name: 2-Butanone, 4-[3-methoxy-4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-
• CAS NO: 223801-42-1
• Molecular Formula: C16H22O4
• Molecular Weight: 278.348
• Mol File: 223801-42-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Butanone, 4-[3-methoxy-4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butanone, 4-[3-methoxy-4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-(223801-42-1)
• EPA Substance Registry System: 2-Butanone, 4-[3-methoxy-4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-(223801-42-1)

Safety Data

• Hazardous Substances Data: 223801-42-1(Hazardous Substances Data)

Upstream product

• 121-33-5 vanillin 
• 896460-67-6 C₁₃H₁₈O₄ 
• 124-63-0 methanesulfonyl chloride 
• 1080-12-2 Dehydrozingerone 
• 110-87-2 3,4-dihydro-2H-pyran 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 61152-59-8 4-hydroxy-4-(4-hydroxy-3-methoxyphenyl)butan-2-one 

Downstream Products

• 336784-92-0 5-hydroxy-1-[3-methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-dodecan-3-one 
• 104186-05-2 trans-10-shogaol 
• 36700-45-5 [8]-shogaol 
• 863780-78-3 (E)-[5]-shogaol 
• 23513-13-5 [6]-shogaol 

Relevant articles and documents

Combined treatment with zingerone and its novel derivative synergistically inhibits TGF-β1 induced epithelial-mesenchymal transition, migration and invasion of human hepatocellular carcinoma cells

The epithelial–mesenchymal transition (EMT) is an important cellular process during which polarized epithelial cells become motile mesenchymal cells, which promote cancer metastasis. Ginger, the rhizome of Zingiber officinale, is extensively used in cooking worldwide and also as a traditional medicinal herb with antioxidant, anti-inflammatory and anticancer properties. Several pungent compounds have been identified in ginger, including zingerone, which has anticancer potential. However, the role of zingerone in EMT is unclear. We investigated the synergistic effect of zingerone and its derivative on EMT. Transforming growth factor-beta 1 (TGF-β1) induces the EMT to promote hepatocellular carcinoma metastasis, including migration and invasion. To understand the repressive role of the combination of zingerone and its derivative (ZD 2) in hepatocellular carcinoma metastasis, we investigated the potential use of each compound of ginger, such as zingerone, ZD 2 and 6-shogaol, or the mixture of zingerone and ZD 2 (ZD 2-1) as inhibitors of TGF-β1 induced EMT development in SNU182 hepatocellular carcinoma cells in vitro. We show that ZD 2-1, but not zingerone, ZD 2 and 6-shogaol significantly increased expression of the epithelial marker E-cadherin and repressed Snail upregulation and expression of the mesenchymal marker N-cadherin during initiation of the TGF-β1 induced EMT. In addition, ZD 2-1 inhibited the TGF-β1 induced increase in cell migration and invasion of SNU182 hepatocellular carcinoma cells. Furthermore, ZD 2-1 significantly inhibited TGF-β1 regulated matrix metalloproteinase-2/9 and activation of Smad2/3. We also found that ZD 2-1 inhibited nuclear translocation of NF-κB, activation of p42/44 MAPK/AP1 signaling pathway in the TGF-β1 induced EMT. Our findings provide new evidence that combined treatment with ZD 2, novel zingerone derivative, and zingerone synergistically suppresses hepatocellular carcinoma metastasis in vitro by inhibiting the TGF-β1 induced EMT.

Side-chain length is important for shogaols in protecting neuronal cells from β-amyloid insult

Ten shogaols were synthesized to evaluate the importance of the side-chain length in protecting cells from βA(1-42) insult using PC12 rat pheochromocytoma and IMR-32 human neuroblastoma cells. The compounds cell protectivity against βA insult was demonstrated using 3-[4,5- dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) reduction assay. The efficacy of cell protection from βA insult by these shogaols was shown to improve as the length of the side chain increase.