narciclasine

narciclasine Structure
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
Molecular Weight:
307.26
MOL File:
29477-83-6.mol
MSDS File:
SDS
Modify Date:
2023/9/4 15:51:00

narciclasine Properties

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

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P301+P310+P330
Hazard Codes  Xn
Risk Statements  46
Safety Statements  36

narciclasine price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) SML2805 Narciclasine ≥98% (HPLC) 29477-83-6 1MG ₹13693.63 2022-06-14 Buy
Sigma-Aldrich(India) SML2805 Narciclasine ≥98% (HPLC) 29477-83-6 5MG ₹56246.7 2022-06-14 Buy
Product number Packaging Price Buy
SML2805 1MG ₹13693.63 Buy
SML2805 5MG ₹56246.7 Buy

narciclasine Chemical Properties,Uses,Production

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 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.

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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narciclasine Spectrum

narciclasine (13β)-1,19-Didehydro-2α,3β,4β,7-tetrahydroxy-11,12-dinor-5,19-secocrinan-6-one (2S)-3,4,4aβ,5-Tetrahydro-2α,3β,4β,7-tetrahydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one Lycorcidinol (2S,3R,4S,4aR)-3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one (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 3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one BRN 1087400 Lycoricidin-A NSC 266535 Narciclasin Narciclasine, 99.9% rciclasin [1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR)- Rho-associated kinase,ROCK,inhibit,Inhibitor,ROK,Narciclasine,Rho-associated protein kinase,Rho-kinase (2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one 29477-83-6