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Armepavine

$504

  • Brand : BIOFRON

  • Catalogue Number : BD-P0321

  • Specification : 95.0%(HPLC)

  • CAS number : 524-20-9

  • Formula : C19H23NO3

  • Molecular Weight : 313.397

  • Volume : 10mg

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Catalogue Number

BD-P0321

Analysis Method

HPLC,NMR,MS

Specification

95.0%(HPLC)

Storage

2-8°C

Molecular Weight

313.397

Appearance

Powder

Botanical Source

Structure Type

Quinolines/Isoquinolines/Alkaloids

Category

SMILES

CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)OC)OC

Synonyms

IUPAC Name

Applications

Density

1.151g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

232.3ºC

Boiling Point

460.5ºC at 760 mmHg

Melting Point

InChl

InChI=1S/C19H23NO3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21H,8-10H2,1-3H3/t17-/m1/s1

InChl Key

ZBKFZIUKXTWQTP-QGZVFWFLSA-N

WGK Germany

RID/ADR

HS Code Reference

2933490000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:524-20-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

25909585

Abstract

A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

Title

Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids

Author

Andrea Ruiz-Olalla 1, Martien A Wurdemann 1, Martin J Wanner 1, Steen Ingemann 1, Jan H van Maarseveen 1, Henk Hiemstra 1

Publish date

2015 May 15

PMID

23634947

Abstract

The Stevens rearrangement of nitrile-stabilized ammonium ylides in conjunction with the reductive removal of the nitrile function permits the facile construction of α-branched amines from α-aminonitriles. We employed this reaction sequence for the preparation of (±)-laudanosine, (±)-laudanidine and (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine from two closely related and readily accessible bicyclic α-aminonitriles. The final products were obtained in high to almost quantitative yields (71-98%) from the quaternary ammonium salts obtained by N-alkylation of these starting materials.

Title

Synthesis of alkaloids by Stevens rearrangement of nitrile-stabilized ammonium ylides: (±)-laudanosine, (±)-laudanidine, (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine

Author

Julio Cesar Orejarena Pacheco 1, Gunther Lahm, Till Opatz

Publish date

2013 May 17;

PMID

22031071

Abstract

Introduction: Visceral leishmaniasis is endemic in 88 countries, with a total of 12 million people infected and 350 million at risk. In the search for new leishmanicidal agents, alkaloids and acetogenins isolated from leaves of Annona squamosa and seeds of Annona muricata were tested against promastigote and amastigote forms of Leishmania chagasi.

Methods: Methanol-water (80:20) extracts of A. squamosa leaves and A. muricata seeds were extracted with 10% phosphoric acid and organic solvents to obtain the alkaloid and acetogenin-rich extracts. These extracts were chromatographed on a silica gel column and eluted with a mixture of several solvents in crescent order of polarity. The compounds were identified by spectroscopic analysis. The isolated compounds were tested against Leishmania chagasi, which is responsible for American visceral leishmaniasis, using the MTT test assay. The cytotoxicity assay was evaluated for all isolated compounds, and for this assay, RAW 264.7 cells were used.

Results: O-methylarmepavine, a benzylisoquinolinic alkaloid, and a C37 trihydroxy adjacent bistetrahydrofuran acetogenin were isolated from A. squamosa, while two acetogenins, annonacinone and corossolone, were isolated from A. muricata. Against promastigotes, the alkaloid showed an IC50 of 23.3 µg/mL, and the acetogenins showed an IC50 ranging from 25.9 to 37.6 µg/mL; in the amastigote assay, the IC50 values ranged from 13.5 to 28.7 µg/mL. The cytotoxicity assay showed results ranging from 43.5 to 79.9 µg/mL.

Conclusions: These results characterize A. squamosa and A. muricata as potential sources of leishmanicidal agents. Plants from Annonaceae are rich sources of natural compounds and an important tool in the search for new leishmanicidal therapies.

Title

Rev Soc Bras Med Trop . 2011 Oct;44(5):567-71. doi: 10.1590/s0037-86822011000500007. Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil

Author

Nadja Soares Vila-Nova 1, Selen Maiade Morais, Maria Jose Cajazeiras Falcão, Lyeghyna Karla Andrade Machado, Claudia Maria Leal Bevilaqua, Igor Rafael Sousa Costa, Nilce Viana Gramosa Pompeu de Sousa Brasil, Heitor Francode Andrade Júnior

Publish date

2011 Oct;