ACENOCOUMAROL

Base Information

• Chemical Name: ACENOCOUMAROL
• CAS No.: 152-72-7
• Molecular Formula: C19H15NO6
• Molecular Weight: 353.331
• Hs Code.: 2932209090
• Mol file: 152-72-7.mol

Synonyms:Acenocoumarol(6CI);Coumarin, 3-(a-acetonyl-p-nitrobenzyl)-4-hydroxy- (8CI);3-(Alpha-acetonyl-4-nitrobenzyl)-4-hydroxycoumarin;3-(a-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin;3-(a-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarin;3-(a-p-Nitrophenyl-b-acetylethyl)-4-hydroxycoumarin;3-[a-(4'-Nitrophenyl)-b-acetylethyl]-4-hydroxycoumarin;3-[a-(p-Nitrophenol)-b-acetylethyl]-4-hydroxycoumarin;4-Hydroxy-2-oxo-3-[3-oxo-1-(4-nitrophenyl)butyl]-2H-chromene;Acenocoumarin;Acitrom;Ascumar;DL-3-(a-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin;G 23,350;Minisintrom;Nicoumalone;Nitrowarfarin;Sinkumar;Sinthrome;Sintrom;Sintrom Mitis;Syncumar;Syntrom;Trombostop;Zotil;

Chemical Property of ACENOCOUMAROL

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 196-199 °C
• Refractive Index: 1.656
• Boiling Point: 592.718 °C at 760 mmHg
• PKA: pKa 4.7 (Uncertain)
• Flash Point: 312.265 °C
• PSA: 113.33000
• Density: 1.427 g/cm³
• LogP: 4.04100
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO, heptane and xylene: ≥17mg/mL

Purity/Quality:

Acenocoumarol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63-22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: R-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant S-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant antimicrobial Anticoagulant agent: Vitamin K antagonist
• Therapeutic Function: Anticoagulant, Vitamin
• Clinical Use: Anticoagulant
• Drug interactions: Potentially hazardous interactions with other drugs There are many significant interactions with coumarins. Prescribe with care with regard to the following: Anticoagulant effect enhanced by: alcohol, amiodarone, anabolic steroids, aspirin, aztreonam, bicalutamide, cephalosporins, chloramphenicol, cimetidine, ciprofloxacin, fibrates, clopidogrel, cranberry juice, danazol, dipyridamole, disulfiram, dronedarone, esomeprazole, ezetimibe, fibrates, fluconazole, flutamide, fluvastatin, grapefruit juice, itraconazole, ketoconazole, levamisole, levofloxacin, macrolides, methylphenidate, metronidazole, miconazole, nalidixic acid, neomycin, norfloxacin, NSAIDs, ofloxacin, omeprazole, pantoprazole, paracetamol, penicillins, propafenone, ritonavir, rosuvastatin, SSRIs, simvastatin, sulfinpyrazone, sulphonamides, tamoxifen, testosterone, tetracyclines, thyroid hormones, tigecycline, toremifene, tramadol, trimethoprim, valproate, vitamin E, voriconazole. Anticoagulant effect decreased by: acitretin, azathioprine, carbamazepine, enteral feeds, enzalutamide, fosphenytoin, griseofulvin, oral contraceptives, phenobarbital, phenytoin, primidone, rifamycins, St John’s wort (avoid), sucralfate, vitamin K. Anticoagulant effects enhanced / reduced by: anion exchange resins, corticosteroids, dietary changes, efavirenz, fosamprenavir, tricyclics. Analgesics: increased risk of bleeding with IV diclofenac and ketorolac - avoid concomitant use. Anticoagulants: increased risk of haemorrhage with apixaban, dabigatran, edoxaban and rivaroxaban - avoid. Antidiabetic agents: enhanced hypoglycaemic effect with sulphonylureas also possible changes to anticoagulant effect. Ciclosporin: there have been a few reports of altered anticoagulant effect; decreased ciclosporin levels have been seen rarely. Cytotoxics: increased risk of bleeding with erlotinib; enhanced anticoagulant effect with capecitabine, etoposide, fluorouracil, ifosfamide, sorafenib and tegafur; reduced effect with mercaptopurine and mitotane.

Technology Process of ACENOCOUMAROL

There total 12 articles about ACENOCOUMAROL 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: 98.0%

4-(p-nitrophenyl)-3-butene-2-one (946-49-6,3490-37-7,30625-98-0) + 4-hydroxydihydrocoumarin → (+)-Acenocoumarol (152-72-7,66556-78-3,70897-81-3,66556-77-2)

Guidance literature:

With (S,S)-N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine; p-Toluic acid; In toluene; at 20 ℃; for 72h; enantioselective reaction;

DOI:10.1039/c2ob26334c

Reference yield: 96.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + (E)-4-(4-nitrophenyl)-3-buten-2-one (946-49-6,3490-37-7,30625-98-0) → acenocoumarol (152-72-7)

Guidance literature:

With polystyrene-divinylbenzene support prepared with 2-ethylhexanoic acid as porogen with immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene; at 100 ℃; for 72h; Reagent/catalyst; Green chemistry;

DOI:10.1016/j.jcat.2013.10.009

Reference yield: 92.0%

4-(p-nitrophenyl)-3-butene-2-one (946-49-6,3490-37-7,30625-98-0) + 4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → acenocoumarol (152-72-7)

Guidance literature:

potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride; In water; for 2h; Product distribution; Heating; var. catalysts;

DOI:10.1002/ardp.19903230815

upstream raw materials:

4-(p-nitrophenyl)-3-butene-2-one

4-hydroxy[1]benzopyran-2-one

2-Methoxypropene

4-nitrobenzaldehdye

Refernces

• 1、 Rayar, Anita Marie,Lagarde, Nathalie,Martin, Frederique,Blanchard, Florent,Liagre, Bertrand,Ferroud, Clotilde,Zagury, Jean-Fran?ois,Montes, Matthieu,Sylla-Iyarreta Veitía, Maité. "New selective cyclooxygenase-2 inhibitors from cyclocoumarol: Synthesis, characterization, biological evaluation and molecular modeling". supporting information. p. 577 - 587. Retrieved 2018/02/10.
• 2、 Ueda, Atsushi,Umeno, Tomohiro,Doi, Mitsunobu,Akagawa, Kengo,Kudo, Kazuaki,Tanaka, Masakazu. "Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights". . p. 6343 - 6356. Retrieved 2016/08/16.