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
• Article Data: 7

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

Description

Desmethylanhydroicaritin is a metabolite of Icariin, a compound derived from the Epimedium genus of plants, commonly known as "horny goat weed." It is a yellow solid with significant biological activities, particularly in the realm of cancer treatment and antiangiogenesis.

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

• 870-63-3 prenyl bromide 
• 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 
• 52589-20-5 3β,5,7,4'-tetrahydroxy-8-<3,3-dimethylallyl>-flavonone 
• 83171-42-0 4,6-dimethoxy-2-(4'-methoxybenzoyloxy)acetophenone 
• 1329801-99-1 3,5-hydroxy-4',7-dimethoxymethylflavone 
• 118075-12-0 2'-hydroxy-4,4',6'-trimethoxymethoxylchalcone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 118525-40-9 icaritin 
• 520-18-3 kaempferol 
• 143724-70-3 5-O-prenyl-3,7,4'-tris-O-methoxymethylkaempferol 
• 143724-66-7 3,4',7-tris-O-methoxymethylkaempferol 
• 852247-44-0 7,4'-bis-O-methoxymethyl-8-prenylkaempferol 

Downstream Products

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

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.

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

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.