Khellin (HCID 3828)

概要

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.

名称と識別子

優先名称: Khellin
IUPAC: 4,9-dimethoxy-7-methylfuro[3,2-g]chromen-5-one
現地名: ケーリン
英語名: KHELLIN
分子式: C14H12O5
分子量: 260.24

名称と別名

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

名称をさらに表示

ケーリンケリン4,9-ジメトキシ-7-メチル-5H-フロ[3,2-g][1]ベンゾピラン-5-オン7-メチル-4,9-ジメトキシ-5H-フロ[3,2-g][1]ベンゾピラン-5-オンビスアンミンケリン(ビサムミン)4,9-ジメトキシ-7-メチル-5H-フロ[3,2-g]クロメン-5-オン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

データベース識別子

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

物性

構造計算による物性

XLogP: 2.3
極性表面積: 57.9 Å²
水素結合供与体数: 0
水素結合受容体数: 5
回転可能結合数: 2
重原子数: 19
形式電荷: 0
複雑度: 405

実験および物理化学的性質

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]

物理化学的性質

融点: 150154 °C · 150154°C
沸点: 180200 °C0.05mm · 180200°C0.05mm Hg
比重(密度): 1.1954 · 1.1954 (rough estimate)
屈折率: 1.456 · 1.4560 (estimate)
貯蔵温度: Sealed in dry,Room Temperature
溶解性: クロロホルム（微量）、メタノール（微量）
外見: 結晶性
色: ライトイエロー
水溶解度: 247.2 g/L · 247.2g/L(25℃)
Merck: 14 · 14,5309
BRN: 263185 · 263185
主な用途: 食品および飲料
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の化学物質情報: Khellin (82-02-0)

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (100%)

安全データ

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

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

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

Drugs used to cause dilation of the blood vessels.

応用分野

使用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.

一般的な説明Khellin, is reported to be an efficient drug for treating vitiligo when combined with ultraviolet A irradiation.

調製方法

純化方法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.]