115063-39-3

Basic information

• Product Name: DESMETHYLXANTHOHUMOL
• Synonyms: DESMETHYLXANTHOHUMOL
• CAS NO: 115063-39-3
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.37
• Product Categories: Miscellaneous Natural Products;Flavaniods
• Mol File: 115063-39-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 154-155 °C
• Boiling Point: 570.7 °C at 760 mmHg
• Flash Point: 313 °C
• Appearance: /
• Density: 1.312 g/cm³
• Vapor Pressure: 1.26E-13mmHg at 25°C
• Refractive Index: 1.679
• PKA: 7.35±0.50(Predicted)
• CAS DataBase Reference: DESMETHYLXANTHOHUMOL(CAS DataBase Reference)
• NIST Chemistry Reference: DESMETHYLXANTHOHUMOL(115063-39-3)
• EPA Substance Registry System: DESMETHYLXANTHOHUMOL(115063-39-3)

Safety Data

• Hazardous Substances Data: 115063-39-3(Hazardous Substances Data)

Usage

Description

DESMETHYLXANTHOHUMOL is a member of the chalcone class, specifically a trans-chalcone derivative with hydroxy groups at positions 4, 2', 4', and 6', and a 3-methylbut-2-en-1-yl group at position 3'. It is a naturally occurring compound with potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
DESMETHYLXANTHOHUMOL is used as a pharmaceutical compound for its potential therapeutic properties. The compound's unique structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Cosmetic Industry:
In the cosmetic industry, DESMETHYLXANTHOHUMOL is used as an active ingredient for its potential benefits to skin health. Its antioxidant and anti-inflammatory properties may contribute to improved skin condition and protection against environmental stressors.
Used in Food and Beverage Industry:
DESMETHYLXANTHOHUMOL can be used as a natural additive in the food and beverage industry, providing flavor and potential health benefits. Its antioxidant properties may help to extend the shelf life of products and enhance their nutritional value.
Used in Research and Development:
DESMETHYLXANTHOHUMOL is used as a research compound for studying its chemical properties, biological activities, and potential applications in various fields. Its unique structure and functional groups make it an interesting subject for scientific investigation and the development of new technologies.

InChI:InChI=1/C20H20O5/c1-12(2)3-9-15-17(23)11-18(24)19(20(15)25)16(22)10-6-13-4-7-14(21)8-5-13/h3-8,10-11,21,23-25H,9H2,1-2H3/b10-6+

Upstream product

• 199393-58-3 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone 
• 68682-01-9 5,7,4'-trihydroxy-6-prenylflavanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 

Downstream Products

• 68682-02-0 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one 
• 68682-01-9 5,7,4'-trihydroxy-6-prenylflavanone 
• 68634-19-5 (+/-)-3,4,8,9-Tetrahydro-5-hydroxy-8-(4-hydroxyphenyl)-2,2-dimethyl-2H,10H-benzo<1,2-b:3,4-b'>dipyran-10-on 
• 68634-18-4 (+/-)-2,3,7,8-Tetrahydro-5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,6H-benzo<1,2-b:5,4-b'>dipyran-4-on 
• 68634-20-8 4',5-dihydroxy-6'',6''-dimethyl-5'',6''-dihydro-4''H-pyrano[2'',3'':7,8]flavanone 
• 521-48-2 isoxanthohumol 

Relevant articles and documents

Sensomics Analysis of Key Bitter Compounds in the Hard Resin of Hops (Humulus lupulus L.) and Their Contribution to the Bitter Profile of Pilsner-Type Beer

Recent brewing trials indicated the occurrence of valuable bitter compounds in the hard resin fraction of hop. Aiming at the discovery of these compounds, hop's ε-resin was separated by means of a sensory guided fractionation approach and the key taste mo

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.

Remedies

The present invention provides a therapeutic agent or prophylactic agent for a disease that requires enhancement of nerve growth factor production, an enhancer for nerve growth factor production, or a food, beverage or feed for enhancing nerve growth fact