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8-β-D-グルコピラノシル-3-(4-ヒドロキシフェニル)-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン

Puerarin

HCID 5281807
ノート反応
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
部分構造検索類似構造を探す

基本情報

CAS
3681-99-0
標準SMILES
O=c1c(-c2ccc(O)cc2)coc2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)ccc12
InChIKey
HKEAFJYKMMKDOR-VPRICQMDSA-N
分子式
C21H20O9
平均分子量
416.4 g/mol
単同位体質量
416.11073221

概要

Puerarin is a hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 7 and 4' and a beta-D-glucopyranosyl residue at position 8 via a C-glycosidic linkage. It has a role as an autophagy inducer, a ferroptosis inhibitor, an antioxidant, an antipyretic, an anti-inflammatory agent, a plant metabolite and a cardioprotective agent. It is a C-glycosyl compound and a hydroxyisoflavone. It is functionally related to an isoflavone. It is a conjugate acid of a puerarin(1-).

名称と識別子

優先名称
Puerarin
IUPAC
7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
現地名
8-β-D-グルコピラノシル-3-(4-ヒドロキシフェニル)-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン
英語名
Puerarin
分子式
C21H20O9
分子量
416.38

名称と別名

Puerarin3681-99-0KakoneinDaidzein-8-C-glucosidePuerarin 80 mmDaidzein 8-c-glucosideNPI 031GCHEBI:8633DTXSID30958020Z9W89974167-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-oneNSC-380711
名称をさらに表示
8-(β-D-グルコピラノシル)-7-ヒドロキシ-3-(4-ヒドロキシフェニル)-4H-1-ベンゾピラン-4-オン4',7-ジヒドロキシ-8-[β-D-グルコピラノシル]イソフラボン8-β-D-グルコピラノシル-3-(4-ヒドロキシフェニル)-7-ヒドロキシ-4H-1-ベンゾピラン-4-オンプエラリン8-(β-D-グルコピラノシル)-4',7-ジヒドロキシイソフラボンプエラリン, HIGH PURITY7-ヒドロキシ-3-(4-ヒドロキシフェニル)-8-[(2S,3R,4R,5S,6R)-3,4,5-トリヒドロキシ-6-(ヒドロキシメチル)オキサン-2-イル]-4H-クロメン-4-オン8-(β-D-グルコピラノシル)-3-(4-ヒドロキシフェニル)-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン4′,7-ジヒドロキシ-8-(β-D-グルコピラノシル)イソフラボン4′,7-ジヒドロキシ-8-[β-D-グルコピラノシル]イソフラボンカコネリン4′-ヒドロキシ-7-ヒドロキシ-8-β-D-グルコピラノシルイソフラボン6-tert-ブチルプエラリンPSYCHOSINEPurerarin

物性

構造計算による物性

XLogP
0
極性表面積
157 Ų
水素結合供与体数
6
水素結合受容体数
9
回転可能結合数
3
重原子数
30
形式電荷
0
複雑度
659

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
LogP1.34
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section · 2 件

209.37 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

196.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
187 · 187-189°C
沸点
688 · 688.0±55.0 °C(Predicted)
比重(密度)
1.614 · 1.614±0.06 g/cm3(Predicted)
貯蔵温度
2 · 2-8°C
溶解性
DMSO(微量)、メタノール(微量)
酸解離定数(Pka)
6.46 · 6.46±0.20(Predicted)
外見
粉
色
ホワイトからオフホワイト
水溶解度
DMSOまたはDMFに可溶。水またはエタノールにわずかに溶ける
BRN

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。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 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 CategoriesSkin Irrit. 2 (50%)

安全データ

F
10
wgk
3
rtecs
UO5216000
hs_code
29389090
risk_code
11-34
hazard_code
F,C
safety_code
22-24/25-45-36/37/39-26-16
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
応用分野 · 3 件

説明Puerarin, also known as pueraria flavonoids, is a kind of flavonoid glycoside extracted from the roots of Pueraria alba or Pueraria thomsonii and is also one of the main effective ingredients of Pueraria lobata. That Pueraria lobate was used to treat diseases has already been recorded in China’s ancient medical books such as Shen Nong’s Materia Medica, Treatise on Miscellaneous Diseases and Medical Dictionary. Kanzu root is widely distributed in our country and of rich resources. It has been reported that puerarin could be extracted from Pueraria lobata (Wild.) Ohwi, Radix Pueraria thomsonii, Pueraria omeiensiswanget Tang, Pueraria edulis Pamp and Pueraria phaseoloides, but the content of puerarin differs. Pueraria has a great value for nutrition and medicine and was considered the south ginseng of China. Puerarin has been widespread concerned over our country for its use of food and medicine in recent years.

来歴In 1959, Japanese chemist Shibata Shoji first studied the chemical production of pueraria root, indicating that isoflavones are the main active ingredients of pueraria root, including puerarin, daidzin and daidzein . Then in 2003, David Lee first total synthesized analogical puerarin . And it was in 1974 that puerarin was first extracted by Fang Qicheng and other chemists in China . Due to its strong activity of anti-cardiovascular and anti-cerebrovascular ischemia and hypoxia, expanding the coronary artery and cerebrovascular, reducing myocardial oxygen consumption, and improving myocardial systolic and microcirculation function, puerarin was approved for clinical use by the Ministry of Health in 1993. In recent years, researchers have synthesized a series of puerarin derivatives, and active research showed that the part of the puerarin derivatives has a good biological activity and bioavailability. In a new dosage form research, researchers have developed several types of dosage forms such as quickrelease solid dispersions, solid from microemulsion preparation, etc., which greatly increase the solubility of puerarin, thus improving bioavailability. In recent years,the research on crystal drug has opened up new ways for the application of puerarin.

使用Puerarin is a naturally occuring isoflavonoid derived from Chinese medical herb kudzu root and has been used for the treatment of various cardiovascular diseases. Recent sutdies have shown the potenti al of puerarin treatment as a novel approach to lowering the risk of or improving function in ischemia-reperfusion brain injury-related disorders.

関連反応

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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
Daidzeine
Puerarine
PUERARIN EXTRACT
Pueraria Root Flavone
8-β-D-Glucopyranosyl-3-(4-hydroxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one
7-HYDROXY-3-[4-HYDROXYPHENYL]-1-BENZOPYRAN-4-ONE 8-[BETA-D-GLUCOPYRANOSIDE
Puerain
4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-7-hydroxy-3-(4-hydroxyphenyl)-7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one7-hydroxy-3-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)chromen-4-one7-hydroxy-3-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)chromen-4-oneRefChem:870306DTXCID0013859407-hydroxy-3-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-oneAC1NQZ4N

データベース識別子

CAS
3681-99-0
PubChem CID
5281807
DTXSID
DTXSID30958020
ChEMBL
CHEMBL486386
ChEBI
CHEBI:8633
UNII
Z9W8997416
EC Number
609-296-1
Nikkaji
J16.365A
64198 · 64198
化粧品成分の機能
抗酸化物質
InChIKey
HKEAFJYKMMKDOR-NCHCSYJDSA-N
SMILES
OC1=CC=C2C(C(C3C=CC(O)=CC=3)=COC2=C1[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)=O |&1:18,19,20,22,24,r|
LogP
0.408 · 0.408 (est)
CAS データベース
3681 · 3681-99-0(CAS DataBase Reference)

化学的性質

化学的特性White powder

上流・下流製品情報

上流原料

7-methoxy-3-(4-methoxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one

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補足説明

定義ChEBI: A hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 7 and 4' and a beta-D-glucopyranosyl residue at position 8 via a C-glycosidic linkage.