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(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン

(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン 化学構造式
519-02-8
CAS番号.
519-02-8
化学名:
(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン
别名:
(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン;マトリジン-15-オン;(+)-マルトリン;(7aα,13aR,13bα,13cα)-ドデカヒドロ-1H,5H,10H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10-オン;α-マトリン;(7aα,13aβ,13bα,13cα)-ドデカヒドロ-1H,5H,10H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10-オン;(+)-マトリン;マトリン;(7aS,13aR,13bR,13cS)-ドデカヒドロ-1H,5H,10H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10-オン;α‐マトリン;ソホカルピジン
英語化学名:
Matrine
英語别名:
Vegard;MATRINE;MATRENE;Matrines;MATRINIUM;MATRINE(P);(+)-MATRINE;Matrine CRS;MASSMARK 1621;alpha-matrine
CBNumber:
CB8284723
化学式:
C15H24N2O
分子量:
248.36
MOL File:
519-02-8.mol

(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン 物理性質

融点 :
77 C
沸点 :
86-88C/2,5Torr
比旋光度 :
D20 +38° (alc)
比重(密度) :
1,191g/cm
屈折率 :
1,536
貯蔵温度 :
Sealed in dry,2-8°C
酸解離定数(Pka):
9.47±0.20(Predicted)
Merck :
14,5759
CAS データベース:
519-02-8(CAS DataBase Reference)
NISTの化学物質情報:
Matrine(519-02-8)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn
Rフレーズ  20/21/22-37/38-41-48-22
Sフレーズ  22-26-36/37/39-45-36/37
WGK Germany  3
RTECS 番号 OQ1754000
HSコード  13021990
絵表示(GHS)
注意喚起語 Warning
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
注意書き
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。

(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン 価格 もっと(15)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00013153 マトリン
Matrine
519-02-8 5mg ¥19100 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00013153 マトリン
Matrine
519-02-8 10mg ¥25200 2021-03-23 購入
東京化成工業 M2120 マトリン >98.0%(GC)(T)
Matrine >98.0%(GC)(T)
519-02-8 200mg ¥14900 2021-03-23 購入
東京化成工業 M2120 マトリン >98.0%(GC)(T)
Matrine >98.0%(GC)(T)
519-02-8 1g ¥51300 2021-03-23 購入
関東化学株式会社(KANTO) 49065-45 マトリン
Matrine
519-02-8 25mg ¥40000 2021-03-23 購入

(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン 化学特性,用途語,生産方法

外観

白色~ほとんど白色粉末~結晶

解説

C15H24N2O(248.37).ソホカルピジンともいう.マメ科マトリグサSophora angustifoliaの根(漢薬の苦参)および同属の植物より得られるアルカロイド.ルピンアルカロイドに属し,ルパニンの構造異性体である.精製方法の違いにより,次の4種類の多形が存在し,これらは相互転換できる."α形は融点77 ℃.β形は融点87 ℃.[α]D"+38°(エタノール).γ形は沸点223°(0.8 kPa).d420"1.088.δ形は融点84 ℃.[α]D"+41°(水).水,ベンゼン,クロロホルム,エーテルに可溶.臭化水素酸塩は融点272~275 ℃.総アルカロイドを水酸化カリウムで加水分解すると,マトリン酸カリウムC15H25N2O2K(融点239 ℃)として容易に精製できる.これを2% 塩酸と処理すると,マトリン塩酸塩となり,アルカリ処理でマトリンを再生する.中枢抑制,抗原虫作用,末梢血管収縮などの薬効が報告されているが,毒性が強いので多量には用いられない.[CAS 519-02-8]
森北出版「化学辞典(第2版)

用途

マトリン(Matrine)は、クララ属の植物に含まれるアルカロイドである。抗がん作用、オピオイド受容体のκ-受容体やµ-受容体へのアゴニスト等、様々な薬理作用を持つ。
マトリンは、in vitroでもin vivoでも強い抗腫瘍作用を示す。マトリンの抗腫瘍作用は、細胞増殖の阻害とアポトーシスの誘導によるものと考えられている。またマトリンは、中国の伝統的な薬草であるクララの成分でもある。
マトリンや関連化合物のオキシマトリンは、イエシロアリに対する摂食阻害の効果がある。

説明

Matrine is extracted by organic solvents from the dry roots, plants, and fruits of kushen 苦参 (Sophora flavescens Ait) and also existed in S. alopecuroides L. and S. subprostrata Chun et T.?Chen.
Chinese medicine Radix sophorae flavescentis have dampness eliminating insecticide and diuretic effects. Sophora flavescens is used for heat dysentery, hemafecia, jaundice and anuria, red leukorrhea, vulva pruritus, eczema, wet sores, skin itching, scabies, ringworm, and trichomonas vaginitis. Sophora flavescens is recorded in the ancient Materia Medica. “Southern Yunnan Materia Medica” also recorded the effects of Saphora flavescens .
Sophora flavescens is a species of Sophora japonica and distributed in temperate and subtropical regions. Sophora flavescens is widely distributed in China, mainly in the north of Hebei, the west of Henan, and southwest of Shandong, Anhui, Hubei, and Guizhou. Matrine is extracted and isolated from the Chinese medicine Sophora flavescens

化学的特性

White solid

物理的性質

Appearance: white, needle-like crystal or crystalline powder that becomes yellow and solid after long-time exposure in air. Solubility: soluble in water, benzene, chloroform, and methanol and slightly soluble in petroleum ether. Melting point: 76?°C (α-matrine), 87?°C (β-matrine), 223?°C (γ-matrine), and 84?°C (δ-matrine). Specific optical rotation: +31 to +36°.

来歴

As early as the 1930s, the Soviet Union began to study Sophora flavescens, and the domestic research began in 1972. Sophora flavescens in the chemical composition are divided into two major categories of alkaloids and flavonoids. Domestic and foreign researches are focused on the alkaloids. So far, there are 23 species of alkaloids isolated and identified in roots, stems, leaves, and flowers of Sophora flavescens. The main components of Sophora flavescens have obvious anti-cancer effects, and oxymatrine has anti-cancer and antiaging effects. Flavonoids are predominantly A-ring isoprenyl-branched. Isopentenyl flavonoids are generally thought to act as plant defensins and play an important physiological role in plant defense. These components are only distributed in plants of legumes, Moraceae, and Asteraceae. Since the 1970s, owing to the multiple pharmacological activities of isopentenyl flavonoids, the studies on these ingredients have attracted more and more attention. So far, the natural separation of these compounds has more than a thousand species. Early chemical work focused on the composition of alkaloids in Sophora flavescens. In recent years, more and more researches were focused on isopentenyl flavonoids, which achieved a lot of results .

使用

antifungal, nematocide

適応症

In clinical settings, matrine injection was used for chronic active hepatitis, and suppository was used for trichomoniasis or Candida vaginitis and chronic cervicitis and can also be used for senile vaginitis and pelvic inflammatory disease.

薬理学

Matrine has antiarrhythmic, anti-inflammatory, anti-fibrosis, and anti-tumor effects. Matrine has significant effects of negative frequency and positive inotropic action, which can enhance myocardial contractility, slow down the heart rate, and extend the PR and QTC interval. Matrine can promote the expression of bcl-2 gene and can improve the ratio of bcl-2/Bax to inhibit apoptosis of myocardial cell caused by myocardial ischemia reperfusion and then reduce myocardial deficiency caused by coronary atherosclerotic heart disease and myocardial infarction to achieve the role of antiarrhythmic. In addition, matrine can also play an anti-pulmonary fibrosis effect by inhibiting the proliferation of lung fibroblasts and the expression of pulmonary interstitial fibroblasts (FN). Studies have found that matrine has anti-allergy and anti-inflammatory effects.Matrine has an inhibitory effect on tumor cells by inhibiting growth and proliferation and inducing apoptosis. Studies have shown that 0.8?g/L and 1.0?g/L matrine could significantly inhibit the growth, proliferation, invasion, and metastasis of human hepatocellular carcinoma SMMC-7721 cells . In addition, 0.0625–0.5?mg/ ml matrine significantly inhibited proliferation of HT29 cells after 48?h incubation. 1?mg/ml matrine significantly induce apoptosis of HT29 cells . Oxymatrine is also an anti-cancer ingredient of Sophora flavescens. In recent years, oxymatrine is widely used in the clinic for treatment of leukopenia and chronic hepatitis B, hepatitis C induced by tumor radiotherapy, and chemotherapy. Oxymatrine can improve liver biochemical indicators by protecting liver cells, reducing cell necrosis, and preventing liver fibrosis. In addition, oxymatrine can treat all kinds of eczema, especially for acute and subacute eczema, and contact dermatitis .

臨床応用

Matrine has multiple pharmacological effects and can treat a variety of diseases in clinical setting. At present, the researches on matrine are mainly focused on antiliver injury and liver fibrosis and anti-tumor and anti-cardiovascular diseases. It was worthy of attention that matrine has other pharmacological activities, such as leukocyte-elevating effects and anti-virus effects, and these effects were necessary for further development and utilization. The pharmacological effects of matrine stayed in the experimental phase, and they need further development and research to promote the development of clinical practice. Improvements in the modern formulation of matrine can improve their clinical application.

(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン 上流と下流の製品情報

原材料

準備製品


(7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン 生産企業

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519-02-8((7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン)キーワード:


  • 519-02-8
  • alpha-matrine
  • SOPHOCARPIDINE
  • (+)-MATRINE
  • MATRINE
  • MATRINIUM
  • MATRENE
  • Alkaloids Sophora Flavescen
  • Matrines
  • MATRINE, 98.0% BY HPLC
  • MATRINE(P)
  • MASSMARK 1621
  • Matrine,Sophocarpidine
  • (7aα,13aR,13bα,13cα)-Dodecahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridine-10-one
  • (7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-Decahydro-1H,5H,8H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridine-10(11H)-one
  • Matrine,Matridin-15-one, Sophocarpidine
  • Matridin-15-one (7aS,13aR,13bR,13cS)-Dodecahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one
  • 7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-6-one
  • Matrine((+)-Matrine)
  • Matrine (alpha-matrine)
  • Matrine 519-02-8
  • Vegard
  • Matrine, froM Sophora flavescens
  • 1H,5H,10H-Dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, dodecahydro-, (7aS,13aR,13bR,13cS)-
  • Matridin-15-one (9CI)
  • Matrine, >=98%
  • Lepidium meyenii Walp extract
  • Matrine, 98%, from Sophora flavescens
  • Matridin-15-one Sophocarpidine
  • Matrine CRS
  • 519-02-8 Matrine Insecticide Biological Pesticides for Formosan subterranean termite
  • (7aα,13aβ,13bα,13cα)-2,3,6,7,7a,12,13,13a,13b,13c-デカヒドロ-1H,5H,8H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10(11H)-オン
  • マトリジン-15-オン
  • (+)-マルトリン
  • (7aα,13aR,13bα,13cα)-ドデカヒドロ-1H,5H,10H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10-オン
  • α-マトリン
  • (7aα,13aβ,13bα,13cα)-ドデカヒドロ-1H,5H,10H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10-オン
  • (+)-マトリン
  • マトリン
  • (7aS,13aR,13bR,13cS)-ドデカヒドロ-1H,5H,10H-ジピリド[2,1-f:3',2',1'-ij][1,6]ナフチリジン-10-オン
  • α‐マトリン
  • ソホカルピジン
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