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8-Epiloganic acid

Cat No.:V58818 Purity: ≥98%
8-Epiloganic acid is an iridoid glycoside extracted from Linaria cymbalaria (Fragrantaceae).
8-Epiloganic acid
8-Epiloganic acid Chemical Structure CAS No.: 82509-41-9
Product category: Terpenoids
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes
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Product Description
8-Epiloganic acid is an iridoid glycoside extracted from Linaria cymbalaria (Fragrantaceae).
8-Epiloganic acid is a naturally occurring iridoid glucoside. It is a stereoisomer of loganic acid, a compound found in various plants including those of the Gentianaceae and Loganiaceae families. 8-Epiloganic acid has been studied for its potential biological activities, including anti-inflammatory and antioxidant properties. It is used in research on plant secondary metabolites and their pharmacological effects.
Biological Activity I Assay Protocols (From Reference)
Targets
The molecular targets of 8-Epiloganic acid are not fully characterized. As an iridoid glucoside, it may exhibit anti-inflammatory activity through inhibition of pro-inflammatory mediators such as NO, TNF-α, and IL-6. Its antioxidant activity involves free radical scavenging. The compound may also interact with enzymes involved in the metabolism of iridoid glycosides. Further research is needed to identify specific molecular targets.
ln Vitro
In vitro studies of 8-Epiloganic acid have demonstrated anti-inflammatory and antioxidant activities. However, specific potency data such as IC₅₀ values are not detailed in the available literature. The compound is primarily a research tool for studying the pharmacology of iridoid glycosides and related natural products. Its in vitro applications include studies of inflammation and oxidative stress.
ln Vivo
Specific in vivo activity data for 8-Epiloganic acid are not available in the consulted sources. As a natural iridoid glucoside from plants used in traditional medicine, it may have potential in vivo efficacy in models of inflammation and oxidative stress. However, systematic in vivo studies have not been reported. Further research is needed to evaluate its pharmacokinetics and efficacy.
Enzyme Assay
Typical in vitro assays for 8-Epiloganic acid include DPPH and ABTS radical scavenging assays for antioxidant activity. Anti-inflammatory activity is assessed by measuring NO production in LPS-stimulated macrophages using the Griess assay. Cytokine levels are measured by ELISA. These protocols are standard for evaluating the biological activities of iridoid glycosides and related natural products.
Cell Assay
Cellular assays for 8-Epiloganic acid typically involve treating macrophages (e.g., RAW 264.7) with the compound at concentrations ranging from 1-100 µM for 24-48 hours. Inflammatory markers such as NO, TNF-α, and IL-6 are measured by ELISA or Griess assay. ROS levels are measured using fluorescent probes. Cell viability is assessed by MTT assay. These cell-based systems allow for analysis of the compound's anti-inflammatory and antioxidant mechanisms.
Animal Protocol
In vivo animal experiments for 8-Epiloganic acid are not detailed in the available literature. For anti-inflammatory studies, typical animal models include carrageenan-induced paw edema or LPS-induced systemic inflammation. For antioxidant studies, models of oxidative stress are used. However, such studies have not been reported for this specific compound.
ADME/Pharmacokinetics
Pharmacokinetic data for 8-Epiloganic acid are limited. As an iridoid glucoside, it would be expected to have poor oral bioavailability due to its size and hydrophilicity. The compound may be hydrolyzed by glycosidases in the intestine. Detailed ADME parameters are not available in the consulted sources.
Toxicity/Toxicokinetics
Toxicological data for 8-Epiloganic acid are limited. As a natural iridoid glucoside from plants, it is generally considered to have low toxicity. However, comprehensive toxicological studies have not been reported. Standard laboratory safety precautions should be followed when handling the compound.
References

[1]. 8-epiloganic acid and 7-beta-hydroxy-8-epiiridodial glucoside. Planta Med. 1982 Sep;46(1):38-41.

Additional Infomation
It has been reported that Rehmannia glutinosa, Trichoderma lithosum, and other organisms with available data contain 8-epidermalin.
8-Epiloganic acid is a naturally occurring iridoid glucoside and stereoisomer of loganic acid, found in various plants including those of the Gentianaceae and Loganiaceae families. It has been studied for its potential anti-inflammatory and antioxidant activities. It is a research compound for studying plant secondary metabolites and their pharmacological effects. It is not approved for any clinical indication.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H24O10
Molecular Weight
376.36
Exact Mass
376.137
CAS #
82509-41-9
PubChem CID
158144
Appearance
White to off-white solid
Melting Point
138-139 °C
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
4
Heavy Atom Count
26
Complexity
565
Defined Atom Stereocenter Count
10
SMILES
O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@H]1OC=C(C(=O)O)[C@H]2C[C@@H]([C@H]([C@@H]12)C)O
InChi Key
JNNGEAWILNVFFD-OZFVSFPVSA-N
InChi Code
InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6-,8+,9-,10-,11-,12+,13-,15+,16+/m1/s1
Chemical Name
(1S,4aS,6S,7S,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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: 50 mg/mL (132.85 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (6.64 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 25.0 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: ≥ 2.5 mg/mL (6.64 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 25.0 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: ≥ 2.5 mg/mL (6.64 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 25.0 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 2.6570 mL 13.2852 mL 26.5703 mL
5 mM 0.5314 mL 2.6570 mL 5.3141 mL
10 mM 0.2657 mL 1.3285 mL 2.6570 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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