7729-23-9

Basic information

• Product Name: Hirsutine
• Synonyms: HIRSUTINE;(e)-16,17-didehydro-17-methoxy-17,18-seco-3-beta-yohimban-16-carboxylicacid;16e)-;18-seco-3-beta-yohimban-16-carboxylicacid,16,17-didehydro-17-methoxy-1met;corynan-16-carboxylicacid,16,17-didehydro-17-methoxy-,methylester,(3-bet;Methyl (E)-2-[(2S,3R,12bR)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[3,2-h]quinolizin-2-yl]-3-methoxyprop-2-enoate;(3β,16E)-16,17-Didehydro-17-methoxycorynan-16-carboxylic acid methyl ester;Methyl (E)-2-[(2
• CAS NO: 7729-23-9
• Molecular Formula: C22H28N2O3
• Molecular Weight: 368.47
• Mol File: 7729-23-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 101 °C
• Boiling Point: 531.7°Cat760mmHg
• Flash Point: 275.4°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 2.18E-11mmHg at 25°C
• Refractive Index: 1.612
• PKA: 18.13±0.60(Predicted)
• CAS DataBase Reference: Hirsutine(CAS DataBase Reference)
• NIST Chemistry Reference: Hirsutine(7729-23-9)
• EPA Substance Registry System: Hirsutine(7729-23-9)

Safety Data

• Hazardous Substances Data: 7729-23-9(Hazardous Substances Data)

Usage

General Description

Hirsutine is an alkaloid compound found in Uncaria species of plants, particularly Uncaria rhynchophylla. It has been traditionally used in Chinese medicine for its neuroprotective and anti-inflammatory properties. Hirsutine has been the subject of scientific research for its potential effects on the central nervous system, including its ability to protect against neuronal damage and reduce the risk of neurodegenerative diseases such as Parkinson's and Alzheimer's. Additionally, hirsutine has been studied for its potential anti-cancer and anti-diabetic effects, as well as its ability to lower blood pressure and cholesterol levels. Overall, hirsutine shows promising potential for a wide range of therapeutic applications and may be a valuable compound in pharmacological research.

InChI:InChI=1/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14-,17-,20+/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 26076-15-3 2-((2R,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-oxo-propionic acid methyl ester 
• 61-54-1 tryptamine 
• 60339-88-0 rac-19-oxo-(15βH)-17-nor-coryn-20-ene-16,16-dicarboxylic acid dimethyl ester 
• 1395097-38-7 C₁₈H₂₂N₂O₃ 
• 1395097-37-6 C₂₄H₂₅N₃O₇S 
• 913524-95-5 C₂₂H₂₁N₃O₆S 
• 1395097-36-5 C₂₇H₂₉N₃O₈S 
• 1395097-35-4 C₂₀H₁₉N₃O₆S 
• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 86980-97-4 1,4,6,7,12,12b-Hexahydroindolo<2,3-a>chinolizin-3-carbonsaeure-ethylester 

Relevant articles and documents

Total synthesis of (±)-hirsutine: Application of phosphine-catalyzed imine-allene [4 + 2] annulation

The total synthesis of the indole alkaloid hirsutine has been achieved, with a key step being the application of our phosphine-catalyzed [4 + 2] annulation of an imine with ethyl α-methylallenoate. From commercially available indole-2-carboxaldehyde, the target was synthesized in 14 steps and 6.7% overall yield.

Short, stereospecific total synthesis of (±)-corynantheidine

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Short syntheses of hirsutine and geissoschizine

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