Acerosin

Base Information

• Chemical Name: Acerosin
• CAS No.: 15835-74-2
• Molecular Formula: C18H16 O8
• Molecular Weight: 360.32
• Hs Code.: 2914509090
• DSSTox Substance ID: DTXSID30166406
• Nikkaji Number: J14.309J
• Wikidata: Q27105652
• Metabolomics Workbench ID: 24556
• ChEMBL ID: CHEMBL3314497
• Mol file: 15835-74-2.mol

Synonyms:Acerosin;15835-74-2;CHEBI:2382;CHEMBL3314497;3',5,7-Trihydroxy-4',6,8-trimethoxyflavone;5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxychromen-4-one;5,7,3'-trihydroxy-6,8,4'-trimethoxyflavone;C09982;SCHEMBL12469965;DTXSID30166406;BDBM50046951;LMPK12111473;XA177971;Q27105652;5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-4H-1-benzopyran-4-one;5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-4H-1-benzopyran-4-one, 9CI;5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-4H-chromen-4-one

Chemical Property of Acerosin

Chemical Property:

• Vapor Pressure: 1.68E-18mmHg at 25°C
• Boiling Point: 668.8°Cat760mmHg
• Flash Point: 246.3°C
• PSA: 118.59000
• Density: 1.461g/cm³
• LogP: 2.60260
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 360.08451746
• Heavy Atom Count: 26
• Complexity: 549

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)O)OC)O)O

Technology Process of Acerosin

There total 3 articles about Acerosin 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: 83.0%

6,8-dibromodiosmetin + sodium methylate (124-41-4) → 5,7,3'-trihydroxy-6,8,4'-trimethoxyflavone (15835-74-2)

Guidance literature:

With copper(I) bromide; In methanol; N,N-dimethyl-formamide; at 120 ℃; for 1h; Reagent/catalyst; Time; Inert atmosphere; Microwave irradiation;

DOI:10.3184/174751914X13966139490181

Reference yield:

(2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one (64726-90-5) → 5,7,3'-trihydroxy-6,8,4'-trimethoxyflavone (15835-74-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sulfuric acid / ethanol; water / 4 h / Reflux

2: iodine; pyridine / 5 h / 95 °C

3: N-Bromosuccinimide / trifluoroacetic acid / 5 h / 20 °C

4: copper(I) bromide / methanol; N,N-dimethyl-formamide / 1 h / 120 °C / Inert atmosphere; Microwave irradiation

With pyridine; N-Bromosuccinimide; sulfuric acid; iodine; copper(I) bromide; In methanol; ethanol; water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.3184/174751914X13966139490181

Reference yield:

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone (520-33-2,41001-90-5,69097-99-0) → 5,7,3'-trihydroxy-6,8,4'-trimethoxyflavone (15835-74-2)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine; pyridine / 5 h / 95 °C

2: N-Bromosuccinimide / trifluoroacetic acid / 5 h / 20 °C

3: copper(I) bromide / methanol; N,N-dimethyl-formamide / 1 h / 120 °C / Inert atmosphere; Microwave irradiation

With pyridine; N-Bromosuccinimide; iodine; copper(I) bromide; In methanol; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.3184/174751914X13966139490181

upstream raw materials:

sodium methylate

(2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone

Refernces