28610-31-3

Basic information

• Product Name: Desmethylanhydroicaritin
• Synonyms: Desmethylanhydroicaritin;3,4',5,7-Tetrahydroxy-8-(3-methyl-2-butenyl)flavone;8-Prenylkaempferol;Desmethylicaritin;Noranhydroicaritin;3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-buten-1-yl)-4H-1-benzopyran-4-one;4'-DesMethylicaritin;De-O-Methylanhydroicaritin
• CAS NO: 28610-31-3
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.35
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 28610-31-3.mol

Chemical Properties

• Melting Point: 220-222°C
• Boiling Point: 605.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.444±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Acetone (Slightly), Methanol (Slightly)
• PKA: 6.45±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Desmethylanhydroicaritin(CAS DataBase Reference)
• NIST Chemistry Reference: Desmethylanhydroicaritin(28610-31-3)
• EPA Substance Registry System: Desmethylanhydroicaritin(28610-31-3)

Safety Data

• Hazardous Substances Data: 28610-31-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Desmethylanhydroicaritin is used as an anticancer agent for its ability to dramatically inhibit the growth of most malignant cells. It targets various types of cancer by disrupting essential cellular processes and signaling pathways, thereby preventing tumor growth and progression.
Additionally, Desmethylanhydroicaritin is used as an antiangiogenesis agent for its significant properties in inhibiting or eliminating the development of new malignant cells. By targeting the formation of new blood vessels that supply nutrients to tumors, it can effectively "starve" cancer cells and hinder their growth.
Used in Drug Delivery Systems:
In the field of drug delivery, Desmethylanhydroicaritin can be employed to improve the efficacy and bioavailability of cancer treatments. Its incorporation into novel drug delivery systems, such as organic and metallic nanoparticles, can enhance its delivery to target cancer cells, leading to improved therapeutic outcomes and reduced side effects.

Upstream product

• 143724-76-9 5-hydroxy-8-prenyl-3,4',7-tris-O-methoxymethylkaempferol 
• 520-18-3 kaempferol 
• 780724-90-5 dimethylallyl diphosphate 
• 852247-44-0 7,4'-bis-O-methoxymethyl-8-prenylkaempferol 
• 143724-66-7 3,4',7-tris-O-methoxymethylkaempferol 
• 143724-70-3 5-O-prenyl-3,7,4'-tris-O-methoxymethylkaempferol 
• 870-63-3 prenyl bromide 
• 118525-40-9 icaritin 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 118075-12-0 2'-hydroxy-4,4',6'-trimethoxymethoxylchalcone 
• 1329801-99-1 3,5-hydroxy-4',7-dimethoxymethylflavone 
• 52589-11-4 C₂₆H₃₀O₁₁ 
• 52589-20-5 (2S,3S)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-2,3-dihydro-4H-chromen-4-one 

Downstream Products

• 28610-36-8 3,5,7-triacetoxy-2-(4-acetoxy-phenyl)-8-(3-methyl-but-2-enyl)-chromen-4-one 
• 28610-34-6 6,6-dimethyldihydropyran (2,3:7,8)-5,4'-dihydroxyflavonol 
• 5240-95-9 8-(3-hydroxy-3-methylbutyl)-5,7,4'-trihydroxyflavonol 
• 520-18-3 kaempferol 
• 118525-40-9 icaritin 

Relevant articles and documents

Method for preparing dewatered icaritin through total-synthesis

The invention provides a method for preparing dewatered icaritin through total-synthesis. The method includes the steps of connecting an isopentene group to 8th-position carbon through ortho-positionrearrangement with methoxybenzoyl chloride, isoprenyl bromide and the like as the raw materials by means of trihydroxyacetophenone, and conducting the forming series reaction of a flavone framework toobtain the dewatered icaritin. The defects that in a traditional method of introducing an isopentene group, the yield is low, catalysts are expensive and lots of byproducts are produced are overcome,and the method is low in cost, simple in operation, good in yield and suitable for industrial production.

Flavanonol Glycosides from Leaves of Phellodendron lavallei Introduced in Georgia

The new flavanonol glycoside (2S,3S)-3,5-dihydroxy-2-(4′-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-3,4-dihydro-2H-chromen-7-yl-β-D-glucopyranosyl-(3→1)-xylopyranoside (lavaloside) (1) and the known compound phellamurin (2) were isolated from leaves o

The first total synthesis of sophoflavescenol, flavenochromane C, and citrusinol

The first total syntheses of sophoflavescenol (1), flavenochromane C (2), and citrusinol (3) were achieved. These three naturally occurring prenylated or prenyl-cyclized flavonoids have important biological activities such as cytotoxicity against some can

Icaritin and desmethylicaritin as anti-cancer agents

The antiproliferative effects of Icaritin or Desmethylicaritin on cancer cell lines, both in vitro, and in vivo, are disclosed. Experimental data show that Icaritin and Desmethylicaritin dramatically inhibit the growth of most malignant cells. In addition, both Icaritin and Desmethylicaritin have significant Anti-agiogenesis properties, inhibiting or eliminating entirely the development of new malignant cells. Further, no obvious side effects including nausea, hair loss or body weight loss were found in the animals treated with Icaritin or Desmethylicaritin, making both highly effective anti cancer drugs.

Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: An SAR study

A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.

Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures

Dimethylallyl diphosphate: naringenin 8-dimethylallyltransferase (EC 2.5.1) was characterized. The enzyme was enantiospecific for (-)-(2S)-naringenin and utilized 3,3-dimethylallyl diphosphate as sole prenyl donor. It required Mg2+ (optimum concentration, 10 mM), and has an optimum pH of 9-10. The apparent K(m) values for 3,3-dimethylallyl diphosphate and naringenin were 120 and 36 μM, respectively. The microsomal fraction prenylated several other flavanones at the C-8 position less effectively as compared with naringenin. Interestingly, when 2'-hydroxynaringenin was used as a prenyl acceptor, the 8-lavandulyl (sophoraflavanone G) and the 6-dimethylallyl derivatives were formed, together with the 8-dimethylallyl derivative, leachianone G. These results suggest that the 2'-hydroxy group of naringenin plays an important role for the formation of a lavandulyl group. (C) 2000 Elsevier Science Ltd.

1H-NMR CHEMICAL SHIFT OF THE FLAVONOL 5-HYDROXY PROTON AS A CHARACTERIZATION OF 6- OR 8-ISOPRENOID SUBSTITUTION

1H Nmr examination of 6- or 8-isoprenoid substituted flavonols has shown that the location of isoprenoid side chain on A ring can be deduced from the chemical shift of the 5-hydroxy proton.The application of this 1H nmr technique to identification of the