582-46-7

Usage

Uses

Used in Organic Synthesis:
TERREIN is used as a compound in organic synthesis for its unique chemical properties and reactivity, which can be utilized in the creation of various organic compounds.
Used in Pharmaceutical Applications:
TERREIN is used as a potential therapeutic agent for reducing melanin synthesis by decreasing tyrosinase production through ERK activation and MITF down-regulation. This application is particularly relevant in the treatment of hyperpigmentation and related skin conditions.
Additionally, TERREIN is used as an inhibitor of human keratinocyte proliferation by inhibiting ERK and decreasing the expression of cyclin B1 and Cdc2 complex. This property makes it a candidate for the development of treatments targeting skin disorders and conditions involving excessive cell proliferation.

InChI:InChI=1/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1

Upstream product

• 582-46-7 (+/-)-Isoterrein 
• 81279-59-6 C₁₃H₁₄O₂ 
• 20476-33-9 1α,4α-dibenzyloxy-2α,3α-epoxycyclopentane 
• 75-07-0 acetaldehyde 
• 19314-92-2 3,4-dihydro-6,8-dihydroxy-3-methylisochromen-1-one 
• 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 
• 126566-35-6 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 
• 81279-58-5 C₁₅H₂₀O₃ 
• 81279-57-4 C₁₃H₁₆O₄ 

Downstream Products

• 64-18-6 formic acid 
• 75-07-0 acetaldehyde 
• 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)

Biosynthesis of Fungal Metabolites. Terrein, a Metabolite of Aspergillus terreus Thom

Terrein, a metabolite of Aspergillus terreus Thom, is biosynthesised from 3,4-dihydro-6,8-dihydroxy-3-methylisocoumarin by contraction of an aryl ring.The direction of the ring contraction has been investigated using acetate as precursor.

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.