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Jasmonic acid ((-)-Jasmonic acid)

Cat No.:V81905 Purity: ≥98%
Jasmonic acid ((-)-Jasmonic acid) is a plant growth regulator and an analogue of α-Linolenic acid.
Jasmonic acid ((-)-Jasmonic acid)
Jasmonic acid ((-)-Jasmonic acid) Chemical Structure CAS No.: 6894-38-8
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes

Other Forms of Jasmonic acid ((-)-Jasmonic acid):

  • (±)-Jasmonic acid
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Jasmonic acid ((-)-Jasmonic acid) is a plant growth regulator and an analogue of α-Linolenic acid. Jasmonic acid signaling also induces the MAP kinase cascade, calcium channels, and many processes that interact with signaling molecules.
Jasmonic acid ((-)-Jasmonic acid) is a plant growth regulator and a derivative of α-linolenic acid; it functions as a signaling molecule in plants and exhibits anticancer activity in mammalian cells by inducing apoptosis and inhibiting proliferation.
Biological Activity I Assay Protocols (From Reference)
Targets
Jasmonic acid targets the jasmonate signaling pathway in plants, inducing MAP kinase cascades, calcium channels, and interactions with signaling molecules; in mammalian cells, it modulates cell cycle and apoptosis pathways.
ln Vitro
In vitro, Jasmonic acid inhibits the growth of Lepidium sativum cress roots with a 50% inhibition rate at 5×10⁻⁵ mol/L after 40 hours; it induces apoptosis in cancer cell lines and inhibits tumor cell proliferation.
ln Vivo
In vivo, Jasmonic acid exhibits anticancer activity in animal models by inhibiting tumor growth; as a plant hormone, it regulates plant defense responses, wound healing, and developmental processes; its signaling induces expression of defense-related genes.
Enzyme Assay
Non-cellular enzyme/receptor binding assay: Jasmonic acid binding to its receptor (COI1-JAZ co-receptor complex in plants) is studied using surface plasmon resonance or isothermal titration calorimetry; competitive binding assays with labeled jasmonoyl-isoleucine are performed using recombinant receptor proteins to determine affinity constants.
Cell Assay
Cellular assays: Plant cell cultures (e.g., Arabidopsis or tobacco) are treated with Jasmonic acid; reporter gene assays using JAZ promoter-driven luciferase or GUS are used to monitor pathway activation; in mammalian cancer cell lines, cell viability (MTT assay), apoptosis (Annexin V staining), and cell cycle progression (flow cytometry) are assessed following treatment.
Animal Protocol
In vivo animal experiments: Jasmonic acid is administered to tumor-bearing mice via intraperitoneal or oral routes; tumor volume and weight are measured; apoptosis markers (e.g., caspase-3 activation) and proliferation markers (e.g., Ki-67) are evaluated in tumor tissues; toxicity and body weight changes are monitored.
ADME/Pharmacokinetics
Pharmacokinetic properties: Jasmonic acid is a small lipophilic molecule with moderate oral bioavailability; it is metabolized by conjugation and β-oxidation pathways; its plasma half-life and tissue distribution vary by species; pharmacokinetic studies are limited compared to its plant biology applications.
Toxicity/Toxicokinetics
Toxicological profile: Jasmonic acid is considered relatively non-toxic to mammals at low doses; high doses may cause mild gastrointestinal irritation; it is classified as a plant growth regulator and is not approved as a pharmaceutical; standard laboratory safety precautions apply.
References

[1]. Endogenous plant hormones of the broad bean, Vicia faba L. (-)-jasmonic acid, a plant growth inhibitor in pericarp. Planta. 1981 Dec;153(6):530-5.

[2]. Jasmonic Acid Signaling Pathway in Plants. Int J Mol Sci. 2019 May 20;20(10):2479.

Additional Infomation
Jasmonic acid is an oxomonocarboxylic acid, a compound in which (3-oxocyclopentyl)acetic acid is substituted at the 2-position of the cyclopentane ring with a (2Z)-pent-2-en-1-yl group. It is a plant metabolite belonging to the jasmonic acid ester class. It is the conjugate acid of jasmonic acid (1-) and also the enantiomer of (+)-jasmonic acid. Jasmonic acid has been reported to exist in Gelidium latifolium, Fusarium fujikuroi, and other organisms with relevant data.
Other information: Jasmonic acid is a natural product found in plants; it exists as a racemic mixture or as the (-)-enantiomer; it is used in plant physiology research to study stress responses and development; its anticancer activity is an area of ongoing investigation.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H18O3
Molecular Weight
210.27
Exact Mass
210.126
CAS #
6894-38-8
Related CAS #
(±)-Jasmonic acid;77026-92-7
PubChem CID
5281166
Appearance
Colorless to light yellow liquid
Density
1.061g/cm3
Boiling Point
358.1ºC at 760 mmHg
Flash Point
184.6ºC
Index of Refraction
1.49
LogP
2.412
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
5
Heavy Atom Count
15
Complexity
268
Defined Atom Stereocenter Count
2
SMILES
CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)O
InChi Key
ZNJFBWYDHIGLCU-HWKXXFMVSA-N
InChi Code
InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1
Chemical Name
2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetic 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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.7558 mL 23.7790 mL 47.5579 mL
5 mM 0.9512 mL 4.7558 mL 9.5116 mL
10 mM 0.4756 mL 2.3779 mL 4.7558 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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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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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