Monocrotalin

Base Information

• Chemical Name: Monocrotalin
• CAS No.: 315-22-0
• Molecular Formula: C16H23NO6
• Molecular Weight: 325.362
• Hs Code.: 29399990
• DSSTox Substance ID: DTXSID20859330
• Wikidata: Q27215982
• ChEMBL ID: CHEMBL2134902
• Mol file: 315-22-0.mol

Synonyms:Monocrotalin;MLS002639247;20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13.alpha.,14.alpha.)-;Oprea1_734543;CHEMBL2134902;DTXSID20859330;CHEBI:125403;QVCMHGGNRFRMAD-UHFFFAOYSA-N;BCP04181;LSM-36888;4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione;SMR001548694;A856086;A 6080;A-6080;A6080;Q27215982;(6-CHLORO-IMIDAZO[1,2-A]PYRIDIN-2-YL)-ACETICACID;14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione, 9CI;(13-.alpha.,14-.alpha.)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione;12.beta.,13.beta.-Dihydroxy-12.alpha.,13.alpha.,14.alpha.-trimethylcrotal-1-enine;14,19-Dihydro-12,13-dihydroxy(13.alpha.,14.alpha.)-20-norcrotalanan-11,15-dione;2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dione deriv.;(2,3,4-gh)pyrrolizine-2,6(3H)-dione,(4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-;4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione #

Chemical Property of Monocrotalin

Chemical Property:

• Appearance/Colour: white to light tan powder
• Vapor Pressure: 8.74E-14mmHg at 25°C
• Melting Point: 204 °C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 537.3 °C at 760 mmHg
• PKA: 12.21±0.60(Predicted)
• Flash Point: 278.7 °C
• PSA: 96.30000
• Density: 1.35 g/cm³
• LogP: -0.45470
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 50 mg/ml with warming), in Ethanol (up to 10 mg/ml with warming) or in organic solvents such as Chloroform (up to 50 mg/ml)
• Water Solubility.: 11.86g/L(temperature not stated)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 325.15253745
• Heavy Atom Count: 23
• Complexity: 575

Purity/Quality:

99% ^*data from raw suppliers

Monocrotaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-40-35
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)O)(C)O
• General Description: Monocrotaline is a macrocyclic dilactone pyrrolizidine alkaloid with significant hepatotoxic and antitumor properties, as well as ecological roles as a defensive compound and pheromone precursor in Danaid butterflies. Its synthesis is challenging due to the tendency for competing γ-lactone formation, but a successful approach involving nucleophilic macrolactonization has been demonstrated, confirming the method's applicability for retronecine-derived dilactones.

Technology Process of Monocrotalin

There total 18 articles about Monocrotalin 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: 86.0%

monocrotaline methylene acetal (110121-56-7,121719-98-0,121720-00-1) → monocrotaline (315-22-0)

Guidance literature:

With trityl tetrafluoroborate; In dichloromethane; for 48h; Heating;

DOI:10.1016/S0040-4020(01)88350-2

Reference yield: 75.0%

C17H23NO6 (110121-56-7,121719-98-0,121720-00-1) → monocrotaline (315-22-0)

Guidance literature:

With hydrogenchloride; In ethylene glycol; at 110 ℃; for 2h;

DOI:10.1021/jo00226a045

Reference yield: 38.0%

Monocrotaline N-oxide (35337-98-5) → monocrotaline (315-22-0)

Guidance literature:

With intestinal gut bacteria in a human fecal suspension; at 37 ℃; for 5h; Enzymatic reaction;

DOI:10.14233/ajchem.2013.13283

upstream raw materials:

grahamine

monocrotaline methylene acetal

C₁₇H₂₃NO₆

(2R,3R,4R)-2,3,4-trimethyl-2,3-methylenedioxypentanedioic anhydride

Downstream raw materials:

Monocrotalic acid

Monocrotaline N-oxide

spectabiline

12,13-diacetoxy-(13βH,14βH)-14,19-dihydro-20-nor-crotalanane-11,15-dione

Refernces

Synthesis of monocrotaline by nucleophilic macrolactonization

10.1021/jo00226a045

The research focuses on the synthesis of monocrotaline, a macrocyclic dilactone pyrrolizidine alkaloid, which is notable for its potent hepatotoxic and antitumor activity, as well as its role as a defensive agent and pheromone precursor in Danaid butterflies. The study addresses the challenges in synthesizing the 11-membered derivative monocrotaline, particularly its tendency for y-lactone formation, which complicates synthetic strategies. The researchers developed a sequence involving the coupling of compounds 10 and 6, followed by nucleophilic ring closure, which includes the displacement of mesylate by a carboxylate ion generated in situ through the desilylation of a β-(trimethylsilyl)ethyl ester 3. Key chemicals used in the process include retronecine derivatives, glutaric anhydride derivative 5, 2-(trimethylsilyl)ethanol, and various reagents for cyclization and deprotection steps. The conclusions of the research confirm the generality of the nucleophilic cyclization method for the synthesis of retronecine-derived dilactones and provide a complete synthesis of monocrotaline, highlighting the effectiveness of the method in the case of pyrrolizidine alkaloids.