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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
Structure of METHYL DIHYDROJASMONATE, CIS-(±)-

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

HIDE SMILES / InChI

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The octadecanoic pathway: signal molecules for the regulation of secondary pathways.
1995 May 9
Evaluation of the developmental toxicity of methyl dihydrojasmonate (MDJ) in rats.
2008
Fragrance material review on methyl dihydrojasmonate.
2012 Oct
Development and characterization of biocompatible isotropic and anisotropic oil-in-water colloidal dispersions as a new delivery system for methyl dihydrojasmonate antitumor drug.
2014
Anti-tumor efficacy of an integrated methyl dihydrojasmonate transdermal microemulsion system targeting breast cancer cells: In vitro and in vivo studies.
2017 Jul 1
Patents

Sample Use Guides

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
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
on Sat Dec 16 15:25:52 GMT 2023
Edited
by admin
on Sat Dec 16 15:25:52 GMT 2023
Record UNII
9MCB9AC6FY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYL DIHYDROJASMONATE, CIS-(±)-
Common Name English
CYCLOPENTANEACETIC ACID, 3-OXO-2-PENTYL-, METHYL ESTER, CIS-
Systematic Name English
CYCLOPENTANEACETIC ACID, 3-OXO-2-PENTYL-, METHYL ESTER, CIS-(±)-
Systematic Name English
CYCLOPENTANEACETIC ACID, 3-OXO-2-PENTYL-, METHYL ESTER, (1R,2S)-REL-
Systematic Name English
Code System Code Type Description
FDA UNII
9MCB9AC6FY
Created by admin on Sat Dec 16 15:25:52 GMT 2023 , Edited by admin on Sat Dec 16 15:25:52 GMT 2023
PRIMARY
PUBCHEM
1738127
Created by admin on Sat Dec 16 15:25:52 GMT 2023 , Edited by admin on Sat Dec 16 15:25:52 GMT 2023
PRIMARY
CAS
93452-03-0
Created by admin on Sat Dec 16 15:25:52 GMT 2023 , Edited by admin on Sat Dec 16 15:25:52 GMT 2023
PRIMARY