Dihydrosanguinarine

Base Information

• Chemical Name: Dihydrosanguinarine
• CAS No.: 3606-45-9
• Molecular Formula: C20H15 N O4
• Molecular Weight: 333.343
• European Community (EC) Number: 807-649-6
• UNII: 3H1ZKG80F7
• DSSTox Substance ID: DTXSID00189627
• Nikkaji Number: J394.144B
• Wikipedia: Dihydrosanguinarine
• Wikidata: Q347588
• Metabolomics Workbench ID: 50814
• ChEMBL ID: CHEMBL465678
• Mol file: 3606-45-9.mol

Synonyms:dihydro-sanguinarine;dihydrosanguinarine

Chemical Property of Dihydrosanguinarine

Chemical Property:

• Vapor Pressure: 7.18E-13mmHg at 25°C
• Melting Point: 190-191 °C
• Boiling Point: 566.9°Cat760mmHg
• PKA: 2.36±0.20(Predicted)
• Flash Point: 176.8°C
• PSA: 40.16000
• Density: 1.426g/cm³
• LogP: 3.97900
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 333.10010796
• Heavy Atom Count: 25
• Complexity: 530

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

DihydroSanguinarine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC2=C(C=CC3=C2OCO3)C4=C1C5=CC6=C(C=C5C=C4)OCO6
• Uses: Dihydrosanguinarine (DHSG) is a metabolite of Sanguinarine (SG) (S112500) with antifungal activity.

Technology Process of Dihydrosanguinarine

There total 39 articles about Dihydrosanguinarine 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: 92.5%

Sanguinarine (2447-54-3) → dihydrosanguinarine (3606-45-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.5h;

DOI:10.1080/14786419.2010.482055

Reference yield: 58.0%

N-((5-bromobenzo[d][1,3]dioxol-4-yl)methyl)-N-methylnaphtho[2,3-d][1,3]dioxol-5-amine → dihydrosanguinarine (3606-45-9)

Guidance literature:

With 2.9-dimethyl-1,10-phenanthroline; potassium tert-butylate; In benzene; at 100 ℃; for 5h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c4cc05209a

Reference yield: 55.0%

sanguinarine chloride (5578-73-4) → dihydrosanguinarine (3606-45-9)

Guidance literature:

With methanol; sodium tetrahydroborate; at 20 ℃; for 0.5h; Darkness;

upstream raw materials:

8-hydroxydihydosanguinarine

13-methyl-6,7,13,14-tetrahydro-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine

sanguinarine chloride

protopine N-oxide

Downstream raw materials:

sanguinarine chloride

Sanguinarine

oxysanguinarine

norsanguinarine

Refernces

• 1、 Li, Qi-Lin,Deng, An-Jun,Ji, Ming,Li, Zhi-Hong,Chen, Xiao-Guang,Qin, Hai-Lin. "Re-engineering and synthesis of cytotoxic 2,3:7,8-di(alkylenedioxy)-extended analogs of quaternary sanguinarine chloride". . p. 1137 - 1153. Retrieved 2018.
• 2、 Savina,Tolkachev. "Disproportionation of the alkaloid sanguinarine on silica gel". . p. 196 - 199. Retrieved 1999.
• 3、 Janovska, Marika,Kubala, Martin,Simanek, Vilim,Ulrichova, Jitka. "Fluorescence of sanguinarine: Spectral changes on interaction with amino acids". . p. 11335 - 11341. Retrieved 2010.
• 4、 Vrublova, Eva,Vostalova, Jitka,Vecera, Rostislav,Klejdus, Borivoj,Stejskal, David,Kosina, Pavel,Zdarilova, Adela,Svobodova, Alena,Lichnovsky, Vaclav,Anzenbacher, Pavel,Dvorak, Zdenek,Vicar, Jaroslav,Simanek, Vilim,Ulrichova, Jitka. "The toxicity and pharmacokinetics of dihydrosanguinarine in rat: A pilot study". . p. 2546 - 2553. Retrieved 2008.
• 5、 -. "Oxidative dehydrogenation method and application of compound with cell nucleus-targeted light-activated imaging and cancer cell killing capabilities". Paragraph 0072; 0078-0081. . Retrieved 2020/06/17.