All Photos(1)
Synonym(s):
(1R,3R)-trans-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropane-1-carboxylic acid
Empirical Formula (Hill Notation):
C10H16O2
CAS Number:
Molecular Weight:
168.23
Beilstein:
4904351
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
Assay
≥97.0% (GC)
optical activity
[α]/D +14±1°, c = 2% in ethanol
refractive index
n20/D 1.477
SMILES string
C\C(C)=C/[C@@H]1[C@@H](C(O)=O)C1(C)C
InChI
1S/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)/t7-,8+/m1/s1
InChI key
XLOPRKKSAJMMEW-SFYZADRCSA-N
Related Categories
General description
(+)-trans-Chrysanthemic acid is the acidic component of synthetic pyrethroid insecticides. It can be prepared from (+)-Δ3-carene.
Application
(+)-trans-Chrysanthemic acid may be used in the preparation of (+)-trans-pyrethric acid, a building block for rethrin II.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Studies on Chrysanthemic Acid: Part VIII. Synthesis of Pyrethric Acids Part IX. Alternate Preparation of (+)-trans-pyrethric Acid and Methyl (+)-trans-2, 2-Dimethyl-3-(2'-carboxy-1' propenyl)-cyclopropanecarboxylate.
Matsui M, et al.
Agricultural and Biological Chemistry, 27(5), 373-380 (1963)
Gabriele Leng et al.
Toxicology letters, 162(2-3), 195-201 (2005-11-01)
Pyrethrum as well as synthetic pyrethroids like allethrin, resmethrin, phenothrin, tetramethrin, cyfluthrin, cypermethrin, deltamethrin or permethrin are among the insecticides most often used worldwide. With a sensitive and valid gas-chromatographic-high resolution mass spectrometric method, it is possible to detect all
Alain Krief et al.
Chemical communications (Cambridge, England), (39)(39), 4753-4755 (2008-10-03)
(1S)-cis-Chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry using regiocontrolled epoxide ring opening, diol mono-oxidation and cyclopropanation.
Mandar Paingankar et al.
Biotechnology letters, 27(23-24), 1909-1913 (2005-12-06)
Allethrin is a major mosquito repellent agent. To degrade allethrin present in used mats and the environment, a bacterium capable of utilizing allethrin was isolated. This isolate, an Acidomonas sp., grew in minimal medium with 16 mM: allethrin as sole
Wolfgang Bicker et al.
Journal of chromatography. A, 1035(1), 37-46 (2004-05-01)
This study reports on the direct HPLC stereoisomer separation of selected pyrethroic acids employing commercial cinchona alkaloid derived chiral stationary phases (CSPs). cis/trans-Chrysanthemic acid (cis/trans-CA), cis/trans-chrysanthemum dicarboxylic acid (cis/trans-CDCA), cis/trans-permethrinic acid (cis/trans-PA), and fenvaleric acid (FA) were resolved into the
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