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T5705

Sigma-Aldrich

Terrein

from Aspergillus terreus, ≥98% (HPLC)

Synonym(s):

(+)Terrein, Terrain

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About This Item

Empirical Formula (Hill Notation):
C8H10O3
CAS Number:
582-46-7
Molecular Weight:
154.16
UNSPSC Code:
12352200
NACRES:
NA.77

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

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

T5705-1MG-PW:
T5705-BULK:
T5705-VAR:
T5705-1MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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