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Geniposidic acid

Alias: Geniposidic acid
Cat No.:V2363 Purity: ≥98%
Geniposidic acid is an iridoid glucoside, used to treat inflammation, jaundice and hepatic disorders.
Geniposidic acid
Geniposidic acid Chemical Structure CAS No.: 27741-01-1
Product category: Apoptosis
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Geniposidic acid is an iridoid glucoside, used to treat inflammation, jaundice and hepatic disorders. When given in doses of 500 mg/kg either alone or in combination with radiation, geniposidic acid exhibits a more notable inhibitory activity factor against implanted tumor growth. In rabbits, geniposidic acid increases the number of intimal foam cells, the intima/media thickness ratio, and plaque area. In rabbits, geniposidic acid (100 μg/mL) alleviates EC shedding and corrects abnormalities in aortic morphology. Rabbits' smooth muscle cell proliferation is significantly slowed down by geniposidic acid (100 μg/mL). The migration of SMCs from the upper chamber is obviously inhibited by geniposidic acid.

Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
ln Vitro
Geniposidic acid increases survival rate of rats with fulminant hepatic failure. Geniposidic acid attenuates the following effects: GalN/LPS increases serum aminotransferase activity, serum tumor necrosis factor-α level and hepatic lipid peroxidation and decreases hepatic glutathione content. Geniposidic acid augmentes increases in serum interleukin-6 level, heme oxygenase-1 and NF-E2-related factor 2 protein expression in rats with fulminant hepatic failure. Geniposidic acid decreases cleaved caspase-8 and caspase-3 protein expression and shows significantly fewer apoptotic cells in rats with fulminant hepatic failure. Geniposidic acid increases Bcl-xL protein expression and decreased Bax protein expression in rats with fulminant hepatic failure. Geniposidic acid treatment enhances phosphorylation of signal transducer and activator of transcription 3 in rats with fulminant hepatic failure.[3]
ln Vivo
Geniposidic acid shows a more remarkable inhibitory activity factor against implanted tumor growth when the doses of 500 mg/kg are given alone or combined with irradiation. [1] In rabbits, geniposidic acid increases the number of intimal foam cells, intima/media thickness ratio, and plaque area. In rabbits, geniposidic acid (100 g/mL) improves aortic morphology disorders and reduces ECs shedding. Rabbits' smooth muscle cell proliferation is significantly inhibited by geniposidic acid (100 g/mL). A clear inhibition of SMC migration from the upper chamber is produced by geniposidic acid.[2] The following effects of geniposidic acid are lessened: GalN/LPS raises serum tumor necrosis factor-α levels, hepatic lipid peroxidation, and serum aminotransferase activity while lowering glutathione levels in the liver. In rats with fulminant hepatic failure, geniposidic acid enhances increases in serum interleukin-6 level, heme oxygenase-1, and NF-E2-related factor 2 protein expression. In rats with fulminant hepatic failure, geniposidic acid significantly reduces cleaved caspase-8 and caspase-3 protein expression and the number of apoptotic cells. In rats with fulminant hepatic failure, geniposidic acid increases Bcl-xL protein expression and decreases Bax protein expression. In rats with fulminant hepatic failure, geniposidic acid treatment increases the phosphorylation of signal transducer and activator of transcription 3.
References

[1]. Cancer Lett . 1997 Feb 26;113(1-2):31-7.

[2]. Pharm Biol . 2015 Feb;53(2):280-5.

[3]. Cancer Lett . 1997 Feb 26;113(1-2):31-7.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H22O10
Molecular Weight
374.34
Exact Mass
374.1213
Elemental Analysis
C, 51.34; H, 5.92; O, 42.74
CAS #
27741-01-1
Related CAS #
27741-01-1
Appearance
Solid powder
SMILES
C1C=C([C@@H]2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)CO
InChi Key
ZJDOESGVOWAULF-OGJQONSISA-N
InChi Code
InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9-,10-,11-,12+,13-,15+,16+/m1/s1
Chemical Name
(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
Synonyms
Geniposidic 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: ~16 mg/mL (~42.7 mM)
Water: <1 mg/mL
Ethanol: ~2 mg/mL (~5.3 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 3 mg/mL (8.01 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 30.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 3 mg/mL (8.01 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 30.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 3 mg/mL (8.01 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 30.0 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 2.6714 mL 13.3568 mL 26.7137 mL
5 mM 0.5343 mL 2.6714 mL 5.3427 mL
10 mM 0.2671 mL 1.3357 mL 2.6714 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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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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