62014-87-3

Basic information

• Product Name: helichrysetin
• Synonyms: helichrysetin;1-(2,4-Dihydroxy-6-methoxy-phenyl)-3-(4-hydroxy-phenyl)-propenone
• CAS NO: 62014-87-3
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.282
• Mol File: 62014-87-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 220 °C (decomp)
• Boiling Point: 532°C at 760 mmHg
• Flash Point: 201°C
• Appearance: /
• Density: 1.369g/cm³
• Vapor Pressure: 6.2E-12mmHg at 25°C
• Refractive Index: 1.684
• PKA: 7.08±0.40(Predicted)
• CAS DataBase Reference: helichrysetin(CAS DataBase Reference)
• NIST Chemistry Reference: helichrysetin(62014-87-3)
• EPA Substance Registry System: helichrysetin(62014-87-3)

Safety Data

• Hazardous Substances Data: 62014-87-3(Hazardous Substances Data)

Usage

General Description

Helichrysetin is a flavonoid compound found in various plants, including helichrysum, the immortelle flower. It is known for its antioxidant and anti-inflammatory properties, and has been studied for its potential health benefits. Research has shown that helichrysetin may have anti-cancer effects by inhibiting the growth of cancer cells and promoting apoptosis, or cell death, in cancerous cells. Additionally, it has been shown to have potential protective effects against neurodegenerative diseases and may also aid in the treatment of skin conditions due to its anti-inflammatory and wound healing properties. Overall, helichrysetin is a promising compound with potential therapeutic applications in the fields of cancer treatment, neurodegenerative diseases, and skin health.

InChI:InChI=1/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 1034276-39-5 C₂₂H₂₆O₈ 
• 1070781-94-0 (2E)-1-[2-methoxy-4,6-bis(2-propenyloxy)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one 
• 108-73-6 3,5-dihydroxyphenol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 404597-94-0 1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 119136-14-0 2,4-bis(benzyloxy)-6-methoxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 

Downstream Products

• 94103-36-3 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 37308-75-1 flavokawain C 

Relevant articles and documents

Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents

Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.

In vitro and in vivo anti-Leishmania activity of polysubstituted synthetic chalcones

The in vitro screening of 43 polysubstituted chalcones against Leishmania amazonensis axenic amastigotes, led to the evaluation of 9 of them in a macrophage-infected model with the two other most infectious Leishmania species prevalent in Peru (L. braziliensis and L. peruviana). The five most active and selective chalcones were studied in vivo, resulting on the identification of two chalcones with high reduction parasite burden percentages.

Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity

A general strategy for the synthesis of 3′-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2′,3,4′,5-tetrahydroxy-6′-methoxy-3′-prenylchalcone (9, IC50 3.2 ± 0.4 μM) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 ± 0.5 μM), were more active in comparison to 1 (IC50 9.4 ± 1.4 μM). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 ± 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 ± 2.1) showed that the prenyl side chain at C-3′ has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4′-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 ± 0.6, 3.8 ± 0.4, and 3.8 ± 0.5 Trolox equivalents, respectively.