TERREIN

Product Name: TERREIN
CAS No.: 582-46-7
Chemical Name: TERREIN
Synonyms: TERREIN;Terrain;NSC 29130;(+)Terrein;NSC-291308;(+) Terrein, NSC 291308;Terrein, Akt and ERK inhibitor;(4S,5R)-4,5-Dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one;(4S,5R)-4,5-Dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one;2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1E)-1-propen-1-yl-, (4S,5R)-
CBNumber: CB51443610
Molecular Formula: C8H10O3
Formula Weight: 154.16
MOL File: 582-46-7.mol

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TERREIN Property

Melting point:: 125-127℃
Boiling point:: 327.2±42.0 °C(Predicted)
Density: 1.449±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: H2O: soluble1-1.10 mg/mL, clear, colorless
pka: 11.77±0.60(Predicted)
form: A solid
biological source: Aspergillus terreus
Water Solubility: H2O: soluble 1-1.10mg/mL, clear, colorless
DMSO: soluble

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Safety

WGK Germany: 3
HS Code: 29419000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: T5705
Product name: Terrein
Purity: ≥98% (HPLC)
Packaging: 1mg
Price: $247
Updated: 2025/07/31

Cayman Chemical

Product number: 23496
Product name: Terrein
Purity: ≥98%
Packaging: 1mg
Price: $121
Updated: 2024/03/01

Cayman Chemical

Product number: 23496
Product name: Terrein
Purity: ≥98%
Packaging: 5mg
Price: $423
Updated: 2024/03/01

Cayman Chemical

Product number: 23496
Product name: Terrein
Purity: ≥98%
Packaging: 10mg
Price: $662
Updated: 2024/03/01

TRC

Product number: T548805
Product name: Terrein
Packaging: 2.5mg
Price: $160
Updated: 2021/12/16

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TERREIN Chemical Properties,Usage,Production

Uses

Terrein is a polar, substituted dihydrocyclopentenone first reported by Raistrick and colleagues in the 1930s and subsequently found in a number of Aspergillus and Penicillium species. For many years the biological profile and mode of action of terrein was unstudied; however, recent research showed that terrein reduces melanin synthesis by reducing tyrosinase production via ERK activation, followed by MITF down-regulation. Terrein also reduces human keratinocyte proliferation by inhibiting ERK and by decreasing the expression of cyclin B1 and Cdc2 complex.

Uses

Terrein (cas# 582-46-7) is a compound useful in organic synthesis.

Definition

ChEBI: Terrein is a polyol.

Biological Activity

Terrein is a bioactive fungal metabolite th at 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 th at 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.

TERREIN Preparation Products And Raw materials

Raw materials

Preparation Products

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TERREIN Suppliers

China 44 United Kingdom 3 United States 14 USA 1 Global 62

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582-46-7, TERREINRelated Search:

BATROXOBIN Aspergillus candidus Link Aspergillus fumigatu Aspergillus oryzae Aspergillus niger turkesterone ANTIOXIDANT 765 DIMEFURON 4,5-dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one (4R)-(+)-HYDROXY-2-CYCLOPENTEN-1-ONE TERREIN

TERREIN

(4S,5R)-4,5-Dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one

NSC-291308

(+) Terrein, NSC 291308

(4S,5R)-4,5-Dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one

NSC 29130

Terrain

2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1E)-1-propen-1-yl-, (4S,5R)-

(+)Terrein

Terrein, Akt and ERK inhibitor

582-46-7

Antibiotic