narciclasine
- Product Name
- narciclasine
- CAS No.
- 29477-83-6
- Chemical Name
- narciclasine
- 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
- CBNumber
- CB41341322
- Molecular Formula
- C14H13NO7
- Formula Weight
- 307.26
- MOL File
- 29477-83-6.mol
narciclasine Property
- 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
- pka
- 7.72±0.70(Predicted)
- form
- Solid
- color
- white to off-white
N-Bromosuccinimide Price
- Product number
- SML2805
- Product name
- Narciclasine
- Purity
- ≥98% (HPLC)
- Packaging
- 1MG
- Price
- $143
- Updated
- 2024/03/01
- Product number
- SML2805
- Product name
- Narciclasine
- Purity
- ≥98% (HPLC)
- Packaging
- 5MG
- Price
- $583
- Updated
- 2024/03/01
- Product number
- PHL82604
- Product name
- Narciclasine
- Purity
- phyproof? Reference Substance
- Packaging
- 10MG
- Price
- $1030
- Updated
- 2024/03/01
- Product number
- 20361
- Product name
- Narciclasine
- Purity
- ≥98%
- Packaging
- 500μg
- Price
- $93
- Updated
- 2024/03/01
- Product number
- 20361
- Product name
- Narciclasine
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $166
- Updated
- 2024/03/01
narciclasine Chemical Properties,Usage,Production
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.
Description
Narciclasine is a plant growth inhibitor that can be isolated from Narcissus bulbs. At 1 μM, it has been shown to induce apoptosis-mediated cytotoxicity in human cancer cells in vitro but not in normal fibroblasts. Narciclasine has been shown to regulate the Rho/Rho kinase/LIM kinase/cofilin signaling pathway by increasing GTPase RhoA activity, as well as inducing actin stress fiber formation in a RhoA-dependent manner.
Uses
Narciclasine is an antiproliferative and pro-apoptotic inducer.
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.
Definition
ChEBI: A natural product found in Narcissus pseudonarcissus.
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)
narciclasine Preparation Products And Raw materials
Raw materials
Preparation Products
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