CAS 1449-05-4|Glycyrrhetinic acid

Introduction：Basic information about CAS 1449-05-4|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. Synonyms

Common Name	Glycyrrhetinic acid
CAS Number	1449-05-4	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	331-333°C
MSDS	/	Flash Point	323.7±26.6 °C

Names

Name	glycyrrhetinate
Synonym	More Synonyms

Glycyrrhetinic acid BiologicalActivity

Description	18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2].
Related Catalog	Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>Inflammation/ImmunologySignaling Pathways >>Metabolic Enzyme/Protease >>ProteasomeResearch Areas >>Neurological Disease
Target	NF-κB Proteasome
In Vitro	18α-Glycyrrhetinic acid (18a-GA) markedly reduces LX-2 cell numbers by 14.8% and 31.2% after 48 h and 72 h of treatment, respectively (P< 0.05). 18α-Glycyrrhetinic acid also significantly increases the percentage of LX-2 cells in phase G0/G1 and decreases it in phase S after treated for 48 h and 72 h compare with the control group. 18α-Glycyrrhetinic acid increases apoptosis to 6.8% at 48 h, compare with control (2.5%), and at 72 h the percentages of apoptotic cells in control and the treatment groups are 3.1% and 15.6%, respectively, in LX-2 cells (P<0.01). Furthermore, 18α-Glycyrrhetinic acid induces expression of PPAR-γ and alters some cell cycle and apoptosis-related proteins. 18α-Glycyrrhetinic acid also inhibits NF-κB DNA-binding activity[1].
In Vivo	18α-Glycyrrhetinic acid (18α-GA) treatment significantly enhances life span of C. elegans strains with the most effective concentration being 20 μg/mL. Results reveal a significant delay of paralysis upon 18α-Glycyrrhetinic acid treatment. 18α-Glycyrrhetinic acid treatment also confers a significant reduction of Aβ deposits[2].
Cell Assay	For the determination of cell cycle, 5×105 cells per well are seeded onto 6-well plates and incubated overnight in complete growth medium (DMEM+10% FBS). After starvation for 24 h, the cells are subsequently stimulated with 10% FBS with or without the presence of 18α-Glycyrrhetinic acid (18a-GA). The final concentration of 18α-Glycyrrhetinic acid is 8.0 mM. The cells are incubated for 24 h, 48 h and 72 h, respectively, and then the flow cytometric analysis is performed. Flow cytometric analysis is performed in triplicate. After being treated with 18α-Glycyrrhetinic acid, the cells are stained and then cell apoptosis status is measured by flow cytometry[1].
Animal Admin	C. elegans strains are used in this study. Synchronized L4 larvae CL2006 animals (100 to 120 animals per condition) are transferred to nematode growth medium (NGM) plates containing either 18α-Glycyrrhetinic acid (18α-GA) or DMSO at 20°C. Synchronized CL4176 animals (150 to 300 animals per condition) are transferred to NGM plates containing either 18α-Glycyrrhetinic acid or DMSO at 16°C for 48 h before temperature upshift to 25°C for transgene induction. Scoring of paralyzed animals is initiated at day 1 of adulthood for CL2006 strain and 24 h after temperature upshift for CL4176 strain. Each paralysis assay is repeated at least thrice. Nematodes are scored as paralyzed if they exhibit halos of cleared bacteria around their heads or fail to undergo half end body wave propagation upon prodding[2].
References	[1]. Zong L et al. 18α-glycyrrhetinic acid extracted from Glycyrrhiza radix inhibits proliferation and promotes apoptosis of the hepatic stellate cell line. J Dig Dis. 2013 Jun;14(6):328-36. [2]. Papaevgeniou N, et al. 18α-Glycyrrhetinic Acid Proteasome Activator Decelerates Aging and Alzheimer's Disease Progression in Caenorhabditis elegans and Neuronal Cultures. Antioxid Redox Signal. 2016 Dec 1;25(16):855-869.

Chemical & Physical Properties

Density	1.1±0.1 g/cm3
Boiling Point	588.3±50.0 °C at 760 mmHg
Melting Point	331-333°C
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-MNEJCTLJSA-N
SMILES	CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2C1
Storage condition	2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RK0190000

CHEMICAL NAME :: 18-alpha-Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-

CAS REGISTRY NUMBER :: 1449-05-4

LAST UPDATED :: 199612

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 -BETA

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 560 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Gastrointestinal - other changes

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 28,3449,1980

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 455 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Gastrointestinal - other changes

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 28,3449,1980

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 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#02068

Safety Information

Hazard Codes	Xn: Harmful;
Risk Phrases	R22
Safety Phrases	S22-S23-S36/37/39
WGK Germany	3
RTECS	RK0190000
HS Code	2938909030

Customs

HS Code	2915900090
Summary	2915900090 other saturated acyclic monocarboxylic acids and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:5.5% General tariff:30.0%

Synonyms

18a-Glycyrrhetic acid

(3β,18α)-3-Hydroxy-11-oxoolean-12-en-29-oic acid

18a-Glycyrrhetinic acid

MFCD00064897

Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,18α)-

Glycyrrhetinic acid

EINECS 215-907-9

Recommended......