Record Information
Version1.0
Creation Date2009-06-23 20:53:48 UTC
Update Date2026-04-03 08:50:12 UTC
Accession NumberCHEM001603
Identification
Common NameCinerin II
ClassSmall Molecule
DescriptionCinerin II is a synthetic pyrethrin. Pyrethrins are naturally-occurring compounds with insecticidal properties that are found in pyrethrum extract from certain chrysanthemum flowers. The pyrethrins are often used in household insecticides and products to control insects on pets or livestock. (3)
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Food Toxin
  • Household Toxin
  • Organic Compound
  • Pesticide
  • Pyrethrin
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
3-(3-Methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl esterChEBI
3-(But-2-enyl)-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylateChEBI
3-(3-Methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethylcyclopropanecarboxylate 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl esterGenerator
3-(But-2-enyl)-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylic acidGenerator
Chemical FormulaC21H28O5
Average Molecular Mass360.444 g/mol
Monoisotopic Mass360.194 g/mol
CAS Registry Number121-20-0
IUPAC Name(1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
Traditional Namecinerin II
SMILESCOC(=O)C(\C)=C\[C@@H]1[C@@H](C(=O)O[C@H]2CC(=O)C(C\C=C/C)=C2C)C1(C)C
InChI IdentifierInChI=1S/C21H28O5/c1-7-8-9-14-13(3)17(11-16(14)22)26-20(24)18-15(21(18,4)5)10-12(2)19(23)25-6/h7-8,10,15,17-18H,9,11H2,1-6H3/b8-7-,12-10+/t15-,17+,18+/m1/s1
InChI KeySHCRDCOTRILILT-WOBDGSLYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
Alternative Parents
Substituents
  • Pyrethroid skeleton
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Carbocyclic fatty acid
  • Cyclopropanecarboxylic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceViscous liquid (5).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling Point183°C at 1.00E-03 mm Hg
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0082 g/LALOGPS
logP4.18ALOGPS
logP4.01ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)18.09ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity100.87 m³·mol⁻¹ChemAxon
Polarizability40.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-1619000000-47ee46d0b16ef7fb0160Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mn-9611000000-c1a301a277b438a20e6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0670-9500000000-55c88b3c2c5bb4e46e0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0309000000-c3dbdcb031acd4333874Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-1934000000-19a10c96c3e74e20c2d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02tl-5910000000-97dd96e6ffc7afba8b53Spectrum
Toxicity Profile
Route of ExposureInhalation (4) ; oral (4) ; dermal (4) ; eye contact (4).
Mechanism of ToxicityPyrethrins exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. (3, 1)
MetabolismFollowing ingestion, pyrethrins are hydrolysed by various digestive enzymes in the gastro-intestinal tract. However, a small portion of the insecticidally active compounds or its derivatives are absorbed, as shown by their toxicity and their effect on the liver. Pyrethrins may also be absorbed following inhalation or dermal contact. They are rapidly distributed to most tissues, particularly to those with a high lipid content, and are concentrated in central and peripheral nervous tissues. Pyrethrins or their metabolites are not known to be stored in the body or to be excreted in the milk, but no study of the matter has employed modern methods. The major metabolic pathways for pyrethrins are hydrolysis of the central ester bond, oxidative attacks at several sites, and conjugation reactions, to produce a complex array of primary and secondary water-soluble metabolites that undergo urinary excretion. Metabolism is believed to involve nonspecific microsomal carboxyesterases and microsomal mixed function oxidases, which are located in nearly all tissue types, with particularly high activities in the liver. Metabolites, such as chrysanthemummonocarboxylic acid, are excreted in the urine and faeces. (3, 6)
Toxicity ValuesLD50: 2370 mg/kg (Oral, Rat) (8) LD50: 1030 mg/kg (Oral, Rat) (8)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBreathing in contaminated air; drinking contaminated water or eating contaminated foods; skin and eye exposure (3).
Minimum Risk LevelNot Available
Health EffectsPyrethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis, can also occur following pyrethrin poisoning. (3)
SymptomsThe clinical manifestations of inhalation exposure to pyrethrins can be local or systemic. Localized reactions confined to the upper respiratory tract include rhinitis, sneezing, scratchy throat, oral mucosal edema, and even laryngeal mucosal edema. Localized reactions of the lower respiratory tract include cough, shortness of breath, wheezing, and chest pain. An asthmalike reaction occurs with acute exposures in sensitized patients. Hypersensitivity pneumonitis characterized by chest pain, cough, dyspnea, and bronchospasm may occur in an individual chronically exposed. Large amounts may cause nausea, vomiting, tinnitus, headache, and other central nervous system disturbances. (2)
TreatmentFollowing oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (7)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003034
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID3707
PubChem Compound ID5281548
Kegg Compound IDC09846
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available