| Identification | Back Directory | [Name]
TERREIN | [CAS]
582-46-7 | [Synonyms]
TERREIN
Terrain
NSC 29130
(+)Terrein
NSC-291308
(+) Terrein, NSC 291308
(4S,5R)-4,5-Dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one
(4S,5R)-4,5-Dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one
2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1E)-1-propen-1-yl-, (4S,5R)- | [Molecular Formula]
C8H10O3 | [MOL File]
582-46-7.mol | [Molecular Weight]
154.164 |
| Chemical Properties | Back Directory | [Melting point ]
125-127℃ | [Boiling point ]
327.2±42.0 °C(Predicted) | [density ]
1.449±0.06 g/cm3(Predicted) | [storage temp. ]
?20°C | [solubility ]
H2O: soluble1-1.10 mg/mL, clear, colorless | [form ]
A solid | [pka]
11.77±0.60(Predicted) | [biological source]
Aspergillus terreus | [Water Solubility ]
H2O: soluble 1-1.10mg/mL, clear, colorless
DMSO: soluble |
| Hazard Information | Back Directory | [Uses]
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. | [Definition]
ChEBI: Terrein is a polyol. | [Biological Activity]
Terrein is a bioactive fungal metabolite th at has plant growth inhibition and antibacterial activities. Terrein reduces melanin levels in a dose-dependent manner as well as tyrosinase protein production. In mammalsthere are three melanocyte-specific enzymes: tyrosinasetyrosinase-related protein-1 (TRP-1)and TRP-2 th at are involved in tyrosine conversion into melanin (melanogenesis). Terrein inhibits melanin synthesis by reducing tyrosinase production via extracellular signal-regulated protein kinase (ERK) activation. ERK activation is followed by microphthalmia-associated transcription factor (MITF) down regulationwhich is required for tyrosinase expression. |
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