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484-12-8

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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.

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.

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. The above information is edited by the lookchem of Dai Xiongfeng.

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.

Description

Cnidium is a Chinese medicine which is used widely by traditional medicine doctors. Cnidium has been recorded in almost all of the pharmaceutical monographs , including Shen Nong’s Classic Materia Medica, New Materia Medica, Compendium of Materia Medica, etc. Osthole is a major bioactivity compound of the Cnidium, which has the effect of dampness dispelling, insecticidal antipruritic,and aphrodisiac and is used for the treatment for pruritus and eczema, lumbago,kidney impotence, and infertility . Osthole is derived from Umbelliferae and Rutaceae plants. Osthole is also distributed in Asteraceae and Leguminosae plants. Osthole is present in 14 genera of Umbelliferae plants: danggui (Angelica L.), gudanggui (Archangelica Hoffm.), mianguoqin (Cachrys L.), shechuang (Cnidium Cusson), awei (Ferula L.), duhuo (Heracleum L.), yanfeng (Libanotis Hill), ouqin (Petroselinum Hill), qianhu (Peucedanum L.), huiqin (Pimpinella L.), liangshechuang (Selinum L.). Shuanchiqin (Prangos Lindl), xifengqin (Seseli L.), oufangfeng (Pastinaca L.). Osthole is present in 17 genera of Rutaceae plants: ganju (Citrus L.), huangpi (Clausena Burm. F.), xiangju (Feronia Correa), jupanmu (Flindersia R. Br.), niyunxiang (Haplophyllum A. Juss.), mizhuyu (Melicope J. R. and G. Forst.), xiaoyunmu (Micromelum Bl.), jiulixiang (Murraya Koenig ex L.), zhi (Poncirus Raf.), yinyu (Skimmia Thunb.), Limonia, Myrtopsis, Pentaceras, Phebalium, Pilocarpus, Thamnosma, Ticorea) .

Physical properties

Appearance: white needlelike crystalline powder. Solubility: soluble in methanol. Melting point: 83–84 °C.

History

Cnidium is a Chinese medicine which is used widely by traditional medicine doctors. Osthole was isolated in 1950 and then its chemical structure was determined . Osthole can be extracted by solvent method, acid-base method, ultrasound, and supercritical and other methods. The main methods for the separation of osthole are recrystallization, chromatography, and so on. With the development of modern pharmacological experimental methods and techniques, the pharmacological effects of osthole have been discovered and developed. It is found that osthole has many pharmacological activities such as anti-osteoporosis, antiplatelet aggregation, antiviral, anti-mutation, anti-allergic reaction, and so on. In recent years, it has been found that osthole has obvious antitumor activity. In addition, osthole also has strong insecticidal and antifungal effects. In the future, osthole is expected to be developed as a new kind of low-toxicity, high-efficiency, and lowresidue pesticide.

Uses

Osthole inhibits the PI3K/Akt pathway thus inhibiting insulin-like growth factor-1 (IGF-1)-induced epithelial-to-mesenchymal transition (EMT) in brain cancer. Osthole may be used in the treatment of Glioblastoma multiforme (GBM).

Indications

Impotence, infertility, uterine cold, wet nose with low back pain, vulva eczema, woman vulvae, trichomonas vaginitis

Definition

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

Pharmacology

1. Osthole can enhance the non-specific immune function of mice. 2. Osthole exhibits protective effect on the heart and circulatory system. Osthole can dilate blood vessels, reduce blood pressure, reduce blood lipid, and inhibit the formation of venous thrombosis. 3. Osthole has a central sedative effect and can improve the learning and memory function of mice. 4. Osthole presents the effect of relieving asthma by regulating the function of hypothalamus-pituitary-adrenal cortex system. 5. Osthole has antiaging and antioxidant effects, which may be related to the direct scavenging of oxygen free radicals. 6. Osthole reduces osteoporosis and bone resorption in ovariectomized rats and increases bone mass. Osthole can effectively prevent osteoporosis in ovariectomized rats, prevent bone loss, and maintain bone metabolism balance. 7. Osthole can relieve itching, which may be related to blocking the Ca2+ channel of mast cells, decreasing the flow of Ca2+, and inhibiting the release of histamine from mast cells. 8. Osthole is a noncompetitive antagonist of Ca2+, which can inhibit the smooth muscle of the uterus. In addition, osthole has a certain androgen-like, estrogen-like effect. 9. Osthole has anti-inflammatory effects on acute and chronic inflammation models, and its anti-inflammatory mechanism is not through the pituitary-adrenal cortex system, but also with the synthesis of PGE. It may be possible to exert anti-inflammatory effects by enhancing non-specific immune function and/or anti-allergic reactions . 10. Accumulating experimental evidences have shown that osthole exhibited antiproliferative properties and induced apoptosis in various kinds of tumor cells. Besides, osthole has broad-spectrum antibacterial and insecticidal effects.

Clinical Use

In vitro and in vivo experimental results have revealed that osthole demonstrates multiple pharmacological actions including neuroprotective, osteogenic, immunomodulatory,anticancer, hepatoprotective, cardiovascular protective, and antimicrobial activities. Osthole is expected to be used in the treatment of cardiovascular system, central nervous system, and immune system diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 484-12-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 4 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 484-12:
(5*4)+(4*8)+(3*4)+(2*1)+(1*2)=68
68 % 10 = 8
So 484-12-8 is a valid CAS Registry Number.
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%

484-12-8Relevant articles and documents

Dreyer,Lee

, p. 1499 (1969)

Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions

Gulías, Moisés,Marcos-Atanes, Daniel,Mascare?as, José L.,Font, Marc

supporting information, p. 1669 - 1673 (2019/09/04)

Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.

Synthesis of Allyl- and Prenylcoumarins via Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination

Schmidt, Bernd,Riemer, Martin

, p. 141 - 149 (2015/12/26)

Allyl, dimethylallyl, crotyl, and prenyl ethers of various aromatic ortho-hydroxy carbonyl compounds undergo a tandem sequence of Claisen rearrangement, carbonyl olefination, and cyclization upon microwave irradiation in the presence of a stabilized ylide. The products are multiply substituted 6- or 8-allylated or prenylated coumarins (2H-chromen-2-ones).

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