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18α-Glycyrrhetinic acid

Cat No.:V32823 Purity: ≥98%
18α-Glycyrrhetinic acid, a dietary-derived compound, is an inhibitor (blocker/antagonist) of NF-kB and an activator of the proteasome, and plays a role in promoting longevity and anti-aggregation factors in multicellular organisms.
18α-Glycyrrhetinic acid
18α-Glycyrrhetinic acid Chemical Structure CAS No.: 1449-05-4
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
Other Sizes

Other Forms of 18α-Glycyrrhetinic acid:

  • Enoxolone
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
18α-Glycyrrhetinic acid, a dietary-derived compound, is an inhibitor (blocker/antagonist) of NF-kB and an activator of the proteasome, and plays a role in promoting longevity and anti-aggregation factors in multicellular organisms. 18α-Glycyrrhetinic acid causes apoptosis.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
After 18α-glycyrrhetinic acid (18a-GA) therapy for 48 hours and 72 hours, the number of LX-2 cells was dramatically reduced by 14.8% and 31.2% correspondingly (P<0.05). Compared with the control group, after 48 and 72 hours of 18α-glycyrrhetinic acid administration, the proportion of LX-2 cells in the G0/G1 phase considerably increased, while the percentage of cells in the S phase decreased. 18α-Glycyrrhetinic acid increased cell apoptosis to 6.8% after 48 hours compared to the control group (2.5%), and at 72 hours, the percentage of apoptotic cells in LX-2 cells in the control and treatment groups were respectively 3.1% and 15.6% (P<0.01). In addition, 18α-glycyrrhetinic acid stimulates the expression of PPAR-γ and modifies several cell cycle and apoptosis-related proteins. 18α-Glycyrrhetinic acid also suppresses NF-κB DNA binding activity [1].
ln Vivo
18α-glycyrrhetinic acid (18α-GA) treatment can greatly increase the longevity of nematode strains; 20 μg/mL is the most effective quantity. The outcomes demonstrated a considerable delay in the onset of paralysis symptoms following treatment with 18α-glycyrrhetinic acid. Treatment with 18α-glycyrrhetinic acid can also considerably lower Aβ deposition [2].
References

[1]. 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]. 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.

Additional Infomation
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 cyclic terpene ketone and a hydroxy monocarboxylic acid. It is a conjugate acid of a glycyrrhetinate. It derives from a hydride of an oleanane.
Enoxolone (glycyrrhetic acid) has been investigated for the basic science of Apparent Mineralocorticoid Excess (AME).
Enoxolone has been reported in Glycyrrhiza uralensis, Glycyrrhiza, and other organisms with data available.
Enoxolone is a pentacyclic triterpenoid aglycone metabolite of glycyrrhizin, which is a product of the plant Glycyrrhiza glabra (licorice), with potential expectorant, and gastrokinetic activities. After administration, enoxolone inhibits the metabolism of prostaglandins by both 15-hydroxyprostaglandin dehydrogenase [NAD(+)] and prostaglandin reductase 2. Therefore, this agent potentiates the activity of prostaglandin E2 and F2alpha, which inhibits gastric secretion while stimulating pancreatic secretion and the secretion of intestinal and respiratory mucus, leading to increased intestinal motility and antitussive effects. Additionally, this agent inhibits 11 beta-hydroxysteroid dehydrogenase and other enzymes involved in the conversion of cortisol to cortisone in the kidneys.
An oleanolic acid from GLYCYRRHIZA that has some antiallergic, antibacterial, and antiviral properties. It is used topically for allergic or infectious skin inflammation and orally for its aldosterone effects in electrolyte regulation.
See also: Glycyrrhizin (is active moiety of); Ammonium Glycyrrhizate (is active moiety of); Glycyrrhiza Glabra (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H46O4
Molecular Weight
470.68384
Exact Mass
470.339
CAS #
1449-05-4
Related CAS #
18β-Glycyrrhetinic acid;471-53-4
PubChem CID
10114
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
588.3±50.0 °C at 760 mmHg
Melting Point
331-333°C
Flash Point
323.7±26.6 °C
Vapour Pressure
0.0±3.7 mmHg at 25°C
Index of Refraction
1.563
LogP
6.57
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
34
Complexity
965
Defined Atom Stereocenter Count
9
SMILES
C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)(C)C(=O)O
InChi Key
MPDGHEJMBKOTSU-YKLVYJNSSA-N
InChi Code
InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
Chemical Name
(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
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~11.36 mg/mL (~24.14 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 1.14 mg/mL (2.42 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 11.4 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1.14 mg/mL (2.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 11.4 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1246 mL 10.6229 mL 21.2459 mL
5 mM 0.4249 mL 2.1246 mL 4.2492 mL
10 mM 0.2125 mL 1.0623 mL 2.1246 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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