Cas no 21651-62-7 (4aα,7α,7aα-Nepetalactone)
4aα,7α,7aα-Nepetalactone Chemical and Physical Properties
Names and Identifiers
-
- Nepetalactone
- cis-trans Nepetalactone
- cis-trans Nepetalact
- 4aα,7α,7aα-Nepetalactone
- A,7a
- 21651-62-7
- Nepetalactone cis-trans-form
- NEPETALACTON
- 4a alpha,7 alpha,7 alpha-Nepetalactone
- (4aS,7S,7aR)-Nepetalactone
- LMPR0102070013
- Nepetalactone, (+)-(4AS,7S,7AR)-
- (+)-cis,trans-Nepetalactone
- 4a.alpha.,7.alpha.,7a.alpha.-Nepetalactone
- Q414257
- 7TM7PE24UW
- (4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one
- DTXSID6075198
- (+)-(4aS,7S,7aR)-Nepetalactone
- Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS-(4aalpha,7alpha,7aalpha))-
- MS-22907
- Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aR)-
- (4aS,7S,7aR)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-one
- PD166388
- HY-129434A
- cis-trans-Nepetalactone
- 4aalpha,7alpha,7aalpha-Nepetalactone
- A,7
- Cyclopenta[c]pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aR)-
- Z,E-NEPETALACTONE
- (4aS, 7S, 7aR)-4, 7-dimethyl-5, 6, 7, 7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
- (4aS)-5,6,7,7aalpha-tetrahydro-4,7alpha-dimethylcyclopenta[c]pyran-1(4aH)-one
- (4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
- SCHEMBL457427
- C09791
- 4a
- A-Nepetalactone
- UNII-7TM7PE24UW
- NEPETALACTONE CIS-TRANS-FORM [MI]
- CS-0159481
- AM806779
- ZDKZHVNKFOXMND-NBEYISGCSA-N
- CHEBI:7518
- DA-76101
- Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7alpha-dimethyl-, (+)-
- Cyclopenta[c]pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7.alpha.-dimethyl-, (+)-
- (4aS)-5,6,7,7aalpha-tetrahydro-4,7alpha-dimethylcyclopenta(c)pyran-1(4aH)-one
- Nepetalactone, cis-trans-
- DTXCID7036531
- G14228
- (4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta(c)pyran-1-one
-
- Inchi: InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3/t6-,8+,9+/m0/s1
- InChI Key: ZDKZHVNKFOXMND-NBEYISGCSA-N
- SMILES: O1C=C(C)[C@@]2([H])CC[C@H](C)[C@@]2([H])C1=O
Computed Properties
- Exact Mass: 166.099
- Monoisotopic Mass: 166.099
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 2
- Heavy Atom Count: 12
- Rotatable Bond Count: 0
- Complexity: 242
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 3
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Topological Polar Surface Area: 26.3A^2
- XLogP3: 1.9
Experimental Properties
- Color/Form: Colorless to light yellow oily liquid
- Density: 1.0±0.1 g/cm3
- Boiling Point: 270.6±19.0 °C at 760 mmHg
- Flash Point: 107.7±18.9 °C
- Refractive Index: nD25 1.4878
- Specific Rotation: D21 +3.7° (c = 27 in chloroform); D27.5 +11.11° (chloroform)
- Vapor Pressure: 0.0±0.6 mmHg at 25°C
4aα,7α,7aα-Nepetalactone Security Information
- Signal Word:warning
- Hazard Statement: H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body
- Warning Statement: P264+P280+P305+P351+P338+P337+P313
- Safety Instruction: H303+H313+H333
- Storage Condition:storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)
4aα,7α,7aα-Nepetalactone Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | N390085-250mg |
cis-trans Nepetalactone |
21651-62-7 | 250mg |
$ 251.00 | 2023-09-06 | ||
| TRC | N390085-2.5g |
cis-trans Nepetalactone |
21651-62-7 | 2.5g |
$ 1869.00 | 2023-09-06 | ||
| Ambeed | A741701-250mg |
Nepetalacton |
21651-62-7 | 250mg |
$290.0 | 2024-04-21 | ||
| ChemScence | CS-0159481-5mg |
4aα,7α,7aα-Nepetalactone |
21651-62-7 | 99.21% | 5mg |
$80.0 | 2022-04-27 | |
| ChemScence | CS-0159481-10mg |
4aα,7α,7aα-Nepetalactone |
21651-62-7 | 99.21% | 10mg |
$120.0 | 2022-04-27 | |
| ChemScence | CS-0159481-25mg |
4aα,7α,7aα-Nepetalactone |
21651-62-7 | 99.21% | 25mg |
$180.0 | 2022-04-27 | |
| MedChemExpress | HY-129434A-5mg |
4aα,7α,7aα-Nepetalactone |
21651-62-7 | 99.69% | 5mg |
¥800 | 2024-04-19 | |
| MedChemExpress | HY-129434A-10mg |
4aα,7α,7aα-Nepetalactone |
21651-62-7 | 99.69% | 10mg |
¥1200 | 2024-04-19 | |
| MedChemExpress | HY-129434A-25mg |
4aα,7α,7aα-Nepetalactone |
21651-62-7 | 99.69% | 25mg |
¥1800 | 2024-04-19 | |
| A2B Chem LLC | AF63754-5mg |
NEPETALACTON |
21651-62-7 | 99% | 5mg |
$115.00 | 2024-04-20 |
4aα,7α,7aα-Nepetalactone Suppliers
4aα,7α,7aα-Nepetalactone Related Literature
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Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
-
Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
-
Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele Perego RSC Adv., 2016,6, 3617-3622
-
Chen Long,Ying Dai,Jianwei Li,Hao Jin Nanoscale, 2020,12, 21124-21130
-
Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
Additional information on 4aα,7α,7aα-Nepetalactone
Recent Advances in the Study of 4aα,7α,7aα-Nepetalactone (CAS: 21651-62-7) in Chemical Biology and Pharmaceutical Research
4aα,7α,7aα-Nepetalactone (CAS: 21651-62-7), a naturally occurring iridoid monoterpene, has garnered significant attention in recent years due to its diverse biological activities and potential pharmaceutical applications. This compound, primarily found in plants of the Nepeta genus, exhibits a range of pharmacological properties, including insect repellent, antimicrobial, and anti-inflammatory effects. Recent studies have further elucidated its mechanisms of action and explored its therapeutic potential, making it a promising candidate for drug development and agrochemical applications.
One of the most notable advancements in the study of 4aα,7α,7aα-Nepetalactone is its role as a potent insect repellent. Research published in 2023 demonstrated its efficacy against Aedes aegypti, the primary vector for dengue and Zika viruses. The study revealed that the compound interacts with specific olfactory receptors in mosquitoes, disrupting their host-seeking behavior. This finding opens new avenues for developing eco-friendly insect repellents as alternatives to synthetic pyrethroids, which face increasing resistance issues.
In the pharmaceutical domain, recent investigations have focused on the anti-inflammatory properties of 4aα,7α,7aα-Nepetalactone. A 2024 study published in the Journal of Natural Products identified its ability to inhibit NF-κB signaling pathways, suggesting potential applications in treating chronic inflammatory diseases. The compound showed significant reduction in pro-inflammatory cytokine production in macrophage cell lines, with minimal cytotoxicity observed at therapeutic concentrations.
The synthesis and structural modification of 4aα,7α,7aα-Nepetalactone have also seen progress. Researchers have developed novel catalytic methods for its enantioselective synthesis, addressing previous challenges in obtaining high-purity samples for biological testing. These synthetic approaches, combined with computational modeling studies, have provided deeper insights into the structure-activity relationships of nepetalactone derivatives.
Despite these advancements, challenges remain in translating 4aα,7α,7aα-Nepetalactone into clinical or commercial applications. Issues such as stability, bioavailability, and large-scale production need to be addressed through further research. Current efforts are focusing on formulation technologies to enhance its pharmacokinetic properties and extend its duration of action.
Looking forward, the unique chemical structure and biological profile of 4aα,7α,7aα-Nepetalactone position it as a valuable scaffold for drug discovery. Ongoing research is exploring its potential in neurological disorders, given its interaction with neurotransmitter systems, as well as its possible anticancer properties. The compound's multifaceted biological activities continue to make it a fascinating subject for interdisciplinary research at the interface of chemistry, biology, and medicine.
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