Glycyrrhetinic acid

Modify Date: 2024-01-03 16:33:14

Glycyrrhetinic acid Structure
Glycyrrhetinic acid structure
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 N/A Flash Point 323.7±26.6 °C

 Use of Glycyrrhetinic acid


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].

 Names

Name glycyrrhetinate
Synonym More Synonyms

 Glycyrrhetinic acid Biological Activity

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
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
Storage condition 2-8℃

 MSDS


Section1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: 18α-Glycyrrhetinic acid
Product name
CAS-No.: 1449-05-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses: Laboratory chemicals, Manufacture of substances



Section2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal wordWarning
Hazard statement(s)
H302Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazardnone
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22Harmful if swallowed.
S-phrase(s)none
Other hazards - none

Section3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: 3β-Hydroxy-11-oxo-18α,20β-olean-12-en-29-oic acid
Synonyms
Formula: C30H46O4
Molecular Weight: 470,68 g/mol
ComponentConcentration
(3β,18α,20β)-3-Hydroxy-11-oxoolean-12-en-29-oic acid
CAS-No.1449-05-4-
EC-No.215-907-9

Section4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
Overexposure can cause sodium retention and potassium loss leading to hypertension, water retention,
and electrolyte imbalance.
Indication of any immediate medical attention and special treatment needed
no data available

Section5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

Section6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

Section7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

Section8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

Section9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) AppearanceForm: solid
b) Odourno data available
c) Odour Thresholdno data available
d) pHno data available
e) Melting point/freezingno data available
point
f) Initial boiling point and no data available
boiling range
g) Flash pointno data available
h) Evaporation rateno data available
i) Flammability (solid, gas) no data available
j) Upper/lowerno data available
flammability or
explosive limits
k) Vapour pressureno data available
l) Vapour densityno data available
m) Relative densityno data available
n) Water solubilityno data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignitionno data available
temperature
q) Decompositionno data available
temperature
r) Viscosityno data available
s) Explosive propertiesno data available
t) Oxidizing propertiesno data available
Other safety information
no data available

Section10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents, Strong bases
Hazardous decomposition products
Other decomposition products - no data available

Section11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Oral - mouse - 560 mg/kg
Remarks: Behavioral:Change in motor activity (specific assay). Gastrointestinal:Other changes.
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC:No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
InhalationMay be harmful if inhaled. May cause respiratory tract irritation.
IngestionHarmful if swallowed.
Skin
May be harmful if absorbed through skin. May cause skin irritation.
EyesMay cause eye irritation.
Signs and Symptoms of Exposure
Overexposure can cause sodium retention and potassium loss leading to hypertension, water retention,
and electrolyte imbalance.
Additional Information
RTECS: RK0190000

Section12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

Section13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

Section14. TRANSPORT INFORMATION
UN number
ADR/RID: -IMDG: -IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA:Not dangerous goods
Transport hazard class(es)
ADR/RID: -IMDG: -IATA: -
Packaging group
ADR/RID: -IMDG: -IATA: -
Environmental hazards
ADR/RID: noIMDG Marine pollutant: noIATA: no
Special precautions for user
no data available

Section15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

Section16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

 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

 Synthetic Route

~46%

Glycyrrhetinic acid Structure

Glycyrrhetinic acid

CAS#:1449-05-4

Literature: Ullah, Nisar; Seebacher, Werner; Haslinger, Ernst; Jurenitsch, Johann; Rauchensteiner, Katharina; Weis, Robert Monatshefte fur Chemie, 2002 , vol. 133, # 2 p. 139 - 150

~85%

Glycyrrhetinic acid Structure

Glycyrrhetinic acid

CAS#:1449-05-4

Literature: Ignatov; Prokof'ev; Ipatova; Timofeev; Medvedeva; Misharin Russian Journal of Bioorganic Chemistry, 2003 , vol. 29, # 4 p. 390 - 394

 Precursor & DownStream

Precursor  1

DownStream  0

 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
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