Galangin

Base Information

• Chemical Name: Galangin
• CAS No.: 548-83-4
• Molecular Formula: C15H10O5
• Molecular Weight: 270.241
• Hs Code.: 29329990
• Mol file: 548-83-4.mol

Synonyms:Flavone,3,5,7-trihydroxy- (7CI,8CI);Galangin (6CI);3,5,7-Trihydroxyflavone;NSC407229;Norizalpinin;

Chemical Property of Galangin

Chemical Property:

• Appearance/Colour: Yellowish needle-like crystal
• Vapor Pressure: 2.24E-11mmHg at 25°C
• Melting Point: 214-215 °C(lit.)
• Refractive Index: 1.747
• Boiling Point: 518.6 °C at 760 mmHg
• PKA: 6.32±0.40(Predicted)
• Flash Point: 202 °C
• PSA: 90.90000
• Density: 1.579 g/cm³
• LogP: 2.57680
• Storage Temp.: room temp
• Solubility.: Acetone (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Galangin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Description: Galangin is a flavonoid naturally found in herbs used in traditional medicine. Like many flavonoids, it has potent antioxidant properties. It also has anti-inflammatory actions related to suppression of signaling through NF-κB in mice. Galangin acts as an antagonist of the aryl hydrocarbon receptor, inducing apoptosis in cancer cells. It also inhibits cytochrome P450 isoform 1A1 with an IC50 value of less than 1 μM.
• Uses: CYP1A1 inhibitor, vasodilator Galangin is a flavanoid found in Alpinia officinarum, galangal rhizome (Alpinia galanga) and in propolis. Galangin has been show to inhibit proliferation of estrogen receptor-positive MCF-7 human brea st cancer cells as well as delay of mammary tumorigenesis. Galangin is a flavanoid found in Alpinia officinarum, galangal rhizome (Alpinia galanga) and in propolis. Galangin has been show to inhibit proliferation of estrogen receptor-positive MCF-7 human breast cancer cells as well as delay of mammary tumorigenesis.

Technology Process of Galangin

There total 27 articles about Galangin 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%

3,5,7-trimethoxyflavone (26964-29-4) → galangin (548-83-4)

Guidance literature:

3,5,7-trimethoxyflavone; With boron tribromide; In dichloromethane; at 20 ℃; for 24h;

With water; In dichloromethane;

DOI:10.5012/bkcs.2012.33.4.1379

Reference yield: 73.0%

5,7-bis(benzyloxy)-3-hydroxy-2-phenyl-4H-chromen-4-one → galangin (548-83-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; dichloromethane; for 6h; under 760.051 Torr;

DOI:10.1021/acs.joc.9b03461

Reference yield:

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) → galangin (548-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. KOH / ethanol / 48 h / Ambient temperature

2: 54 percent Turnov_. / air, methylene blue / methanol / 81 h / Irradiation

With potassium hydroxide; air; methylene blue; In methanol; ethanol;

upstream raw materials:

potassium acetate

acetic anhydride

2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone

benzoic acid anhydride

Downstream raw materials:

5,7-dihydroxy-3-methoxy-6-methyl-2-phenyl-chromen-4-one

isalpinin

5,7-dihydroxy-3-methoxyflavone

5-hydroxy-3,7-dimethoxyflavone

Refernces

• 1、 Kim, Sugyeom,Lannigan, Deborah A.,Li, Yu,Lin, Lin,O'Doherty, George A.,Sayasith, Peyton R.,Tarr, Ariel T.,Wright, Eric B.,Yasmin, Sharia. "Synthesis and Biological Evaluation of 4-Substituted Kaempfer-3-ols". . p. 4279 - 4288. Retrieved 2020/04/09.
• 2、 Lee, Hyo Seon,Park, Kwang-Su,Lee, Chaewoon,Lee, Bokhui,Kim, Dong-Eun,Chong, Youhoon. "7-O-Arylmethylgalangin as a novel scaffold for anti-HCV agents". scheme or table. p. 5709 - 5712. Retrieved 2010/11/04.