Terrein
SIGMA/T5705 - from Aspergillus terreus, ≥98% (HPLC)
Synonym: (+)Terrein; Terrain
CAS Number: 582-46-7
Empirical Formula (Hill Notation): C8H10O3
Molecular Weight: 154.16
Linear Formula: C8H10O3
Product Type: Chemical
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| assay | ≥98% (HPLC) |
| biological source | Aspergillus terreus |
| InChI | 1S/C8H10O3/c1-2-3-5-4-6(9 |
| InChI key | MHOOPNKRBMHHEC-NSCUHMNNSA |
| Quality Level | 200  |
| SMILES string | OC1C(C(=O)C=C1C=CC)O |
| solubility | DMSO: soluble |
| H2O: soluble 1-1.10 mg/mL, clear, colorless | |
| storage condition | protect from light |
| storage temp. | −20°C |
| 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. |
| 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 | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (HPLC) |
| Storage Temp. | −20°C |
| UNSPSC | 12352200 |