15358-48-2

Basic information

• Product Name: 13-hydroxylupanine
• Synonyms: 13-hydroxylupanine;(7S,7aβ,9β,14S,14aα)-Dodecahydro-9-hydroxy-7,14-methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one
• CAS NO: 15358-48-2
• Molecular Formula: C₁₅H₂₄N₂O₂
• Molecular Weight: 264.367
• Mol File: 15358-48-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 169-170°
• Boiling Point: 407.59°C (rough estimate)
• Flash Point: 236.6°C
• Appearance: /
• Density: 1.0200 (rough estimate)
• Vapor Pressure: 1.03E-10mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.82±0.20(Predicted)
• CAS DataBase Reference: 13-hydroxylupanine(CAS DataBase Reference)
• NIST Chemistry Reference: 13-hydroxylupanine(15358-48-2)
• EPA Substance Registry System: 13-hydroxylupanine(15358-48-2)

Safety Data

• Hazardous Substances Data: 15358-48-2(Hazardous Substances Data)

Usage

Description

13-Hydroxylupanine, also known as (+)-13α-Hydroxylupanine, is an alkaloid derived from the Lupinus genus of plants, specifically L. lanatus. It possesses unique chemical properties and biological activities, making it a subject of interest for various applications.

Uses

Used in Analytical Chemistry:
13-Hydroxylupanine is used as a chemical marker for the determination of Lupinus polyphyllus through thin-layer chromatography and fluorescence analysis. This application aids in the identification and classification of different Lupinus species based on the presence and concentration of this alkaloid.
Used in Pharmaceutical Research:
As an inhibitor of ganglionic transmission, 13-Hydroxylupanine holds potential for pharmaceutical research and development. Its ability to interfere with ganglionic transmission may lead to the discovery of new therapeutic approaches for conditions related to the nervous system.

InChI:InChI=1/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2/t10-,11-,12+,13-,14-/m1/s1

Upstream product

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

Downstream Products

• 7732-18-5 water 
• 550-90-3 (+)-lupanine 

Related news

On the structure and spectroscopic properties of two 13-hydroxylupanine (cas 15358-48-2) epimers08/07/2019

The crystal structures of 13α- and 13β-hydroxylupanines present a rare case of unexpected configuration and conformation of bis-quinolizidine alkaloid free bases. The configuration of A/B and C/D ring junctions is trans–cis and quasi trans–cis in α and β epimers, respectively. Ring C adopt...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.