(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one

Product Name: (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one
CAS No.: 27495-40-5
Chemical Name: (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one
Synonyms: Protostemonine;(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl;(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl];(5Z)-5-[(1S,3aR,8S,10aS,10bR)-Decahydro-1-methyl-8-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-4-methoxy-3-methyl-2(5H)-furanone;2(5H)-Furanone,5-[(1S,3aR,8S,10aS,10bR)-decahydro-1-Methyl-8-[(2S,4S)-tetrahydro-4-Methyl-5-oxo-2-furanyl]-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-4-Methoxy-3-Methyl-,(5Z)-;(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one;(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one USP/EP/BP
CBNumber: CB72418817
Molecular Formula: C23H31NO6
Formula Weight: 417.5
MOL File: 27495-40-5.mol

More

Less

(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one Property

Melting point:: 172℃
Boiling point:: 594.1±50.0 °C(Predicted)
Density: 1.27
pka: 8.77±0.60(Predicted)

More

Less

Hazard and Precautionary Statements (GHS)

More

Less

N-Bromosuccinimide Price

Usbiological

Product number: 361863
Product name: Protostemonine
Packaging: 10mg
Price: $439
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb594223
Product name: Protostemonine
Packaging: 10mg
Price: $499.8
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb105798
Product name: protostemonine
Purity: >98%,Standard References Grade
Packaging: 20mg
Price: $569.5
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb594223
Product name: Protostemonine
Packaging: 20mg
Price: $591.6
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 74005
Product name: Protostemonine
Purity: 98%
Packaging: 20mg
Price: $600
Updated: 2021/12/16

More

Less

(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one Chemical Properties,Usage,Production

Description

The roots of Sternona japonica contain this complex alkaloid which forms colourless crystals from MeOH containing solvent of crystallization. The base is dextrorotatory with [α]_D + 147.8° and the ultraviolet spectrum shows a broad absorption maximum at 305 m/J.. The picrolonate has been prepared as yellow needles, m.p. 237°C. The structure given above is based upon X-ray crystallo_x0002_graphic analysis of the MeOH solvate and on the already established configuration of Stemonine (q.v.).

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from Stemona bulbs.

Uses

Protostemonine is an alkaloid which provided protective effects of protostemonine in LPS/GalN-induced acute liver failure.

Definition

ChEBI: Protostemonine is an alkaloid. It has a role as a metabolite.

Synthesis

Tragacanth crushed into coarse powder (8.5 kg), with 8 times the amount of volume fraction of 90% ethanol heating reflux extraction 3 times, each time 1 h, combined with the extract, filtered. The filtrate was recovered to thick extract under reduced pressure, and the concentrated solution was dissolved with 1 times the amount of 1% hydrochloric acid, and the acid-water solution was centrifuged. Take the supernatant, alkalized with concentrated ammonia to pH 10, chloroform extraction for 3 times, concentrated under reduced pressure to obtain the crude extract of Morinda citrifolia (75 g). Take 10 g of the crude extract of Trachelium, dissolve with 4% hydrochloric acid 200 mL, filtered, the filtrate with ammonia to adjust the pH of 8 ~ 8.5, chloroform extraction, until the filtrate does not react with bismuth potassium iodide, decompression recovery of chloroform and the filtrate, drying, to get the total alkaloids 6.0 g. Take the total alkaloids of the above Trachelium through the Sephedex LH -20, rinsed with methanol, to remove pigmentation, collection of alkaloid-containing fractions, decompression recovery, and the total alkaloid-containing fractions. The fraction was collected and recovered under reduced pressure, and the solid was mixed with silica gel, loaded onto a silica gel H (200-300 mesh, 200 g) column, and eluted with a gradient of petroleum ether-acetone (3:1, 2:1, 1:1, pure acetone). After repeated forward chromatography, compound I was isolated as pale yellow crystals (650 mg), which was structurally identified as protostemonine (p rotostemonine).

References

Kondo, Satomi.,J. Pharrn. Soc., Japan, 67, 182, 185, 188 (1947)
Structure: Irie et al., Chern. Pharrn. Bull., 21, 451 (1973)

(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one Preparation Products And Raw materials

Raw materials

Preparation Products

More

Less

(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one Suppliers

CHINA 94 United States 7 Global 101

Hangzhou Yuhao Chemical Technology Co., Ltd

Tel: 0571-82693216
Fax: +86-571-82880190
Email: info@yuhaochemical.com
Country: China
ProdList: 6387
Advantage: 52

Dalian Meilun Biotech Co., Ltd.

Tel: 0411-62910999 13889544652
Email: sales@meilune.com
Country: China
ProdList: 4790
Advantage: 58

Chengdu Climax Biotech Co., Ltd.

Tel: 028-83311324 1278112614
Fax: 028-83311324
Email: climaxbiotech@gmail.com
Country: China
ProdList: 925
Advantage: 58

Beijing HuaMeiHuLiBiological Chemical

Tel: 010-56205725
Fax: 010-65763397
Email: waley188@sohu.com
Country: China
ProdList: 12335
Advantage: 58

Shanghai Tauto Biotech Co., Ltd.

Tel: 021-51320588
Fax: 0086-21-51320502
Email: tauto@tautobiotech.com
Country: China
ProdList: 3988
Advantage: 66

Cheng Du Pufeide Biotechnology Co., Ltd.

Tel: 028-82610909 13388174823
Fax: 8171-1798
Email: scglp@glp-china.com
Country: China
ProdList: 1064
Advantage: 58

Chengdu Herbpurify Co.Ltd.

Tel: 2355253622; 18981954830
Fax: 086-28-85377358
Email: 2355253622@qq.com;
Country: China
ProdList: 1089
Advantage: 58

Shanghai BeiZhuo Biotech Co., Ltd.

Tel: 021-61119791,13386096464
Fax: 021-50190009
Email: bzswkf@foxmail.com
Country: China
ProdList: 3921
Advantage: 50

Shanghai Zhanshu Chemical Technology Co., Ltd

Tel: +86-21-58589556
Fax: +86-21-58589557
Country: China
ProdList: 413
Advantage: 55

Shanghai JONLN Reagent Co., Ltd.

Tel: 400-0066400 13621662912
Fax: 021-55660885
Email: 422131432@qq.com
Country: China
ProdList: 9979
Advantage: 55

More

Less

View Lastest Price from (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one manufacturers

Shaanxi Haibo Biotechnology Co., Ltd

Product: Protostemonine 27495-40-5
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 2000ton
Release date: 2023-08-24

Shanghai Standard Technology Co., Ltd.

Product: Protostemonine 27495-40-5
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2020-02-25

27495-40-5, (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-oneRelated Search:

Xanthophyll morusin RHOIFOLIN ISOEUGENOL Ginkgolide C Alpinetin Panaxatriol ISOPIMPINELLIN Brassinolide HOMOORIENTIN Folic acid Panaxadiol Tectorigenin Diacerein Securinol A lithospermic acid HEXABROMOBENZENE tuberostemonine

(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one

Protostemonine

(5Z)-5-[(1S,3aR,8S,10aS,10bR)-Decahydro-1-methyl-8-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-4-methoxy-3-methyl-2(5H)-furanone

2(5H)-Furanone,5-[(1S,3aR,8S,10aS,10bR)-decahydro-1-Methyl-8-[(2S,4S)-tetrahydro-4-Methyl-5-oxo-2-furanyl]-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-4-Methoxy-3-Methyl-,(5Z)-

(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]

(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl

(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one USP/EP/BP

27495-40-5

reagent

standard substance