| Identification | Back Directory | [Name]
narciclasine | [CAS]
29477-83-6 | [Synonyms]
rciclasin
NSC 266535
Narciclasin
BRN 1087400
Lycorcidinol
narciclasine
Lycoricidin-A
Narciclasine, 99.9%
(13β)-1,19-Didehydro-2α,3β,4β,7-tetrahydroxy-11,12-dinor-5,19-secocrinan-6-one
3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one
(2S)-3,4,4aβ,5-Tetrahydro-2α,3β,4β,7-tetrahydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one
(2S,3R,4S,4aR)-3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one
[1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR)-
(2S-(2-alpha,3-beta,4-beta,4a-beta))-3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one | [Molecular Formula]
C14H13NO7 | [MDL Number]
MFCD01729949 | [MOL File]
29477-83-6.mol | [Molecular Weight]
307.257 |
| Chemical Properties | Back Directory | [Melting point ]
250-252℃ | [Boiling point ]
447.77°C (rough estimate) | [density ]
1.85±0.1 g/cm3 (20 ºC 760 Torr) | [refractive index ]
1.5300 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: ≥10mg/mL | [form ]
Solid | [pka]
7.72±0.70(Predicted) | [color ]
white to off-white | [InChI]
InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1 | [InChIKey]
LZAZURSABQIKGB-AEKGRLRDSA-N | [SMILES]
C1=C2[C@@]([H])(NC(=O)C3C2=CC2OCOC=2C=3O)[C@H](O)[C@H](O)[C@H]1O | [Uses]
Narciclasine is reasonably abundant in some Narcissus spp. and has served as a very useful intermediate for synthetic conversion into (+)-pancratistatin and to conduct a series of structure–activity relationship studies . Bicolorine, another member of the narciclasine series, is an unusual, completely aromatized quaternary alkaloid with an N-methyl group. |
| Hazard Information | Back Directory | [Definition]
ChEBI: A natural product found in Narcissus pseudonarcissus. | [Description]
The bulbs of several Narcissus species contain this alkaloid which crystallizes in
the form of pale yellow needles with a pronounced yellow-green fluorescence. It
is best purified by recrystallization from either acetic acid or an aqueous mixture
of methoxyethyl alcohol. It is dextrorotatory with [α]589 + 145° or [Qh64 +
983° (c 1.5, EtOH). The ultraviolet spectrum in neutral solution (EtOH) has
absorption maxima at 252, 302 and 329 mil, while that in alkaline solution
(0.01 N/NaOH) has the maxima at 219, 249,310 and 355 mil. The O-methyl
ether forms shiny needles which also exhibit a strong blue fluorescence. The tri_x0002_acetate has been prepared as an amorphous, non-crystallizable substance. With
FeC13 the alkaloid gives a violet colour. | [Chemical Properties]
White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from narcissus. | [target]
Immunology & Inflammation related | [storage]
Store at -20°C | [References]
Ceriotti., Nature, 213,595 (1967)
Piozzi et al., Tetrahedron, 24, 1119 (1968)
Revised structure:
Mondon, Krohn., Tetrahedron Lett., 2123 (1970)
Savona, Piozzi, Marino., Chern. Cornrnun., 1006 (1970)
Absolute configuration:
Fuganti, Mazza.,J. Chern. Soc., Chern. Cornrnun., 239 (1972)
Crystal structure:
Immirzi, Fuganti., J. Chern. Soc., Chern. Cornrnun., 240 (1972)
Stereochemistry:
Mondon, Krohn., Tetrahedron Lett., 2085 (1972) |
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