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2,3,9,10-テトラメトキシ-5H,6H-ジベンゾ[a,g]キノリジン-7-イウム

Palmatine

HCID 19009
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
3486-67-7
標準SMILES
COc1cc2c(cc1OC)-c1cc3ccc(OC)c(OC)c3c[n+]1CC2
InChIKey
QUCQEUCGKKTEBI-UHFFFAOYSA-N
分子式
C21H22NO4+
平均分子量
352.4 g/mol
単同位体質量
352.15488318

概要

Palmatine is a berberine alkaloid and an organic heterotetracyclic compound. It has a role as a plant metabolite.

名称と識別子

優先名称
Palmatine
IUPAC
2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium
現地名
2,3,9,10-テトラメトキシ-5H,6H-ジベンゾ[a,g]キノリジン-7-イウム
英語名
Palmatine
分子式
C21H22NO4+
分子量
352.4

名称と別名

Palmatine3486-67-7BerbericinineO,O-Dimethyldemethyleneberberine5,6-Dihydro-2,3,9,10-tetramethoxydibenzo[a,g]quinoliziniumpalmatine ionpalmatine cation7,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxyberbiniumDTXSID9048065G50C0342175,6-Dihydro-2,3,9,10-tetramethoxydibenzo(a,g)quinoliziniumCHEBI:16096
名称をさらに表示
7,8,13,13a-テトラデヒドロ-2,3,9,10-テトラメトキシベルビニウム2,3,9,10-テトラメトキシ-5,6-ジヒドロジベンゾ[a,g]キノリジニウム2,3,9,10-テトラメトキシ-5H,6H-ジベンゾ[a,g]キノリジン-7-イウム5,6-ジヒドロ-2,3,9,10-テトラメトキシジベンゾ[a,g]キノリジニウムブラサインベルベリシニンパルマチン3,4,10,11-テトラメトキシ-7,8-ジヒドロ-6λ5-アザテトラフェン-6-イリウムプソイドデヒドロコリダリン7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-berbiniug)quinolizinium,5,6-dihydro-2,3,9,10-tetramethoxy-dibenzo(2,3,9,10-TETRAMETHOXY-5,6-DIHYDRO-ISOQUINO[3,2-A]ISOQUINOLINYLIUMmatinePalatine
2,3,9,10-tetramethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium2,3,9,10-tetramethoxy-5,6-dihydroisoquino(3,2-a)isoquinoliniumRefChem:44890DTXCID0028036PalmatinBurasaineDibenzo[a,g]quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium

物性

構造計算による物性

XLogP
3.7
極性表面積
40.8 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
4
重原子数
26
形式電荷
1
複雑度
475

実験および物理化学的性質

SpringerMaterials PropertiesChemical shift
Collision Cross Section183.2 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
205 °C · 205°C
貯蔵温度
2 · under inert gas (nitrogen or Argon) at 2-8°C
溶解性
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
外見
Powder
色
Yellow
化粧品成分の機能
抗酸化物質
InChI
InChI=1S/C21H22NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,9-12H,7-8H2,1-4H3/q+1
InChIKey
QUCQEUCGKKTEBI-UHFFFAOYSA-N
SMILES
C12=CC3=C(C(OC)=C(OC)C=C3)C=[N+]1CCC1C=C(OC)C(OC)=CC2=1
LogP
-1.12 · -1.120 (est)
CAS データベース
3486 · 3486-67-7(CAS DataBase Reference)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

安全データ

毒性
mouse,LD50,subcutaneous,135mg/kg (135mg/kg),Russian Pharmacology and Toxicology Vol. 31, Pg. 129, 1968.

化学と産業

用途と製造

Household ProductsInformation on 2 consumer products that contain Palmatine in the following categories is provided:
応用分野 · 2 件

説明This quaternary alkaloid occurs frequently in the Rhoeadales, being found in Cop tis japonica Mak. (Ranunculaceae); Berberis heteropoda Schrenk; B. vulgaris L. (Berberidaceae); Coscinium blumeatum Miers; Fibrauria chloroleuca Miers;Jatrorrhiza palmata (Lam.) Miers. (Menispermaceae); and Phellodendron amurense Rupr. (Rutcaeae). The base is usually obtained as the iodide dihydrate forming orange-yellow needles from H20, m.p. 241°C (dec.). Other salts that have been prepared include the chloride, green-yellow needles from H20, m.p. 205°C (dec.); nitrate, yellow needles, from H20, m.p. 239°C (dec.); perchlorate, m.p. 262°C (dec.); sulphate, m.p. 250°C; platinichloride, m.p. 236°C and the thiocyanate, m.p. 210°C (dec.). The alkaloid resembles berberine in yielding addition compounds with CHCl3 and Me2CO. On catalytic hydrogenation it gives tetrahydropalmatine, while on oxidation with alkaline KMn04 it furnishes corydaldine and hemipinic acid.

来歴In the middle of the last century, Garrison health team of China and Honghe state hospital interviewed to explore the medicinal use of Huangteng in the screen edge of ethnic minority areas firstly and found its detoxification and anti-inflammatory effect of antibacterial. Then, it was promoted to be used in Yunnan province after the initial clinical validation. Palmatine on the market is mostly natural, which is mainly obtained from the extraction of dry rattan of Huangteng, one plant of Menispermaceae. The palmatine is abundant in the dry rattan of Huangteng with more than 2% palmatine chloride . It is an important part of technological research to obtain natural palmatine with high quality and high purityHonghe state in Yunnan province isolated and extracted palmatine from Huangteng firstly and then produced needle, tablets, ointment and topical solution, and other dosage forms for the treatment of various suppurative infections. It is now believed that the optimum conditions for the extraction of palmatine should be acid water decocting, firstly extracted from the rattan of Huangteng and then adjusted to pH 9-10, and NaCl salting out, which is obtained by precipitation purifica tion step by step, while ultrasonic can be used as an auxiliary means of extraction.The growth period of Huangteng is very long so that the extraction of natural palmatine cannot meet the market demand. Therefore, in order to alleviate the con tradiction of resources, researchers began to explore the method of chemical synthe sis of palmatine and its active derivatives in place of natural palmatine. At present, the improved synthetic method using berberine as raw material is the one with high yield, the total yield of which is 54%, and the purity of palmatine is 99%

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
3486-67-7
PubChem CID
19009
DTXSID
DTXSID9048065
ChEMBL
CHEMBL206106
ChEBI
CHEBI:16096
UNII
G50C034217
Nikkaji
J12.970D

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定義本品は、次の化学式で表される有機化合物である。