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18509

Sigma-Aldrich

(+)-trans-Chrysanthemic acid

≥97.0% (GC)

Synonym(s):

(1R,3R)-trans-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropane-1-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H16O2
CAS Number:
4638-92-0
Molecular Weight:
168.23
Beilstein/REAXYS Number:
4904351
EC Number:
225-067-5
MDL number:
MFCD01941572
UNSPSC Code:
12352002
PubChem Substance ID:
57647664
NACRES:
NA.22

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

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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
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
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.
(+)-Trans-chrysanthemic acid from (+)-?3-carene.
Sobti R and Dev S.
Tetrahedron, 30(16), 2927-2929 (1974)
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