Imperialine
Basic information
- CAS
61825-98-7- Standard SMILES
C[C@H]1CC[C@@H]2N(C1)C[C@H]1[C@@H]3C[C@H]4[C@@H](CC(=O)[C@H]5C[C@@H](O)CC[C@@]54C)[C@@H]3CC[C@H]1[C@]2(C)O- InChIKey
IQDIERHFZVCNRZ-LRCDAWNTSA-N- Molecular formula
- C27H43NO3
- Average molar mass
- 429.6 g/mol
- Monoisotopic mass
- 429.32429423
Overview
Sipeimine is an alkaloid.
Names & identifiers
- Preferred name
- Imperialine
- IUPAC
- (1R,2S,6S,9S,10S,11R,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one
- English name
- IMPERIALINE
- Molecular formula
- C27H43NO3
- Molecular weight
- 429.64
Names & synonyms
Imperialinesipeimine61825-98-7JKN43410XZCevan-6-one, 3,20-dihydroxy-, (3-beta,5-alpha,17-beta)-(1R,2S,6S,9S,10S,11R,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-oneNSC-282170(1R,2S,6S,9S,10S,11R,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo(12.11.0.02,11.04,9.015,24.018,23)pentacosan-17-oneRefChem:1087262Cevan-6-one, 3,20-dihydroxy-, (3beta,5alpha)-QUB07U6VTQKashmirine
Show more names
RADDEAMINEPregn-4-ene-3sipeimine(Kashmirine)Raddeamine, SipeimineImperialine (Sipeimine)Sipeimine, 10 mM in DMSO
MFCD00171661(3S,4aS,6aS,6bS,8aR,9S,9aS,12S,15aS,15bR,16aS,16bR)-3,9-dihydroxy-9,12,16b-trimethyldocosahydrobenzo[4,5]indeno[1,2-h]pyrido[1,2-b]isoquinolin-5(1H)-oneC27H43NO3UNII-JKN43410XZImperialinBenzo[7,8]fluoreno[2,1-b]quinolizine, cevan-6-one deriv.; Kashmirine; NSC 282170Sipeimine;Sipeimine (Standard)(3-beta,5-alpha,17-beta)-3,20-Dihydroxycevan-6-one
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 60.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 755
Physicochemical properties
- Melting point
- 267 °C · 267 °C(Solv: methanol (67-56-1))
- Boiling point
- 567.1 · 567.1±50.0 °C(Predicted)
- Density
- 1.18 · 1.18±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Ethanol (Slightly)
- pka
- 14.56 · 14.56±0.70(Predicted)
- form
- solid
- color
- White to Off-White
- InChIKey
- IQDIERHFZVCNRZ-LRCDAWNTSA-N
- FDA UNII
- 43410 XZ · JKN43410XZ
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- RTECS
- 5830000 · FL5830000
- HS Code
- 29389090 · 29389090
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302+H312+H332 (100%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- rtecs
- FL5830000
- hs_code
- 29389090
- safety_code
- 24/25
Chemistry & industry
Applications
DescriptionA steroidal alkaloid isolated from the bulbs of Fritillaria irnperialis L. and Petiliurn eduardi, the base crystallizes in short, colourless needles and has [α]D - 35.4° (CHCI3). It yields crystalline salts and with sucrose gives a sequence of characteristic colours on addition of dilute H2S04 from yellowgreen, through pale green, pink, cherry red, to dark violet. The structure has been determined from mass spectrometry and the NMR spectrum, the latter proving the presence of tertiary hydroxyl and methyl groups at C-20.
OccurrenceA steroidal alkaloid, kashmirine has been obtained from Fritillaria raylei. It furnishes colourless needles when crystallized from EtOH and is laevorotatory with a specific rotation of [α]D -40.4° (CHCI3).
UsesImperialine is an isosteroidal alkaloid from Fritillaria thunbergii.
Additional notes
DefinitionChEBI: Sipeimine is an alkaloid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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