T5705

Terrein

from Aspergillus terreus, ≥98% (HPLC)

• Synonym(e): (+)Terrein, Terrain
• Empirische Formel (Hill-System): C₈H₁₀O₃
• CAS-Nummer: 582-46-7
• Molekulargewicht: 154.16
• UNSPSC-Code: 12352200
• NACRES: NA.77

Eigenschaften

• Biologische Quelle: Aspergillus terreus
• Qualitätsniveau: 200
• Assay: ≥98% (HPLC)
• Lagerbedingungen: protect from light
• Löslichkeit: H₂O: soluble 1-1.10 mg/mL, clear, colorless; DMSO: soluble
• Lagertemp.: −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+
• InChIKey: MHOOPNKRBMHHEC-NSCUHMNNSA-N

Beschreibung

Biochem./physiol. Wirkung

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.

Angaben zur Herstellung

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.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable