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

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

Uses

Used in Organic Synthesis:
Imperatorin is used as a compound in organic synthesis for its unique chemical properties and potential applications in the development of new molecules and compounds.
Used in Pharmaceutical Research:
Imperatorin is used as a research tool in the pharmaceutical industry for its anti-hypertrophic, anti-convulsant, and HIV-1 inhibitory effects. It can be further studied and potentially utilized in the development of drugs targeting these conditions.
Used in HIV-1 Research:
Imperatorin is used as an inhibitor of HIV-1 replication in primary T lymphocytes and transformed cell lines, as well as in HeLa cells. Its inhibitory effect on the virus makes it a valuable compound for research in the development of antiretroviral therapies.
Used in Cancer Research:
Imperatorin has been shown to induce apoptosis in human promyelocytic leukemia cells, making it a potential compound for research in cancer treatment and the development of anti-cancer drugs.
Used in Acetylcholinesterase Inhibition:
Imperatorin acts as an acetylcholinesterase inhibitor, which can be useful in the research and development of drugs targeting neurological disorders related to acetylcholinesterase activity.

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

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

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

Downstream Products

• 2009-24-7 8-hydroxypsoralen 
• 152441-79-7 Isogosferol 
• 642-05-7 Alloimperatorin 
• 35740-18-2 Prangenin 
• 135366-52-8 9-(3'-Hydroperoxy-3'-methyl-1'-butenyloxy)furo<3,2-g><1>benzopyran-7-one 
• 135366-51-7 9-(2'-Hydroperoxy-3'-methyl-3'-butenyloxy)furo<3,2-g><1>benzopyran-7-one 
• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 
• 10386-19-3 O-acetylxanthotoxol 
• 31575-93-6 heraclenol 
• 484-20-8 bergapten 
• 1428263-43-7 C₁₆H₂₀O₇ 
• 1428263-44-8 C₁₇H₂₂O₇ 
• 1428263-45-9 C₁₆H₁₈O₆ 
• 1428263-47-1 C₁₆H₁₈O₆ 

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.

Natural oxyprenylated coumarins are modulators of melanogenesis

Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor β and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses.

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.