Synonym
Dihydrojasmone; dihydro-jasmone; NSC 71928; NSC71928; NSC-71928;
IUPAC/Chemical Name
3-methyl-2-pentylcyclopent-2-en-1-one
InChi Key
YCIXWYOBMVNGTB-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H18O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h3-8H2,1-2H3
SMILES Code
CCCCCC1=C(C)CCC1=O
Purity
>98% (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
>2 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
2934.99.9001
Biological target:
Dihydrojasmone, a constituent of bergamot oil, is an important perfume ingredient.
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
100.0 |
601.45 |
|
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
166.26
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.
| 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 |
1: Gliszczyńska A, Semba D, Szczepanik M, Dancewicz K, Gabryś B. Alkyl-Substituted δ-Lactones Derived from Dihydrojasmone and Their Stereoselective Fungi-Mediated Conversion: Production of New Antifeedant Agents. Molecules. 2016 Sep 13;21(9). pii: E1226. doi: 10.3390/molecules21091226. PubMed PMID: 27649116.
2: Belloir C, Miller-Leseigneur ML, Neiers F, Briand L, Le Bon AM. Biophysical and functional characterization of the human olfactory receptor OR1A1 expressed in a mammalian inducible cell line. Protein Expr Purif. 2017 Jan;129:31-43. doi: 10.1016/j.pep.2016.09.006. Epub 2016 Sep 15. PubMed PMID: 27642093.
3: Ahmad S, Ullah F, Zeb A, Ayaz M, Ullah F, Sadiq A. Evaluation of Rumex hastatus D. Don for cytotoxic potential against HeLa and NIH/3T3 cell lines: chemical characterization of chloroform fraction and identification of bioactive compounds. BMC Complement Altern Med. 2016 Aug 24;16:308. doi: 10.1186/s12906-016-1302-y. PubMed PMID: 27552817; PubMed Central PMCID: PMC4995757.
4: Gliszczyńska A, Gładkowski W, Dancewicz K, Gabryś B. Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity. Curr Microbiol. 2015 Jul;71(1):83-94. doi: 10.1007/s00284-015-0831-9. Epub 2015 May 10. PubMed PMID: 25958072.
5: Erden I, Ocal N, Song J, Gleason C, Gärtner C. Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides. Tetrahedron. 2006 Nov 13;62(46):10676-10682. PubMed PMID: 17998948; PubMed Central PMCID: PMC1905889.
6: Trost BM, Pinkerton AB. A three-component coupling approach to cyclopentanoids. J Org Chem. 2001 Nov 16;66(23):7714-22. PubMed PMID: 11701026.
7: Nakashita Y, Hesse M. Conversion of nitroheptane to dihydrojasmone. Planta Med. 1985 Aug;51(4):349-50. PubMed PMID: 17340535.
8: Bakuzis P, Bakuzis ML. Synthesis of 2-alkylcyclopentenones. Jasmone, dihydrojasmone, and a prostaglandin precursor. J Org Chem. 1977 Jul 8;42(14):2362-5. PubMed PMID: 874613.
9: Katsure J, Matsui M. Synthetic studies on cyclopentane derivatives. Pt. 1. Alternative routes to dl-prostaglandin-B1 and dihydrojasmone. Agric Biol Chem. 1969;33(7):1078-86. PubMed PMID: 12262299.
