TERREIN Chemical Properties

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

pka

11.77±0.60(Predicted)

form 

A solid

biological source

Aspergillus terreus

Water Solubility 

H2O: soluble 1-1.10mg/mL, clear, colorless
DMSO: soluble

Safety Information

WGK Germany 

3

HS Code 

29419000

TERREIN Usage And Synthesis

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.

Uses

Terrein (cas# 582-46-7) is a compound useful in organic synthesis.

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 mammals, there are three melanocyte-specific enzymes: tyrosinase, tyrosinase-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 regulation, which is required for tyrosinase expression.

TERREIN(582-46-7)Related Product Information

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