Rubiadin

Base Information

• Chemical Name: Rubiadin
• CAS No.: 117-02-2
• Molecular Formula: C15H10O4
• Molecular Weight: 254.242
• Hs Code.: 29146990
• European Community (EC) Number: 683-093-6
• UNII: CY0UH3X06R
• DSSTox Substance ID: DTXSID90151651
• Nikkaji Number: J10.078A
• Wikipedia: Rubiadin
• Wikidata: Q15633911
• Metabolomics Workbench ID: 68151
• ChEMBL ID: CHEMBL251251
• Mol file: 117-02-2.mol

Synonyms:1,3-dihydroxy-2-methyl-9,10-anthracenedione;rubiadin

Chemical Property of Rubiadin

Chemical Property:

• Vapor Pressure: 1E-11mmHg at 25°C
• Melting Point: 290℃
• Refractive Index: 1.709
• Boiling Point: 527.1 °C at 760 mmHg
• PKA: 7.22±0.20(Predicted)
• Flash Point: 286.6 °C
• PSA: 74.60000
• Density: 1.476 g/cm³
• LogP: 2.18160
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 254.05790880
• Heavy Atom Count: 19
• Complexity: 405

Purity/Quality:

98%,99%, ^*data from raw suppliers

Rubiadin analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C2C(=C1O)C(=O)C3=CC=CC=C3C2=O)O
• Description: Rubiadin is an anthraquinone that is a minor component of certain Rubia species, as well as other plants. It demonstrates antioxidant activity.
• Uses: Rubiadin is a dihydroxy anthraquinone isolated from Rubia cordifolia. Rubiadin exhibits anti-epileptic activity in mice.

Technology Process of Rubiadin

There total 16 articles about Rubiadin 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: 82.0%

phthalic anhydride (85-44-9) + 2-methylbenzene-1,3-diol (608-25-3) → rubiadin (117-02-2)

Guidance literature:

With aluminum (III) chloride; sodium chloride; at 125 - 175 ℃; for 2h;

Reference yield:

3,5-dihydroxy-4-methylbenzoic acid (28026-96-2) + benzoic acid (65-85-0,8013-63-6) → rubiadin (117-02-2)

Guidance literature:

With sulfuric acid; at 120 ℃;

DOI:10.1038/120729b0

Reference yield:

1-hydroxy-3-methoxy-2-methyl-9,10-anthraquinone (22170-89-4) → rubiadin (117-02-2)

Guidance literature:

With aluminium trichloride; at 200 ℃; durch langsames Erhitzen;

upstream raw materials:

1,3-dimethoxy-2-methylanthraquinone

1-hydroxy-3-methoxy-2-methyl-9,10-anthraquinone

rubiadin-1-methyl ether

3,5-dihydroxy-4-methylbenzoic acid

Downstream raw materials:

lucidin dimethyl ether

rubiadin-1-methyl ether

Refernces

• 1、 Yeap, Sweekeong,Akhtar, Muhammad Nadeem,Lim, Kian Lam,Abu, Nadiah,Ho, Wan Yong,Zareen, Seema,Roohani, Kiarash,Ky, Huynh,Tan, Sheau Wei,Lajis, Nordin,Alitheen, Noorjahan Banu. "Synthesis of an anthraquinone derivative (DHAQC) and its effect on induction of G2/M arrest and apoptosis in breast cancer MCF-7 cell line". . p. 983 - 992. Retrieved 2015.
• 2、 -. "Method for synthesizing 2,6-dihydroxytoluene by using waste acid". Paragraph 0029. . Retrieved 2021/08/07.
• 3、 -. "Rubiadin A ring glycosylated derivative as well as preparation method and application of Rubiadin A ring glycosylated derivative". Paragraph 0081; 0083-0084. . Retrieved 2020/11/26.