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Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, [1R-[1alpha[S*(Z)],3beta]]-

PubChem CID
56660531
Structure
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, [1R-[1alpha[S*(Z)],3beta]]-_small.png
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, [1R-[1alpha[S*(Z)],3beta]]-_3D_Structure.png
Molecular Formula
Synonyms
  • Chrysanthemummonocarboxylic acid pyrethrolone ester
  • (1S)-2-Methyl-4-oxo-3-[(2Z)-2,4-pentadienyl]-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, (1R,3R)-
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, [1R-[1.alpha.[S*(Z)],3.beta.]]-
Molecular Weight
328.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2012-03-06
  • Modify:
    2025-01-18
See also: Pyrethrin I (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, [1R-[1alpha[S*(Z)],3beta]]-.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-methyl-4-oxo-3-[(2Z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C21H28O3/c1-7-8-9-10-15-14(4)18(12-17(15)22)24-20(23)19-16(11-13(2)3)21(19,5)6/h7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8-
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

ROVGZAWFACYCSP-HJWRWDBZSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C)C/C=C\C=C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H28O3
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
328.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3
Property Value
5.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
328.20384475 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
328.20384475 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
43.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
642
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

3.2 Experimental Properties

3.2.1 Kovats Retention Index

Semi-standard non-polar
2297 , 2314

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Instrument Name
Jeol PS-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
NIST Number
67512
Library
Main library
Total Peaks
102
m/z Top Peak
123
m/z 2nd Highest
41
m/z 3rd Highest
81
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2 of 2
NIST Number
15322
Library
Replicate library
Total Peaks
83
m/z Top Peak
123
m/z 2nd Highest
41
m/z 3rd Highest
43
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6 Patents

6.1 Depositor-Supplied Patent Identifiers

6.2 WIPO PATENTSCOPE

7 Information Sources

  1. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, [1R-[1.alpha.[S*(Z)],3.beta.]]-
    http://www.nist.gov/srd/nist1a.cfm
  2. SpectraBase
  3. PubChem
  4. PATENTSCOPE (WIPO)
CONTENTS