Terrein

Base Information

• Chemical Name: Terrein
• CAS No.: 582-46-7
• Molecular Formula: C8H10 O3
• Molecular Weight: 154.166
• Hs Code.: 29419000
• UNII: 3I47HPE16N
• DSSTox Substance ID: DTXSID101017469
• Nikkaji Number: J16.229I,J431.505G
• Wikipedia: Terrein
• Wikidata: Q27257243
• ChEMBL ID: CHEMBL506722
• Mol file: 582-46-7.mol

Synonyms:terrein

Chemical Property of Terrein

Chemical Property:

• Vapor Pressure: 1.55E-05mmHg at 25°C
• Melting Point: 125-127℃
• Boiling Point: 327.2°Cat760mmHg
• PKA: 11.77±0.60(Predicted)
• Flash Point: 165.9°C
• PSA: 57.53000
• Density: 1.449g/cm³
• LogP: -0.20660
• Storage Temp.: ?20°C
• Solubility.: H2O: soluble1-1.10 mg/mL, clear, colorless
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 228

Purity/Quality:

98% ^*data from raw suppliers

Terrein ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=CC1=CC(=O)C(C1O)O
• Isomeric SMILES: C/C=C/C1=CC(=O)[C@@H]([C@H]1O)O
• 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. Terrein (cas# 582-46-7) is a compound useful in organic synthesis.

Technology Process of Terrein

There total 47 articles about Terrein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(+/-)-trans-5-hydroxy-3-(E-1-propenyl)-4-(2-trimethylethoxy)-2-cyclopenten-1-one (131149-30-9,131233-97-1,131234-00-9) → (+/-)-terrein (582-46-7,54192-03-9,63903-20-8,63903-21-9,131233-98-2)

Guidance literature:

With zinc chloride diethyl ether; In dichloromethane; for 16h;

DOI:10.1016/S0957-4166(00)86329-6

Reference yield: 86.0%

(4S,5R)-4,5-bis[[tert-butyldimethylsilyl]oxy]-(1-(E)-propenyl)cyclopent-2-enone → (+)-terrein (582-46-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In water; acetonitrile; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1016/j.bmc.2014.07.047

Reference yield: 86.0%

(-)-(4S,5R)-5-hydroxy-3-(E-1-propenyl)-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one (131234-00-9) → (+)-terrein (582-46-7)

Guidance literature:

With zinc chloride diethyl ether; In dichloromethane; for 16h;

DOI:10.1016/S0957-4166(00)86329-6

upstream raw materials:

3,4-dihydro-6,8-dihydroxy-3-methylisochromen-1-one

(-)-(4S,5R)-5-hydroxy-3-(E-1-propenyl)-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one

[(4R,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclopent-1-enylmethyl]-phosphonic acid diethyl ester

acetaldehyde

Downstream raw materials:

(+/-)-terrein

formic acid

acetaldehyde

Refernces

• 1、 Mandai, Hiroki,Omori, Kazuhiro,Yamamoto, Daisuke,Tsumura, Toki,Murota, Kyouta,Yamamoto, Satoshi,Mitsudo, Koichi,Ibaragi, Soichiro,Sasaki, Akira,Maeda, Hiroshi,Takashiba, Shogo,Suga, Seiji. "Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts". . p. 5338 - 5344. Retrieved 2014/12/11.
• 2、 Kolb,Martin,Hoffmann. "A total synthesis of racemic and optically active terrein (trans-4,5-dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one)". . p. 237 - 250. Retrieved 2007/10/02.