EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

(Z,E)-nepetalactone cis-trans-form
nepetalactone, (4aalpha,7alpha,7abeta)-isomer

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Name:(4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
CAS Number: 21651-62-7Picture of molecule3D/inchi
Other(deleted CASRN):123357-09-5
FDA UNII: 7TM7PE24UW
Nikkaji Web:J15.869K
XlogP3-AA:1.90 (est)
Molecular Weight:166.21998000
Formula:C10 H14 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 1834 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Nepetalacton
The Perfumery
Nepetalactone Isolate WS (10% nepetalactone
products/catalog/WSCHNepeta
Flavor: characteristic
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (Z,E)-nepetalactone cis-trans-form usage levels up to:
 not for fragrance use.
 
Recommendation for (Z,E)-nepetalactone cis-trans-form flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :161367
National Institute of Allergy and Infectious Diseases:Data
(4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
Chemidplus:0021651627
 
References:
 (4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):161367
Pubchem (sid):135256369
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C09791
HMDB (The Human Metabolome Database):HMDB35063
FooDB:FDB014964
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 cyclopenta[c]pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aR)-
(4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
(4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one
cis,trans-nepetalactone
 nepetalactone cis-trans-form
 nepetalactone, (4aalpha,7alpha,7abeta)-isomer
(4aS-(4aalpha,7alpha,7aalpha))-5,6,7,7a-tetrahydro-4,7-dimethyl cyclopenta(c)pyran-1(4ah)-one
 

Articles:

PubMed:Evaluation of a Push-Pull Approach for Aedes aegypti (L.) Using a Novel Dispensing System for Spatial Repellents in the Laboratory and in a Semi-Field Environment.
PubMed:Response of Aphidius colemani to aphid sex pheromone varies depending on plant synergy and prior experience.
PubMed:Aphid Sex Pheromone Compounds Interfere with Attraction of Common Green Lacewings to Floral Bait.
PubMed:Simultaneous UHPLC/DAD/(+/-)HESI-MS/MS analysis of phenolic acids and nepetalactones in methanol extracts of Nepeta species: a possible application in chemotaxonomic studies.
PubMed:Evaluation of the repellent effects of Nepeta parnassica extract, essential oil, and its major nepetalactone metabolite against mosquitoes.
PubMed:Chemical composition and antimicrobial activities of essential oil of nepeta cataria L. Against common causes of oral infections.
PubMed:Do asexual morphs of the peach-potato aphid, Myzus persicae, utilise the aphid sex pheromone? Behavioural and electrophysiological responses of M. persicae virginoparae to (4aS,7S,7aR)-nepetalactone and its effect on aphid performance.
PubMed:Evaluation of the antinociceptive and anti-inflammatory effects of essential oil of Nepeta pogonosperma Jamzad et Assadi in rats.
PubMed:Chemical Composition and Antimicrobial Activities of Essential Oils from Nepeta cataria L. against Common Causes of Food-Borne Infections.
PubMed:The sex pheromones of mealy plum (Hyalopterus pruni) and leaf-curl plum (Brachycaudus helichrysi) aphids: identification and field trapping of male and gynoparous aphids in prune orchards.
PubMed:Genotoxic effects of catmint (Nepeta meyeri Benth.) essential oils on some weed and crop plants.
PubMed:Composition of the essential oils and antibacterial activities of Hymenocrater yazdianus, Stachys obtusicrena and Nepeta asterotricha three Labiatae herbs growing wild in Iran.
PubMed:Interference in foraging behaviour of European and American house dust mites Dermatophagoides pteronyssinus and Dermatophagoides farinae (Acari: Pyroglyphidae) by catmint, Nepeta cataria (Lamiaceae).
PubMed:Determination of chemical composition and genotoxic effects of essential oil obtained from Nepeta nuda on Zea mays seedlings.
PubMed:Anticandidal activity of the essential oil of Nepeta transcaucasica Grossh.
PubMed:Essential oil composition and antioxidant activity of different extracts of Nepeta betonicifolia C.A. Meyer and Nepeta saccharata Bunge.
PubMed:Essential oil of Nepeta x faassenii Bergmans ex Stearn (N. mussinii Spreng. x N. nepetella L.): a comparison study.
PubMed:Nepetalactones from essential oil of Nepeta cataria represent a stable fly feeding and oviposition repellent.
PubMed:Patent literature on mosquito repellent inventions which contain plant essential oils--a review.
PubMed:Repellency of a wax-based catnip-oil formulation against stable flies.
PubMed:Repellent activity of catmint, Nepeta cataria, and iridoid nepetalactone isomers against Afro-tropical mosquitoes, ixodid ticks and red poultry mites.
PubMed:Attraction of Chrysoperla carnea complex and Chrysopa spp. lacewings (Neuroptera: Chrysopidae) to aphid sex pheromone components and a synthetic blend of floral compounds in Hungary.
PubMed:Antioxidant activity of Nepeta nuda L. ssp. nuda essential oil rich in nepetalactones from Greece.
PubMed:Nepetalactone content and antibacterial activity of the essential oils from different parts of Nepeta persica.
PubMed:Nepetalactone content in shoot cultures of three endemic Nepeta species and the evaluation of their antimicrobial activity.
PubMed:Dihydronepetalactones deter feeding activity by mosquitoes, stable flies, and deer ticks.
PubMed:Antimicrobial and antioxidant activity of the essential oil and methanol extract of Nepeta cataria.
PubMed:Antibacterial activity and composition of the essential oil of Nepeta menthoides from Iran.
PubMed:Female-induced increase of host-plant volatiles enhance specific attraction of aphid male Dysaphis plantaginea (Homoptera: Aphididae) to the sex pheromone.
PubMed:Dolichodial: a new aphid sex pheromone component?
PubMed:Fast gas chromatography characterisation of purified semiochemicals from essential oils of Matricaria chamomilla L. (Asteraceae) and Nepeta cataria L. (Lamiaceae).
PubMed:Parnapimarol and nepetaparnone from Nepeta parnassica.
PubMed:Semiochemicals related to the aphid Cinara pilicornis and its host, Picea abies: a method to assign nepetalactone diastereomers.
PubMed:Structure, ratios and patterns of release in the sex pheromone of an aphid, Dysaphis plantaginea.
PubMed:Quantification of nepetalactones in catnip (Nepeta cataria L.) by HPLC coupled with ultraviolet and mass spectrometric detection.
PubMed:The Effect of Natural Mulches on Crop Performance, Weed Suppression and Biochemical Constituents of Catnip and St. John's Wort.
PubMed:An evaluation of the allelopathic potential of selected perennial groundcovers: foliar volatiles of catmint (Nepeta x faassenii) inhibit seedling growth.
PubMed:Iridodial: a powerful attractant for the green lacewing, Chrysopa septempunctata (Neuroptera: Chrysopidae).
PubMed:Feeding deterrent effects of catnip oil components compared with two synthetic amides against Aedes aegypti.
PubMed:Simplified isolation procedure and interconversion of the diastereomers of nepetalactone and nepetalactol.
PubMed:Comparison of contact and spatial repellency of catnip oil and N,N-diethyl-3-methylbenzamide (deet) against mosquitoes.
PubMed:Electroantennogram responses of the three migratory forms of the damson-hop aphid, Phorodon humuli, to aphid pheromones and plant volatiles.
PubMed:Semiochemistry of the goldeneyed lacewing Chrysopa oculata: attraction of males to a male-produced pheromone.
PubMed:Identification of two sex pheromone components of the potato aphid, Macrosiphum euphorbiae (Thomas).
PubMed:Electrophysiological characterisation of olfactory sensilla in the black bean aphid, Aphis fabae.
PubMed:Responses of the aphids Phorodon humuli and Rhopalosiphum padi to sex pheromone stereochemistry in the field.
PubMed:Chemical composition and biological activity of Nepeta parnassica oils and isolated nepetalactones.
PubMed:Catnip essential oil as a barrier to subterranean termites (Isoptera: Rhinotermitidae) in the laboratory.
PubMed:Electroantennogram and behavioural responses of different forms of the bird cherry-oat aphid, Rhopalosiphum padi, to sex pheromone and a plant volatile.
PubMed:Functional specialisation and polyphenism in aphid olfactory sensilla.
PubMed:Aphid sex pheromones: from discovery to commercial production.
PubMed:Characterization of (1'R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis.
PubMed:Behavioral activity of catnip (Lamiaceae) essential oil components to the German cockroach (Blattodea: Blattellidae).
PubMed:Determination of nepetalactone in Nepeta cataria by reversed phase high performance liquid chromatography.
PubMed:Composition of the essential oil of two Nepeta species and in vitro evaluation of their activity against Helicobacter pylori.
PubMed:Nepetalactone: a new opioid analgesic from Nepeta caesarea Boiss.
PubMed:The aphid sex pheromone cyclopentanoids: synthesis in the elucidation of structure and biosynthetic pathways.
PubMed:Chemical composition and biological activity of leaf exudates from some Lamiaceae plants.
PubMed:Sex attractant pheromone of damson-hop aphid Phorodon humuli (Homoptera, aphididae).
PubMed:Constituents of Essential Oil of Nepeta nepetella.
PubMed:Behavioral and toxicological studies of cyclopentanoid monoterpenes from Nepeta cataria.
PubMed:Feline attractant, cis,trans-nepetalactone: metabolism in the domestic cat.
PubMed:Cyclopentanoid terpene biosynthesis in a phasmid insect and in catmint.
PubMed:CATNIP: ITS RAISON D' ETRE.
 
Notes:
Constit. of catnip from the catmint plant Nepeta cataria
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