Imperatorin

Base Information

• Chemical Name: Imperatorin
• CAS No.: 482-44-0
• Deprecated CAS: 70102-00-0
• Molecular Formula: C16H14O4
• Molecular Weight: 270.285
• Hs Code.: 29419090
• European Community (EC) Number: 207-581-1
• NSC Number: 402949
• UNII: K713N25C78
• DSSTox Substance ID: DTXSID8048737
• Nikkaji Number: J25.135F
• Wikipedia: Imperatorin
• Wikidata: Q1649534
• NCI Thesaurus Code: C63672
• Pharos Ligand ID: PSM3XMRCLX2A
• Metabolomics Workbench ID: 46512
• ChEMBL ID: CHEMBL453805
• Mol file: 482-44-0.mol

Synonyms:5-hydroxy-8-(1,1-dimethylallyl)psoralen;8-isoamylenoxypsoralen;imperatorin

Chemical Property of Imperatorin

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 3.13E-08mmHg at 25°C
• Melting Point: 98-100 °C
• Refractive Index: 1.606
• Boiling Point: 448.319 °C at 760 mmHg
• Flash Point: 224.936 °C
• PSA: 52.58000
• Density: 1.243 g/cm³
• LogP: 3.88420
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥5mg/mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 436

Purity/Quality:

99% ^*data from raw suppliers

Imperatorin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C
• Description: Imperatorin is a kind of furocoumarin and phytochemical that present in citrus fruits. It could be isolated from Urena lobata L. (Malvaceae). It is biosynthesized from Umbelliferae in vivo. It has been found that it has anti-hypertrophic and anti-convulsant effects, and is useful in the HIV-1 research. Previous studies have shown that Imperatorin requires the transcription factor Sp1 to exert its inhibitory effect on the HIV-1. It can further inhibit the expression of cyclin D1 to cause cell cycle arrest at G1 stage. Moreover, it can suppress the HIV-1 replication inside the primary T lymphocytes and transformed cell lines. This inhibitory effect on HIV-1 can also be effectively observed in the HeLa cells. In addition, it has also been shown that it can cause apoptosis of human promyelocytic leukaemia via the cytochrome c/caspase-9 pathway.
• Uses: Imperatorin (cas# 482-44-0) is a compound useful in organic synthesis.

Technology Process of Imperatorin

There total 3 articles about Imperatorin 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: 77.0%

O-acetylxanthotoxol (10386-19-3) + 3,3-dimethyl-allyl chloride (503-60-6) → imperatorin (482-44-0)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In acetone; for 0.5h; Heating;

DOI:10.1039/c39820000815

Reference yield: 58.7%

8-hydroxypsoralen (2009-24-7) + prenyl bromide (870-63-3) → imperatorin (482-44-0)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 5h;

Reference yield:

9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one (298-81-7) → imperatorin (482-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1: boron tribromide / dichloromethane / 4 h / 10 °C

2: sodium carbonate / N,N-dimethyl-formamide / 5 h / 50 °C

With boron tribromide; sodium carbonate; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

8-hydroxypsoralen

prenyl bromide

O-acetylxanthotoxol

3,3-dimethyl-allyl chloride

Downstream raw materials:

Isogosferol

8-hydroxypsoralen

Alloimperatorin

Prangenin

Refernces

• 1、 Fiorito, Serena,Epifano, Francesco,Preziuso, Francesca,Cacciatore, Ivana,di Stefano, Antonio,Taddeo, Vito Alessandro,de Medina, Philippe,Genovese, Salvatore. "Natural oxyprenylated coumarins are modulators of melanogenesis". . p. 274 - 282. Retrieved 2018/05/14.