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Fructus Cnidii Extract
Cas No: 484-12-8
USD $ 15.5-15.5 / Kilogram 1 Kilogram 300 Kilogram/Month Greenutra Resource Inc Contact Supplier
Cnidium Fruit Extract
Cas No: 484-12-8
USD $ 1119.0-1139.0 / Kilogram 1 Kilogram 300 Metric Ton/Month Weihai Moochun Bio-Tech Co., Ltd. Contact Supplier
E-0091 Osthole
Cas No: 484-12-8
No Data No Data Metric Ton/Day shanghai Tauto Biotech Co., Ltd Contact Supplier
Osthole Manufacturer/High quality/Best price/In stock
Cas No: 484-12-8
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Osthole Powder CAS 484-12-8
Cas No: 484-12-8
USD $ 18.0-100.0 / Kilogram 1 Kilogram 3000 Kilogram/Month Kono Chem Co.,Ltd Contact Supplier
Osthole
Cas No: 484-12-8
USD $ 1.0-3.0 / Metric Ton 1 Metric Ton 10 Metric Ton/Day Hebei yanxi chemical co.,LTD. Contact Supplier
Whole Sale Male Health Cnidium Monieri Seed Extract Osthole Powder 50:1
Cas No: 484-12-8
USD $ 13.1-21.3 / Kilogram 25 Kilogram 1000 Kilogram/Year Xi'an Quanao Biotech Co., Ltd. Contact Supplier
High Content Natural Extract Osthole HACCP manufacturer
Cas No: 484-12-8
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
Bacopa Monnieri Extract 10%-50% Bacopaside Bacopa Monnieri Powder CAS 484-12-8
Cas No: 484-12-8
USD $ 60.0-80.0 / Kilogram 1 Kilogram 5000 Metric Ton/Month Xi'an Julong Bio-Tech Co., Ltd. Contact Supplier
Osthole extract CAS# 484-12-8
Cas No: 484-12-8
No Data 1 Kilogram 50 Metric Ton/Year ORCHID CHEMICAL SUPPLIES LTD Contact Supplier

484-12-8 Usage

Plant extracts

Osthole is a substance extracted from the fruit of the annual Umbelliferae plant Fructus Cnidii. It appears as yellow-green to white crystalline powder. It is insoluble in cold water and petroleum ether, easily soluble in acetone, methanol, ethanol, chloroform and ethyl acetate and soluble in boiling petroleum ether. It has various effects including antispasmodic, hypotensive, anti-arrhythmic, enhancing immune function and broad-spectrum antimicrobial effect. It is clinically mainly used for the treatment of men impotence, scrotal wet itchy, women prurUus Yulvae and cold uterus and infertility, rheumatism, scabies, eczema and trichomonas vaginitis. Osthole can also be used to make field insecticides, fungicides with contact killing action being the primary effect and stomach poisoning being the auxiliary effect. The drug liquid can be absorbed through body surface and enter into the body and further act on the nervous system of pests, causing the non-functional muscle contraction of the pests and eventually leading to death due to energy exhaustion. It has a relative excellent contact-killing effect on various kinds of pests such as cabbage caterpillar, tea looper, cotton bollworm, beet armyworm and any kinds of aphids.

Pharmacological effects

Osthole has various kinds of effects of antispasmodic, hypotensive, anti-arrhythmic and enhancing immune function and broad-spectrum antimicrobial effect. Osthole can not only have efficacy such as anti-hypertensive, anti-arrhythmic, anti-inflammatory, anti-tumor and anti-osteoporosis effect, but can also act as a new type of biological pesticides with significant efficacy in treating pests and plant pathogens.

Definition

ChEBI: A natural product found in Peucedanum ostruthium and Angelica pubescens.

Physical and Chemical Properties

Osthole belongs to coumarin compounds. It is prismatic-like crystals (diethyl ether) and needle-like crystals (Ethanol) with the melting point being 83~84 ℃ and the boiling point being 145~150 ℃. It is soluble in alkaline solution, methanol, ethanol, chloroform, acetone, ethyl acetate, and boiling petroleum ether but insoluble in water and petroleum ether.

Botanical insecticides

Osthole is a class of natural coumarin compound which had been initially extracted from Umbelliferae plants. The dried ripe fruit of Fructus Cnidii in the Umbelliferae plant, Cnidium monnieri has a relative high content, hence obtaining the name. Related research has shown that Osthole is also presented in other kinds of plants, including Umbelliferae including Angelica, Archangelica Hoffm and Cnidium as well as rutaceous plant such as citrus, clausena, Limonia acidissima and Haplophyllum A. Juss. In addition, it is also distributed in a few species of Asteraceae and legumes. Osthole has its chemical name being 7-methoxy-8-isopenteylcoumarin with the core structure consisting of benzene and pyrone ring. As a member of coumarins compounds, Osthole, in addition to containing the core structure of coumarin, also has isopentenyl structure. Compound containing isopentenyl structure, as a phytoalexin, plays an important role in fighting against disease. Osthole, as a kind of botanical pesticide, has contact-killing effect being the primary effect and stomach poisoning effect being the auxiliary effect. The drug liquid can be absorbed into the insect body through body surface and acts on the nervous system of pests, causing non-functional muscle contraction and final death due to energy exhaustion. Indoor activity virulence tests have showed that it has a higher activity against Pieris rapae (LD50 is 6.2258 mg/kg). It is demonstrated through the field efficacy trials that it has excellent efficacy in the treatment of Pieris rapae of cruciferous vegetables and tea and tea looper caterpillar. The drug dosage for prevention and treatment of the Pieris rapae of cruciferous vegetables has the active ingredient be 4.8~7.2g/hm (equals to 80~120 mL per acre if converted to 0.4% Osthole cream commercialized product); the drug dosage against tea mites has the active ingredient be 6 to 7.2 g/hm (equals to 100~120 mL per acre if converted to 0.4% Osthole cream commercialized product). Apply the drug liquid at an amount of 50~75 kg per acre with uniform spray; the period of validity is about 7d. It is safe for crop within the dose range with no drug injury.
InChI:InChI=1/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

484-12-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (O0426)  Osthole  >98.0%(GC) 484-12-8 250mg 650.00CNY Detail
TCI America (O0426)  Osthole  >98.0%(GC) 484-12-8 1g 1,690.00CNY Detail
TCI America (O0426)  Osthole  >98.0%(GC) 484-12-8 5g 4,900.00CNY Detail
Sigma-Aldrich (Y0001207)  Osthole  European Pharmacopoeia (EP) Reference Standard 484-12-8 Y0001207 1,880.19CNY Detail
Sigma-Aldrich (02150595)  Osthole  primary pharmaceutical reference standard 484-12-8 02150595-10MG 5,257.98CNY Detail

484-12-8Synthetic route

7-methoxy-8-iodo-2H-chromen-2-one
65763-01-1

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

prenyl bromide
870-63-3

prenyl bromide

osthole
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%
8-allyl-7-methoxy-2H-chromen-2-one
55136-74-8

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

3-chloro-3-methyl-1-butene
2190-48-9

3-chloro-3-methyl-1-butene

osthole
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

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

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

osthole
484-12-8

osthole

Conditions
ConditionsYield
With N,N-diethylaniline at 250℃; for 1h; Microwave irradiation; Sealed tube;68%
7-methoxy-8-iodo-2H-chromen-2-one
65763-01-1

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

prenyl tributylstannane
104108-29-4

prenyl tributylstannane

osthole
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%
prenyl tributylstannane
104108-29-4

prenyl tributylstannane

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

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

osthole
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%
2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)benzaldehyde
37761-53-8

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

acetic anhydride
108-24-7

acetic anhydride

osthole
484-12-8

osthole

Conditions
ConditionsYield
With sodium acetate at 160℃;
osthenol

osthenol

osthole
484-12-8

osthole

Conditions
ConditionsYield
With diethyl ether
2-Hydroxy-4-methoxybenzaldehyde
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

osthole
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
7-hydroxy-2H-chromen-2-one
93-35-6

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

osthole
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
7-hydroxy-8-allylcoumarin
55136-72-6

7-hydroxy-8-allylcoumarin

osthole
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
7-allyloxycoumarin
31005-03-5

7-allyloxycoumarin

osthole
484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethylene glycol / 6 h / Reflux
2: potassium carbonate; potassium iodide / acetone / 5 h / 20 °C
3: 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
(ethoxycarbonylmethyl)triphenylphosphonium chloride
17577-28-5

(ethoxycarbonylmethyl)triphenylphosphonium chloride

osthole
484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium hydroxide / ethanol / 1.5 h / 80 °C
2: potassium carbonate; potassium iodide / acetone / 22 h / 60 °C
3: ethylene glycol / 6 h / Reflux
4: potassium carbonate; potassium iodide / acetone / 5 h / 20 °C
5: 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
triphenylphosphine
603-35-0

triphenylphosphine

osthole
484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: ethanol / 4 h / 80 °C
2: potassium hydroxide / ethanol / 1.5 h / 80 °C
3: potassium carbonate; potassium iodide / acetone / 22 h / 60 °C
4: ethylene glycol / 6 h / Reflux
5: potassium carbonate; potassium iodide / acetone / 5 h / 20 °C
6: 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
7-hydroxy-8-iodocoumarin
65763-00-0

7-hydroxy-8-iodocoumarin

osthole
484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetone / 5 h / Reflux
2.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -20 °C / Schlenk technique; Inert atmosphere; Green chemistry
2.2: 10.5 h / -20 - 20 °C / Schlenk technique; Inert atmosphere; Green chemistry
View Scheme
4-methoxy-2-((2-methylbut-3-en-2-yl)oxy)benzaldehyde

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

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

osthole
484-12-8

osthole

Conditions
ConditionsYield
In toluene at 220℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube;928 mg
C13H14O3

C13H14O3

osthole
484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / ethyl acetate / 12 h / 20 °C / 760.05 Torr
2: toluene / 1 h / 220 °C / Inert atmosphere; Microwave irradiation; Sealed tube
View Scheme
3-bromo-2-hydroxy-4-methoxybenzaldehyde
63638-85-7

3-bromo-2-hydroxy-4-methoxybenzaldehyde

osthole
484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / Reflux
1.2: 12 h / 0 °C
2.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate / acetonitrile / 16 h / 85 °C
3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 5 h / 125 °C / Schlenk technique; Inert atmosphere
View Scheme
2-bromo-3-methoxy-6-vinylphenol
1358063-31-6

2-bromo-3-methoxy-6-vinylphenol

osthole
484-12-8

osthole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate / acetonitrile / 16 h / 85 °C
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 5 h / 125 °C / Schlenk technique; Inert atmosphere
View Scheme
osthole
484-12-8

osthole

methyl iodide
74-88-4

methyl iodide

(Z)-2,4-dimethoxy-3-prenyl cinnamalic acid
73490-51-4

(Z)-2,4-dimethoxy-3-prenyl cinnamalic acid

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) 15 min, 2.) 10 h;98%
With potassium hydroxide 1.) DMSO, 1 h, 2.) (Osthol : CH3I = 1:1) 12 h; Yield given. Multistep reaction;
Stage #1: osthole; methyl iodide With potassium hydroxide In ethanol at 90℃; for 24h;
Stage #2: With hydrogenchloride In ethanol; water pH=3 - 4;
Stage #1: osthole; methyl iodide With ethanol; potassium hydroxide at 90℃;
Stage #2: With hydrogenchloride In ethanol; water pH=3 - 4;
osthole
484-12-8

osthole

8-(3-hydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one
69219-24-5

8-(3-hydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one

Conditions
ConditionsYield
Stage #1: osthole With mercury(II) diacetate; water In tetrahydrofuran; dichloromethane for 3h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; dichloromethane
97%
With sulfuric acid; water In acetic acid at 0 - 5℃; for 1h;80%
With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;71%
With boron trifluoride diethyl etherate; water In dichloromethane Ambient temperature;52%
osthole
484-12-8

osthole

propargyl bromide
106-96-7

propargyl bromide

(Z)-3-(4-methoxy-3-(3-methylbut-2-enyl)-2-(prop-2-ynyloxy)phenyl)acrylic acid

(Z)-3-(4-methoxy-3-(3-methylbut-2-enyl)-2-(prop-2-ynyloxy)phenyl)acrylic acid

Conditions
ConditionsYield
Stage #1: osthole With sodium hydroxide In dimethyl sulfoxide at 25℃; for 0.5h;
Stage #2: propargyl bromide In dimethyl sulfoxide at 20℃; for 2h;
96%
osthole
484-12-8

osthole

7-methoxy-8-((3,3-dimethyloxiran-2-yl)methyl)-2H-chromen-2-one
489-53-2

7-methoxy-8-((3,3-dimethyloxiran-2-yl)methyl)-2H-chromen-2-one

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -5℃; for 2h;93%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;88%
With Perbenzoic acid; chloroform
Multi-step reaction with 2 steps
1: 180 mg / N-bromosuccinimide, DMSO, water / 1 h / Ambient temperature
2: 120 mg / sodium borohydride / dimethylsulfoxide / Ambient temperature
View Scheme
osthole
484-12-8

osthole

8-isopentyl-7-methoxy-chroman-2-one
181303-71-9

8-isopentyl-7-methoxy-chroman-2-one

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 16h;92%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 16h;92%
With palladium on activated charcoal; acetic acid Hydrogenation;
osthole
484-12-8

osthole

8-isopentyl-7-methoxy-2H-chromen-2-one
6619-22-3

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

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen In ethanol at 20℃;91%
With palladium; ethyl acetate Hydrogenation;
With acetic acid Hydrogenation;
Multi-step reaction with 2 steps
1: 66 percent / H2 / Pd/C / CH2Cl2; ethanol
2: 72 percent / Pd/C / 1,3,5-trimethyl-benzene / Heating
View Scheme
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C / 760.05 Torr
2: palladium 10% on activated carbon / 1,3,5-trimethyl-benzene / 16 h / 166 °C / Inert atmosphere
View Scheme
osthole
484-12-8

osthole

7-methoxy-8-(2',3'-dihydroxy-3'-methylbutyl)coumarin
5673-37-0

7-methoxy-8-(2',3'-dihydroxy-3'-methylbutyl)coumarin

Conditions
ConditionsYield
Stage #1: osthole With methanesulfonamide; AD-mix β In water; tert-butyl alcohol at 20℃; for 12h;
Stage #2: With sodium sulfite In water; tert-butyl alcohol at 20℃; for 0.5h;
90%
Multi-step reaction with 2 steps
1: 88 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 °C
2: 73 percent / H2O, H2SO4 / tetrahydrofuran / Ambient temperature
View Scheme
osthole
484-12-8

osthole

N'-(3-methoxybenzylidene)-2-nitrobenzenesulfonohydrazide

N'-(3-methoxybenzylidene)-2-nitrobenzenesulfonohydrazide

7-methoxy-8-((3-(3-methoxyphenyl)-2,2-dimethylcyclopropyl)methyl)-2H-chromen-2-one

7-methoxy-8-((3-(3-methoxyphenyl)-2,2-dimethylcyclopropyl)methyl)-2H-chromen-2-one

Conditions
ConditionsYield
Stage #1: N'-(3-methoxybenzylidene)-2-nitrobenzenesulfonohydrazide With sodium hydride In dichloromethane at 20℃; for 1h; Inert atmosphere; Sealed tube;
Stage #2: osthole With silver trifluoromethanesulfonate In dichloromethane at 40℃; for 18h; Inert atmosphere; Sealed tube;
85%
osthole
484-12-8

osthole

tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

(E)-tert-butyl 4-(7-methoxy-2-oxo-2H-chromen-8-yl)but-2-enoate
1299490-72-4

(E)-tert-butyl 4-(7-methoxy-2-oxo-2H-chromen-8-yl)but-2-enoate

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide In diethyl ether at 35℃; for 24h; Inert atmosphere; diastereoselective reaction;81%
osthole
484-12-8

osthole

ethyl iodide
75-03-6

ethyl iodide

3-(2-ethoxy-4-methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid
73490-52-5

3-(2-ethoxy-4-methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) 15 min, 2.) heating;80%
With potassium hydroxide 1.) DMSO, 1 h, 2.) (Osthol : C2H5I = 1:1) 12 h; Yield given. Multistep reaction;
osthole
484-12-8

osthole

osthenol
484-14-0

osthenol

Conditions
ConditionsYield
With L-Cysteine; sodium hydride In N,N-dimethyl-formamide for 3h; Reflux;77%
With aluminium trichloride; dimethylsulfide In dichloromethane at 30℃; for 24h;62%
Stage #1: osthole With aluminum (III) chloride; dimethylsulfide In dichloromethane at 0 - 30℃;
Stage #2: With hydrogenchloride In dichloromethane; water
62%
With aluminum (III) chloride; dimethylsulfide In dichloromethane at 0 - 30℃; for 24h;59%
osthole
484-12-8

osthole

7,8-(11,11-dimethyl pyrano)coumarin
2221-66-1

7,8-(11,11-dimethyl pyrano)coumarin

Conditions
ConditionsYield
With aluminium trichloride; ethanethiol In dichloromethane at 30℃; for 24h;76%
With phosphorus; hydrogen bromide
osthole
484-12-8

osthole

thioosthole

thioosthole

Conditions
ConditionsYield
With Lawessons reagent In tetrahydrofuran for 24h; Reflux;76%
With Lawessons reagent In tetrahydrofuran at 66℃; for 24h;351 mg
osthole
484-12-8

osthole

A

8-isopentyl-7-methoxy-2H-chromen-2-one
6619-22-3

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

B

8-isopentyl-7-methoxy-chroman-2-one
181303-71-9

8-isopentyl-7-methoxy-chroman-2-one

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol; dichloromethaneA 21%
B 66%
osthole
484-12-8

osthole

(E)-2-hydroxy-4-methoxy-3-isopentenyl-cinnamic acid

(E)-2-hydroxy-4-methoxy-3-isopentenyl-cinnamic acid

Conditions
ConditionsYield
Stage #1: osthole With water; sodium hydroxide for 8h; Reflux;
Stage #2: With hydrogenchloride In water at 20℃; pH=2 - 3;
65.7%
osthole
484-12-8

osthole

(2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-enal
73292-92-9

(2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-enal

Conditions
ConditionsYield
With selenium(IV) oxide; acetic acid for 3h;60%
osthole
484-12-8

osthole

dimethyl sulfate
77-78-1

dimethyl sulfate

(Z)-2,4-dimethoxy-3-isopentenyl-cinnamic acid

(Z)-2,4-dimethoxy-3-isopentenyl-cinnamic acid

Conditions
ConditionsYield
Stage #1: osthole With water; sodium hydroxide for 0.5h; Reflux;
Stage #2: dimethyl sulfate With sodium hydroxide In water at 20℃; for 1.5h; Reflux;
Stage #3: With hydrogenchloride In water at 20℃; pH=2 - 3;
55.4%
osthole
484-12-8

osthole

A

(2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-enal
73292-92-9

(2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-enal

B

4'-hydroxylosthole
73292-93-0

4'-hydroxylosthole

Conditions
ConditionsYield
With selenium(IV) oxide In ethanol for 0.75h; Heating;A 22%
B 55%
osthole
484-12-8

osthole

dimethyl sulfate
77-78-1

dimethyl sulfate

(E)-2,4-dimethoxy-3-isopentenyl-cinnamic acid

(E)-2,4-dimethoxy-3-isopentenyl-cinnamic acid

Conditions
ConditionsYield
Stage #1: osthole With water; sodium hydroxide Reflux;
Stage #2: dimethyl sulfate With sodium hydroxide In water at 20℃; for 3.5h; Reflux;
Stage #3: With hydrogenchloride In water at 20℃; pH=2 - 3;
52.2%
osthole
484-12-8

osthole

7-methoxy-8-(3'-formylbut-2'-enyl) coumarin

7-methoxy-8-(3'-formylbut-2'-enyl) coumarin

Conditions
ConditionsYield
With selenium(IV) oxide; acetic acid for 3h;50%
With selenium(IV) oxide In ethanol at 65℃; for 10h; Inert atmosphere;
With selenium(IV) oxide In 1,4-dioxane at 60 - 80℃; for 1.5h;
osthole
484-12-8

osthole

sodium difluoromethanesulfinate
275818-95-6

sodium difluoromethanesulfinate

3-difluoromethyl-7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

3-difluoromethyl-7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Conditions
ConditionsYield
With eosin y In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; Irradiation;47%
osthole
484-12-8

osthole

1,1,1-trifluoro-2-iodoethane
353-83-3

1,1,1-trifluoro-2-iodoethane

7-methoxy-8-(3-methylbut-2-en-1-yl)-3-(2,2,2-trifluoroethyl)-2H-chromen-2-one

7-methoxy-8-(3-methylbut-2-en-1-yl)-3-(2,2,2-trifluoroethyl)-2H-chromen-2-one

Conditions
ConditionsYield
With tris[2-phenylpyridinato-C2,N]iridium(III); potassium carbonate In dimethyl sulfoxide at 20℃; for 12h; Schlenk technique; Irradiation; Inert atmosphere;43%
osthole
484-12-8

osthole

ethanethiol
75-08-1

ethanethiol

A

7,8-(11,11-dimethyl pyrano)coumarin
2221-66-1

7,8-(11,11-dimethyl pyrano)coumarin

B

7-hydroxy-8-(3-methyl-3-thioethylbutyl)-coumarin

7-hydroxy-8-(3-methyl-3-thioethylbutyl)-coumarin

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 30℃; for 12h;A 20%
B 40%
osthole
484-12-8

osthole

8-(2,3-dibromo-3-methyl-butyl)-7-methoxy-coumarin

8-(2,3-dibromo-3-methyl-butyl)-7-methoxy-coumarin

Conditions
ConditionsYield
With bromine In dichloromethane at 0℃;34%
With tetrachloromethane; bromine
osthole
484-12-8

osthole

dimethyl sulfate
77-78-1

dimethyl sulfate

2,4-dimethoxy-3-isopentenyl-cinnamic acid

2,4-dimethoxy-3-isopentenyl-cinnamic acid

Conditions
ConditionsYield
Stage #1: osthole With water; sodium hydroxide at 20℃; Reflux;
Stage #2: dimethyl sulfate In water at 20℃; for 3h; Reflux;
Stage #3: With hydrogenchloride In water at 20℃; pH=2 - 3;
31.25%
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