131233-98-2

Upstream product

• 131149-30-9 (+/-)-trans-5-hydroxy-3-(E-1-propenyl)-4-(2-trimethylethoxy)-2-cyclopenten-1-one 
• 81279-60-9 (1R,5R)-((E)-4-Propenyl)-6-oxa-bicyclo[3.1.0]hex-3-en-2-one 
• 582-46-7 (+/-)-Isoterrein 
• 126566-35-6 6-(2-trimethylsilylethoxy)-2,3-dihydro-6H-pyran-3-one 
• 75-07-0 acetaldehyde 
• 62644-49-9 6-acetoxy-2H-pyran-3(6H)-one 
• 71443-31-7 6-t-butoxy-2,3-dihydro-6H-pyrano-3-one 
• 20476-33-9 1α,4α-dibenzyloxy-2α,3α-epoxycyclopentane 
• 131149-29-6 (2R,3S)-2-Hydroxy-5-phenylselanyl-4-((E)-propenyl)-3-(2-trimethylsilanyl-ethoxy)-cyclopentanone 
• 131149-28-5 (+/-)-trans-2-benzeneselenenyl-5-hydroxy-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one 
• 131149-33-2 5-(E-1-propenyl)-6-(2-trimethylsilylethoxy)-2,3-dihydro-6H-pyran-3-one 
• 126566-40-3 trans-5-hydroxy-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one 
• 131166-65-9 4-Phenylselanyl-5-((E)-propenyl)-6-(2-trimethylsilanyl-ethoxy)-dihydro-pyran-3-one 
• 131149-31-0 4-benzeneselenenyl-6-(2-trimethylsilylethoxy)-2,3-dihydro-6H-pyran-3-one 

Downstream Products

• 582-46-7 (+/-)-terrein 

Relevant academic research and scientific papers

Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts

Interleukin (IL)-6 is a proinflammatory cytokine that performs a wide variety of biological functions, including important roles in the progression of chronic inflammatory diseases such as periodontal disease. (+)-Terrein, a secondary bioactive fungal metabolite isolated from Aspergillus terreus, has various biological activities; however, its anti-inflammatory effects are still unknown. The purpose of this study was to examine the effect of synthetic (+)-terrein on IL-6 signaling and related protein production in human gingival fibroblasts. To our knowledge, this study is the first to report that synthetic (+)-terrein is not cytotoxic at concentrations less than 20 μM and suppresses IL-6/soluble IL-6 receptor (sIL-6R)-induced phosphorylation of signal transducer and activator of transcription-3, extracellular signal-regulated kinase 1/2, and c-jun N-terminal kinase 1/2 - signaling proteins that are downstream of IL-6 signaling. In addition, synthetic (+)-terrein suppresses IL-6/sIL-6R-induced vascular endothelial growth factor (VEGF) secretion in a concentration-dependent manner (p 0.01). These data suggest that synthetic (+)-terrein has potential anti-IL-6 signaling activity and suppresses VEGF-associated inflammatory disease progression.

Synthesis and melanin biosynthesis inhibitory activity of (±)-terrein produced by Penicillium sp. 20135

Terrein was isolated from Penicillium sp. 20135, prepared by a practical synthetic way, and evaluated first time for its melanin biosynthesis inhibitory activity. Terrein was isolated from Penicillium sp. 20135, prepared by a practical synthetic way, and evaluated first time for its melanin biosynthesis inhibitory activity.

A total synthesis of racemic and optically active terrein (trans-4,5-dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one)

Two routes to terrein (1), employing a novel ring contraction of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (5, 13) are described. Separation into enantiomers was carried out by classical resolution via diastereomeric camphanic acid ester intermediates (14, 15)

AN EFFICIENT STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-) TERREIN

Flash vacuum pyrolysis of functionalized tricyclo2,6>decenone epoxide 5, and acetals 3 and 4 affords cyclopentadienone epoxide 6 and acetals 10 and 8, respectively.These epoxides are suitable precursors for the synthesis of (+/-) terrein.