484-51-5

Basic information

• Product Name: KHELLINONE
• Synonyms: KHELLINONE;1-(6-HYDROXY-4,7-DIMETHOXY-BENZOFURAN-5-YL)-ETHANONE;6-hydroxy-4,7-dimethoxybenzofuran-5-yl methyl ketone;KHELLINONE 97%;Khellinone,97%;4,7-Dimethoxy-5-acetylbenzofuran-6-ol;1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)ethanone
• CAS NO: 484-51-5
• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.22
• EINECS: 207-607-1
• Mol File: 484-51-5.mol
• Article Data: 32

Chemical Properties

• Melting Point: 90-101 °C
• Boiling Point: 366.3°Cat760mmHg
• Flash Point: 175.3°C
• Appearance: /
• Density: 1.281g/cm³
• Vapor Pressure: 7.02E-06mmHg at 25°C
• Refractive Index: 1.583
• PKA: 7.67±0.50(Predicted)
• CAS DataBase Reference: KHELLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: KHELLINONE(484-51-5)
• EPA Substance Registry System: KHELLINONE(484-51-5)

Safety Data

• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• Hazardous Substances Data: 484-51-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 5823, 1985 DOI: 10.1021/ja00306a052The Journal of Organic Chemistry, 53, p. 4166, 1988 DOI: 10.1021/jo00253a002

InChI:InChI=1/C12H12O5/c1-6(13)8-9(14)12(16-3)11-7(4-5-17-11)10(8)15-2/h4-5,14H,1-3H3

Upstream product

• 668-10-0 Ammiol 
• 67-56-1 methanol 
• 88897-95-4 1-(6-hydroxy-7-methoxy-5-benzofuranyl)-ethanone 
• 87145-72-0 methyl 4,7-dimethoxy-6-hydroxybenzofuran-5-carboxylate 
• 75-16-1 methylmagnesium bromide 
• 98362-17-5 5-acetyl-4,7-dimethoxy-6-ethoxybenzofuran 
• 85518-13-4 3-acetyl-5,9-dimethoxy-2-methyl-4H-furo[3,2-g]chromen-4-one 
• 99059-07-1 4,7-dimethoxy-benzofuran-6-ol 
• 854898-32-1 6-benzyloxy-4,7-dimethoxy-benzofuran-2-carboxylic acid ethyl ester 
• 40512-23-0 1-(4,6,7-trimethoxybenzofuran-5-yl)ethan-1-one 
• 6274-74-4 2,6-dibenzyloxy-1,4-dimethoxybenzene 
• 20032-42-2 2,5-dimethoxyresorcinol 
• 42528-81-4 2,6-bis-benzyloxy-benzene-1,4-diol 
• 52249-81-7 4-benzyloxy-2-hydroxy-3,6-dimethoxybenzaldehyde 

Downstream Products

• 76301-19-4 4,9-Dimethoxy-7--5H-furo<3,2-g><1>benzopyran-5-one 
• 76301-20-7 4,9-Dimethoxy-7-<(phenylthio)methyl>-5H-furo<3,2-g><1>benzopyran-5-one 
• 85517-98-2 (5-Acetyl-4,7-dimethoxy-6-benzofuranyl)-4-trifluormethyl-benzoat 
• 85517-97-1 (5-Acetyl-4,7-dimethoxy-6-benzofuranyl)-4-nitrobenzoat 
• 82-02-0 Khellin 
• 92663-30-4 C₂₄H₂₁O₅P 
• 102830-32-0 2-benzoyl-3-methyl-4,8-dimethoxybenzo<1,2-b:5,4-b>difuran-2,6-dione 
• 85517-96-0 (5-Acetyl-4,7-dimethoxy-6-benzofuranyl)-2-nitrobenzoat 
• 89820-31-5 4',9'-Dimethoxy-spiro[cyclohexane-1,7'-[7H]furo[3,2-g][1]benzopyran]-5'(6'H)-one 
• 49572-86-3 4,9-dimethoxy-7-(4-methoxy-phenyl)-furo[3,2-g]chromen-5-one 
• 62061-97-6 4,9-dimethoxy-7-(4-methoxy-phenyl)-6,7-dihydro-furo[3,2-g]chromen-5-one 
• 49572-87-4 7-(3,4-dimethoxy-phenyl)-4,9-dimethoxy-furo[3,2-g]chromen-5-one 
• 110442-47-2 4,8-dimethoxy-3-methyl-benzo[1,2-b;5,4-b']difuran-2-carboxylic acid anilide 
• 856814-19-2 1-(3,4-dimethoxy-phenyl)-3-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-propane-1,3-dione 

Relevant articles and documents

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Non-ulcerogenic pyrazolyl 2-hydroxychalcones and pyrazolylpyrazolines derived from naturally existing furochromone (khellin): semi-synthesis, docking study and anti-inflammatory activity

Novel pyrazolyl 2-hydroxychalcone derivatives 3a–e and pyrazolylpyrazoline derivatives 4a–e and 5a–j derived from the naturally existing furochromone (Khellin) were synthesized and evaluated for their in?vivo anti-inflammatory activity. Most of the synthesized compounds showed better or comparable activity to that of Diclofenac as reference drug. Twelve compounds were evaluated for their ulcerogenic potential and exhibited no ulcerogenic effect. In addition compounds 3c, 5c and 5h as examples showed PGE2 inhibition % 88.86, 65.87 and 44.06, respectively and TNFα inhibition % 48.62, 31.11 and 16.02, respectively in rat serum samples. Compounds 3c, 5c, 5h and Celecoxib were subjected to in?vitro COX-1 and COX-2 inhibition assay, showed selectivity index 45.04, 102.04, 131.58 and 185.18, respectively. The computational finding supported those of in?vitro, where the pyrazolylpyrazolines interacted with the COX-2 enzyme in a similar orientation to that of Celecoxib, while chlacones were found to exhibit similar orientation to that of Diclofenac.

Natural chalcone derivative as well as preparation method and application thereof

The invention provides a natural chalcone derivative as well as a preparation method and application thereof, and belongs to the technical field of chemical medicines. The natural chalcone derivative is a compound represented by formula (I), or a salt thereof, or a stereoisomer thereof, or a hydrate thereof. The derivative has remarkable inhibitory activity on IL-1beta and can effectively inhibit release of IL-1beta, and the inhibitory effect of the derivative is even superior to that of compounds with a similar structure in the prior art, wherein the compound 19, the compound 27, the compound 30, the compound 32 and the compound 40 have the optimal inhibition effect on IL-1beta. The derivative can be used as an IL-1beta inhibitor, is used for preparing medicines for treating inflammation and inflammation-related diseases, such as medicines for treating neurological inflammation, Alzheimer's disease, systemic lupus erythematosus, atherosclerosis, allergic asthma, arthritis, colitis and other diseases, and has a good application prospect.

FURANOCHALCONES AS INHIBITORS OF CYP1A1, CYP1A2 AND CYP1B1 FOR CANCER CHEMOPREVENTION

The present invention relates to the furanochalcone class of compounds of general formula A. The present invention particularly relates to the synthesis of furanochalcones and their CYP1A1, CYP1A2 and CYP1B1 inhibitory activity. In addition, the invention relates to the prevention or treatment of cancer caused by polyaromatic hydrocarbons (PAHs), 4-nitroquinoline-1-oxide, and N-nitroso-N- methylurea, heterocyclic amines, estrogen and 17β-estradiol, resulting from the inhibition of CYP1A1, CYP1A2 and CYP1B1 enzymes.