52358-58-4

Basic information

• Product Name: (+)-Erysotramidine
• Synonyms: (+)-Erysotramidine;(13bS)-1,2,8,9-Tetrahydro-2β,11,12-trimethoxy-6H-indolo[7a,1-a]isoquinoline-6-one;1,2,6,7-Tetradehydro-3β,15,16-trimethoxyerythrinan-8-one;3β,15,16-Trimethoxy-1,2,6,7-tetradehydroerythrinan-8-one;(3beta)-1,2,6,7-Tetradehydro-3,15,16-trimethoxyerythrinan-8-one
• CAS NO: 52358-58-4
• Molecular Formula: C19H21NO4
• Molecular Weight: 327.37
• Mol File: 52358-58-4.mol

Chemical Properties

• Boiling Point: 565.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• PKA: -2.06±0.40(Predicted)
• CAS DataBase Reference: (+)-Erysotramidine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Erysotramidine(52358-58-4)
• EPA Substance Registry System: (+)-Erysotramidine(52358-58-4)

Safety Data

• Hazardous Substances Data: 52358-58-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Erysotramidine is used as an antifungal and antibacterial agent for its ability to combat fungal and bacterial infections due to its inherent antimicrobial properties.
Used in Anti-inflammatory Applications:
(+)-Erysotramidine is used as an anti-inflammatory agent for its potential to reduce inflammation by inhibiting the production of reactive oxygen species and other inflammatory mediators.
Used in Antioxidant Applications:
(+)-Erysotramidine is used as an antioxidant agent for its capacity to neutralize harmful reactive oxygen species, thereby protecting cells from oxidative damage and related diseases.
Used in Anticancer Applications:
(+)-Erysotramidine is used as a cytotoxic agent for its demonstrated effects on cancer cells, showing potential in the development of novel anticancer therapies.
Used in Cosmetics Industry:
(+)-Erysotramidine could be used as an ingredient in cosmetic products for its anti-inflammatory and antioxidant properties, potentially benefiting skin health and appearance by reducing inflammation and oxidative stress.

Upstream product

• 74-88-4 methyl iodide 
• 156567-10-1 (4aS,5S,13bR)-5-Methanesulfonyloxy-11,12-dimethoxy-2,6-dioxo-1,2,5,6,8,9-hexahydro-indolo[7a,1-a]isoquinoline-4a-carboxylic acid methyl ester 
• 156567-05-4 (4aS,5R,13bR)-5-Methanesulfonyloxy-11,12-dimethoxy-2,6-dioxo-1,2,5,6,8,9-hexahydro-indolo[7a,1-a]isoquinoline-4a-carboxylic acid methyl ester 
• 1666-13-3 diphenyl diselenide 
• 129112-90-9 3α,15,16-Trimethoxy-8-oxo-Δ¹-cis-erythrinan 
• 81750-70-1 (2R,13bS)-2-hydroxy-11,12-dimethoxy-8,9-dihydro-1H-indolo[7a,1-a]isoquinolin-6(2H)-one 
• 110452-14-7 2-phenylthiocyclohexanone 
• 94997-16-7 1-[2-(3,4-dimethoxyphenyl)ethyl]-1,4,5,6-tetrahydro-2H-indol-2-one 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 81755-01-3 1,2-Didehydro-7β-hydroxy-15,16-dimethoxy-6-methoxycarbonyl-3,8-dioxoerythrinan 
• 112342-31-1 (5R*,6R*,7S*)-7-methanesulfonyloxy-15,16-dimethoxy-6-methoxycarbonyl-3,8-dioxoerythrin-1-ene 
• 79641-54-6 (1S*,5R*,6R*)-15,16-dimethoxy-6-methoxycarbonyl-7,8-dioxo-1,3-bis(trimethylsilyloxy)-erythrin-2-ene 
• 69111-30-4 15,16-dimethoxy-1,7-cyclo-cis-erythrinan-2,8-dione 
• 95456-80-7 3,3,15,16-tetramethoxy-1,7-cyclo-cis-erythrinan-2,8-dione 

Downstream Products

• 27740-43-8 erysotrine 
• 51666-26-3 11β-hydroxyerysotrine (erythrartine) 
• 27740-43-8 (+/-)-erysotrine 
• 28619-41-2 (+/-)-erythristemine 
• 27740-43-8 (+)-erysotrine 
• 27740-43-8 (+/-)-3-epierysotrine 

Relevant articles and documents

An asymmetric synthesis of (+)-erysotramidine

A new asymmetric total synthesis of the erythrinan alkaloid erysotramidine is described, which uses chiral base desymmetrisation, N-acyliminium addition, and 6-exo-trig radical cyclisation as the key steps. Georg Thieme Verlag Stuttgart.

Total Synthesis of (+)-3-Demethoxyerythratidinone and (+)-Erysotramidine via the Oxidative Amidation of a Phenol

Oxidative amidation chemistry provides a unified route to aromatic Erythrina alkaloids through a sequence that illustrates new principles and improved conditions to effect a crucial eliminative Curtius-Schmidt rearrangement.

Synthesis of the erythrina alkaloid erysotramidine

A concise synthesis of erysotramidine (an alkaloid belonging to the erythrina family) was achieved starting with an inexpensive phenol and amine derivative. The synthesis is based on oxidative phenol dearomatizations mediated by a hypervalent iodine reage

General and efficient strategy for erythrinan and homoerythrinan alkaloids: Syntheses of (±)-3-demethoxyerythratidinone and (±)- erysotramidine

A general and efficient strategy to both aromatic-type and nonaromatic-type erythrinan and homoerythrinan alkaloids has been developed. This approach involves a key two-step sequence, an alkylation of a ketone with various N-substituted iodoacetamides fol

Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans

Several 2-imido substituted furans were found to undergo a rapid intramolecular [4 + 2]-cycloaddition to deliver oxabicyclo adducts in good to excellent yields. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, it was possible t

Electrophilic-induced cyclization reaction of hexahydroindolinone derivatives and its application toward the synthesis of (±)- erysotramidine

A convenient synthesis of variously substituted octahydroindolo[7a,1a]- isoquinolinones has been achieved by an acid-induced cyclization of hexahydroindolinones bearing tethered phenethyl groups. The formation of a single lactam diastereomer is the result

Efficient synthesis of (+/-)-erysotramidine using an NBS-promoted cyclization reaction of a hexahydroindolinone derivative.

An NBS-promoted intramolecular electrophilic aromatic substitution reaction of a hexahydroindolinone derivative was used to assemble the tetracyclic core of the erythrinane skeleton. The resulting cyclized product was transformed into (+/-)-erysotramidine

Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxy-erythrinans: Total synthesis of an alkenoid-type erythrinan alkaloid, (±)-erythratidine

Four stereoisomers of 1,2-epoxy-3-hydroxyerythrinans were synthesized and their stereochemistries were determined. The 1,2α-epoxy-3α-alcohol was converted to the alkenoid-type alkaloid, (±)-erythratidine utilizing reductive migration of an α, β-unsaturate

Chiral synthesis of Erythrina alkaloids. I. Total synthesis of (+)-erysotrine via asymmetric Diels-Alder reaction under high pressure

(S)-(+)-3,4-Dimethoxyphenylalanine methyl ester (1b) was converted, in 3 steps, into (5S)-(-)-8,9-dimethoxy-1,5-dimethoxycarbonyl-2,3-dioxo-2,3,5,6-tetrahy dropyrrolo[2,1-a]isoquinoline (2b). Diels-Alder reaction of 2b with 1-methoxy-3-trimethylsilyloxybu

TOTAL SYNTHESIS OF (+)-ERYSOTRINE VIA ASYMMETRIC DIELS-ALDER REACTION UNDER SUPER HIGH PRESSURE

The first total synthesis of (+)-erysotrine in a chiral form was achieved through application of Diels-Alder reaction of a chiral dioxopyrroline with 1-methoxy-3-trimethylsilyloxybutadiene under a 10 Kbar pressure.