Nardosinone

Base Information

• Chemical Name: Nardosinone
• CAS No.: 23720-80-1
• Molecular Formula: C15H22 O3
• Molecular Weight: 250.338
• Hs Code.: 29145090
• UNII: 5VA93HYL8U
• DSSTox Substance ID: DTXSID50946520
• Nikkaji Number: J16.437B
• Wikipedia: Nardosinone
• Wikidata: Q15425798
• Metabolomics Workbench ID: 125598
• ChEMBL ID: CHEMBL1933702
• Mol file: 23720-80-1.mol

Synonyms:nardosinone

Chemical Property of Nardosinone

Chemical Property:

• Vapor Pressure: 0.000169mmHg at 25°C
• Melting Point: 108-110℃
• Boiling Point: 330.2°Cat760mmHg
• Flash Point: 142°C
• PSA: 35.53000
• Density: 1.11g/cm³
• LogP: 3.04700
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 250.15689456
• Heavy Atom Count: 18
• Complexity: 424

Purity/Quality:

99.5% ^*data from raw suppliers

Nardosinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC=C2C1(C3C(CC2=O)OOC3(C)C)C
• Isomeric SMILES: C[C@@H]1CCC=C2[C@]1([C@H]3[C@@H](CC2=O)OOC3(C)C)C
• Uses: Nardosinone reduces neuronal injury and protects H9c2 cardiac cells from angiotensin II-induced hypertrophy which may give rise to heart failure. Enhancer of nerve growth factor (NGF).

Technology Process of Nardosinone

There total 5 articles about Nardosinone 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: 50.0%

aristol-1(10)-en-9-one (114339-93-4) → nardosinone diol (20489-11-6) + Desoxo-Narchinol A (53859-06-6,127843-31-6) + nardosinone (23720-80-1)

Guidance literature:

With α-naphthol; oxygen; In acetone; at 80 ℃; for 24h;

DOI:10.1002/ardp.19903230308

Reference yield: 50.0%

aristol-1(10)-en-9-one (114339-93-4) → nardosinone (23720-80-1)

Guidance literature:

With α-naphthol; oxygen; at 80 ℃;

DOI:10.1016/S0040-4039(00)80585-7

Reference yield: 5.0%

aristol-1(10)-en-9-one (114339-93-4) → nardosinone (23720-80-1) + kanshone C (117634-64-7) + 1(10)-Aristolen-9-on-2β-hydroperoxid (127843-30-5) + 1(10)-Aristolen-9-on-2α-hydroperoxid (127912-18-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); oxygen; at 80 ℃; for 8h;

DOI:10.1002/ardp.19903230308

upstream raw materials:

aristol-1⁽¹⁰⁾-en-9-one

Downstream raw materials:

(4S,4aR,5R)-4-Isopropenyl-2-methoxy-4a,5-dimethyl-4a,5,6,7-tetrahydro-4H-naphthalen-1-one

2-Hydroxy-4a,5-dimethyl-4-isopropyl-decahydro-naphthalin-1-on

1-Hydroxy-4,5-dimethyl-5,6,7,8-tetrahydro-naphthalin

(4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one

Refernces

• 1、 Rucker,Shide,Olbrich. "Peroxides as plant constituents, VII: Formation of the sesquiterpeneperoxide nardosinone from an aristolane precursor". . p. 171 - 175. Retrieved 2007/10/02.