Olomoucin

Base Information

• Chemical Name: Olomoucin
• CAS No.: 87414-49-1
• Molecular Formula: C₂₄H₂₄O₇
• Molecular Weight: 424.45
• Hs Code.: 29419000
• UNII: HKM4266XIK
• Wikidata: Q27279976
• Mol file: 87414-49-1.mol

Synonyms:olomoucin;HKM4266XIK;[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-methyl-5-oxofuran-2-carboxylate;methyl 4-hydroxy-2-[[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate;UNII-HKM4266XIK;SCHEMBL17508567;HB3820;Q27279976;2-FURANCARBOXYLIC ACID, 2,5-DIHYDRO-4-HYDROXY-2-((4-HYDROXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)METHYL)-3-(4-HYDROXYPHENYL)-5-OXO-, METHYL ESTER, (2R)-;ALPHA-OXO-BETA-(4-HYDROXYPHENYL)-GAMMA-(4-HYDROXY-M-3,3- DIMETHYLALLYLBENZYL)-GAMMA-METHOXYCARBONYL-GAMMA- BUTYROLACTONE

Chemical Property of Olomoucin

Chemical Property:

• Vapor Pressure: 2.22E-18mmHg at 25°C
• Melting Point: 74℃
• Boiling Point: 661.1°Cat760mmHg
• PKA: 8.59±0.40(Predicted)
• Flash Point: 228°C
• PSA: 113.29000
• Density: 1.342g/cm³
• LogP: 3.58690
• Sensitive.: Light Sensitive
• Solubility.: Soluble in ethanol at 25mg/ml or DMSO at 10mg/ml
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 424.15220310
• Heavy Atom Count: 31
• Complexity: 743

Purity/Quality:

99% ^*data from raw suppliers

ButyrolactoneI ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=CC(=C1)COC(=O)C2(C(=C(C(=O)O2)O)C3=CC=C(C=C3)O)C)O)C
• Isomeric SMILES: CC(=CCC1=C(C=CC(=C1)COC(=O)[C@]2(C(=C(C(=O)O2)O)C3=CC=C(C=C3)O)C)O)C
• Uses: Butyrolactone I is one of a family of three butyrolactones isolated from Aspergillus fumigatus, first reported in 1983. Butyrolactone I exhibits antitumor activity, inhibiting the cell cycle at the G1/S and G2/M transitions. Butyrolactone I is a selective inhibitor of cyclin-dependent kinases CDK1/cyclin B, CDK2 and CDK5, and is an important bioprobe for understanding the cellular roles of CDKs.

Technology Process of Olomoucin

There total 5 articles about Olomoucin 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:

α-oxo-β-(p-hydroxyphenyl)-γ-(p-hydroxybenzyl)-γ-methoxycarbonyl-γ-lactone (87414-44-6) → Butyrolactone I (65372-42-1,87414-49-1)

Guidance literature:

With potassium fluoride; dimethylallyl diphosphate; sodium carbonate; In water; at 30 ℃; for 3h; pH 8.0;

DOI:10.1248/cpb.31.1528

Reference yield:

4-hydroxyphenylpiruvic acid (156-39-8) → Butyrolactone I (65372-42-1,87414-49-1)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether / 0.08 h

2: sat. Na₂CO₃ / diethyl ether / 1 h / Ambient temperature

3: 40 mg / dimethylallyl-pyrophosphate (DMAPP), 1percent Na₂CO₃, KF / H₂O / 3 h / 30 °C / pH 8.0

With potassium fluoride; dimethylallyl diphosphate; sodium carbonate; In diethyl ether; water;

DOI:10.1248/cpb.31.1528

Reference yield:

methyl 2-oxo-3-(4-hydroxyphenyl)propionate (154722-74-4) → Butyrolactone I (65372-42-1,87414-49-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sat. Na₂CO₃ / diethyl ether / 1 h / Ambient temperature

2: 40 mg / dimethylallyl-pyrophosphate (DMAPP), 1percent Na₂CO₃, KF / H₂O / 3 h / 30 °C / pH 8.0

With potassium fluoride; dimethylallyl diphosphate; sodium carbonate; In diethyl ether; water;

DOI:10.1248/cpb.31.1528

upstream raw materials:

α-oxo-β-(p-hydroxyphenyl)-γ-(p-hydroxybenzyl)-γ-methoxycarbonyl-γ-lactone

4-hydroxyphenylpiruvic acid

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

butyrolactone IIa

Downstream raw materials:

methyl 4-acetoxy-2-(4-acetoxy-3-(3-methylbut-2-enyl)benzyl)-3-(4-acetoxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

Refernces

• 1、 Nitta,Fujita,Yoshimura,et al.. "Metabolic products of Aspergillus terreus. IX. Biosynthesis of butyrolactone derivatives isolated from strains IFO 8835 and 4100". . p. 1528 - 1533. Retrieved 2007/10/02.