Aristolone

Base Information

• Chemical Name: Aristolone
• CAS No.: 6831-17-0
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• DSSTox Substance ID: DTXSID10987838
• Nikkaji Number: J17.033J
• Wikidata: Q82976182
• Metabolomics Workbench ID: 141085
• ChEMBL ID: CHEMBL512374
• Mol file: 6831-17-0.mol

Synonyms:aristolone;aristolone, (-)-isomer

Chemical Property of Aristolone

Chemical Property:

• Vapor Pressure: 0.00067mmHg at 25°C
• Boiling Point: 308.7°C at 760 mmHg
• Flash Point: 136.5°C
• PSA: 17.07000
• Density: 1.02g/cm³
• LogP: 3.59400
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 390

Purity/Quality:

98% ^*data from raw suppliers

Aristolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCCC2=CC(=O)C3C(C12C)C3(C)C
• Isomeric SMILES: C[C@@H]1CCCC2=CC(=O)[C@@H]3[C@H]([C@@]12C)C3(C)C

Technology Process of Aristolone

There total 15 articles about Aristolone 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: 18.7%

β-gurjunene (17334-55-3) → aristolone (3293-43-4,6831-17-0,20536-71-4,22419-46-1,25274-27-5,27779-52-8) + (1aR)-5-oxo-1.1.7c.7ac-tetramethyl-(1arH.7bcH)-1a.2.3.5.6.7.7a.7b-octahydro-1H-cyclopropa[a]naphthalene (28398-06-3,808102-61-6) + (1aR,3R,7R,7aR,7bS)-3-hydroxy-1,1,7,7a-tetramethyl-1,1a,2,3,6,7,7a,7b-octahydro-5H-cyclopropa[α]naphthalen-5-one (26808-51-5)

Guidance literature:

With culture medium of Chlorella fusca var. vacuocola IAMC-28; Noro medium; at 25 ℃; for 528h;

DOI:10.1248/cpb.54.861

Reference yield:

2,3-dimethylcyclohexanone (13395-76-1) → (+/-)-Aristolon (3293-43-4,6831-17-0,20536-71-4,22419-46-1,25274-27-5,27779-52-8)

Guidance literature:

Multi-step reaction with 6 steps

1: (i) NaOMe, (ii) /BRN= 906769/

2: TsOH

3: (i) KOtBu, (ii) aq. KOH

4: TsOH

5: (i) NaH, (ii) aq. KOH

With toluene-4-sulfonic acid;

DOI:10.1139/v69-132

Reference yield:

2,3-dimethylcyclohexanone (13395-76-1) → (+/-)-6.7-Epi-aristolon (3293-43-4,6831-17-0,20536-71-4,22419-46-1,25274-27-5,27779-52-8)

Guidance literature:

Multi-step reaction with 6 steps

1: (i) NaOMe, (ii) /BRN= 906769/

2: TsOH

3: (i) KOtBu, (ii) aq. KOH

4: TsOH

5: (i) NaH, (ii) aq. KOH

With toluene-4-sulfonic acid;

DOI:10.1139/v69-132

upstream raw materials:

(?)-aristolene

β-gurjunene

diazomethane

2,3-dimethylcyclohexanone

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.