Fallacinol

Base Information

• Chemical Name: Fallacinol
• CAS No.: 569-05-1
• Molecular Formula: C16H12O6
• Molecular Weight: 300.2629
• DSSTox Substance ID: DTXSID80205430
• Nikkaji Number: J11.355G
• Wikidata: Q83079009
• Mol file: 569-05-1.mol

Synonyms:Fallacinol;Teloschistin;Phallacinol;569-05-1;1,8-dihydroxy-3-(hydroxymethyl)-6-methoxyanthracene-9,10-dione;Chrysazin, 3-(hydroxymethyl)-6-methoxy-;1,8-Dihydroxy-3-(hydroxymethyl)-6-methoxy-9,10-anthracenedione;Anthraquinone, 1,8-dihydroxy-3-(hydroxymethyl)-6-methoxy-;9,10-Anthracenedione, 1,8-dihydroxy-3-(hydroxymethyl)-6-methoxy-;SCHEMBL16225969;DTXSID80205430;CHEBI:144153;AKOS040734727

Chemical Property of Fallacinol

Chemical Property:

• Vapor Pressure: 9.12E-17mmHg at 25°C
• Boiling Point: 630.5°Cat760mmHg
• Flash Point: 241.4°C
• PSA: 104.06000
• Density: 1.549g/cm³
• LogP: 1.37410
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 300.06338810
• Heavy Atom Count: 22
• Complexity: 464

Purity/Quality:

≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)CO

Technology Process of Fallacinol

There total 20 articles about Fallacinol 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: 100.0%

fallacinol ω-acetate (20194-61-0) → 1,8-dihydroxy-3-hydroxymethyl-6-methoxy-anthraquinone (569-05-1)

Guidance literature:

With potassium hydroxide; In ethanol; for 0.166667h; Heating;

DOI:10.1021/jo00201a033

Reference yield: 92.0%

1,8-Diacetoxy-3-acetoxymethyl-6-methoxyanthrachinon (42981-61-3) → 1,8-dihydroxy-3-hydroxymethyl-6-methoxy-anthraquinone (569-05-1)

Guidance literature:

With sodium hydroxide; at 75 ℃; for 0.5h;

Reference yield:

2-chloro-1,4-dimethoxybenzene (2100-42-7) → 1,8-dihydroxy-3-hydroxymethyl-6-methoxy-anthraquinone (569-05-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 75 percent / hexamethylenetetramine / 12 h / Heating

2: 65 percent / NaH / EtOH / toluene / 1 h / Ambient temperature

3: 70 percent / NaOAc / 3 h / 140 °C

4: 78 percent / LiAlH₄ / tetrahydrofuran / 24 h / Ambient temperature

5: 90 percent / Et₃N, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

6: 90 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 3 h / Ambient temperature

7: 84 percent / AlCl₃ / CH₂Cl₂ / 1 h / Ambient temperature

8: 75 percent / 1 h / 100 °C

9: 95 percent / AlCl₃ / CH₂Cl₂ / 24 h / Ambient temperature

10: 98 percent / 10percent aq. NaOH / 24 h / Ambient temperature

With dmap; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; ammonium cerium(IV) nitrate; hexamethylenetetramine; sodium acetate; sodium hydride; triethylamine; ethanol; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo00079a042

upstream raw materials:

physcion diacetate

1,8-Diacetoxy-3-acetoxymethyl-6-methoxyanthrachinon

citreorosein

dimethyl sulfate

Downstream raw materials:

4,5-dihydroxy-7-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

citreorosein

Refernces

• 1、 Koyama, Junko,Takeuchi, Atsuko,Morita, Izumi,Nishino, Yu,Shimizu, Maki,Inoue, Munetaka,Kobayashi, Norihiro. "Characterization of emodin metabolites in Raji cells by LC-APCI-MS/MS". scheme or table. p. 7493 - 7499. Retrieved 2011/02/23.
• 2、 Benfaremo, Nicholas,Cava, Michael P.. "Studies in Anthracycline Synthesis: SImple Diels-Alder Routes to Pachybasin, ω-Hydroxypachybasin, Aloe-emodin, and Fallacinol". . p. 139 - 141. Retrieved 2007/10/02.