Butyrolactone II

Base Information

• Chemical Name: Butyrolactone II
• CAS No.: 87414-44-6
• Molecular Formula: C19H16O7
• Molecular Weight: 356.32600
• Hs Code.: 29419000
• DSSTox Substance ID: DTXSID301017691
• Nikkaji Number: J3.646.196I
• Wikidata: Q76415606
• Metabolomics Workbench ID: 133114
• ChEMBL ID: CHEMBL3753562
• Mol file: 87414-44-6.mol

Synonyms:Butyrolactone II;(4R)-Butyrolactone I;CHEMBL3753562;87414-44-6;Methyl (2~{r})-3-(4-Hydroxyphenyl)-2-[(4-Hydroxyphenyl)methyl]-4-Oxidanyl-5-Oxidanylidene-Furan-2-Carboxylate;XBU;DTXSID301017691;BDBM50453561;AKOS040734181;Methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-5-oxo-furan-2-carboxylate;HY-111238;CS-0034725;J3.646.196I;(R)-4-Hydroxy-3-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-5-oxo-2,5-dihydrofuran-2-carboxylic acid methyl ester;methyl (R)-4-hydroxy-2-(4-hydroxybenzyl)-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

Chemical Property of Butyrolactone II

Chemical Property:

• Melting Point: 91-94 °C
• Boiling Point: 640.5±55.0 °C(Predicted)
• PKA: 8.61±0.40(Predicted)
• PSA: 113.29000
• Density: 1.497±0.06 g/cm3(Predicted)
• LogP: 2.07820
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 356.08960285
• Heavy Atom Count: 26
• Complexity: 583

Purity/Quality:

>95% ^*data from raw suppliers

ButyrolactoneII ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(C(=C(C(=O)O1)O)C2=CC=C(C=C2)O)CC3=CC=C(C=C3)O
• Isomeric SMILES: COC(=O)[C@]1(C(=C(C(=O)O1)O)C2=CC=C(C=C2)O)CC3=CC=C(C=C3)O
• Description: Butyrolactone II is a butenolide fungal metabolite that has been found in A. terreus. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) and ABTS free radicals (EC50s = 11.5 and 68.5 μM, respectively). It inhibits 5-lipoxygenase (5-LO; IC50 = 21.43 μg/ml) and α-glucosidase (IC50 = 0.126 mM).
• Uses: Butyrolactone II is an antibiotic, a 5-LOX inhibitor and has shown DPPH radical-scavening activity.

Technology Process of Butyrolactone II

There total 7 articles about Butyrolactone II 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: 61.0%

methyl 2-oxo-3-(4-hydroxyphenyl)propionate (154722-74-4) → α-oxo-β-(p-hydroxyphenyl)-γ-(p-hydroxybenzyl)-γ-methoxycarbonyl-γ-lactone (87414-44-6)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃;

DOI:10.1039/b403052d

Reference yield:

butyrolactone IIa (87414-48-0) → α-oxo-β-(p-hydroxyphenyl)-γ-(p-hydroxybenzyl)-γ-methoxycarbonyl-γ-lactone (87414-44-6)

Guidance literature:

With S-(+)-adenosylmethionine; sodium carbonate; In water; at 30 ℃; for 3h;

DOI:10.1248/cpb.31.1528

Reference yield:

2-hydroxy-3-(4-hydroxyphenyl)-2-propenoic acid (10589-28-3) → α-oxo-β-(p-hydroxyphenyl)-γ-(p-hydroxybenzyl)-γ-methoxycarbonyl-γ-lactone (87414-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / DBU / dimethylformamide / 2.5 h / 0 °C

2: 61 percent / K₂CO₃ / acetone / 20 °C

With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; acetone;

DOI:10.1039/b403052d

upstream raw materials:

methyl 2-oxo-3-(4-hydroxyphenyl)propionate

butyrolactone IIa

2-hydroxy-3-(4-hydroxyphenyl)-2-propenoic acid

4-hydroxyphenylpiruvic acid

Downstream raw materials:

Butyrolactone I

4-(4-hydroxyphenyl)-5-(4-hydroxyphenylmethyl)-3-hydroxyfurane-2-one

butyrolactone IIa

3-Hydroxy-4-(4-hydroxy-phenyl)-5-(2-isopropyl-benzofuran-5-ylmethyl)-5H-furan-2-one