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4aα,7α,7aα-Nepetalactone

CAT: 0013-GTR19212910-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19212910-01Size:1 mg
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Description
4aα,7α,7aα-Nepetalactone is a terpenoid lactone with demonstrated antibacterial properties against pathogens including E. coli, P. aeruginosa, and S. aureus. It serves as a valuable research tool for in vitro studies exploring novel antimicrobial mechanisms and natural product chemistry.
CAS Number
21651-62-7
Product Name Alternative
(4aS,7S,7aR) -Nepetalactone, Nepetalactone cis-trans-form
Field of Research
Infectious Disease & Virology
Purity
99.94% (May vary between batches)
Smiles
CC=1[C@@]2 ([C@@] ([C@@H] (C) CC2) (C (=O) OC1) [H]) [H]
Molecular Formula
C10H14O2
Molecular Weight
166.22
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

nepetalactone cis-trans-form

Cis-trans-nepetalactone is a cyclopentapyran that is (4aS,7aR)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aS,7S,7aR-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It is an aphid sex pheromone and cat attractant, and exhibits antibacterial, antifungal, and analgesic properties. It has a role as an insect attractant, a pheromone, an antibacterial agent, an analgesic, an antifungal agent, an insect repellent and a plant metabolite. It is a cyclopentapyran and an iridoid monoterpenoid.

CAS Number21651-62-7
PubChem CID161367
IUPAC Name(4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
Molecular FormulaC10H14O2
Molecular Weight166.22
XLogP1.9
Topological Polar Surface Area26.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Heavy Atom Count12
Formal Charge0
Complexity242
SMILES
C[C@H]1CC[C@H]2[C@@H]1C(=O)OC=C2C
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
InChIKey
ZDKZHVNKFOXMND-NBEYISGCSA-N
Chemical Structure
2D Structure
2D structure of nepetalactone cis-trans-form
CAS: 21651-62-7
CID: 161367
Formula: C10H14O2
MW: 166.22
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight166.22
XLogP31.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass166.099379685
Monoisotopic Mass166.099379685
Topological Polar Surface Area26.3 Ų
Heavy Atom Count12
Formal Charge0
Complexity242
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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