(+)-Hydrastine

Base Information

• Chemical Name: (+)-Hydrastine
• CAS No.: 29617-43-4
• Molecular Formula: C21H21 N O6
• Molecular Weight: 383.401
• European Community (EC) Number: 204-233-0
• DSSTox Substance ID: DTXSID1045611
• Nikkaji Number: J1.238.122K,J417.756H
• Wikipedia: Hydrastine
• Wikidata: Q27115728
• NCI Thesaurus Code: C76031
• Metabolomics Workbench ID: 123492
• ChEMBL ID: CHEMBL1441048
• Mol file: 29617-43-4.mol

Synonyms:beta-hydrastine;hydrastine;hydrastine hydrochloride, (S-(R*,S*))-isomer;hydrastine, (R-(R*,R*))-isomer;hydrastine, (R-(R*,S*))-isomer;isocoryne

Chemical Property of (+)-Hydrastine

Chemical Property:

• Vapor Pressure: 4.28E-12mmHg at 25°C
• Refractive Index: 1.614
• Boiling Point: 548.8°Cat760mmHg
• Flash Point: 285.7°C
• PSA: 66.46000
• Density: 1.339g/cm³
• LogP: 2.81110
• Storage Temp.: −20°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 383.13688739
• Heavy Atom Count: 28
• Complexity: 601

Purity/Quality:

99%min ^*data from raw suppliers

(+)-β-Hydrastine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C=C2[C@H]1[C@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3

Technology Process of (+)-Hydrastine

There total 26 articles about (+)-Hydrastine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

5-((R)-4,5-Dimethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium (78179-06-3) → meconin (569-31-3) + (-)-β-hydrastine (118-08-1,4370-85-8,29617-43-4,53950-51-9,60594-55-0,60827-73-8,73554-66-2,85280-16-6,85280-18-8)

Guidance literature:

With hydrogen; platinum(IV) oxide; In methanol;

Reference yield: 80.0%

5-((R)-4,5-Dimethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium (78179-06-3) → (-)-β-hydrastine (118-08-1,4370-85-8,29617-43-4,53950-51-9,60594-55-0,60827-73-8,73554-66-2,85280-16-6,85280-18-8)

Guidance literature:

With hydrogen; platinum(IV) oxide; In methanol;

Reference yield:

(-)-β-hydrastine (118-08-1,4370-85-8,29617-43-4,53950-51-9,60594-55-0,60827-73-8,73554-66-2,85280-16-6,85280-18-8) → hydrastine (118-08-1) + (+)-Hydrastine (29617-43-4)

Guidance literature:

With potassium methanolate; In methanol; at 20 ℃; Overall yield = 65 percent; enantioselective reaction;

DOI:10.1039/d0ra03038d

upstream raw materials:

hydrastine

(+)-β-hydrastine hydrochloride

5-((R)-4,5-Dimethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium

tert-butyl (2-(6-iodobenzo[d][1,3]dioxol-5-yl)ethyl)carbamate

Downstream raw materials:

(-)-Ophiocarpin

hydrastine

meconin

(+/-)-Adlumidine

Refernces

• 1、 Shono, Tatsuya,Hamaguchi, Hiroshi,Sasaki, Manji,Fujita, Shumei,Nagami, Kimihiko. "Novel Zinc-Promoted Alkylation of Iminium Salts. New Synthesis of Benzylisoquinoline, Phthalidylisoquinoline, and Protoberberine Alkaloids and Related Compounds". . p. 1621 - 1628. Retrieved 2007/10/02.
• 2、 Shono, Tatsuya,Usui, Yoshihiro,Hamaguchi, Hiroshi. "NEW ELECTROREDUCTIVE SYNTHESIS OF PHTHALIDE ALKALOIDS". . p. 1351 - 1354. Retrieved 2007/10/02.