Jarin-1 is a jasmonate-amide synthetase (JAR1) inhibitor (antagonist) with IC50 of 3.8 μM. Jarin-1 specifically inhibits the biosynthesis of the bioactive JA-Ile in Arabidopsis and other plants.

Physicochemical Properties

Molecular Formula	C28H29N3O4
Molecular Weight	471.547567129135
Exact Mass	471.215
CAS #	1212704-51-2
PubChem CID	7142742
Appearance	White to off-white solid powder
LogP	2.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Heavy Atom Count	35
Complexity	883
Defined Atom Stereocenter Count	2
SMILES	COCCC(=O)N1C[C@@H]2C[C@H](C1)C3=CC=C(C(=O)N3C2)NC(=O)C4=CC=C(C=C4)C5=CC=CC=C5
InChi Key	LMVUVKIGGHXSJX-WMZHIEFXSA-N
InChi Code	InChI=1S/C28H29N3O4/c1-35-14-13-26(32)30-16-19-15-23(18-30)25-12-11-24(28(34)31(25)17-19)29-27(33)22-9-7-21(8-10-22)20-5-3-2-4-6-20/h2-12,19,23H,13-18H2,1H3,(H,29,33)/t19-,23+/m0/s1
Chemical Name	N-[(1R,9S)-11-(3-methoxypropanoyl)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-5-yl]-4-phenylbenzamide
Synonyms	Jarin1; Jarin 1; Jarin-1
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)

Biological Activity

ln Vitro

Strawberries treated with MeJA had higher peel and anthocyanin levels than those treated with Jarin-1; these differences were accompanied by the activation of the FaANS and FaUFGT genes. As it turned out, fruits treated with Jarin-1 and MeJA + Jarin-1 had higher proanthocyanidin (PA) contents than fruits treated with MeJA. Treatment with MeJA + Jarin-1 increased the expression of FaANR and associated transcription factors, including FabHLH33, FaMYB9/11, FaJMT, and FaJAR1.2. The FaMYB1/9/10/11 genes' promoter region had JA response elements. Strawberries accumulate more PA because extracting Jarin-1 from MeJA-treated fruits can control genes involved in PA production [1].

References

[1]. Delgado LD, et al. Application of a JA-Ile Biosynthesis Inhibitor to Methyl Jasmonate-Treated Strawberry Fruit Induces Upregulation of Specific MBW Complex-Related Genes and Accumulation of Proanthocyanidins. Molecules. 2018 Jun 13;23(6). pii: E1433. [2]. Meesters C, et al. A chemical inhibitor of jasmonate signaling targets JAR1 in Arabidopsis thaliana. Nat Chem Biol. 2014 Oct;10(10):830-6.

Solubility Data

Solubility (In Vitro)

DMSO : ~33.33 mg/mL (~70.68 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.30 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 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 (5.30 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (5.30 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	2.1207 mL	10.6033 mL	21.2067 mL
	5 mM	0.4241 mL	2.1207 mL	4.2413 mL
	10 mM	0.2121 mL	1.0603 mL	2.1207 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.