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MedKoo Cat#: 558496 | Name: Methyl dihydrojasmonate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methyl dihydrojasmonate is an aroma compound used to prepare hydrogels as delivery systems for the slow release of bioactive carbonyl derivatives.

Chemical Structure

Methyl dihydrojasmonate
Methyl dihydrojasmonate
CAS#24851-98-7

Theoretical Analysis

MedKoo Cat#: 558496

Name: Methyl dihydrojasmonate

CAS#: 24851-98-7

Chemical Formula: C13H22O3

Exact Mass: 226.1569

Molecular Weight: 226.32

Elemental Analysis: .C, 68.99; H, 9.80; O, 21.21

Price and Availability

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25g USD 350.00 2 weeks
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Synonym
Methyl dihydrojasmonate; Hedione; Kharismal;
IUPAC/Chemical Name
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester
InChi Key
KVWWIYGFBYDJQC-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3
SMILES Code
O=C(OC)CC1C(CCCCC)C(CC1)=O
Appearance
Liquid (cis- and trans- mixture)
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methyl dihydrojasmonate is a fragrance ingredient with a jasmine-like odor, used in many fragrance mixtures.
In vitro activity:
In this work, biocompatible MEs of appropriate diameter size for intravenous route administration, loaded and unloaded with methyl dihydrojasmonate (MJ), were developed and described in a pseudo-ternary phase diagram. The results showed that the droplet size decreased with both MJ incorporation and oil phase/surfactant ratio. Almost all MJ-unloaded MEs presented anisotropic characteristics, but some formulations became isotropic, especially in the presence of MJ. Reference: Int J Nanomedicine. 2014 Feb 11;9:867-76. https://pubmed.ncbi.nlm.nih.gov/24596463/
In vivo activity:
In this context, microemulsions are reported as one of the most favored carriers for successful transdermal drug delivery. Thereby, these nano-carriers were utilized in this study for the delivery of a phytochemical, namely methyl dihydrojasmonate (MDHJ), which has previously demonstrated an anticancer effect. In vivo investigations were performed using Ehlirch solid carcinoma and histopathological examination of the tumor cells evaluating the tumor volume differences, tumor inhibition percentages and the necrotic effect of the formulation compared to control, placebo and pure drug. Reference: Colloids Surf B Biointerfaces. 2017 Jul 1;155:512-521. https://pubmed.ncbi.nlm.nih.gov/28486181/
Solvent mg/mL mM comments
Solubility
DMSO 100.0 441.86
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 226.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. da Silva GB, Scarpa MV, Rossanezi G, do Egito ES, de Oliveira AG. Development and characterization of biocompatible isotropic and anisotropic oil-in-water colloidal dispersions as a new delivery system for methyl dihydrojasmonate antitumor drug. Int J Nanomedicine. 2014 Feb 11;9:867-76. doi: 10.2147/IJN.S46055. PMID: 24596463; PMCID: PMC3930478. 2. Yehia R, Hathout RM, Attia DA, Elmazar MM, Mortada ND. Anti-tumor efficacy of an integrated methyl dihydrojasmonate transdermal microemulsion system targeting breast cancer cells: In vitro and in vivo studies. Colloids Surf B Biointerfaces. 2017 Jul 1;155:512-521. doi: 10.1016/j.colsurfb.2017.04.031. Epub 2017 Apr 23. PMID: 28486181. 3. Politano VT, Lewis EM, Hoberman AM, Christian MS, Diener RM, Api AM. Evaluation of the developmental toxicity of methyl dihydrojasmonate (MDJ) in rats. Int J Toxicol. 2008;27(3):295-300. doi: 10.1080/10915810802210158. PMID: 18569171.
In vitro protocol:
1. da Silva GB, Scarpa MV, Rossanezi G, do Egito ES, de Oliveira AG. Development and characterization of biocompatible isotropic and anisotropic oil-in-water colloidal dispersions as a new delivery system for methyl dihydrojasmonate antitumor drug. Int J Nanomedicine. 2014 Feb 11;9:867-76. doi: 10.2147/IJN.S46055. PMID: 24596463; PMCID: PMC3930478.
In vivo protocol:
1. Yehia R, Hathout RM, Attia DA, Elmazar MM, Mortada ND. Anti-tumor efficacy of an integrated methyl dihydrojasmonate transdermal microemulsion system targeting breast cancer cells: In vitro and in vivo studies. Colloids Surf B Biointerfaces. 2017 Jul 1;155:512-521. doi: 10.1016/j.colsurfb.2017.04.031. Epub 2017 Apr 23. PMID: 28486181. 2. Politano VT, Lewis EM, Hoberman AM, Christian MS, Diener RM, Api AM. Evaluation of the developmental toxicity of methyl dihydrojasmonate (MDJ) in rats. Int J Toxicol. 2008;27(3):295-300. doi: 10.1080/10915810802210158. PMID: 18569171.
1: Scognamiglio J, Jones L, Letizia CS, Api AM. Fragrance material review on methyl dihydrojasmonate. Food Chem Toxicol. 2012 Oct;50 Suppl 3:S562-71. doi: 10.1016/j.fct.2012.03.036. Epub 2012 Mar 17. Review. PubMed PMID: 22449534. 2: Api AM, Belsito D, Bhatia S, Bruze M, Calow P, Dagli ML, Dekant W, Fryer AD, Kromidas L, La Cava S, Lalko JF, Lapczynski A, Liebler DC, Miyachi Y, Politano VT, Ritacco G, Salvito D, Shen J, Schultz TW, Sipes IG, Wall B, Wilcox DK. RIFM fragrance ingredient safety assessment, methyl dihydrojasmonate, CAS registry number 24851-98-7. Food Chem Toxicol. 2015 Aug;82 Suppl:S114-21. doi: 10.1016/j.fct.2015.01.006. Epub 2015 Jan 28. Review. PubMed PMID: 25636727. 3: da Silva GB, Scarpa MV, Rossanezi G, do Egito ES, de Oliveira AG. Development and characterization of biocompatible isotropic and anisotropic oil-in-water colloidal dispersions as a new delivery system for methyl dihydrojasmonate antitumor drug. Int J Nanomedicine. 2014 Feb 11;9:867-76. doi: 10.2147/IJN.S46055. eCollection 2014. PubMed PMID: 24596463; PubMed Central PMCID: PMC3930478. 4: da Silva GB, Scarpa MV, Carlos IZ, Quilles MB, Lia RC, do Egito ES, de Oliveira AG. Oil-in-water biocompatible microemulsion as a carrier for the antitumor drug compound methyl dihydrojasmonate. Int J Nanomedicine. 2015 Jan 12;10:585-94. doi: 10.2147/IJN.S67652. eCollection 2015. PubMed PMID: 25609963; PubMed Central PMCID: PMC4298349. 5: Fontal M, van Drooge BL, Grimalt JO. A rapid method for the analysis of methyl dihydrojasmonate and galaxolide in indoor and outdoor air particulate matter. J Chromatogr A. 2016 May 20;1447:135-40. doi: 10.1016/j.chroma.2016.04.028. Epub 2016 Apr 13. PubMed PMID: 27113676. 6: Porta A, Vidari G, Zanoni G. A general enantioselective approach to jasmonoid fragrances: synthesis of (+)-(1R,2S)-methyl dihydrojasmonate and (+)-(1R,2S)-magnolione. J Org Chem. 2005 Jun 10;70(12):4876-8. PubMed PMID: 15932335. 7: Politano VT, Lewis EM, Hoberman AM, Christian MS, Diener RM, Api AM. Evaluation of the developmental toxicity of methyl dihydrojasmonate (MDJ) in rats. Int J Toxicol. 2008;27(3):295-300. doi: 10.1080/10915810802210158. PubMed PMID: 18569171. 8: Perrard T, Plaquevent JC, Desmurs JR, Hébrault D. Enantioselective synthesis of both enantiomers of methyl dihydrojasmonate using solid-liquid asymmetric phase-transfer catalysis. Org Lett. 2000 Sep 21;2(19):2959-62. PubMed PMID: 10986082. 9: Hijosa-Valsero M, Reyes-Contreras C, Domínguez C, Bécares E, Bayona JM. Behaviour of pharmaceuticals and personal care products in constructed wetland compartments: Influent, effluent, pore water, substrate and plant roots. Chemosphere. 2016 Feb;145:508-17. doi: 10.1016/j.chemosphere.2015.11.090. Epub 2015 Dec 15. PubMed PMID: 26702554. 10: Dobbs DA, Vanhessche KP, Brazi E, Rautenstrauch V V, Lenoir JY, Genêt JP, Wiles J, Bergens SH. Industrial Synthesis of (+)-cis-Methyl Dihydrojasmonate by Enantioselective Catalytic Hydrogenation; Identification of the Precatalyst. Angew Chem Int Ed Engl. 2000 Jun 2;39(11):1992-1995. PubMed PMID: 10941007. 11: Oku K, Weldegergis BT, Poelman EH, De Jong PW, Dicke M. Altered volatile profile associated with precopulatory mate guarding attracts spider mite males. J Chem Ecol. 2015 Feb;41(2):187-93. doi: 10.1007/s10886-015-0547-0. Epub 2015 Jan 23. PubMed PMID: 25612522. 12: Hijosa-Valsero M, Matamoros V, Sidrach-Cardona R, Pedescoll A, Martín-Villacorta J, García J, Bayona JM, Bécares E. Influence of design, physico-chemical and environmental parameters on pharmaceuticals and fragrances removal by constructed wetlands. Water Sci Technol. 2011;63(11):2527-34. PubMed PMID: 22049744. 13: Herrera-Cárdenas J, Navarro AE, Torres E. Effects of porous media, macrophyte type and hydraulic retention time on the removal of organic load and micropollutants in constructed wetlands. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2016;51(5):380-8. doi: 10.1080/10934529.2015.1120512. Epub 2016 Jan 28. PubMed PMID: 26817393. 14: Baldwin IT, Schmelz EA, Zhang ZP. Effects of octadecanoid metabolites and inhibitors on induced nicotine accumulation inNicotiana sylvestris. J Chem Ecol. 1996 Jan;22(1):61-74. doi: 10.1007/BF02040200. PubMed PMID: 24226983. 15: Zeng F, Xu P, Tan K, Zarbin PHG, Leal WS. Methyl dihydrojasmonate and lilial are the constituents with an "off-label" insect repellence in perfumes. PLoS One. 2018 Jun 19;13(6):e0199386. doi: 10.1371/journal.pone.0199386. eCollection 2018. PubMed PMID: 29920544; PubMed Central PMCID: PMC6007898. 16: Reyes-Contreras C, Hijosa-Valsero M, Sidrach-Cardona R, Bayona JM, Bécares E. Temporal evolution in PPCP removal from urban wastewater by constructed wetlands of different configuration: a medium-term study. Chemosphere. 2012 Jun;88(2):161-7. doi: 10.1016/j.chemosphere.2012.02.064. Epub 2012 Mar 20. PubMed PMID: 22436587. 17: Yehia R, Hathout RM, Attia DA, Elmazar MM, Mortada ND. Anti-tumor efficacy of an integrated methyl dihydrojasmonate transdermal microemulsion system targeting breast cancer cells: In vitro and in vivo studies. Colloids Surf B Biointerfaces. 2017 Jul 1;155:512-521. doi: 10.1016/j.colsurfb.2017.04.031. Epub 2017 Apr 23. PubMed PMID: 28486181. 18: da Silva GBRF, Alécio AC, Scarpa MVC, do Egito EST, Sequinel R, Hatanaka RR, Oliveira JE, Oliveira AG. An analytical GC-MS method to quantify methyl dihydrojasmonate in biocompatible oil-in-water microemulsions: physicochemical characterization and in vitro release studies. Pharm Dev Technol. 2018 Feb;23(2):151-157. doi: 10.1080/10837450.2017.1337792. Epub 2017 Jun 21. PubMed PMID: 28565943. 19: Zhu S, Zhang Q, Chen K, Jiang H. Synergistic Catalysis: Metal/Proton-Catalyzed Cyclization of Alkynones Toward Bicyclo[3.n.1]alkanones. Angew Chem Int Ed Engl. 2015 Aug 3;54(32):9414-8. doi: 10.1002/anie.201504964. Epub 2015 Jul 3. PubMed PMID: 26138939. 20: Li J, Wang J, Wu X, Liu D, Li J, Li J, Liu S, Gao W. Jasmonic acid and methyl dihydrojasmonate enhance saponin biosynthesis as well as expression of functional genes in adventitious roots of Panax notoginseng F.H. Chen. Biotechnol Appl Biochem. 2017 Mar;64(2):225-238. doi: 10.1002/bab.1477. Epub 2016 Apr 25. PubMed PMID: 26777985.