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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:
4904351
EC Number:
225-067-5
MDL number:
MFCD01941572
UNSPSC Code:
12352002
PubChem Substance ID:
57647664
NACRES:
NA.22

Quality Level

100

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

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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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
[Evaluation of the toxicity of chrysanthemic acid and its derivatives].
A I Gurova et al.
Gigiena i sanitariia, (1)(1), 16-18 (1986-01-01)
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)
M Dondi et al.
Journal of chromatography. A, 859(2), 133-142 (1999-11-26)
The direct enantioseparation of chrysanthemic acid [2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylic acid] and its halogen-substituted analogues was systematically studied by HPLC using a terguride-based chiral stationary phase in combination with a UV diode array and chiroptical detectors. Isomers with (1R) configuration always eluted before
M Nishizawa et al.
Applied and environmental microbiology, 61(9), 3208-3215 (1995-09-01)
The gene coding for a novel esterase which stereoselectively hydrolyzes the (+)-trans (1R,3R) stereoisomer of ethyl chrysanthemate was cloned from Arthrobacter globiformis SC-6-98-28 and overexpressed in Escherichia coli. The cellular content of the active enzyme reached 33% of the total
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