CAS 471-53-4|Glycyrrhetinic acid

Introduction：Basic information about CAS 471-53-4|Glycyrrhetinic acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Glycyrrhetinic acid BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles4
8. Synonyms

Common Name	Glycyrrhetinic acid
CAS Number	471-53-4	Molecular Weight	470.684
Density	1.1±0.1 g/cm3	Boiling Point	588.3±50.0 °C at 760 mmHg
Molecular Formula	C₃₀H₄₆O₄	Melting Point	292 - 295ºC
MSDS	/	Flash Point	323.7±26.6 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	Enoxolone
Synonym	More Synonyms

Glycyrrhetinic acid BiologicalActivity

Description	18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhizae Radix and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties.
Related Catalog	Research Areas >>CancerResearch Areas >>Inflammation/ImmunologyNatural Products >>Terpenoids and Glycosides
Target	Human Endogenous Metabolite
In Vitro	18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhizae Radix and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties. MTS assay demonstrates that 24 h treatment of 18β-Glycyrrhetinic acid suppresses cell proliferation in both cell lines in a dose-dependent manner. 18β-Glycyrrhetinic acid at 160 μM significantly decreases the percentage of viable cells to around 40.5±10.5% in A549 and 38.3±4.6% in NCI-H460 (p<0.01 respectively). When the cells are treated with 320 μM 18β-Glycyrrhetinic acid, a greater inhibitory effects on cell proliferation is shown, as the percentage of viable cells is below 30% compare with untreated controls (p<0.001). Treatment with 18β-Glycyrrhetinic acid at 160 μM and 320 μM decreases the levels of full-length PARP and increases the levels of cleaved-PARP[1].
In Vivo	Rats in 18β-Glycyrrhetinic acid+Triptolide (TP) group which receive low-dose 18β-Glycyrrhetinic acid (50 mg/kg) have significant reductions in the three serum parameters when compare with TP rats. Rats in 18β-Glycyrrhetinic acid+TP group which receive the high-dose 18β-Glycyrrhetinic acid (100 mg/kg) have slightly lowered the levels of three liver enzymes, the reductions do not reach statistical significance compare with TP group. Contrastingly, preadministration of low-dose 18β-Glycyrrhetinic acid protects animals from TP-induced hepatic lesions. On the contrary, low-dose 18β-Glycyrrhetinic acid (50 mg/kg) markedly suppresses the release of the four cytokines above[3].
Cell Assay	Primary microglia cultures are used in this study. For treatment assay, microglia are incubated with complete DMEM and stimulated with or without 100 ng/mL IFN-γ in the presence or absence of 18β-Glycyrrhetinic acid (25 μM and 50 μM) at 37°C in a humidified incubator with 5% CO2. For cell migration assay, the isolated primary microglia that seeded in complete DMEM medium are stimulated with or without IFN-γ (100 ng/mL), and treated with different doses of 18β-Glycyrrhetinic acid, 24 h later, the microglia culture supernatants are collected and added to the lower chambers of Transwell inserts[2].
Animal Admin	Healthy Wistar rats (male, 200±20 g) are used and divided into five groups with 10 individuals for each group randomly. Animals in normal control (NC) group receive distilled water for 6 days and 0.5% CMC-Na for the last 3 days. Rats in Triptolide model group (TP), 18β-Glycyrrhetinic acid low-dose group (GAL+TP), and 18β-Glycyrrhetinic acid high-dose group (GAH+TP) receive distilled water, 18β-Glycyrrhetinic acid (50 mg/kg, p.o., dissolved in distilled water), or 18β-Glycyrrhetinic acid (100 mg/kg, p.o., dissolved in distilled water) for consecutive 6 days, respectively, and liver injury is induced by TP (2.4 mg/kg, p.o., suspended in 0.5% CMC-Na) for the last 3 days. Animals in the above three groups receive TP 6 hours after distilled water or 18β-Glycyrrhetinic acid treatment on the last 3 days[3].
References	[1]. Huang RY, et al. 18β-Glycyrrhetinic acid suppresses cell proliferation through inhibiting thromboxane synthase in non-small cell lung cancer. PLoS One. 2014 Apr 2;9(4):e93690. [2]. Zhou J, et al. 18β-glycyrrhetinic acid suppresses experimental autoimmune encephalomyelitis through inhibition of microglia activation and promotion of remyelination. Sci Rep. 2015 Sep 2;5:13713. [3]. Yang G, et al. Protective Effect of 18β-Glycyrrhetinic Acid against Triptolide-Induced Hepatotoxicity in Rats. Evid Based Complement Alternat Med. 2017;2017:3470320.

Chemical & Physical Properties

Density	1.1±0.1 g/cm3
Boiling Point	588.3±50.0 °C at 760 mmHg
Melting Point	292 - 295ºC
Molecular Formula	C₃₀H₄₆O₄
Molecular Weight	470.684
Flash Point	323.7±26.6 °C
Exact Mass	470.339600
PSA	74.60000
LogP	6.57
Vapour Pressure	0.0±3.7 mmHg at 25°C
Index of Refraction	1.563
InChIKey	MPDGHEJMBKOTSU-YKLVYJNSSA-N
SMILES	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2C1

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RK0180000

CHEMICAL NAME :: Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-

CAS REGISTRY NUMBER :: 471-53-4

BEILSTEIN REFERENCE NO. :: 2229654

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C30-H46-O4

MOLECULAR WEIGHT :: 470.76

WISWESSER LINE NOTATION :: L F6 E6 B666 CV DUTJ A1 HVQ H1 K1 N1 O1 S1 S1 TQ -ALPHA

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 308 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,319,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#02067

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302-H319
Precautionary Statements	P301 + P312 + P330-P305 + P351 + P338
Hazard Codes	Xn: Harmful;
Risk Phrases	R22;R36
Safety Phrases	22-24/25
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	RK0180000
HS Code	2938909030

Customs

HS Code	2918990090
Summary	2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles4

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Prevention of cisplatin-induced ototoxicity by the inhibition of gap junctional intercellular communication in auditory cells. Kim YJ, Kim J, Tian C, et al.

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Synonyms

MFCD00003706

(3β)-3-Hydroxy-11-oxoolean-12-en-30-oic acid

Glycyrrhetinic acid

(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-Hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-2-picenecarboxylic acid

18-beta-Glycyrrhetinic acid

Arthrodont

EINECS 207-444-6

18-β-Glycyrrhetinic Acid

glycyrrhetin

GM 1658

Uralenic acid

3β-Hydroxy-11-oxoolean-12-en-30-oic acid

18b-Glycyrrhetic acid

Biosone

Olean-12-en-30-oic acid, 3β-hydroxy-11-oxo-

18β-Glycyrrhetinic acid

STX 352

Glycyrrhetic Acid

PO 12

Olean-12-en-30-oic acid, 3-hydroxy-11-oxo-, (3β)-

3b-Hydroxy-11-oxoolean-12-en-30-oic Acid

18b-Glycyrrhetinic Acid

Glycyrrhetinate

(3b,20b)-3-Hydroxy-11-oxoolean-12-en-29-oic Acid

ENOLOXONE

enoxolone

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