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BioViotica
Terrein
130
CHF
CHF 130.00
In stock
BVT-0193-M0011 mgCHF 130.00
BVT-0193-M0055 mgCHF 420.00
BVT-0193-M01010 mgCHF 755.00
| Product Details | |
|---|---|
| Synonyms | NSC 291308; 4,5-Dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one |
| Product Type | Chemical |
| Properties | |
| Formula |
C8H10O3 |
| MW | 154.2 |
| CAS | 582-46-7 |
| Source/Host Chemicals | Isolated from Aspergillus terreus. |
| Purity Chemicals | ≥98% (HPLC) |
| Appearance | White to off-white solid. |
| Solubility | Soluble in methanol or DMSO. |
| Identity | Determined by 1H-NMR and UV. |
| InChi Key | MHOOPNKRBMHHEC-HZIBQTDNSA-N |
| Smiles | C\C=C\C1=CC(=O)[C@H](O)[C@H]1O |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Protect from light. |
| Use/Stability |
Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Antibacterial. Phytotoxin [3, 4 , 5].
- Melanogenesis inhibitor by reducing tyrosinase production via extracellular signal-regulated protein kinase (ERK) activation [4, 5].
- Keratinocyte and epidermis proliferation inhibitor [6, 9].
- Mycotoxin [7].
- Anti-inflammatory modulator in pulpal inflammation [8].
- Angiogenesis inhibitor through angiogenin secretion inhibition [10].
- Collagen-induced platelet aggregation inhibitor [11].
- Antioxidant agent that enhances osseointegration by decreasing the level of ROS and having a potentially synergistic effect on osteoblast differentiation [13].
- Proteasome inhibitor [12, 14].
Product References
- Studies in the biochemistry of micro-organisms: The metabolic products of Aspergillus terreus Thom. A new mould metabolic product-terrein: H. Raistrick & G. Smith; Biochem. J. 29, 606 (1935)
- The constitution and stereochemistry of Terrein: D.H.R. Barton & E. Miller; J. Chem. Soc. 1955, 1028 (1955)
- Bioactive metabolites from a marine-derived strain of the fungus Emericella variecolor: J. Malmstrom, et al.; J. Nat. Prod. 65, 364 (2002)
- Terrein: a new melanogenesis inhibitor and its mechanism: S.H. Park, et al.; Cell Mol. Life Sci. 61, 2878 (2004)
- Synthesis and melanin biosynthesis inhibitory activity of (+/-)-terrein produced by Penicillium sp. 20135: S. Lee, et al.; Bioorg. Med. Chem. Lett. 15, 471 (2005)
- Terrein, a fungal metabolite, inhibits the epidermal proliferation of skin equivatents: D.S. Kim, et al.; J. Dermatol. Sci. 46, 65 (2007)
- Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati: T. O. Larsen, et al.; Med. Mycol. 45, 225 (2007)
- Terrein reduces pulpal inflammation in human dental pulp cells: J.C. Lee, et al.; J. Endod. 34, 433 (2008)
- Terrein inhibits keratinocyte proliferation via ERK inactivation and G2/M cell cycle arrest: D.S. Kim, et al.; Exp. Dermatol. 17, 312 (2008)
- A new terrein glucoside, a novel inhibitor of angiogenin secretion in tumor angiogenesis: M. Arakawa, et al.; J. Antibiot. (Tokyo) 61, 442 (2008)
- Inhibitory effects of dihydroterrein and terrein isolated from Aspergillus novofumigatus on platelet aggregation: T. Hosoe, et al.; Mycotoxins 59, 75 (2009)
- Long-term suppression of tyrosinase by terrein via tyrosinase degradation and its decreased expression: S.H. Park, et al.; Exp. Dermatol. 18, 562 (2009)
- Enhancement of osteoblast biocompatibility on titanium surface with Terrein treatment: Y.H. Lee, et al.; Cell. Biochem. Funct. 28, 678 (2010)
- Studies on terrein as a new class of proteasome inhibitors: M. Demasi, et al.; J. Braz. Chem. Soc. 21, 299 (2010)
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