Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H22O3 |
Molecular Weight | 226.312 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@@H]1[C@H](CC(=O)OC)CCC1=O
InChI
InChIKey=KVWWIYGFBYDJQC-WDEREUQCSA-N
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/t10-,11+/m0/s1
Molecular Formula | C13H22O3 |
Molecular Weight | 226.312 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
(-)-cis-methyl dihydrojasmonate is one of the four isomers of the aroma compound methyl dihydrojasmonate. Racemic mixtures have a floral and citrus aroma while epimerized mixtures exhibit a dense fatty floral odor. Methyl dihydrojasmonates have attracted investigational interest as anticancer compounds.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
The octadecanoic pathway: signal molecules for the regulation of secondary pathways. | 1995 May 9 |
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Evaluation of the developmental toxicity of methyl dihydrojasmonate (MDJ) in rats. | 2008 |
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Fragrance material review on methyl dihydrojasmonate. | 2012 Oct |
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Development and characterization of biocompatible isotropic and anisotropic oil-in-water colloidal dispersions as a new delivery system for methyl dihydrojasmonate antitumor drug. | 2014 |
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Anti-tumor efficacy of an integrated methyl dihydrojasmonate transdermal microemulsion system targeting breast cancer cells: In vitro and in vivo studies. | 2017 Jul 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18569171
Methyl dihydrojasmonate (MDJ) was evaluated for developmental toxicity in presumed pregnant Sprague-Dawley rats at oral dosages of 0,40, 80 or 120 mg/kg/day in corn oil administered on gestational days 7 to 20. MDJ-related maternal clinical signs included an increased incidence of sparse hair coat and ungroomed appearance at 120 mg/kg/day. Two dams in this group also had tan areas in the liver and a pale spleen. The 120 mg/kg/day dosage also caused reduced mean maternal body weight gains and body weights during the dosage period and reduced absolute and relative maternal feed consumption for the entire dosage period. It was concluded that MDJ is not a developmental toxicant in rats under the conditions of this study.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28486181
Human MCF-7 breast cancer cells were incubated for 24 hours to allow cell adhesion before exposure to methyl dihydrojasmonate to concentrations of 0, 5, 12.5, 25, and 50 microL/mL (delivered in its pure form as an oily liquid). and 0, 25, 50, 75, 100 microL/mL (delivered as a microemulsion formula including 39% Oleic acid: MDHJ, 1% water and 60% Labrasol: Transcutol P). Monolayer cells were incubated with methyl dihydrojasmonates for 48 hours at 37 deg-C and in an atmosphere of 5% CO2. After 48 hours cells were fixed, washed, and stained with Sulfo-Rhodamine-B (SRB). The survival curve was determined from the surviving fraction and the drug concentration. The formulated methyl dihydrojasmonate demonstrated an IC50 of 42.2 micro-L/mL compared to 3.85 micro-L/mL for the pure compound.
Substance Class |
Chemical
Created
by
admin
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Edited
Sat Dec 16 15:25:52 GMT 2023
by
admin
on
Sat Dec 16 15:25:52 GMT 2023
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Record UNII |
9MCB9AC6FY
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Record Status |
Validated (UNII)
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Record Version |
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