550-43-6

Basic information

• Product Name: angustifoline
• Synonyms: angustifoline;(1S,11aβ)-Decahydro-4β-(2-propenyl)-1β,5β-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one;Jamaicensine;Mixture of (-)-Angustifoline and Isoangustifoline
• CAS NO: 550-43-6
• Molecular Formula: C₁₄H₂₂N₂O
• Molecular Weight: 234.34
• Mol File: 550-43-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 79-80 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 377.6°Cat760mmHg
• Flash Point: 182.1°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 6.69E-06mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.07±0.40(Predicted)
• CAS DataBase Reference: angustifoline(CAS DataBase Reference)
• NIST Chemistry Reference: angustifoline(550-43-6)
• EPA Substance Registry System: angustifoline(550-43-6)

Safety Data

• Hazardous Substances Data: 550-43-6(Hazardous Substances Data)

Usage

Uses

(-)-Angustifoline is used in biological studies to determine the toxicity of dietary lupin alkaloids and its adverse effect.

InChI:InChI=1/C14H22N2O/c1-2-4-12-11-7-10(8-15-12)13-5-3-6-14(17)16(13)9-11/h2,10-13,15H,1,3-9H2/t10-,11-,12+,13-/m1/s1

Upstream product

• 1476-39-7 1,5-diaminopentane dihydrochloride 

Downstream Products

• 550-90-3 (+)-lupanine 

Related news

Further investigation of the chemistry and structure of angustifoline (cas 550-43-6) and its derivatives07/14/2019

Most of the structural assignments presented in this paper were based on the conformation of angustifoline selectively deuterated at the 13β position (13β2H I). To confirm the absolute stereoselectivity of the reaction introducing 2H at 13C on the β face, 13β2H I was transformed into four de...detailed

Relevant articles and documents

Synthesis of Cadaverine and its Incorporation into five Quinolizidine Alkaloids

Cadaverine dihydrochloride (13) was synthesised by the sequential introduction of two equivalents of sodium cyanide to a C3 precursor, and it was fed to Lupinus luteus and L. polyphyllus plants.Complete labelling patterns were obtained in five quinolizidine alkaloids by 13C n.m.r. spectroscopy.The 13C-13C doublets observed in the spectra of (-)-lupinine (3), (-)-sparteine (4), (+)-lupanine (5), (+)-13α-hydroxylupanine (6), and (+)-angustifoline (7) derived biosynthetically from the doubly labelled precursor (13) confirm the intact, specific incorporation of two cadaverine units into the tetracyclic quinolizidine alkaloid skeletons.The cadaverine (13) units are incorporated to about the same extent into each part of the quinolizidine alkaloids (3)-(7).Two of the 13C chemical shifts for lupanine (5) have been reassigned.The labelling pattern of the tricyclic alkaloid angustifoline (7) indicates that the allyl group originates by degradation of one ring of a tetracyclic precursor.