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
• Article Data: 7

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

Different sources of media describe the Uses of 82-02-0 differently. You can refer to the following data:
1. vasodilator (coronary), photosensitizer
2. Khellin has been used as a reference standard for supercritical fluid extraction of khellin from Ammi visnaga L. fruits to understand the various medicinal effects of γ-Pyrones by reversed phase HPLC method.

Brand name

Ammivin (Marion Merrell Dow); Khelloyd (Hoechst-Roussel).

Synthesis Reference(s)

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

General Description

Khellin, is reported to be an efficient drug for treating vitiligo when combined with ultraviolet A irradiation.

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

• 115249-37-1 5-benzyloxykhellin 
• 119104-31-3 1-(4-benzyloxy-6-hydroxy-7-methoxy-benzofuran-5-yl)-ethanone 
• 86397-43-5 4,9-diethoxy-7-methyl-furo[3,2-g]chromen-5-one 
• 55165-10-1 9-benzyloxy-4-hydroxy-7-methyl-furo[3,2-g]chromen-5-one 
• 1026891-49-5 9-(4-benzoyl-benzyloxy)-4-hydroxy-7-methyl-furo[3,2-g]chromen-5-one 
• 1026457-89-5 9-(4-benzyloxy-benzyloxy)-4-hydroxy-7-methyl-furo[3,2-g]chromen-5-one 
• 1026676-52-7 4-hydroxy-7-methyl-9-(3-trifluoromethoxy-benzyloxy)-furo[3,2-g]chromen-5-one 

Relevant articles and documents

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FACILE CHROMONE RING-OPENING OF KHELLIN

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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.

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.