Synonyms: (+)Terrein; Terrain
CAS Number: 582-46-7
Formula: C8H10O3
Formula Weight: 154.16
Linear Formula: C8H10O3
Purity: >=98% (HPLC)
Storage: -20C
UNSPSC Code: 12352200
Biochem/physiol Actions: Terrein is a bioactive fungal metabolite that 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 that 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.
Preparation Note: Terrein is soluble in water at 1-1.10 mg/ml and yields a clear, colorless solution. It is also soluble in DMSO. Hence, the product may be reconstituted in water or DMSO.
RIDADR: NONH for all modes of transport
WGK Germany: 3