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
• Description: Monocrotaline (MCT) is a toxic 11-membered macrocyclic pyrrolizidine alkaloid (PA) derived from the seeds of the Crotalaria spectabilis plant. It poisons livestock and humans through the ingestion of contaminated grains and other foods. Pyrrolizidine alkaloid is activated by cytochrome P450 to the reactive pyrrole metabolite dehydromonocrotaline (MCTP) in the liver. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Monocrotaline is produced for research use. It is used in rat model to investigate human pulmonary hypertension as it offers technical simplicity, reproducibility, and low cost compared with other models of pulmonary hypertension. A hepatotoxic alkaloid of the pyrrolizidine group obtained from Crotalaria retusa and C. spectabilis, the base is laevorotatory with [α]26D - 55.7° (CHCI3). It may be characterized as the hydrochloride, m.p. 184°C ldec.); [α]28D - 38.4° (H20) and the methiodide which crystallizes from MeOH with 3 moles of solvent, m.p. 205°C (dry, dec.); [α]28D + 23.4° (MeOH). Hydrolysis with boiling Ba(OHh furnishes retronecine and monocrotic acid, C7H120 3, b.p. 145-6°C/ 18 mm which is optically inactive. This acid yields a methyl ester, b.p. 94-6°Cj 18 mm, a p-bromophenacyl ester, m.p. 78°C and a 2:4-dinitrophenylhydrazone, m.p. 95-6°C. Hydrogenation in the presence of Pt02 as catalyst yields retro_x0002_necanol and monocrotalic acid, CSH120S' m.p. 181-2°C; [α]28D - 5.33° (H20) which gives a methyl ester, m.p. 79-800 C; [α]30D - 16.2° (EtOH) and a pbromophenacyl ester, m.p. 162-3°C.
• Physical properties: Appearance: white prism crystal. Solubility: soluble in methanol, ethanol, and chloroform; slightly soluble in benzene, water, ether, and acetone; insoluble in petroleum ether. Melting point: 197–198 °C. Specific optical rotation: ?54.7 ° (in chloroform).
• Uses: Crotaline has been used in hydrochloric acid (HCl) and injected into experimental animals to induce-pulmonary hypertension. A toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary diseases in rats. antineoplastic, insect sterilant
• Indications: This product is available in the Pharmacopoeia of the People’s Republic of China (1977).Clinical available formulations include gel and liposome transdermal preparations. It is effective in treating skin cancer, basal cell carcinoma, acute leukemia, and cervical and penile cancer.
• Clinical Use: Monocrotaline injection shows well therapeutic effect for treating squamous cell carcinoma and basal cell carcinoma. In folk, the fresh pulp or dry powder of the herb has been also used for treating squamous cell carcinoma and basal cell carcinoma .

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:

1,2-Dihydro-1α,2α-epoxymonocrotalin

1,2-Dihydro-1β,2β-epoxy-monocrotalin

spectabiline

(7R,7aR)-7-Hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carbaldehyde

Refernces

• 1、 Niwa, Haruki,Ogawa, Takeshi,Okamoto, Osamu,Yamada, Kiyoyuki. "Total synthesis of optically active monocrotaline, a carcinogenic pyrrolizidine alkaloid possessing an eleven-membered retronecine dilactone". . p. 10531 - 10548. Retrieved 2007/10/02.
• 2、 Vedejs,Ahmad,Larsen,Westwood. "Synthesis of monocrotaline by nucleophilic macrolactonization". . p. 3937 - 3938. Retrieved 2007/10/02.