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
Grundinformationen
- CAS
315-22-0- Standard-SMILES
CC1C(=O)OC2CCN3CC=C(COC(=O)C(C)(O)C1(C)O)C23- InChIKey
QVCMHGGNRFRMAD-UHFFFAOYSA-N- Summenformel
- C16H23NO6
- Durchschnittliche Molmasse
- 325,36 g/mol
- Monoisotopische Masse
- 325,15253745
Überblick
LSM-36888 is a member of pyrrolizines.
Namen und Bezeichner
- Bevorzugter Name
- 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
- IUPAC
- 5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
- Englischer Name
- MONOCROTALINE
- Summenformel
- C16H23NO6
- Molmasse
- 325.36
Namen und Synonyme
MLS00263924720-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13.alpha.,14.alpha.)-Oprea1_734543CHEMBL2134902DTXSID20859330CHEBI:125403QVCMHGGNRFRMAD-UHFFFAOYSA-N(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-LSM-368884,5-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)-dioneLS-14523SMR001548694
Weitere Namen anzeigen
CROTALINEMONOCROTALINA 6080CROTALINNSC 28693NCI-C56462Bulbus LiliiMONOCROTALINEMonccrotalireMONOCRATALINE
NS00015471Q2721598214,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione, 9CI(13-.alpha.,14-.alpha.)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione12.beta.,13.beta.-Dihydroxy-12.alpha.,13.alpha.,14.alpha.-trimethylcrotal-1-enine14,19-Dihydro-12,13-dihydroxy(13.alpha.,14.alpha.)-20-norcrotalanan-11,15-dione2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dione deriv.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 #
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,7
- Polarare Oberfläche (TPSA)
- 96,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 575
Experimentelle und physikochemische Eigenschaften
Melting Point202 - 203 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 204 °C · 204 °C (dec.) (lit.)
- Siedepunkt
- 463.55 °C · 463.55°C (rough estimate)
- Dichte
- 1.1512 · 1.1512 (rough estimate)
- Brechungsindex
- 1.55 · 1.5500 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 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)
- Aggregatzustand
- Solid
- pka
- 12.21 · 12.21±0.60(Predicted)
- Farbe
- White
- Wasserlöslichkeit
- 11.86 g/L · 11.86g/L(temperature not stated)
- Merck
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 1544 6.1/PG 3
- hs_code
- 29399990
- RTECS-Nr.
- QB3140000
- risk_code
- 25-40-35
- Toxizität
- LD50 orally in rats: 71 mg/kg (Newberne)
- hazard_code
- T
- safety_code
- 36/37/39-45
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Giftige Stoffe Daten
- 315-22-0(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 3 OralCarc. 2
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsCytoplasm
Anwendungen
BeschreibungA 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.
HistoryIn 1935, W.M. Neil and L.L. Russoff isolated monocrotaline from Crotalaria sessiliflora L.Monocrotaline showed anticancer activity invivo, especially for treating squamous cell carcinoma, cervical cancer, and leukemia. However, since many pyrrolizidine alkaloid compounds have hepatotoxicity, further development of these compounds is restricted.China began the research of monocrotaline, as early as 1943. Crotalaria sessiliflora L. was also recorded in the 1977 edition of the Pharmacopoeia of the People’s Republic of China. But monocrotaline was reported for its liver toxicity; teratogenic, allergic reactions; and other side effects, limiting its further clinical applications. In 1992, the Ministry of Health stopped the clinical application of monocrotaline injection. Further pharmacology study is essential for monocrotaline .
VerwendenA toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary diseases in rats.
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