General Information of Natural Product (ID: NP0814)
  Natural Product Name
Nepetalactone Cis-Trans-Form
  Synonyms
Nepetalactone cis-trans-form; 21651-62-7; (+)-cis,trans-Nepetalactone; (4aS,7S,7aR)-Nepetalactone; UNII-7TM7PE24UW; 7TM7PE24UW; (4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one; 4aalpha,7alpha,7aalpha-Nepetalactone; (+)-(4aS,7S,7aR)-Nepetalactone; NEPETALACTON; 4a.alpha.,7.alpha.,7a.alpha.-Nepetalactone; (4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one; Cyclopenta[c]pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aR)-; cis-trans-Nepetalactone; Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aR)-; cis,trans-Nepetalactone; SCHEMBL457427; CHEBI:7518; DTXSID6075198; 4a; A,7; A,7a; A-Nepetalactone; ZINC4098346; HY-129434A; LMPR0102070013; AM806779; C09791; Q414257; (4aS)-5,6,7,7aalpha-tetrahydro-4,7alpha-dimethylcyclopenta[c]pyran-1(4aH)-one; Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS-(4aalpha,7alpha,7aalpha))-
Click to Show/Hide
  Formula C10H14O2
  Weight 166.22
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  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
  Isomeric SMILES C[C@H]1CC[C@H]2[C@@H]1C(=O)OC=C2C
  Canonical SMILES CC1CCC2C1C(=O)OC=C2C
  External Links PubChem ID 161367
CAS ID 21651-62-7

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Achillea biebersteinii
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
Fresh aerial parts of A. biebersteinii were collected in May and June 2009 at different developmental stages (vegetative, floral budding, flowering and fruit set)from its natural habitat in the Dizin zone, northwest of Tehran, Iran (Latitude: 36° 4′ 52″N, Longitude: 51° 22′ 46″ E, Altitude: 2325-2425 m).
Click to Show/Hide
               Factor Function
All oil samples from different plant parts and phenological stages were mostly made up of monoterpenoid compounds (88.6 - 99.6%), especially oxygenated ones (52.4 - 82.4%). The oil of the vegetative stage contained high amounts of limonene, 4a-alpha,7-alpha,7a-alpha-nepetalactone, p-cymene and 1,8-cineole. The major constituents in the flower budding stage oil were found to be limonene, 1,8-cineole and 4aalpha-7beta-7aalpha-nepetalactone. In the oil of the fruit set stage, gamma-terpinene, p-cymene and cis-chrysanthenyl acetate were the predominant constituents. On the other hand, the most important compounds from the stem oil were 4a-alpha,7-alpha,7a-alpha-nepetalactone, 1,8-cineole, 4aalpha-7beta-7aalpha-nepetalactone and camphor. 4aalpha-7alpha-7aalpha-nepetalactone, limonene, 1,8-cineole and cis-p-menth-2-en-1-ol were found in high concentration in the oil of leaves, whereas 4aalpha-7alpha-7aalpha-nepetalactone, 4aalpha-7beta-7aalpha-nepetalactone, limonene and p-cymene were present in large amounts in the oil of flowers.
Click to Show/Hide
               Factor Part Location NP Content
 
Aerial part: Vegetative satge
Aerial parts Tehran, Iran
NP Content: 5.7 %
 
Aerial part: Floral Budding satge
Aerial parts Tehran, Iran
NP Content: 3.5 %
 
flower: flowering stage
Flowers Tehran, Iran
NP Content: 33.6 %
 
leaf: Flowering stage
Leaves Tehran, Iran
NP Content: 34.1 %
 
Stem: flowering stage
Stems Tehran, Iran
NP Content: 32.7 %
References
1 Essential oil content and composition of Achillea biebersteinii Afan. in different plant parts and phenological stages