- Terrein
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- $296.00
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2026-07-15
- CAS:582-46-7
- Purity:
- Supply Ability: 10g
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| | TERREIN Basic information |
| Product Name: | TERREIN | | Synonyms: | 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)- | | CAS: | 582-46-7 | | MF: | C8H10O3 | | MW: | 154.16 | | EINECS: | | | Product Categories: | Antibiotic | | Mol File: | 582-46-7.mol |  |
| | TERREIN Chemical Properties |
| 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 | | Cosmetics Ingredients Functions | SKIN CONDITIONING | | 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 | | SMILES | OC1C(C(=O)C=C1\C=C\C)O |
| WGK Germany | 3 | | HS Code | 29419000 | | Storage Class | 11 - Combustible Solids |
| | TERREIN Usage And Synthesis |
| Uses | Terrein (cas# 582-46-7) is a compound useful in organic synthesis. | | 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. | | 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 |
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