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글리시레티닉애씨드

Glycyrrhetinic Acid

HCID 10114
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
471-53-4
표준 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
분자식
C30H46O4
평균 분자량
470.7 g/mol
단동위원소 질량
470.33960994

개요

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.

이름 및 식별자

우선 이름
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
현지명
글리시레티닉애씨드
영어명
18β-Glycyrrhetinic Acid
분자식
C30H46O4
분자량
470.68

이름 및 동의어

enoxolone471-53-4Glycyrrhetic acidGLYCYRRHETINIC ACIDUralenic acid18-beta-Glycyrrhetinic acidJintanRhetinic AcidEnoxolonaEnoxolonum3beta-Hydroxy-11-oxoolean-12-en-30-oic acidDTXSID9020669
이름 더 보기
글리시레티닉애씨드18B-GLYCYRRHETINIC ACIDGlycyrrhetinateGlycyrrhetinicbiosone18β-Glycyrrhetic acidglycyrrhetin
(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

데이터베이스 식별자

CAS
471-53-4
PubChem CID
10114
DTXSID
DTXSID9020669
ChEMBL
CHEMBL230006

물성

구조 계산 물성

XLogP
6.4
극성 표면적
74.6 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
4
회전 가능 결합 수
1
무거운 원자 수
34
형식 전하
0
복잡도
965

실험 및 물리화학적 성질

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

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

Skin conditioning

Personal care product -> emollient

Collision Cross Section · 2건

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]

물리화학적 성질

녹는점
292 · 292-295 °C(lit.)
끓는 점
492.11 °C · 492.11°C (rough estimate)
밀도
0.9967 · 0.9967 (rough estimate)
증기압
10 · 10-220Pa at 20-50℃
굴절률
162 ° · 162 ° (C=1, MeOH)
저장 조건
2 · 2-8°C
용해도
물에 거의 녹지 않으며, 에탄올에 녹고, 염화메틸렌에는 거의 녹지 않습니다.
산도 계수 (pKa)
5.56 · pKa 5.56±0.1 (Uncertain)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 3건

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%)

독성 정보

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

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
RK0180000
독성
mouse,LD50,intraperitoneal,308mg/kg (308mg/kg),Drugs in Japan Vol. -, Pg. 319, 1990.
HS 번호
29189900
risk_code
22-36
hazard_code

화학 및 산업

약리 정보

ATC Code · 2건

D - Dermatologicals

QD - Dermatologicals

MeSH Pharmacological ClassificationSubstances that reduce or suppress INFLAMMATION.

용도 및 제조

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
응용 분야 · 4건

개요Extracting 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.

역사Glycyrrhetic 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.

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
ChEBI
CHEBI:30853
UNII
P540XA09DR
EC Number
207-444-6
Nikkaji
J5.943I
물리적 상태
결정성 분말
색상
흰색에서 황백색까지
수용성
아세트산에 용해됨
Merck
14 · 14,3590
BRN
2229654 · 2229654
화장품 원료 기능
피부 컨디셔닝
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℃
EPA
Enoxolone (471-53-4)

화학적 성질

white or greyish-white crystalline powder

Xn
safety_code
22-24/25
기존화학 물질
KE-20783
스토리지 클래스
11 - Combustible Solids

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

일반 설명18β-Glycyrrhetinic acid is a pentacyclic triterpenoid found in the Glycyrrhiza glabra L.(liquorice) roots. It is the key metabolite of glycyrrhizin and glycyrrhizic acid.

상·하류 제품 정보

상류 원료

글리시리진SIS에틸알코올Triammonium glycyrrhizinate수크로스(설탕)DGLEthanol solution18α-글리실리진물염산

하류 제품

스테아릴글리시레티네이트

공급사100 곳

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추가 설명

정의ChEBI: 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.