4,9-Dimethoxy-7-methyl-5H-furo-(3,2-g)(1)benzo-pyran-5-on

Khellin

HCID 3828CAS 82-02-0

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Grundinformationen

Standard-SMILES: COc1c2occc2c(OC)c2c(=O)cc(C)oc12
InChIKey: HSMPDPBYAYSOBC-UHFFFAOYSA-N
Summenformel: C14H12O5
Durchschnittliche Molmasse: 260,24 g/mol
Monoisotopische Masse: 260,06847348

Überblick

Khellin is a furanochrome in which the basic tricyclic skeleton is substituted at positions 4 and 9 with methoxy groups and at position 7 with a methyl group. A major constituent of the plant Ammi visnaga it is a herbal folk medicine used for various illnesses, its main effect being as a vasodilator. It has a role as a bronchodilator agent, a cardiovascular drug, a vasodilator agent and an anti-asthmatic agent. It is a furanochromone, an organic heterotricyclic compound and an oxacycle. It is functionally related to a 5H-furo[3,2-g]chromen-5-one.

Namen und Bezeichner

Bevorzugter Name: Khellin
IUPAC: 4,9-dimethoxy-7-methylfuro[3,2-g]chromen-5-one
Lokaler Name: 4,9-Dimethoxy-7-methyl-5H-furo-(3,2-g)(1)benzo-pyran-5-on
Englischer Name: KHELLIN
Summenformel: C14H12O5
Molmasse: 260.24

Namen und Synonyme

khellin82-02-0VisamminViscardanKhelloydAmmivinKellinaKhellineKhellinumQuelina4,9-Dimethoxy-7-methyl-5H-furo(3,2-g)(1)benzopyran-5-oneDTXSID9045267

Weitere Namen anzeigen

VISNAGINeskelnorkelKHELINkeloidchellinkelaminkelicor

4,9-Dimethoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one4,9-Dimethoxy-7-methyl-5-oxofuro(3,2-g)-1,2-chromenekelina5H-Furo[3,2-g][1]benzopyran-5-one, 4,9-dimethoxy-7-methyl-CHEBI:6133NSC-25509NSC-377445G117T0TJZ

Datenbank-Bezeichner

CAS: 82-02-0
PubChem CID: 3828
DTXSID: DTXSID9045267
ChEMBL: CHEMBL44746
ChEBI: CHEBI:6133
UNII: 5G117T0TJZ
EC Number: 201-392-8
Nikkaji: J24.827D

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,3
Polarare Oberfläche (TPSA): 57,9 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 2
Schwere Atome: 19
Formalladung: 0
Komplexität: 405

Experimentelle und physikochemische Eigenschaften

LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Benzopyranoids [PK1311]

Collision Cross Section151.6 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID9045267]

Physikochemische Eigenschaften

Schmelzpunkt: 150154 °C · 150154°C
Siedepunkt: 180200 °C0.05mm · 180200°C0.05mm Hg
Dichte: 1.1954 · 1.1954 (rough estimate)
Brechungsindex: 1.456 · 1.4560 (estimate)
storage temp.: Sealed in dry,Room Temperature
Löslichkeit: Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand: crystalline
Farbe: light yellow
Wasserlöslichkeit: 247.2 g/L · 247.2g/L(25 ºC)
Merck: 14 · 14,5309
BRN: 263185 · 263185
Major Application: food and beverages
InChI: 1S/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
InChIKey: HSMPDPBYAYSOBC-UHFFFAOYSA-N
SMILES: COc1c2OC(C)=CC(=O)c2c(OC)c3ccoc13
LogP: 1.77 · 1.770 (est)
EPA chemische Informationen: Khellin (82-02-0)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P280, P301+P316, P302+P352, P321, P330, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Sicherheitsdaten

wgk: 3
ridadr: UN 2811 6.1/PG 3
hs_code: 2932.99.7000
RTECS-Nr.: LV1050000
risk_code: 25-38-36/37/38-23/24/25
Toxizität: LD50 in mice, rats (mg/kg): 30.6, 34.4 i.v.; 50.8, 68.8 orally (Busch)
hazard_code: T
safety_code: 36/37/39-45-26
hazard_class: 6.1(b)
packing_group: III
Speicherklasse: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Agents that cause an increase in the expansion of a bronchus or bronchial tubes.

Drugs used to cause dilation of the blood vessels.

Anwendungen

VerwendenKhellin 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.