Digitolutein

Base Information

• Chemical Name: Digitolutein
• CAS No.: 477-86-1
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.269
• DSSTox Substance ID: DTXSID30197255
• Nikkaji Number: J12.556C
• Wikidata: Q83070179
• Mol file: 477-86-1.mol

Synonyms:digitolutein

Chemical Property of Digitolutein

Chemical Property:

• Vapor Pressure: 2.29E-10mmHg at 25°C
• Boiling Point: 493.6°Cat760mmHg
• Flash Point: 189.4°C
• PSA: 63.60000
• Density: 1.356g/cm³
• LogP: 2.48460
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 268.07355886
• Heavy Atom Count: 20
• Complexity: 419

Purity/Quality:

99%+, ^*data from raw suppliers

Digitolutein ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C1O)OC)C(=O)C3=CC=CC=C3C2=O

Technology Process of Digitolutein

There total 12 articles about Digitolutein 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: 92.0%

(3R,4S,4aS,9aR)-4a,9a-Dichloro-4-methoxy-3-methyl-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione (127042-44-8) → digitolutein (477-86-1)

Guidance literature:

methanolate;

DOI:10.1016/S0040-4039(01)93478-1

Reference yield: 81.0%

1-methoxy-2-methoxymethoxy-3-methylanthraquinone (73484-75-0) → digitolutein (477-86-1)

Guidance literature:

With sulfuric acid; acetic acid; at 70 - 80 ℃; for 24h;

DOI:10.1080/00397919608003861

Reference yield:

1,2-dimethoxy-3-methylbenzene (4463-33-6) → digitolutein (477-86-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / trimethylsilyl iodide / CHCl₃ / 48 h / Ambient temperature

2: 32 percent / aluminum chloride, sodium chloride / 0.75 h / 165 °C

3: 38 percent / K₂CO₃ / acetone / 48 h / Ambient temperature

4: 86 percent / K₂CO₃ / acetone / 60 h / Ambient temperature

5: 81 percent / acetic acid, sulphuric acid / 24 h / 70 - 80 °C

With aluminium trichloride; trimethylsilyl iodide; sulfuric acid; potassium carbonate; acetic acid; sodium chloride; In chloroform; acetone;

DOI:10.1080/00397919608003861

upstream raw materials:

2-acetoxy-1-methoxy-3-methyl-anthraquinone

(3R,4S,4aS,9aR)-4a,9a-Dichloro-4-methoxy-3-methyl-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione

1-methoxy-2-methoxymethoxy-3-methylanthraquinone

1,2-dimethoxy-3-methylbenzene

Downstream raw materials:

1,2-dimethoxy-3-methyl-anthraquinone

Refernces

• 1、 Camerom, Donald W.,Feutrill, Geoffrey I.,Keep, Philip L. C.. "DICHLORO QUINONES AS DIENOPHILES; SYNTHESIS OF ALIZARIN DERIVATIVES". . p. 5173 - 5176. Retrieved 2007/10/02.