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471-53-4

471-53-4 structure
471-53-4 structure
  • Name: Glycyrrhetinic acid
  • Chemical Name: Enoxolone
  • CAS Number: 471-53-4
  • Molecular Formula: C30H46O4
  • Molecular Weight: 470.684
  • Catalog: Food additive Sweetener
  • Create Date: 2018-04-02 08:00:00
  • Modify Date: 2024-01-02 13:26:30
  • 18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhizae Radix and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties.
Name Enoxolone
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
Description 18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhizae Radix and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties.
Related Catalog
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.
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

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
Symbol GHS07
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
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%

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