T5705
Terrein
from Aspergillus terreus, ≥98% (HPLC)
Synonym(s):
(+)Terrein, Terrain
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
biological source
Aspergillus terreus
assay
≥98% (HPLC)
storage condition
protect from light
solubility
H2O: soluble 1-1.10 mg/mL, clear, colorless, DMSO: soluble
storage temp.
−20°C
Quality Level
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.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Yanqing Wu et al.
Oncology letters, 13(4), 2805-2810 (2017-04-30)
Terrein is a bioactive fungal metabolite isolated from
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