Osthole

Base Information

• Chemical Name: Osthole
• CAS No.: 484-12-8
• Deprecated CAS: 1440642-68-1
• Molecular Formula: C15H16O3
• Molecular Weight: 244.29
• Hs Code.: 29322090
• European Community (EC) Number: 610-421-7
• NSC Number: 31868
• UNII: XH1TI1759C
• DSSTox Substance ID: DTXSID20197507
• Nikkaji Number: J12.542C
• Wikipedia: Osthol
• Wikidata: Q4338679
• RXCUI: 1547630
• Pharos Ligand ID: WR3L9L1BLPYJ
• Metabolomics Workbench ID: 67592
• ChEMBL ID: CHEMBL52229
• Mol file: 484-12-8.mol

Synonyms:7-methoxy-8-(3-methylpent-2-enyl)coumarin;osthol;osthole

Chemical Property of Osthole

Chemical Property:

• Appearance/Colour: Fine White Powder
• Vapor Pressure: 1.67E-06mmHg at 25°C
• Melting Point: 83-84 °C
• Refractive Index: 1.556
• Boiling Point: 396.7 °C at 760 mmHg
• Flash Point: 167.6 °C
• PSA: 39.44000
• Density: 1.126 g/cm³
• LogP: 3.31030
• Storage Temp.: room temp
• Solubility.: methanol: soluble10mg/mL, clear, colorless
• Water Solubility.: 12mg/L(25 oC)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 244.109944368
• Heavy Atom Count: 18
• Complexity: 366

Purity/Quality:

98%, ^*data from raw suppliers

Osthol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCC1=C(C=CC2=C1OC(=O)C=C2)OC)C
• 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.
• 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
• 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.

Technology Process of Osthole

There total 19 articles about Osthole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

7-methoxy-8-iodo-2H-chromen-2-one (65763-01-1) + prenyl bromide (870-63-3) → osthole (484-12-8)

Guidance literature:

7-methoxy-8-iodo-2H-chromen-2-one; With isopropylmagnesium chloride; In tetrahydrofuran; at -20 ℃; for 1h; Schlenk technique; Inert atmosphere; Green chemistry;

prenyl bromide; With copper(l) iodide; lithium chloride; In tetrahydrofuran; at -20 - 20 ℃; for 10.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Green chemistry;

DOI:10.1002/cjoc.201500620

Reference yield: 77.65%

8-allyl-7-methoxy-2H-chromen-2-one (55136-74-8) + 3-chloro-3-methyl-1-butene (2190-48-9) → osthole (484-12-8)

Guidance literature:

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;

DOI:10.1016/j.ejmech.2012.06.009

Reference yield: 68.0%

4-methoxy-2-((2-methylbut-3-en-2-yl)oxy)benzaldehyde + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → osthole (484-12-8)

Guidance literature:

With N,N-diethylaniline; at 250 ℃; for 1h; Microwave irradiation; Sealed tube;

DOI:10.1055/s-0035-1560501

upstream raw materials:

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

acetic anhydride

diazomethane

2-Hydroxy-4-methoxybenzaldehyde

Downstream raw materials:

8,8-dimethyl-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-2-one

7-Methoxy-8-(3-methylbutyl)-cumarin

7-hydroxy-8-(3-methyl-3-phenyl-butyl)-coumarin

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

Refernces

• 1、 Yin, Qiang,Yan, Han,Zhang, Yaqin,Wang, Yige,Zhang, Guojin,He, Yuxiang,Zhang, Weihua. "Palladium-catalyzed synthesis of 8-allyl or 8-prenylcoumarins by using organotin reagents as multicoupling nucleophiles". . p. 85 - 88. Retrieved 2013.
• 2、 Konrádová, Daniela,Kozubíková, Hana,Dole?al, Karel,Pospí?il, Ji?í. "Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol". supporting information. p. 5204 - 5213. Retrieved 2017/09/29.
• 3、 Liu, Ming,Liu, Yang,Hua, Xuewen,Wu, Changchun,Zhou, Sha,Wang, Baolei,Li, Zhengming. "Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes". . p. 1353 - 1358. Retrieved 2016/02/18.