28619-41-2

Basic information

• Product Name: (+)-Erythristemine
• Synonyms: (+)-Erythristemine;(10bS)-6α,8,9,12β-Tetramethoxy-1,10b-[1]buteno-3,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinoline;1,2,6,7-Tetradehydro-3β,11α,15,16-tetramethoxyerythrinan;Erythristemine;(3beta,11alpha)-1,2,6,7-Tetradehydro-3,11,15,16-tetramethoxyerythrinan
• CAS NO: 28619-41-2
• Molecular Formula: C20H25NO4
• Molecular Weight: 343.42
• Mol File: 28619-41-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Erythristemine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Erythristemine(28619-41-2)
• EPA Substance Registry System: (+)-Erythristemine(28619-41-2)

Safety Data

• Hazardous Substances Data: 28619-41-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Erythristemine is used as a potential therapeutic agent for neurodegenerative diseases such as Alzheimer's due to its ability to inhibit the activity of acetylcholinesterase, an enzyme involved in the breakdown of the neurotransmitter acetylcholine.
Used in Pain Management:
(+)-Erythristemine is used as an analgesic agent for its potential pain-relieving properties, which have been recognized in traditional folk medicine.
Used in Anti-Inflammatory Applications:
(+)-Erythristemine is used as an anti-inflammatory agent, leveraging its traditional use in folk medicine to reduce inflammation.
Used in Immunomodulation:
(+)-Erythristemine is used as an immunomodulatory agent for its potential to modulate the immune system, with promising results in preliminary investigations.

Upstream product

• 125145-68-8 (+/-)-11β-methoxyerysotramidine 
• 129112-90-9 3α,15,16-Trimethoxy-8-oxo-Δ¹-cis-erythrinan 
• 52358-58-4 (+/-)-3α,15,16-trimethoxy-8-oxo-Δ^1,6-erythrinan 
• 125145-65-5 (4aR,9R,13bS)-9,11,12-Trimethoxy-4a,5,8,9-tetrahydro-indolo[7a,1-a]isoquinoline-2,6-dione 
• 125145-67-7 (2R,4aR,9R,13bS)-2,9,11,12-Tetramethoxy-1,2,4a,5,8,9-hexahydro-indolo[7a,1-a]isoquinolin-6-one 
• 95456-80-7 3,3,15,16-tetramethoxy-1,7-cyclo-cis-erythrinan-2,8-dione 
• 125145-63-3 C₂₁H₂₇NO₇ 
• 125145-61-1 (+/-)-3,3,11β,15,16-pentamethoxy-1,7-cyclo-cis-erythrinan-2,8-dione 
• 125145-64-4 C₂₃H₂₉NO₇S₂ 
• 125145-66-6 (2R,4aR,9R,13bS)-2-Hydroxy-9,11,12-trimethoxy-1,2,4a,5,8,9-hexahydro-indolo[7a,1-a]isoquinolin-6-one 
• 80153-98-6 O-methyl-erythrartine-N-oxide 
• 51666-26-3 erythrartine 
• 74-88-4 methyl iodide 
• 27740-43-8 erysotrine 

Relevant articles and documents

Stereoselective introduction of oxygen functionalities at the 11β- position of erythrinan skeleton: Total syntheses of (±)-erythristemine and (+)-erythrartine

Oxidation of 8-oxoerythrinan and 8-oxo-1,7-cycloerythrinan derivatives with 2 mol eq of ceric ammonium nitrate in alcohols or acetic acid gave the corresponding 11β-alkoxy or acetoxy compounds in moderate yield. Thus, (±)- 3,3,15,16-tetramethoxy-1,7-cycloerythrinan-2,8-dione and (+)-erysotramidine gave the corresponding 11β-methoxy and 11β-acetoxy derivatives on oxidation in methanol and in acetic acid, respectively. Those compounds were respectively converted into (±)-erythristemine and (+)-erythrartine in several steps, thus achieving the total synthesis of these alkaloids.

ALKALOID CONSTITUENTS FROM ERYTHRINA XBIDWILLII FLOWERS

The alkaloids present in the flowers of Erythrina xbidwillii have been screened by GC-MS.A novel alkaloid, erythristemine-N-oxide has been isolated and its structure established by spectroscopic methods.

Stereoselective Methoxylation at the 11β-Position of the Erythrinan Skeleton: Total Synthesis of (+/-)-Erythristemine

Treatment of cis-erythrinan-8-one or 1,7-cyclo-cis-erythrinan-8-one with ceric ammonium nitrate in methanol gave the appreciable yields of the corresponding 11β-methoxy compounds; these were converted into the natural 11-oxygenated erythrinan alkaloid, erythristemine, in high yield.