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ベルゲニン

Bergenin

HCID 66065
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
477-90-7
標準SMILES
COc1c(O)cc2c(c1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC2=O
InChIKey
YWJXCIXBAKGUKZ-HJJNZUOJSA-N
分子式
C14H16O9
平均分子量
328.27 g/mol
単同位体質量
328.07943208

概要

Bergenin is a natural product found in Cenostigma gardnerianum. It has a role as a metabolite.

名称と識別子

優先名称
Bergenin
IUPAC
(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
現地名
ベルゲニン
英語名
Bengenin
分子式
C14H16O9
分子量
328.27

名称と別名

bergenin477-90-7YanbaicaisuBergeninumL84RBE4IDCNSC-661749NSC-757796(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-oneDTXSID40481414-Methoxy-2-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)pyran-2-yl)alpha-resorcylic acid gamma lactone(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano(3,2-c)isochromen-6-one(-)-Bergenin
名称をさらに表示
ベルゲニンベルゲニン (JAN)2α-(ヒドロキシメチル)-3β,4α,8,10-テトラヒドロキシ-9-メトキシ-2,3,4,4aα,6,10bβ-ヘキサヒドロピラノ[3,2-c][2]ベンゾピラン-6-オン(2S,4R,5S,6S,7R)-5,6,12,14-テトラヒドロキシ-4-(ヒドロキシメチル)-13-メトキシ-3,8-ジオキサトリシクロ[8.4.0.02,7]テトラデカ-1(14),10,12-トリエン-9-オン(+)-ベルゲニン1β,2-O-(4,6-ジヒドロキシ-5-メトキシ-1,2-フェニレンカルボニル)-1-デオキシ-β-D-グルコピラノース(2R)-3,4,4aα,10bβ-テトラヒドロ-3β,4α,8,10-テトラヒドロキシ-2α-(ヒドロキシメチル)-9-メトキシピラノ[3,2-c][2]ベンゾピラン-6(2H)-オンVakerinEngeninGoldate

物性

構造計算による物性

XLogP
-1
極性表面積
146 Ų
水素結合供与体数
5
水素結合受容体数
9
回転可能結合数
2
重原子数
23
形式電荷
0
複雑度
458

実験および物理化学的性質

Collision Cross Section · 2 件

163.07 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

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

物理化学的性質

融点
237 · 237-240 °C(lit.)
比旋光度
18 · D18 -37.7° (c = 1.96 in ethanol); D24 -45.3° (c = 0.51 for anhydr in water)
沸点
386.03 °C · 386.03°C (rough estimate)
比重(密度)
1.3901 · 1.3901 (rough estimate)
屈折率
1.655 · 1.6550 (estimate)
貯蔵温度
-20 °C · -20°C
溶解性
DMSO(微量)、メタノール(微量)
外見
Solid
酸解離定数(Pka)
8.26 · 8.26±0.70(Predicted)
色
ホワイトからオフホワイト
主な用途
メタボロミクスビタミン、栄養補助食品、天然製品
化粧品成分の機能
スキンコンディショニング
InChI
1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1

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 · 4 件

Warning

H315 (100%): 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 39 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 (100%)

安全データ

wgk
3
rtecs
UQ0337200
hs_code
29329990
risk_code
36/37/38-20/21/22
hazard_code
Xi,Xn
safety_code
26-36
ストレージクラス
11 - Combustible Solids

化学と産業

応用分野 · 4 件

説明The plant resources of bergenin are rich, mainly from Rock cabbage (Bergenia purpurascens) and thick leafy rock cabbage (Astilbe macroflora) from Saxifragaceae and the roots, stems, and leaves of bai liang jin (Ardisia crispa) from Ardisia japonica (Thunb.) Blume. In Chinese medicine Rock cabbage (Bergenia purpurascens) is the common folk medicine, with nourishing, stanching bleeding, relieving a cough, and other effects. Its earliest record is contained in the classified herbal in Qing Dynasty .There are ten kinds of Rock cabbage (Bergenia purpurascens) in Asia, mainly growing in East Asia, north of South Asia, and southeastern Central Asia. There are seven species (including three endemic species) in China, mainly distributed in Shaanxi (Qinling), Xinjiang, Sichuan, Yunnan, and Tibet .

来歴In 1958, Hay and Haynes first reported the complete synthesis of bergenin, using 4-methoxy gallate and A-D-bromo-2, 3, 4, 6-tetraacetylglucose as raw materials to synthesize bergenin successfully .In 1987, Chen Wendou determined the content of bergenin as 5.8% in the alcohol extract of Astilbe chinensis (Maxim.), Franch. et Savat.(Luoxinfu), and Rock cabbage (Bergenia purpurascens) by using high-performance liquid chromatography. In 1991, Wang Junping determined the content of bergenin in the alcohol extract of Rodgersia podophylla as 19.17% with spectrophotometry.By doing thin layer qualitative analysis, Liu Nunian discovered that bergenin could be found in seven kinds of plants including sour moss (Ardisia solanacea), Luosan tree (Ardisia quinquegona Bl.), Cinnabar root (Ardisia crenata Sims), Zijinniu (Ardisia japonica), Lianzuozijinniu (Ardisia primulaefolia), Jiujielong (Ardisia pusilla), and Xinyezijinniu (Ardisia maclurei) from Ardisia. In addition, Zhang Yi determined the content of bergenin in the medicinal plants from Ardisiawith high-performance liquid chromatography, and results showed that there were four species of plants with the content of bergenin of more than 1%, having great resource utilization value. There are 11 species of plants with the content of bergenin less than 1%, such as Xiaoqiaomuzijinniu (Ardisia arborescens), twist fruit, fine umbrella (Ardisia affinis Hemsl.), and so on. They had some useful value as well .In recent years, it has been found that both 8, 10-dimethylca bergenin and 11-0-gallate betaine had weak inhibitory effects on the tumor in mice, and their effects were stronger than that of bergenin. The effect of acetylated bergenin was stronger than that of bergenin on liver injury induced by chloroform in mice. The new bergenin derivatives from the Ardisia gigantifolia stapf had a certain degree of free radical-scavenging effect and anti-HIV viral activity .

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
Bergenit
Ai Cha Su
NSC 661749
Bergenitol
RefChem:567029GlyTouCan:G67862GTDTXCID0028113G67862GT803-760-9BengeninCuscutinMFCD00133120

データベース識別子

CAS
477-90-7
PubChem CID
66065
DTXSID
DTXSID4048141
ChEMBL
CHEMBL273019
ChEBI
CHEBI:69499
UNII
L84RBE4IDC
EC Number
803-760-9
Nikkaji
J475.124H
InChIKey
YWJXCIXBAKGUKZ-HJJNZUOJSA-N
SMILES
O1[C@@H]2[C@H](OC(=O)c3c2c(c(c(c3)O)OC)O)[C@H]([C@@H]([C@H]1CO)O)O
LogP
-1.398 · -1.398 (est)
CAS データベース
477 · 477-90-7(CAS DataBase Reference)

化学的性質

化学的特性White powder

使用A herbal remedy with antioxidant, antimicrobial and antiinflammatory properties.

一般的な説明This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

上流・下流製品情報

上流原料

Ethanol solution

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補足説明

定義ChEBI: A natural product found in Cenostigma gardnerianum.