글리시레티닉애씨드

글리시레티닉애씨드
글리시레티닉애씨드 구조식 이미지
카스 번호:
471-53-4
한글명:
글리시레티닉애씨드
동의어(한글):
글리시레티닉애씨드
상품명:
18β-Glycyrrhetinic Acid
동의어(영문):
GLYCYRRHETINIC ACID;ENOXOLONE;GLYCYRRHETIC ACID;Glycyrrhetinic;Glycyrrhetinate;biosone;URALENIC ACID;18β-Glycyrrhetic acid;18B-GLYCYRRHETINIC ACID;(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
CBNumber:
CB8474793
분자식:
C30H46O4
포뮬러 무게:
470.69
MOL 파일:
471-53-4.mol
MSDS 파일:
SDS

글리시레티닉애씨드 속성

녹는점
292-295 °C(lit.)
알파
165 º (c=1, CHCl3,on dry ba)
끓는 점
492.11°C (rough estimate)
밀도
0.9967 (rough estimate)
증기압
10-220Pa at 20-50℃
굴절률
162 ° (C=1, MeOH)
저장 조건
2-8°C
용해도
물에 거의 녹지 않으며, 에탄올에 녹고, 염화메틸렌에는 거의 녹지 않습니다.
산도 계수 (pKa)
pKa 5.56±0.1 (Uncertain)
물리적 상태
결정성 분말
색상
흰색에서 황백색까지
optical activity
[α]22/D +170.0°, c = 1 in chloroform
수용성
아세트산에 용해됨
Merck
14,3590
BRN
2229654
LogP
4.5 at 20℃
CAS 데이터베이스
471-53-4(CAS DataBase Reference)
EPA
Enoxolone (471-53-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn
위험 카페고리 넘버 22-36
안전지침서 22-24/25
WGK 독일 3
RTECS 번호 RK0180000
HS 번호 29189900
독성 mouse,LD50,intraperitoneal,308mg/kg (308mg/kg),Drugs in Japan Vol. -, Pg. 319, 1990.
기존화학 물질 KE-20783
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 GHS hazard pictograms P264, P270, P301+P312, P330, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
예방조치문구:
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P301+P312 삼켜서 불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P330 입을 씻어내시오.
P501 ...에 내용물 / 용기를 폐기 하시오.
NFPA 704
0
1 0

글리시레티닉애씨드 MSDS


18-beta-Glycyrrhetinic acid

글리시레티닉애씨드 C화학적 특성, 용도, 생산

개요

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.

화학적 성질

white or greyish-white crystalline powder

물리적 성질

Solubility: insoluble in water; it exists in crystal with methanol and chloroform. Melting point: the compound melts at 292–295?°C. Specific optical rotation: under the condition of 20?°C, 589.3?nm, and 1?dm, polarized light rotates at 68° when it passes through the chloroform with a concentration of 64? mol/L.? Both 18α-glycyrrhetic acid and 18β-glycyrrhetic acid are chiral isomers of glycyrrhetic acid.

역사

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.

용도

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

Indications

Treatment of Addison’s disease, deoxycorticosterone

정의

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.

일반 설명

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.

Pharmacology

Thirty percent of glycyrrhetinic acid can be effectively used by the body; both 18α-glycyrrhetic acid and 18β-glycyrrhetic acid reduce by half in 2.24 h and 11.5 h separately. CYP3A promotes metabolism with hydroxyl added to 22α and 24α .There are lots of pharmacological activities : it plays an anti-inflammatory role by inhibiting the activity of phospholipase A2 and lipoxygenase to reduce mediators of inflammation; the compound promotes antiulcer activity through the production of more PGE2 and secretion of gastric mucus; it also provokes proliferation of gastric cell to protect the mucosa from ulceration. The complex which consists of glycyrrhetinic acid and carotenoid plays antioxidation by scavenging free radical. Glycyrrhetinic acid inhibits the replication of viral DNA to achieve an antiviral effect at the concentration of 4×10?5 mol/L; it also inhibits proliferation of tumor cell and promotes apoptosis and differentiation. The decreasing ability of invasion exerts an antitumor effect. Glycyrrhetinic acid is considered to have extensive antiarrhythmic effects through inhibition of L-type calcium channel. In addition, glycyrrhetinic acid functions as an anticholinesterase (1.7×10?5 mol/L), anticoagulant, and antitetanus toxin; it also improves inner ear hearing (100 mg/kg, intramuscular injection) and improves absorption of insulin.

Clinical Use

Glycyrrhetic acid has not been applied in clinical treatment till now. Meanwhile, the ramification has come into the market for the property of antiulcer. However, with large doses and long-term usage, the drug gives rise to hypertension, sodium retention, and hypokalemia. When renin-angiotensin-aldosterone system fails to function properly, liquorice-induced pseudoaldosteronism threatens human health .

Anticancer Research

Glycyrrhetinic acid in combinationwith etoposide inhibits thetopoisomerase 2α and inducesapoptosis
Cai et al.(2017)

글리시레티닉애씨드 준비 용품 및 원자재

원자재

준비 용품


글리시레티닉애씨드 공급 업체

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