T5705

Terrein

from Aspergillus terreus, ≥98% (HPLC)

• Synonym(s): (+)Terrein, Terrain
• Empirical Formula (Hill Notation): C₈H₁₀O₃
• CAS Number: 582-46-7
• Molecular Weight: 154.16
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• biological source: Aspergillus terreus
• Quality Level: 200
• Assay: ≥98% (HPLC)
• storage condition: protect from light
• solubility: H₂O: soluble 1-1.10 mg/mL, clear, colorless; DMSO: soluble
• storage temp.: −20°C
• SMILES string: OC1C(C(=O)C=C1\C=C\C)O
• InChI: 1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+
• InChI key: MHOOPNKRBMHHEC-NSCUHMNNSA-N

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable