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Osthole
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Name

Osthole

 EINECS 1532714-185-1
CAS No. 484-12-8 Density 1.126 g/cm3
PSA 39.44000 LogP 3.31030
Solubility 12mg/L(25 oC) Melting Point 83-84 °C
Formula C15H16O3 Boiling Point 396.7 °C at 760 mmHg
Molecular Weight 244.29 Flash Point 167.6 °C
Transport Information N/A Appearance Fine White Powder
Safety Risk Codes R36/37/38; R20/21/22
Molecular Structure Molecular Structure of 484-12-8 (Osthole) Hazard Symbols Xi,Xn
Synonyms

8-(3-Methyl-2-butenyl)herniarin;2H-1-Benzopyran-2-one, 7-methoxy-8-(3-methyl-2-butenyl)-;7-Methoxy-8-isopentenylcoumarin;7-methoxy-8-(3-methylbut-2-enyl)chromen-2-one;Coumarin, 7-methoxy-8- (3-methyl-2-butenyl)-;2H-1-Benzopyran-2-one,7-methoxy-8-(3- methyl-2-butenyl)-;Ostol;Coumarin, 7-methoxy-8-(3-methyl-2-butenyl)-;Cnidium monnieri P.E.- Osthole;Common Cnidium Fruit P. E.;Fructus Cnidii;

Article Data 11

Osthole Synthetic route

65763-01-1

7-methoxy-8-iodo-2H-chromen-2-one

870-63-3

prenyl bromide

484-12-8

osthole

Conditions
ConditionsYield
Stage #1: 7-methoxy-8-iodo-2H-chromen-2-one With isopropylmagnesium chloride In tetrahydrofuran at -20℃; for 1h; Schlenk technique; Inert atmosphere; Green chemistry;
Stage #2: prenyl bromide With copper(l) iodide; lithium chloride In tetrahydrofuran at -20 - 20℃; for 10.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Green chemistry;		80%
55136-74-8

8-allyl-7-methoxy-2H-chromen-2-one

2190-48-9

3-chloro-3-methyl-1-butene

484-12-8

osthole

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 45℃; for 2h; Inert atmosphere;77.65%

4-methoxy-2-((2-methylbut-3-en-2-yl)oxy)benzaldehyde

1099-45-2

ethyl (triphenylphosphoranylidene)acetate

484-12-8

osthole

Conditions
ConditionsYield
With N,N-diethylaniline at 250℃; for 1h; Microwave irradiation; Sealed tube;68%
65763-01-1

7-methoxy-8-iodo-2H-chromen-2-one

104108-29-4

prenyl tributylstannane

484-12-8

osthole

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; lithium chloride In N,N-dimethyl-formamide at 80℃; for 6h; Stille Cross Coupling; Inert atmosphere; Schlenk technique;66.1%
104108-29-4

prenyl tributylstannane

8-bromo-7-methoxy-2H-chromen-2-one

484-12-8

osthole

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 125℃; for 5h; Stille Cross Coupling; Schlenk technique; Inert atmosphere;32%
37761-53-8

2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)benzaldehyde

108-24-7

acetic anhydride

484-12-8

osthole

Conditions
ConditionsYield
With sodium acetate at 160℃;
186581-53-3, 908094-01-9

diazomethane

osthenol

osthenol

484-12-8

osthole

Conditions
ConditionsYield
With diethyl ether
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium; benzene / anschliessend mit 4-Brom-2-methyl-buten-(2)
2: sodium acetate / 160 °C
View Scheme
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / dichloromethane / 0.25 h / -20 °C
1.2: -20 - 20 °C
2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / Reflux
2.2: 12 h / 0 °C
3.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate / acetonitrile / 16 h / 85 °C
4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 5 h / 125 °C / Schlenk technique; Inert atmosphere
View Scheme
93-35-6

7-hydroxy-2H-chromen-2-one

484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate; potassium iodide / acetone / 22 h / 60 °C
2: ethylene glycol / 6 h / Reflux
3: potassium carbonate; potassium iodide / acetone / 5 h / 20 °C
4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 45 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: iodine; potassium iodide; ammonium hydroxide / water / 24.5 h
2.1: potassium carbonate / acetone / 5 h / Reflux
3.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Schlenk technique; Inert atmosphere; Green chemistry
3.2: 10.5 h / -20 - 20 °C / Schlenk technique; Inert atmosphere; Green chemistry
View Scheme
55136-72-6

7-hydroxy-8-allylcoumarin

484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; potassium iodide / acetone / 5 h / 20 °C
2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 45 °C / Inert atmosphere
View Scheme

Osthole Chemical Properties

IUPAC Name: 7-Methoxy-8-(3-methylbut-2-enyl)chromen-2-one 
Following is the structure of Osthole (CAS NO.484-12-8):
                       
Empirical Formula: C15H16O3
Molecular Weight: 244.2857 g/mol
Index of Refraction: 1.556
Molar Refractivity: 69.79 cm3
Molar Volume: 216.8 cm3
Density: 1.126 g/cm3
Flash Point: 167.6 °C
Melting point: 83-84 °C
Surface Tension: 40.3 dyne/cm
Enthalpy of Vaporization: 64.71 kJ/mol
Boiling Point: 396.7 °C at 760 mmHg
Vapour Pressure of Osthole (CAS NO.484-12-8): 1.67E-06 mmHg at 25 °C 
Product Categories of Osthole (CAS NO.484-12-8): Standard extract; Natural Plant Extract; Steroids
Water Solubility of Osthole (CAS NO.484-12-8): 12 mg/L at 30 °C
Canonical SMILES: CC(=CCC1=C(C=CC2=C1OC(=O)C=C2)OC)C
InChI: InChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3
InChIKey: MBRLOUHOWLUMFF-UHFFFAOYSA-N

Osthole Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD intravenous > 40mg/kg (40mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 150, Pg. 425, 1964.
guinea pig LD oral > 1gm/kg (1000mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 150, Pg. 425, 1964.
mouse LD50 intraperitoneal 190mg/kg (190mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Indian Journal of Medical Research. Vol. 55, Pg. 241, 1967.
mouse LD50 subcutaneous 16mg/kg (16mg/kg)   Pharmaceutical Chemistry Journal Vol. 11, Pg. 331, 1977.
rabbit LD subcutaneous > 70mg/kg (70mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 400, 1962.
rabbit LDLo intravenous 25mg/kg (25mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 400, 1962.
rat LD50 intraperitoneal 600mg/kg (600mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Indian Journal of Medical Research. Vol. 55, Pg. 241, 1967.
rat LD50 oral 2905mg/kg (2905mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Indian Journal of Medical Research. Vol. 55, Pg. 241, 1967.

Osthole Specification

  Osthole , its cas register number is 484-12-8. It also can be called 7-Methoxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one ; 7-Methoxy-8-(3-methyl-2-butenyl)-coumarin ; 7-Methoxy-8-isopentenylcoumarin ; and 8-(3-Methyl-2-butenyl)herniarin . Adjuvants, immunologic; Calcium channel blockers; Cardiovascular Agents; Drug / Therapeutic Agent; Immunologic Factors and Membrane Transport Modulators.

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