82-02-0

Basic information

• Product Name: KHELLIN
• Synonyms: 2-g)(1)benzopyran-5-one,4,9-dimethoxy-7-methyl-5h-furo(;4,9-dimethoxy-7-methyl-5-oxo-1,8-dioxabenz-(f)indene;ammispasmin;ammivin;ammivisnagen;benecardin;cardio-khellin;chellin
• CAS NO: 82-02-0
• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.24
• EINECS: 201-392-8
• Product Categories: Herb extract;AMIVIN;Inhibitors
• Mol File: 82-02-0.mol

Chemical Properties

• Melting Point: 150154°C
• Boiling Point: 180200°C0.05mm Hg
• Flash Point: 218.8 °C
• Appearance: light yellow/crystalline
• Density: 1.1954 (rough estimate)
• Vapor Pressure: 1.88E-09mmHg at 25°C
• Refractive Index: 1.4560 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: 247.2g/L(25 oC)
• Merck: 14,5309
• BRN: 263185
• CAS DataBase Reference: KHELLIN(CAS DataBase Reference)
• NIST Chemistry Reference: KHELLIN(82-02-0)
• EPA Substance Registry System: KHELLIN(82-02-0)

Safety Data

• Hazard Codes: T
• Statements: 25-38-36/37/38-23/24/25
• Safety Statements: 36/37/39-45-26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: LV1050000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 82-02-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
KHELLIN is used as a vasodilator for its ability to dilate blood vessels, particularly in the coronary arteries, which helps improve blood flow and alleviate symptoms of angina and other cardiovascular conditions.
KHELLIN is also used as a photosensitizer, which makes it useful in photodynamic therapy for the treatment of various conditions, including certain types of cancer and age-related macular degeneration.
Used in Analytical Chemistry:
KHELLIN serves as a reference standard for supercritical fluid extraction, allowing researchers to study the medicinal effects of γ-Pyrones using reversed phase HPLC methods. This application aids in understanding the therapeutic potential of KHELLIN and related compounds.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 26, p. 1672, 1983 DOI: 10.1021/jm00366a002

Purification Methods

Crystallise khellin from H2O, MeOH, pet ether or Et2O. The hydrochloride has m 98o(dec) (from EtOH/HCl). [Beilstein 19 II 236, 19 III/IV 2816, 19/6 V 320.]

InChI:InChI=1/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

Upstream product

• 2159-83-3 4,9-Dihydroxy-7-methyl-5H-furo<3,2-g><1>benzopyran-5-one 
• 478-42-2 khellinol 
• 26239-04-3 4,9-dimethoxy-7-methyl-2,3-dihydro-furo[3,2-g]chromen-5-one 
• 37833-19-5 6-hydroxy-4,7-dimethoxy-5-acetoacetylbenzofuran 
• 853930-62-8 (6-formyl-5,8-dimethoxy-2-methyl-4-oxo-4H-chromen-7-yloxy)-acetic acid 
• 481-71-0 NSC₃₃₀₇₉₆ 
• 74-88-4 methyl iodide 
• 484-51-5 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran 
• 141-78-6 ethyl acetate 
• 85518-13-4 3-acetyl-5,9-dimethoxy-2-methyl-4H-furo[3,2-g]chromen-4-one 
• 98362-17-5 5-acetyl-4,7-dimethoxy-6-ethoxybenzofuran 
• 98393-99-8 4,7-dimethoxy-6-ethoxy-5-(1-hydroxyethyl)benzofuran 
• 98362-16-4 5-<1-<(tert-butyldimethylsilyl)oxy>ethyl>-4,7-dimethoxy-6-ethoxybenzofuran 
• 98362-14-2 4-acetoxy-5-<1-<(tert-butyldimethylsilyl)oxy>ethyl>-6-ethoxy-7-methoxybenzofuran 

Downstream Products

• 112115-91-0 4,9-dimethoxy-7-(4t-phenyl-buta-1,3-dien-t-yl)-furo[3,2-g]chromen-5-one 
• 113113-95-4 4,9-dimethoxy-7-(4-methyl-trans-styryl)-furo[3,2-g]chromen-5-one 
• 110435-55-7 4,9-dimethoxy-7-(4-nitro-trans-styryl)-furo[3,2-g]chromen-5-one 
• 481-71-0 NSC₃₃₀₇₉₆ 
• 484-51-5 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran 
• 478-42-2 khellinol 
• 23036-39-7 4,9-dimethoxy-7-trans-styryl-furo[3,2-g]chromen-5-one 
• 34959-30-3 4,11-dimethoxy-9-methylene-5-oxo-8,9-dihydro-5H,6H-spiro[furo[3',2':6,7]chromeno[3,2-c]pyridinium-7,1'-piperidinium]; chloride 
• 92611-82-0 7-hydroxy-5,8-dimethoxy-2-methyl-4(H)-oxo-1-benzopyran-6-carboxaldehyde 
• 2159-83-3 4,9-Dihydroxy-7-methyl-5H-furo<3,2-g><1>benzopyran-5-one 
• 3380-63-0 5,8-Dimethoxy-2-methyl-furo<3',2':6,7>chromanon-(4) 
• 61348-53-6 khellin oxime 
• 25944-27-8 5,8-dimethoxy-4',5'-furo-6,7-chromone-2-carboxaldehyde 

Relevant articles and documents

t-BUTYL LITHIOACETATE ON ORTHO-HYDROXYPHENONES PROVIDING 2-METHYLCHROMONES. AN EASY ACCESS TO KHELLIN

Reaction of t-butyl lithioacetate with several kinds of poly-substituted ortho-hydroxyphenones including khellinone and subsequent acid hydrolysis of the resulting hemiacetals provide the corresponding 2-methylchromone derivatives in excellent overall yields.

Synthetic routes to benzofurans and benzothiophenes and intermediates therefor

The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and other furochromone analogues, which have demonstrated antiatherosclerotic activity. These novel intermediates and processes can also be used for the preparation of benzofurans and benzothiophenes which inhibit the synthesis of leukotriene and/or lipoxygenase.

Synthesis of precursors of anti-atherosclerotic furochromones

The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and analogues thereof, which have demonstrated antiatherosclerotic activity.