ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
化工社オープンプロジェクト:[email protected]AIアクセス:llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
  1. ホーム
  2. /化合物

グリチルレチン酸

Glycyrrhetinic Acid

HCID 10114
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
471-53-4
標準SMILES
CC1(C)[C@@H](O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12
InChIKey
MPDGHEJMBKOTSU-YKLVYJNSSA-N
分子式
C30H46O4
平均分子量
470.7 g/mol
単同位体質量
470.33960994

概要

Glycyrrhetinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30. It has a role as an immunomodulator and a plant metabolite. It is a pentacyclic triterpenoid, a hydroxy monocarboxylic acid and a cyclic terpene ketone. It is a conjugate acid of a glycyrrhetinate. It derives from a hydride of an oleanane.

名称と識別子

優先名称
Glycyrrhetinic Acid
IUPAC
(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
現地名
グリチルレチン酸
英語名
18β-Glycyrrhetinic Acid
分子式
C30H46O4
分子量
470.68

名称と別名

enoxolone471-53-4Glycyrrhetic acidGLYCYRRHETINIC ACIDUralenic acid18-beta-Glycyrrhetinic acidJintanRhetinic AcidEnoxolonaEnoxolonum3beta-Hydroxy-11-oxoolean-12-en-30-oic acidDTXSID9020669
名称をさらに表示
グリチルレチン酸ハイデルマートβ-グリチルレチン酸(20S)-3β-ヒドロキシ-11-オキソ-5α-オレアナ-12-エン-29-酸18β-グリチルレチン酸デルマクリンA(18β)-3β-ヒドロキシ-11-オキソオレアナ-12-エン-30-酸ビオソングリシルレチンウラレン酸デルマクリンエノキソロングリシルレチン酸3β-ヒドロキシ-11-オキソオレアナ-12-エン-30-酸18β-グリシルレチン酸18Β‐グリチルレチン酸18-Β-グリチルレチン酸18Β-グリチルレチン酸, 99+%(HPLC)18B-グリシルレチン酸グリチルレチン酸, 18BETA-18B-GLYCYRRHETINIC ACIDGlycyrrhetinateGlycyrrhetinicbiosone

物性

構造計算による物性

XLogP
6.4
極性表面積
74.6 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
1
重原子数
34
形式電荷
0
複雑度
965

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Cosmetics · 3 件

Cosmetic ingredients (Glycyrrhetinic Acid) -> CIR (Cosmetic Ingredient Review)

Skin conditioning

Personal care product -> emollient

Collision Cross Section · 2 件

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

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

物理化学的性質

融点
292 · 292-295 °C(lit.)
比旋光度
165 · 165 º (c=1, CHCl3,on dry ba)
沸点
492.11 °C · 492.11°C (rough estimate)
比重(密度)
0.9967 · 0.9967 (rough estimate)
蒸気圧
10 · 10-220Pa at 20-50℃
屈折率
162 ° · 162 ° (C=1, MeOH)
貯蔵温度
2 · 2-8°C
溶解性
水にほとんど溶けず、エタノールに溶け、塩化メチレンにやや溶けにくい。

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 35.6% (26 of 73) of reports.

Warning

H302 (64.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 73 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

Regulatory Information · 3 件

Chemical: Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-

REACH registered substance: Enoxolone (EC: 207-444-6)

Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (64.4%)

毒性情報

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

安全データ

wgk
3
tsca
TSCA listed
rtecs
RK0180000
毒性
mouse,LD50,intraperitoneal,308mg/kg (308mg/kg),Drugs in Japan Vol. -, Pg. 319, 1990.
hs_code
29189900
risk_code
22-36
化審法

化学と産業

薬理情報

ATC Code · 2 件

D - Dermatologicals

QD - Dermatologicals

MeSH Pharmacological ClassificationSubstances that reduce or suppress INFLAMMATION.

用途と製造

UsesCIR ingredient: Glycyrrhetinic Acid
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationOlean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-: ACTIVE
応用分野 · 5 件

用途食品中のグリチルリチン酸定量用標準品。

説明Extracting from liquorice (Glycyrrhiza uralensis Fisch, Gan Cao), glycyrrhetic acid also can be detected in other plants, such as Abrus cantoniensis Hance and Herba Abri fruticulosi. As one of traditional Chinese medicines, liquorice has been applied clinically for a long period. Due to its extensive usage, it plays an extremely important role in traditional Chinese medicine formula mainly as “guide” drug. As is recorded in Shen Nong’s Herbal Classic and later in pharmaceutical monographs, liquorice is able to strengthen bones and muscles and enhance metabolism and detoxification. Also, abnormal symptoms of the body and wound can be improved. Glycyrrhetic acid, the most important and potent ingredient of liquorice, has been recorded in Pharmacopoeia of the People’s Republic of China.

来歴Glycyrrhetic acid originates from hydrolysis of glycyrrhizin, which has a therapeutic effect on disease. Dating back to the 1930s, the chemical structure of glycyrrhetic acid was demonstrated . Subsequently, the discovery of antiulcer activity promotes following research . The ramification of glycyrrhetic acid, carbenoxolone sodium, has a therapeutic effect on ulcer. In 2010, followed by the approval of raw materials, batches of tablets and capsules were approved in 2009, respectively. In foreign countries, 18β-glycyrrhetic acid was studied for anti-inflammatory effect on arthritis, rheumatoid disease, and periodontitis in BioNetWorks. The company applied for the patent of 18β-glycyrrhetic acid in 1999. Also, after joining the leading worldwide market in 2006, phase III clinical trials would be carried out in 2007. However, the progress was hindered in 2008. To detecting more indications, its carbenoxolone sodium was studied by other three companies: after conducting phase III clinical trials in the UK, the project of RB intending to improve nonspecific inflammatory bowel disease was given up in 1992. York Pharma expected to make progress in psoriasis with gel or cream; however, the project has been in a standstill after phase II clinical trials was conducted from 2005 to 2009. Canada pharmaceutical company, Oxalys Pharmaceuticals, research it for treating Huntington’s disease, and it was included in the orphan drug list by the USA in 2014. Till now, phase I clinical trials are still continuing.

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

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
18β-Glycyrrhetic acid
glycyrrhetin
(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acidNSC-353473-beta-Hydroxy-11-oxoolean-12-en-30-oic acidP540XA09DROlean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3beta,20beta)-DTXCID50669CHEBI:30853Glyciram

データベース識別子

CAS
471-53-4
PubChem CID
10114
DTXSID
DTXSID9020669
ChEMBL
CHEMBL230006
ChEBI
CHEBI:30853
UNII
P540XA09DR
EC Number
207-444-6
Nikkaji
J5.943I
酸解離定数(Pka)
5.56 · pKa 5.56±0.1 (Uncertain)
外見
結晶性粉末
色
ホワイトからオフホワイト
水溶解度
酢酸に可溶
Merck
14 · 14,3590
BRN
2229654 · 2229654
化粧品成分の機能
スキンコンディショニング
InChIKey
MPDGHEJMBKOTSU-YKLVYJNSSA-N
SMILES
CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]3(C)[C@@H]2C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(O)=O
LogP
4.5 at · 4.5 at 20℃
CAS データベース
471 · 471-53-4(CAS DataBase Reference)
EPAの化学物質情報
Enoxolone (471-53-4)

化学的性質

化学的特性white or greyish-white crystalline powder

(8)-507, (9)-399
hazard_code
Xn
safety_code
22-24/25
ストレージクラス
11 - Combustible Solids

使用The product may be used as a starting material to prepare 18β-glycyrrhetinic acid derivatives, which show anti-inflammatory and antioxidant properties.

一般的な説明18β-Glycyrrhetinic acid is a pentacyclic triterpenoid found in the Glycyrrhiza glabra L.(liquorice) roots. It is the key metabolite of glycyrrhizin and glycyrrhizic acid.

上流・下流製品情報

上流原料

グリチルリチンSISエタノールTriammonium glycyrrhizinateD-(+)-サッカロースDGLEthanol solution[(18α)-20β-カルボキシ-11-オキソ-30-ノルオレアナ-12-エン-3β-イル]2-O-β-D-グルコピラヌロノシル-α-D-グルコピラノシドウロン酸水和物塩酸

下流製品

(20S)-3β-ヒドロキシ-11-オキソ-5α-オレアナ-12-エン-29-酸オクタデシル

サプライヤー100 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Shaanxi Huike Botanical Development Co., Ltd+86-29-62663046 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
右玉县安德益源生物科技有限公司03498026555; 15110806857 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
成都健腾生物技术有限公司86-28-85159085 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
陕西帕尼尔生物科技有限公司13720616393;029-84385017-8003 13720616393 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
湖南华腾制药有限公司400-8592883 15367835770 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
上海洽凡生化科技有限公司+86-021-61654350 · [email protected]

補足説明

定義本品は、グリチルリチン酸(*)から得られる物質であり、次の化学式で表される。参照表示名称:グリチルリチン酸

定義ChEBI: A pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30.