Terrein
| Code | Size | Price |
|---|
| BVT-0193-M001 | 1 mg | £130.00 |
Quantity:
| BVT-0193-M005 | 5 mg | £385.00 |
Quantity:
| BVT-0193-M010 | 10 mg | £685.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Further Information
Alternate Names/Synonyms:
NSC 291308; 4,5-Dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one
Appearance:
White to off-white solid.
CAS:
582-46-7
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light.
Hazards:
H302, H319
InChi:
InChi=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1
InChiKey:
MHOOPNKRBMHHEC-HZIBQTDNSA-N
Long Description:
Chemical. CAS: 582-46-7. Formula: C8H10O3. MW: 154.2. Isolated from Aspergillus terreus. Antibacterial. Phytotoxin. Melanogenesis inhibitor by reducing tyrosinase production via extracellular signal-regulated protein kinase (ERK) activation. Keratinocyte and epidermis proliferation inhibitor. Mycotoxin. Anti-inflammatory modulator in pulpal inflammation. Angiogenesis inhibitor through angiogenin secretion inhibition. Collagen-induced platelet aggregation inhibitor. Antioxidant agent that enhances osseointegration by decreasing the level of ROS and having a potentially synergistic effect on osteoblast differentiation. Proteasome inhibitor.
MDL:
MFCD09752761
Molecular Formula:
C8H10O3
Molecular Weight:
154.2
Package Type:
Plastic Vial
Precautions:
P270, P280, P301, P312, P305, P351, P338
Product 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].
Purity:
>98% (HPLC)
Signal word:
Warning
SMILES:
CC=CC1=CC(=O)[C@H](O)[C@H]1O
Solubility Chemicals:
Soluble in methanol or DMSO.
Source / Host:
Isolated from Aspergillus terreus.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.
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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