2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

• ChemBase ID: 105120
• Molecular Formular: C19H26O3
• Molecular Mass: 302.40794
• Monoisotopic Mass: 302.18819469
• SMILES: CC(=CC1C(C(=O)OC2CC(=O)C(=C2C)CC=C)C1(C)C)C
• Canonical SMILES: C=CCC1=C(C)C(CC1=O)OC(=O)C1C(C1(C)C)C=C(C)C
• InChI: InChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3
• InChIKey: ZCVAOQKBXKSDMS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• IUPAC Traditional name: pyrethrin
• Synonyms: Allylcinerine; Allethrin; Bioallethrin; D-trans-Allethrin; BIOALLETHRIN; ALLETHRIN; 3-Allyl-2-methyl-4-oxo-2-cyclopentenyl chrysanthemate; Esbiothrin; Allethrine; 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-cyclopropanecarboxylic Acid 2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl Ester; Allyl cinerin I; EBT; ENT 17510; Esbiothrine; Exthrin; Matox; NSC 11782; OMS 3045; Pynamin forte; Pyresyn; RU 27436; Wasp Stopper CF; Chrysanthemummonocarboxylic Acid 2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one Ester; dl-Allethrin; trans-Allethrin; 丙烯除虫菊; 丙烯菊酯; D-丙烯菊酯; 3-烯丙基-2-甲基-4-氧代-2-环戊烯基菊酯; Es-生物烯丙菊酯

Database IDs

• CAS Number: 584-79-2; 22431-63-6
• EC Number: 209-542-4
• MDL Number: MFCD00045443
• Beilstein Number: 2294836
• PubChem SID: 24860206; 162092522; 24868814; 24860101
• PubChem CID: 11442

CALCULATED PROPERTIES

• Acid pKa: 18.088175
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.0561905
• LogD (pH = 7.4): 4.0561905
• Log P: 4.0561905
• Molar Refractivity: 88.71 cm^3
• Polarizability: 34.379314 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 150.8 °F; 66 °C

Safety Information

• Storage Condition: -20°C
• RTECS: GZ1925000
• European Hazard Symbols: Nature polluting (N); Toxic (T); Harmful (Xn)
• UN Number: 2810; 3082
• German water hazard class: 3
• Hazard Class: 6.1; 9
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 20/22-50/53; R:25
• Safety Statements: 36-60-61; S:28-36/37/39-45-53
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H332-H410
• GHS Precautionary statements: P273-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3082 9/PG 3

Product Information

• Grade: PESTANAL®, analytical standard
• Description: mixture of stereo isomers
• Empirical Formula (Hill Notation): C19H26O3

DETAILS

MP Biomedicals - 02159010

(Allethrin I)
Mixture of 8 isomers
A Type I pyrethrin which demonstrates very weak active negative control properties for calcineurin (protein phosphatase 2B) inhibition by Type II pyrethrins.

MP Biomedicals - 02158873

Mixture of isomers
Bioallethrin is a Type I pyrethrin and it mimics Type II pyrethrins on the inhibition of calcineurin (protein phosphatase 2B). It is a more potent inhibitor of calcineurin than allethrin and other Type I pyrethrins.

Sigma Aldrich - 33309

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 33396

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 31489

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - A542200

Allethrin is a synthetic pyrethroid derivative used as an insecticide. Allethrin is commonly used in many household insecticide products due to its low toxicity towards humans.

REFERENCES

• Dua, V.K. et al.: Bull. Environ. Contam. Toxicol., 75, 747 (2005)
• Jiang, M. et al.: Nanj. Nong. Dax. Xue., 18, 110 (2005)