Retrorsine-N-oxide, HPLC Grade
Grundinformationen
- CAS
15503-86-3- Standard-SMILES
C/C=C1\C[C@H](C)[C@](O)(CO)C(=O)OCC2=CC[N+]3([O-])CC[C@@H](OC1=O)[C@@H]23- InChIKey
IDIMIWQPUHURPV-DWIABFLBSA-N- Summenformel
- C18H25NO7
- Durchschnittliche Molmasse
- 367,4 g/mol
- Monoisotopische Masse
- 367,16310214
Überblick
See also: Isatidine (annotation moved to).
Namen und Bezeichner
- Bevorzugter Name
- Retrorsine-N-oxide, HPLC Grade
- IUPAC
- (1R,4E,6S,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
- Englischer Name
- isatidine
- Summenformel
- C18H25NO7
- Molmasse
- 367.39
Namen und Synonyme
Retrorsine-N-oxide , HPLC Grade15503-86-3MFCD00074872isatidineRetrorsin-N-oxidRETRORSINE-N-OXIDERetrorsine N-oxide (Standard)Retrorsine-N-oxide 100 μg/mL in Water12,18-Dihydroxysenecionane-11,16-dione 4-oxide12,18-Dihydroxy-11,16-dioxosenecionane 4-oxide[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3Z,5R,6S,14aR,14bR)-
Datenbank-Bezeichner
- CAS
15503-86-3- PubChem CID
- 168009744
- EC Number
- 805-145-0
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0
- Polarare Oberfläche (TPSA)
- 111 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 672
Physikochemische Eigenschaften
- Schmelzpunkt
- 145 °C · 145°C
- Siedepunkt
- 497.95 °C · 497.95°C (rough estimate)
- Dichte
- 1.3204 · 1.3204 (rough estimate)
- Brechungsindex
- 1.51 · 1.5100 (estimate)
- pka
- 11.96 · 11.96±0.40(Predicted)
- EPA chemische Informationen
- Isatidine (15503-86-3)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P264, P270, P301+P316, P319, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Sicherheitsdaten
- ridadr
- 1544
- hazard_class
- 6.1(a)
- packing_group
- II
- Giftige Stoffe Daten
- 15503-86-3(Hazardous Substances Data)
Chemie und Industrie
Anwendungen
BeschreibungThis hepatotoxic alkaloid occurs in certain Senecio species and was first isolated from S. isatideus D.C. It occurs abundantly in S. retrorsus D.C. and S. scleratus Schw. The alkaloid crystallizes in rhombic prisms as the dihydrate and has [α]27D . 8.25° (H 20). It is soluble in MeOH, hot EtOH and hot H20 but virtually insoluble in Et 20, Me2CO or CHCl 3. On reduction it absorbs 4 molecules of H2 to give hexahydrodeoxyisatidine which melts at l15-l20°C and then remelts at l83-4°C following an intermediate solidification. This compound gives a hydrochloride, m.p. 218°C (dec.); [α]20D - 52.5° (H20) and may be hydrolyzed with Ba(OHh to give a basic product, tetrahydroisatinecine, CSH1703N, m.p. l74.5°C; [α]20D - 88° (H 20). The alkaloid itself, on hydrolysis with Ba(OHh yields isatinecine and two acid products, isatinecic acid and the monolactone, the latter almost certainly being formed by the action of the base upon the acid.
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