| Identification | Back Directory | [Name]
IMPERIALINE | [CAS]
61825-98-7 | [Synonyms]
SIPEIMINE
RADDEAMINE
kashmirine
IMPERIALINE
Raddeamine, Sipeimine
Imperialine (Sipeimine)
Sipeimine（Kashmirine,Imperialine）
(5α,17β)-3β,20-Dihydroxycevan-6-one
(5α,17β)-3β,20β-Dihydroxycevane-6-one
Cevan-6-one, 3,20-dihydroxy-, (3β,5α,17β)-
Sipeimine, 98%, from Fritillaria cirrhosa Don.
(3-beta,5-alpha,17-beta)-3,20-dihydroxycevan-6-one
3,20-dihydroxy-,(3-beta,5-alpha,17-beta)-cevan-6-on | [Molecular Formula]
C27H43NO3 | [MDL Number]
MFCD00171661 | [MOL File]
61825-98-7.mol | [Molecular Weight]
429.64 |
| Chemical Properties | Back Directory | [Occurrence]
A 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). | [Melting point ]
267 °C(Solv: methanol (67-56-1)) | [Boiling point ]
567.1±50.0 °C(Predicted) | [density ]
1.18±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Ethanol (Slightly) | [form ]
solid
| [pka]
14.56±0.70(Predicted) | [color ]
White to Off-White | [InChIKey]
IQDIERHFZVCNRZ-LRCDAWNTSA-N |
| Hazard Information | Back Directory | [Description]
A 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. | [Chemical Properties]
White needle-shaped crystals, easily soluble in chloroform and ethyl acetate, soluble in methanol, ethanol, acetone, and ether, insoluble in water and petroleum ether, derived from Fritillaria cirrhosa. | [Uses]
Imperialine is an isosteroidal alkaloid from Fritillaria thunbergii. | [Definition]
ChEBI: Sipeimine is an alkaloid. | [References]
Fragner., Ber., 28,3284 (1888)
Structure:
Nuriddinov, Shakirov, Yunusov., Khirn. Prir. Soedin., 3,316 (1967) |
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