2H-Pyran-2-one, 4-hydroxy-6-(2-oxoheptyl)-

Base Information

• Chemical Name: 2H-Pyran-2-one, 4-hydroxy-6-(2-oxoheptyl)-
• CAS No.: 327175-05-3
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.257
• Mol file: 327175-05-3.mol

Synonyms:HTAL;hexanoyltriacetic acid lactone;

Chemical Property of 2H-Pyran-2-one, 4-hydroxy-6-(2-oxoheptyl)-

Chemical Property:

• Boiling Point: 363.0±42.0 °C(Predicted)
• PSA: 67.51000
• Density: 1.175±0.06 g/cm3(Predicted)
• LogP: 2.03730

Purity/Quality:

4-Hydroxy-6-(2-oxoheptyl)-2H-pyran-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Hydroxy-6-(2-oxoheptyl)-2H-pyran-2-one is a product of Type III Polyketide Synthases in Mycobacterium tuberculosis.

Technology Process of 2H-Pyran-2-one, 4-hydroxy-6-(2-oxoheptyl)-

There total 5 articles about 2H-Pyran-2-one, 4-hydroxy-6-(2-oxoheptyl)- 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: 54.0%

S-2-acetamidoethyl hexanethioate → 4-hydroxy-6-pentyl-2H-pyrone (81017-02-9) + 4-hydroxy-6-(2-oxoheptyl)-2-pyrone (327175-05-3)

Guidance literature:

With 1,4-dithio-D,L-threitol; chalcone synthase, immobilized onto Ni-nitrilotriacetic acid agarose; malonyl-CoA synthetase, immobilized onto glutathione-sepharose; sodium malonate; adenosine 5'-triphosphate disodium salt; coenzyme A; magnesium chloride; at 22 ℃; for 72h; pH=7.5; Tris-HCl buffer; Enzymatic reaction;

DOI:10.1021/ol901243e

Reference yield:

malonyl coenzyme A + hexanoyl-CoA ester (21708-76-9) → 4-hydroxy-6-pentyl-2H-pyrone (81017-02-9) + 4-hydroxy-6-(2-oxoheptyl)-2-pyrone (327175-05-3)

Guidance literature:

With type III polyketide synthase RppA from S_. griseus; 2-hydroxyethanethiol; In various solvent(s); at 37 ℃; for 2h; pH=7.5;

DOI:10.1021/ja0441559

Reference yield:

S-(hydrogen malonyl)coenzyme A (524-14-1) + S-hexanoyl-coenzyme-A (5060-32-2,21708-76-9) → 4-hydroxy-6-pentyl-2H-pyrone (81017-02-9) + 4-hydroxy-6-(2-oxoheptyl)-2-pyrone (327175-05-3)

Guidance literature:

S-(hydrogen malonyl)coenzyme A; S-hexanoyl-coenzyme-A; With recombinant N-His-tagged hexaketide synthase of Drosophyllum lusitanicum Link; pH=7.0; aq. buffer; Enzymatic reaction;

Acidic aq. solution;

DOI:10.1016/j.phytochem.2008.03.013

upstream raw materials:

hexanoyl-CoA ester

malonyl-CoA

hexanoyl-CoA

S-(hydrogen malonyl)coenzyme A

Refernces

• 1、 Matsuzawa, Miku,Katsuyama, Yohei,Funa, Nobutaka,Horinouchi, Sueharu. "Alkylresorcylic acid synthesis by type III polyketide synthases from rice Oryza sativa". experimental part. p. 1059 - 1067. Retrieved 2011/03/20.
• 2、 Jindaprasert, Aphacha,Springob, Karin,Schmidt, Juergen,De-Eknamkul, Wanchai,Kutchan, Toni M.. "Pyrone polyketides synthesized by a type III polyketide synthase from Drosophyllum lusitanicum". experimental part. p. 3043 - 3053. Retrieved 2009/04/11.