582-46-7

Basic information

• Product Name: TERREIN
• Synonyms: TERREIN;(4S,5R)-4,5-Dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one;NSC-291308;(+) Terrein, NSC 291308;(4S,5R)-4,5-Dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one;NSC 29130;Terrain
• CAS NO: 582-46-7
• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 154.164
• Product Categories: Antibiotic
• Mol File: 582-46-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 125-127℃
• Boiling Point: 327.2°Cat760mmHg
• Flash Point: 165.9°C
• Appearance: /
• Density: 1.449g/cm³
• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.713
• Storage Temp.: ?20°C
• Solubility: H2O: soluble1-1.10 mg/mL, clear, colorless
• PKA: 11.77±0.60(Predicted)
• CAS DataBase Reference: TERREIN(CAS DataBase Reference)
• NIST Chemistry Reference: TERREIN(582-46-7)
• EPA Substance Registry System: TERREIN(582-46-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 582-46-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 582-46-7 differently. You can refer to the following data:
1. Terrein is a polar, substituted dihydrocyclopentenone first reported by Raistrick and colleagues in the 1930s and subsequently found in a number of Aspergillus and Penicillium species. For many years the biological profile and mode of action of terrein was unstudied; however, recent research showed that terrein reduces melanin synthesis by reducing tyrosinase production via ERK activation, followed by MITF down-regulation. Terrein also reduces human keratinocyte proliferation by inhibiting ERK and by decreasing the expression of cyclin B1 and Cdc2 complex.
2. Terrein (cas# 582-46-7) is a compound useful in organic synthesis.

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

• 81279-60-9 (1R,5R)-((E)-4-Propenyl)-6-oxa-bicyclo[3.1.0]hex-3-en-2-one 
• 131149-30-9 (+/-)-trans-5-hydroxy-3-(E-1-propenyl)-4-(2-trimethylethoxy)-2-cyclopenten-1-one 
• 124224-84-6 [(4R,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclopent-1-enylmethyl]-phosphonic acid diethyl ester 
• 75-07-0 acetaldehyde 
• 131234-00-9 (-)-(4S,5R)-5-hydroxy-3-(E-1-propenyl)-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one 
• 19314-92-2 3,4-dihydro-6,8-dihydroxy-3-methylisochromen-1-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 
• 126566-35-6 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 

Downstream Products

• 582-46-7 (+/-)-terrein 
• 75-07-0 acetaldehyde 
• 64-18-6 formic acid 

Relevant articles and documents

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.

Synthese von (+)-Terrein aus L-Weinsaeure

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