trans,cis-Nepetalactone

CAT: 0572-TRC-N390055-250MGSize: 250 mgDry Ice: NoHazardous: No

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CAT#:0572-TRC-N390055-250MGSize:250 mg

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CAS Number

17257-15-7

Synonyms

[4aS-(4aα,7α,7aβ)]-5,6,7,7a-Tetrahydro-4,7-dimethyl-cyclopenta[c]pyran-1(4aH)-one; 5,6,7,7aβ-Tetrahydro-4,7α-dimethyl-cyclopenta[c]pyran-1(4aαH)-one; (4aS,7S,7aS)-5,6,7,7a-Tetrahydro-4,7-dimethylcyclopenta[c]pyran-1(4aH)-one; (+)-trans,cis-Nepetalactone; (4aS,7S,7aS)-Nepetalactone; 4aα,7α,7aβ-Nepetalactone; Epinepetalactone; Isonepetalactone

Hazard Statement

Harmful if swallowed.

Purity

>95% (HPLC)

Smiles

CC(=O)NC1[C@@H](OC(CO)[C@H](O)C1O)Oc2cc3c(cc2)C(C)=CC(=O)O3

Molecular Formula

C10H14O2

Molecular Weight

166.22

Shipping Conditions

Room Temperature

Storage Conditions

+4°C

Chemical Information

4aalpha,7alpha,7abeta-Nepetalactone

Trans-cis-nepetalactone is a cyclopentapyran that is (4aS,7aS)-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,7aS-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It exhibits potent repellant activity against house dust mites and mosquitoes. It has a role as an antibacterial agent, an antifungal agent, an insect repellent and a plant metabolite. It is a cyclopentapyran and an iridoid monoterpenoid.

CAS Number	17257-15-7
PubChem CID	442430
IUPAC Name	(4aS,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
Molecular Formula	C10H14O2
Molecular Weight	166.22
XLogP	1.9
Topological Polar Surface Area	26.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Heavy Atom Count	12
Formal Charge	0
Complexity	242

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-ZQARSLAVSA-N

Chemical Structure

2D Structure

CAS: 17257-15-7

CID: 442430

Formula: C10H14O2

MW: 166.22

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	166.22
XLogP3	1.9
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	166.099379685
Monoisotopic Mass	166.099379685
Topological Polar Surface Area	26.3 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	242
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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C818005	Crotamiton (Cis/Trans Mixture)

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163140	Cis-trans Nepetalactone
SAA25715-01	Trans, cis-nepetalactone
RM-N052701-01	Nepetalactone Cis-Trans-Form
GTR19193366	Nepetalactone
285467-01	Nerolidol (cis/trans)
T72436-01	Cis, trans-Germacrone
sc-506178B	Cis/trans-Nepetalactol
sc-257255	δ- (cis-trans) -Phenothrin
MBS5814830	cis,trans-Germacrone
72301743	Citral (cis + trans)

trans,cis-Nepetalactone

Chemical Information

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