27740-43-8

Usage

Uses

Used in Pharmaceutical Applications:
Erysotrine is used as a pharmaceutical agent for its DPPH radical scavenging properties. These properties indicate that Erysotrine may have potential benefits in the development of treatments for various health conditions, particularly those related to oxidative stress and free radical damage.
Used in Antioxidant Formulations:
In the field of cosmetics and personal care products, Erysotrine is used as an antioxidant for its ability to scavenge DPPH radicals. This application helps to protect the products from oxidation, thereby extending their shelf life and maintaining their efficacy.
Used in Nutraceutical Applications:
Erysotrine's DPPH radical scavenging properties also make it a potential candidate for use in the development of nutraceuticals, which are products derived from food sources with extra health benefits. These nutraceuticals could be used to support overall health and well-being by combating oxidative stress and promoting a balanced antioxidant system in the body.
Used in Research and Development:
Erysotrine's unique properties also make it a valuable compound for further research and development in various scientific fields. Its potential applications in pharmaceuticals, cosmetics, and nutraceuticals warrant continued investigation to fully understand its capabilities and optimize its use in these industries.

InChI:InChI=1/C19H23NO3/c1-21-15-5-4-14-7-9-20-8-6-13-10-17(22-2)18(23-3)11-16(13)19(14,20)12-15/h4-5,7,10-11,15H,6,8-9,12H2,1-3H3/t15-,19-/m0/s1

Upstream product

• 52358-58-4 (+)-erysotramidine 
• 136945-69-2 (+)-11β-acetoxyerysotramidine 
• 112342-30-0 (5R*,6S*,7S*)-7-acetoxy-15,16-dimethoxy-6-methoxycarbonyl-3,8-dioxoerythrin-1-ene 
• 112342-25-3 6,7-dimethoxy-1-(Z)-(methoxycarbonyl)-methylidene-1,2,3,4-tetrahydroisoquinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 129112-90-9 3α,15,16-Trimethoxy-8-oxo-Δ¹-cis-erythrinan 
• 79641-54-6 (1R*,5R*,6R*)-15,16-dimethoxy-6-methoxycarbonyl-7,8-dioxo-1,3-bis(trimethylsilyloxy)-erythrin-2-ene 
• 79648-95-6 (1R*,5R*,6R*)-1,15,16-trimethoxy-6-methoxycarbonyl-7,8-dioxo-3-trimethylsilyloxyerythrin-2-ene 
• 79641-44-4 methyl 2-(3,4-dihydro-6,7-dimethoxy-2H-isoquinoline-1-ylidene)acetate 
• 81750-70-1 (2R,13bS)-2-hydroxy-11,12-dimethoxy-8,9-dihydro-1H-indolo[7a,1-a]isoquinolin-6(2H)-one 
• 112342-31-1 (5R*,6R*,7S*)-7-methanesulfonyloxy-15,16-dimethoxy-6-methoxycarbonyl-3,8-dioxoerythrin-1-ene 
• 81755-01-3 1,2-Didehydro-7β-hydroxy-15,16-dimethoxy-6-methoxycarbonyl-3,8-dioxoerythrinan 
• 79641-47-7 methyl 8,9-dimethoxy-2,3-dioxo-2,3,5,6-tetrahydropyrrolo<2,1-a>isoquinoline-1-carboxylate 
• 79641-42-2 N-<2-(3,4-dimethoxyphenyl)-ethyl>methoxycarbonylacetamide 

Downstream Products

• 28619-41-2 erythristemine 

Relevant academic research and scientific papers

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

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.

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.

SYNTHESIS OF 11β-HYDROXY ERYTHRINA ALKALOID, ERYTHRARTINE, AND ITS O-ACETATE (ERYTHRASCINE?)

Oxidation of an erythrinan alkaloid erysotramidine (4) with CAN in AcOH-MeCN gave, in moderate yield, the 11β-acetoxy derivative (5b), which was transformed into erythrartine (8).Its O-acetate (O-acetylerythrartine) was not identical with erythrascine in the 1H-nmr spectra, presenting an ambiguity on the reported structure of erythrascine.

CONFORMATIONAL DIFFERENCE BETWEEN ERYTHRINAN- AND HOMOERYTHRINAN-3-ONES: TOTAL SYNTHESIS OF (+/-)-SCHELHAMMERIDINE AND (+/-)-3-EPISCHELHAMMERIDINE

Erythrinan- and homoerythrinan-3-ones behave differently toward hydride reductions suggesting their conformational difference: for example, Δ1-erythrinan-3-one gives 3α-alcohol and Δ1-homoerythrinan-3-one gives 3β-alcohol stereoselectively on reduction with NaBH4-CeCl3 in methanol.Based on these observations, total syntheses of homoerythrinan alkaloids, schelhammeridine and 3-epischelhammeridine, and an erythrinan alkaloid, 8-oxoerysotrine, were accomplished.

SYNTHESES OF ERYTHRINA AND RELATED ALKALOIDS (6) TOTAL SYNTHESIS OF ERYSOTRINE AND ERYTHRALINE

An efficiently stereocontrolled synthesis of the erythrina alkaloids, erysotrine and erythraline was described.