Imperatorin

Modify Date: 2024-01-02 10:11:38

Imperatorin Structure
Imperatorin structure
 Common Name Imperatorin
CAS Number 482-44-0 Molecular Weight 270.280
Density 1.2±0.1 g/cm3 Boiling Point 448.3±45.0 °C at 760 mmHg
Molecular Formula C16H14O4 Melting Point 98-100ºC
MSDS Chinese USA Flash Point 224.9±28.7 °C
Purity Quantity Budget Inquiry

 Use of Imperatorin


Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol). Imperatorin is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM.

 Names

Name imperatorin
Synonym More Synonyms

 Imperatorin Biological Activity

Description Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol). Imperatorin is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM.
Related Catalog
Target

IC50: 9.2 μmol (NO synthesis), 31.4 μmol (BChE)[1]EC50: 12.6±3.2 μM (TRPV1)[2]

In Vitro Imperatorin is a plant secondary metabolite belonging to the coumarins-specifically the furanocoumarins. Imperatorin enhances the GABA-induced chloride ion current (IGABA) through the α1β2γ2S receptors. Imperatorin potentiates IGABA at 100 μmol by 50.5±16.3 % and at 300 μmol by 109.8±37.7 %, respectively. Imperatorin, together with Phellopterin, found in the roots of A. dahurica, inhibit [3H]diazepam binding to the benzodiazepine site of the rat brain GABAA receptor in vitro with an IC50 of 12.3 μmol for Imperatorin and 400 nmol for Phellopterin. Imperatorin, in a concentration ranging from 3.5 to 14 mmol, significantly and irreversibly inhibits GABA-T in a time-dependent and concentration-dependent manner, by irreversibly binding with the active site of GABA-T.Imperatorin is a reversible acetylcholinesterase (AChE) inhibitor, and acts in dose-dependent manner. The AChE and BChE inhibitory activities of Imperatorin and a crude extract from the fruits of Angelica archangelica L. is tested by the spectrophotometric method at concentrations of 12.5, 25, 50, and 100 μg/mL. Imperatorin displays low inhibition towards AChE (13.75-46.11 %), whereas it has remarkable inhibitory effect against BChE (37.46-83.98 %). Imperatorin shows selectivity toward BChE rather than AChE, with an IC50 for BChE of 31.4 μmol. Imperatorin, together with (+)-Byakangelicol, are found to be the most effective BACE-1 inhibitors, with IC50s of 91.8 and 104.9 μmol, respectively. Imperatorin (IC50=9.2 μmol) is also effective as an inhibitor of NO synthesis[1]. Imperatorin is a weak agonist of TRPV1, a channel implicated in detecting several noxious stimuli, exhibiting EC50 of 12.6±3.2 μM[2].
In Vivo At doses of 10 and 20 mg/kg and 30 min after injection, Imperatorin shows an anxiolytic effect and improved different stages of memory and learning processes-both acquisition and consolidation. It is also shown that acute administration Imperatorin at doses of 10 and 20 mg/kg reduced the anxiogenic effect of nicotine (0.1 mg/kg, subcutaneous, s.c.). At 30 and 40 mg/kg, i.p. Imperatorin significantly potentiates the anticonvulsant activity of carbamazepine against maximal electroshock-induced seizures expressed by lowering the ED50 from 10.8 to 6.8 mg/kg (by 34 %) and 6 mg/kg (by 42 %), respectively. Moreover, Imperatorin at 30 mg/kg and carbamazepine at 6.8 mg/kg shows increases the total brain concentration of carbamazepine from 1.260 to 2.328 μg/mL (by 85%), which may be caused by modifying the blood-barrier permeability or acting like an inhibitor of multi-drug resistance proteins[1]. Imperatorin, a naturally occurring furanocoumarin, inactivates gamma-aminobutyric acid transaminase and inhibits acetylcholinesterase activity. Imperatorin administered acutely at the doses of 5 and 10 mg/kg prior to the injection of scopolamine (1 mg/kg) improves memory acquisition and consolidation impaired by scopolamine. Furthermore, repeatable (7 days, twice daily) administration of the highest dose of Imperatorin (10 mg/kg) significantly attenuates the effects of scopolamine on memory acquisition, whereas the doses of 5 and 10 mg/kg of this furanocoumarin are effective when memory consolidation is measured [3].
Animal Admin Mice[3] The experiments are carried out on naive male Swiss mice weighing 20-25 g. Drugs are administered intraperitoneally (i.p.) at the volume of 10 mL/kg. Fresh drug solutions are prepared on each day of experimentation. Control groups receive saline injections of the same volume and via the same route of administration. During the acute treatment, the animals are allocated to the following drug groups: saline, rivastigmine (0.5 mg/kg, i.p.), scopolamine (1 mg/kg, i.p.), Imperatorin (1, 5, 10 mg/kg, i.p.), or Imperatorin coadministered with scopolamine. To measure the memory acquisition processes, scopolamine is administered 20 min before the pretest, whereas Imperatorin and rivastigmine are administered 30 min before the pretest. To measure the memory consolidation processes, rivastigmine or scopolamine (1 mg/kg) is administered immediately after the pretest, whereas Imperatorin is administered 15 min after pretest or after scopolamine injection. On the second day, the mice are retested. In the second set of the experiments, animals are randomly allocated to receive 6 days of i.p. injections of Imperatorin (1, 5, and 10 mg/kg, i.p.) or saline, twice daily (8:00 a.m. and 8:00 p.m.). On the seventh day, these animals are subjected to saline, scopolamine (1 mg/kg, i.p.), Imperatorin (1, 5, and 10 mg/kg, i.p.), or Imperatorin coadministered with scopolamine. To measure the memory acquisition processes, scopolamine is administered 20 min before the pretest and Imperatorin 30 min before the pretest. To measure the memory consolidation processes, scopolamine (1 mg/kg) is administered immediately after the pretest, whereas Imperatorin is administered 15 min after the pretest or after scopolamine injection. On the eighth day, the mice are retested.
References

[1]. Kozioł E, et al. Imperatorin-pharmacological meaning and analytical clues: profound investigation. Phytochem Rev. 2016;15:627-649.

[2]. Chen X, et al. Furanocoumarins are a novel class of modulators for the transient receptor potential vanilloid type 1 (TRPV1) channel. J Biol Chem. 2014 Apr 4;289(14):9600-10.

[3]. Budzynska B, et al. Effects of imperatorin on scopolamine-induced cognitive impairment and oxidative stress in mice. Psychopharmacology (Berl). 2015 Mar;232(5):931-42.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 448.3±45.0 °C at 760 mmHg
Melting Point 98-100ºC
Molecular Formula C16H14O4
Molecular Weight 270.280
Flash Point 224.9±28.7 °C
Exact Mass 270.089203
PSA 52.58000
LogP 3.81
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.606
Storage condition 2-8°C

 MSDS

Section1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name: Imperatorin
Section2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a dangerous substance according to GHS.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none
Section3. COMPOSITION/INFORMATION ON INGREDIENTS
Synonyms: 9-[(3-Methyl-2-buten-1-yl)oxy]-7h-furo[3,2-g][1]benzopyran-7-one
Ammidin
Marmelide
Marmelosin
NSC 402949
Formula: C16H14O4
Molecular Weight: 270,28 g/mol
CAS-No.EC-No.Index-No.ClassificationConcentration
9-(3-Methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one
482-44-0207-581-1---
Section4. FIRST AID MEASURES
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Section5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.
Section6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Section7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire
protection.
Conditions for safe storage
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Section8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Personal protective equipment
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use
type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved
under appropriate government standards such as NIOSH (US) or CEN (EU).
Hand protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without
touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves
after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Eye protection
Use equipment for eye protection tested and approved under appropriate government standards such as
NIOSH (US) or EN 166(EU).
Skin and body protection
Choose body protection in relation to its type, to the concentration and amount of dangerous substances,
and to the specific work-place., The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Hygiene measures
General industrial hygiene practice.
Section9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Formsolid
Colouroff-white, light brown
Safety data
pHno data available
Melting point98 - 100 °C
Boiling pointno data available
Flash pointno data available
Ignition temperatureno data available
Lower explosion limitno data available
Upper explosion limitno data available
Water solubilityno data available
Partition coefficient:log Pow: 3,72
n-octanol/water
Section10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
no data available
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides
Section11. TOXICOLOGICAL INFORMATION
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
InhalationMay be harmful if inhaled. May cause respiratory tract irritation.
IngestionMay be harmful if swallowed.
Skin
May be harmful if absorbed through skin. May cause skin irritation.
EyesMay cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: Not available
Section12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
PBT and vPvB assessment
no data available
Other adverse effects
no data available
Section13. DISPOSAL CONSIDERATIONS
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.
Section14. TRANSPORT INFORMATION
ADR/RID
Not dangerous goods
IMDG
Not dangerous goods
IATA
Not dangerous goods
Section15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Section16. OTHER INFORMATION
Further information
Copyright 2010 Co. License granted to make unlimited paper copies for internal use only.
The above information is believed to be correct but does not purport to be all inclusive and shall be used
only as a guide. The information in this document is based on the present state of our knowledge and is
applicable to the product with regard to appropriate safety precautions. It does not represent any guarantee
of the properties of the product. Co., shall not be held liable for any damage resulting from
handling or from contact with the above product. See reverse side of invoice or packing slip for additional
terms and conditions of sale.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LV1575000
CHEMICAL NAME :
7H-Furo(3,2-g)(1)benzopyran-7-one, 9-((3-methyl-2-butenyl)oxy)-
CAS REGISTRY NUMBER :
482-44-0
LAST UPDATED :
199410
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C16-H14-O4
MOLECULAR WEIGHT :
270.30
WISWESSER LINE NOTATION :
T C566 DO LVOTJ BO2UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
330 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
5 mg/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 43,1054,1983

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
RIDADR NONH for all modes of transport

 Articles29

More Articles
Simultaneous determination of imperatorin and its 2 metabolites in dog plasma by using liquid chromatography-tandem mass spectrometry.

J. Pharm. Biomed. Anal. 70 , 640-6, (2012)

In this study, 2 metabolites of imperatorin, imperatorin hydroxylate (IMH) and imperatorin epoxide (IME), were identified for the first time in dog plasma. A sensitive, specific, and accurate high-per...

A potential calcium antagonist and its antihypertensive effects.

Fitoterapia 82(7) , 988-96, (2011)

Imperatorin (Imp) as a hypotensive active ingredient, its hypotensive effect was evaluated in the SHRs, its calcium antagonism and affinity to L-type calcium channel was also confirmed. The results sh...

F420H2-dependent degradation of aflatoxin and other furanocoumarins is widespread throughout the actinomycetales.

PLoS ONE 7(2) , e30114, (2012)

Two classes of F(420)-dependent reductases (FDR-A and FDR-B) that can reduce aflatoxins and thereby degrade them have previously been isolated from Mycobacterium smegmatis. One class, the FDR-A enzyme...

 Synonyms

Pentosalen
Imperatorin
Enoxypsoralen
MFCD00016881
7H-Furo[3,2-g][1]benzopyran-7-one, 9-[(3-methyl-2-buten-1-yl)oxy]-
MARMELOSIN
AMMIDIN
9-[(3-Methyl-2-buten-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
Marmelide
8-ISOAMYLEN
9-[(3-Methyl-2-buten-1-yl)oxy]-7H-furo[3,2-g]chromen-7-on
EINECS 207-581-1
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