482-44-0

Basic information

• Product Name: Imperatorin
• Synonyms: 2-g)(1)benzopyran-7-one,9-((3-methyl-2-butenyl)oxy)-7h-furo(;6-hydroxy-7-((3-methyl-2-butenyl)oxy)-5-benzofuranacrylicacidelta-lacto;6-hydroxy-7-((3-methyl-2-butenyl)oxy)-5-benzofuranacrylicacidelta-lactone;6-hydroxy-7-(3-methyl-2-butenyloxy)-5-benzofuranacrylicacidomega-lactone;8-isopentenyloxypsoralene;9-((3-methyl-2-butenyl)oxy)-7h-furo(3,2-g)(1)benzopyran-7-one;9-[(3-methyl-2-butenyl)oxy]-7h-furo[3,2-g][1]benzopyran-7-one;IMPERATORIN
• CAS NO: 482-44-0
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28
• EINECS: 207-581-1
• Product Categories: Coumarins;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 482-44-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 98-100°C
• Boiling Point: 333.4°C (rough estimate)
• Flash Point: 224.936 °C
• Appearance: off-white to light brown/
• Density: 1.1311 (rough estimate)
• Vapor Pressure: 3.13E-08mmHg at 25°C
• Refractive Index: 1.4350 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥5mg/mL
• Merck: 14,4925
• CAS DataBase Reference: Imperatorin(CAS DataBase Reference)
• NIST Chemistry Reference: Imperatorin(482-44-0)
• EPA Substance Registry System: Imperatorin(482-44-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: LV1575000
• Hazardous Substances Data: 482-44-0(Hazardous Substances Data)

Usage

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.

References

https://www.scbt.com/scbt/product/imperatorin-482-44-0 https://pubchem.ncbi.nlm.nih.gov/compound/imperatorin#section=Top https://en.wikipedia.org/wiki/Imperatorin

Chemical Properties

White Solid

Uses

Imperatorin (cas# 482-44-0) is a compound useful in organic synthesis.

Definition

ChEBI: A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Imperatorin is a modulator of p38, ERK pathway. Imperatorin increases BMP-2 expression (mRNA) and increases bone density/volume and mineralization in vivo.

InChI:InChI=1/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3

Synthetic route

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

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetone for 0.5h; Heating;	77%

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

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 50℃; for 5h;	58.7%
With methanol; diethyl ether; sodium methylate
Williamson Ether Synthesis;

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

Conditions	Yield
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 View Scheme

imperatorin (482-44-0) → 8-hydroxypsoralen (2009-24-7)

Conditions	Yield
With hydrogenchloride In methanol; water	100%
With ferrous(II) sulfate heptahydrate; dipotassium hydrogenphosphate; magnesium sulfate heptahydrate; D-glucose; potassium chloride; water; Sucrose In dimethyl sulfoxide at 27℃; for 288h;	64%
With hydrogenchloride In ethanol for 2h; Heating;	7.0 g

imperatorin (482-44-0) → Prangenin (35740-18-2)

Conditions	Yield
With dihydrogen peroxide In ethanol at 0℃; for 6.66667h; γ-Irradiation;	100%
With 3,3-dimethyldioxirane In acetone at 0℃; for 2h;	99%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 2h;	85%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 2h;	67%

imperatorin (482-44-0) → 5-bromo-8-hydroxypsoralen (1930-60-5)

Conditions	Yield
With bromine In acetic acid at 20℃; for 5h; Bromination;	98%

imperatorin (482-44-0) → furo<3,2-g><1>benzopyran-4,7,9-trione (483-36-3)

Conditions	Yield
With nitric acid In acetic acid for 1h; Oxidation; Heating;	70%

imperatorin (482-44-0) → Prangenin (35740-18-2) + C16H14O5

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 0.625h; γ-Irradiation;	A 66% B 34%

imperatorin (482-44-0) → heraclenol (31575-93-6, 118407-74-2, 139079-42-8) + bergapten (484-20-8) + C16H20O7 (1428263-43-7) + C17H22O7 (1428263-44-8) + C16H18O6 (1428263-45-9) + C16H18O6 (1428263-47-1) + C17H20O6 (1428417-34-8) + C16H20O6 (1428263-46-0) + C16H18O6 (1428417-33-7) + 6,7-furano-5-isopentylcoumarin 8-O-β-D-glucoside

Conditions	Yield
With Penicillium janthinellum AS; liquid potato medium In acetone at 27℃; for 120h; Microbiological reaction;	A 3.1% B 0.63% C 1% D 0.5% E 0.63% F 3 mg G 0.4% H 0.37% I 0.75% J 0.56%

...Expand

imperatorin (482-44-0) → 9-hydroxy-2,3,5,6-tetrahydro-furo[3,2-g]chromen-7-one (25957-84-0) + 9-isopentyloxy-2,3,5,6-tetrahydro-furo[3,2-g]chromen-7-one

Conditions	Yield
With palladium on activated charcoal; acetic acid Hydrogenation;

imperatorin (482-44-0) → Isogosferol (152441-79-7) + 8-hydroxypsoralen (2009-24-7) + Claucoumarin A

Conditions	Yield
With oxygen; methylene blue In methanol for 24h; Irradiation;
With oxygen; methylene blue In methanol for 24h; Product distribution; Mechanism; Irradiation; light and other sensitizers, effects of D2O and DABCO; further time;

imperatorin (482-44-0) → 8-hydroxypsoralen (2009-24-7) + Alloimperatorin (642-05-7)

Conditions	Yield
In acetic acid at 25 - 30℃; for 100h; Irradiation;	A 246 mg B 23 mg
In acetone at 25 - 30℃; for 100h; Irradiation;	A 26 mg B 25 mg

imperatorin (482-44-0) → 8-hydroxypsoralen (2009-24-7) + Alloimperatorin (642-05-7) + imperatorin dimer

Conditions	Yield
In methanol at 25 - 30℃; for 100h; Mechanism; Irradiation; different solvents;	A 73 mg B 22 mg C 11 mg
In methanol at 25 - 30℃; for 100h; Irradiation;	A 73 mg B 22 mg C 11 mg

imperatorin (482-44-0) → Alloimperatorin (642-05-7)

Conditions	Yield
In various solvent(s) for 1h; Heating;	4.6 g
With N,N-diethylaniline for 1h; Heating;

imperatorin (482-44-0) → 9-(3'-Hydroperoxy-3'-methyl-1'-butenyloxy)furo<3,2-g><1>benzopyran-7-one (135366-52-8) + 9-(2'-Hydroperoxy-3'-methyl-3'-butenyloxy)furo<3,2-g><1>benzopyran-7-one (135366-51-7)

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane at -10℃; for 2.5h; Yield given. Yields of byproduct given;

imperatorin (482-44-0) → alloimperatorin

Conditions	Yield
at 200℃; under 0.5 Torr;

imperatorin (482-44-0) → 9-(2'-Hydroperoxy-3'-methyl-3'-butenyloxy)furo<3,2-g><1>benzopyran-7-one (135366-51-7) + 9-(3'-hydroperoxy-3'-methyl-1'-butenyloxy)furo[3,2-g][1]benzopyran-7-one

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin In chloroform at 0℃; for 4h; γ-Irradiation;

imperatorin (482-44-0) → Dihydro-8-hydroxypsoralen (68123-30-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr; for 0.5h;

imperatorin (482-44-0) → 9-isopentyloxy-2,3,5,6-tetrahydro-furo[3,2-g]chromen-7-one

Conditions	Yield
With hydrogen; palladium on activated charcoal In hexane at 20℃; for 2h;

imperatorin (482-44-0) → (+/-)-5-(3''-bromo-2''-hydroxy-3''-methylbutanoxy)-psoralen (159973-49-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / MCPBA / CHCl3 / 2 h / 0 °C 2: 70 percent / HBr / diethyl ether; benzene / 1 h / 5 °C View Scheme

imperatorin (482-44-0) → (+)-(2S)-5-<3''-bromo-2''-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3''-methylbutanoxy>-psoralen

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / MCPBA / CHCl3 / 2 h / 0 °C 2: 70 percent / HBr / diethyl ether; benzene / 1 h / 5 °C 3: pyridine / 24 h / Ambient temperature View Scheme

imperatorin (482-44-0) → (-)-(2S)-5-<3''-bromo-2''-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3''-methylbutanoxy>-psoralen

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / MCPBA / CHCl3 / 2 h / 0 °C 2: 70 percent / HBr / diethyl ether; benzene / 1 h / 5 °C 3: pyridine / 24 h / Ambient temperature View Scheme

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

Conditions	Yield
Multi-step reaction with 2 steps 1: 26 mg / acetone / 100 h / 25 - 30 °C / Irradiation 2: potassium carbonate / acetone / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water; methanol 2: potassium carbonate / acetone / Reflux; Inert atmosphere View Scheme

imperatorin (482-44-0) → O-acetylxanthotoxol (10386-19-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 26 mg / acetone / 100 h / 25 - 30 °C / Irradiation 2: 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 7.0 g / dil. HCl / ethanol / 2 h / Heating 2: 2.1 g / CH3COONa / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 14.5 g / HCl / ethanol / 2 h / Heating 2: pyridine / Heating View Scheme

imperatorin (482-44-0) → allo-imperatorin acetate (65161-82-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 25 mg / acetone / 100 h / 25 - 30 °C / Irradiation 2: 2 h / Heating View Scheme

imperatorin (482-44-0) → 9-(phenylmethoxy)-7H-furo[3,2-g][1]benzopyran-7-one (42207-40-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 14.5 g / HCl / ethanol / 2 h / Heating 2: K2CO3 / acetone / Heating View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water; methanol 2: potassium carbonate / acetone / Reflux; Inert atmosphere View Scheme

imperatorin (482-44-0) → Alloimperatorin methyl ether (10523-54-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-diethylaniline / 1 h / Heating 2: K2CO3 / acetone / 24 h / Heating View Scheme

imperatorin (482-44-0) → 9-(2-propen-1-yloxy)-7H-furo[3,2-g][1]benzopyran-7-one (62188-89-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 14.5 g / HCl / ethanol / 2 h / Heating 2: K2CO3 / acetone / Heating View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water; methanol 2: potassium carbonate / acetone / Reflux; Inert atmosphere View Scheme

imperatorin (482-44-0) → 4-Allyl-9-hydroxy-furo[3,2-g]chromen-7-one (65161-79-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 14.5 g / HCl / ethanol / 2 h / Heating 2: K2CO3 / acetone / Heating 3: N,N-diethylaniline / 1 h / Heating View Scheme

imperatorin (482-44-0) → 4-Allyl-9-methoxy-furo[3,2-g]chromen-7-one (65161-80-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 14.5 g / HCl / ethanol / 2 h / Heating 2: K2CO3 / acetone / Heating 3: N,N-diethylaniline / 1 h / Heating 4: K2CO3 / acetone / 24 h / Heating View Scheme

Upstream product

• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 
• 10386-19-3 O-acetylxanthotoxol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 2009-24-7 8-hydroxypsoralen 
• 870-63-3 prenyl bromide 

Downstream Products

• 135366-51-7 9-(2'-Hydroperoxy-3'-methyl-3'-butenyloxy)furo<3,2-g><1>benzopyran-7-one 
• 31575-93-6 heraclenol 
• 484-20-8 bergapten 
• 1428263-43-7 C₁₆H₂₀O₇ 
• 1428263-44-8 C₁₇H₂₂O₇ 
• 1428263-45-9 C₁₆H₁₈O₆ 
• 1428263-47-1 C₁₆H₁₈O₆ 
• 1428417-34-8 C₁₇H₂₀O₆ 
• 1428263-46-0 C₁₆H₂₀O₆ 
• 1428417-33-7 C₁₆H₁₈O₆ 
• 56201-56-0 8-methoxypsoralen-5-sulphonyl chloride 
• 1930-56-9 4-nitro-9-methoxy-7H-furo<3,2-g><1>benzopyran-7-one 
• 1930-54-7 4-bromo-9-methoxy-7H-furo[3,2-g]chromen-7-one 
• 62188-91-4 4-Nitro-benzoic acid 7-oxo-7H-furo[3,2-g]chromen-9-yl ester 

Relevant articles and documents

Structural modifier of 8-methoxypsoralen as well as preparation method and application of structural modifier

The invention discloses a structural modifier of 8-methoxypsoralen as well as a preparation method and application of the . The structural modifier of the 8-methoxypsoralen provided by the invention is a compound B20 shown as a formula 1 or a compound A10 shown as a formula 2. The bacteriostatic activity of the compound B20 for enterotoxigenic escherichia coli at the concentration of 64 mu g/mL is2.3 times of that of the 8-methoxypsoralen; the bacteriostatic activity of the compound A10 for enterotoxigenic escherichia coli at the concentration of 64 mu g/mL is 2.4 times of the 8-methoxypsoralen. The compound B20 and the compound A10 can be applied to the preparation of a medicament for treating and/or preventing piglet diarrhea. The formula 1 and the formula 2 are shown in the description.

A Simple One-step Synthesis of Phenyl Ethers from Phenyl Acetates

Phenyl acetates when refluxed with alkyl halides in acetone solution in the presence of a crown ether and anhydrous potassium carbonate undergo alkylation yielding phenyl ethers.