Chrysanthemic acid

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 592039

CAS#: 10453-89-1

Description: Chrysanthemic acid is an insecticide.

Chemical Structure

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Chrysanthemic acid
CAS# 10453-89-1
Instruction

Theoretical Analysis

MedKoo Cat#: 592039
Name: Chrysanthemic acid
CAS#: 10453-89-1
Chemical Formula: C10H16O2
Exact Mass: 168.12
Molecular Weight: 168.240
Elemental Analysis: C, 71.39; H, 9.59; O, 19.02

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Chrysanthemic acid; NSC 11779; NSC-11779; NSC11779

IUPAC/Chemical Name: 2,2-Dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid

InChi Key: XLOPRKKSAJMMEW-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)

SMILES Code: O=C(C1C(C)(C)C1/C=C(C)\C)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 168.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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6: Khan S, Upadhyay S, Khan F, Tandon S, Shukla RK, Ghosh S, Gupta V, Banerjee S, Ur Rahman L. Comparative transcriptome analysis reveals candidate genes for the biosynthesis of natural insecticide in Tanacetum cinerariifolium. BMC Genomics. 2017 Jan 9;18(1):54. doi: 10.1186/s12864-016-3409-4. PubMed PMID: 28068903; PubMed Central PMCID: PMC5220608.

7: Fan J, Zareyan S, Zhao W, Shimizu Y, Pfeifer TA, Tak JH, Isman MB, Van den Hoven B, Duggan ME, Wood MW, Wellington CL, Kulic I. Identification of a Chrysanthemic Ester as an Apolipoprotein E Inducer in Astrocytes. PLoS One. 2016 Sep 6;11(9):e0162384. doi: 10.1371/journal.pone.0162384. eCollection 2016. PubMed PMID: 27598782; PubMed Central PMCID: PMC5012716.

8: Sakamori K, Ono N, Ihara M, Suzuki H, Matsuura H, Tanaka K, Ohta D, Kanaya S, Matsuda K. Selective regulation of pyrethrin biosynthesis by the specific blend of wound induced volatiles in Tanacetum cinerariifolium. Plant Signal Behav. 2016;11(4):e1149675. doi: 10.1080/15592324.2016.1149675. PubMed PMID: 26918634; PubMed Central PMCID: PMC4883863.

9: Ferroni C, Bassetti L, Borzatta V, Capparella E, Gobbi C, Guerrini A, Varchi G. Polyenylcyclopropane carboxylic esters with high insecticidal activity. Pest Manag Sci. 2015 May;71(5):728-36. doi: 10.1002/ps.3842. Epub 2014 Jul 3. PubMed PMID: 24899413.

10: Ramirez AM, Stoopen G, Menzel TR, Gols R, Bouwmeester HJ, Dicke M, Jongsma MA. Bidirectional secretions from glandular trichomes of pyrethrum enable immunization of seedlings. Plant Cell. 2012 Oct;24(10):4252-65. doi: 10.1105/tpc.112.105031. Epub 2012 Oct 26. PubMed PMID: 23104830; PubMed Central PMCID: PMC3517248.

11: Kikuta Y, Ueda H, Takahashi M, Mitsumori T, Yamada G, Sakamori K, Takeda K, Furutani S, Nakayama K, Katsuda Y, Hatanaka A, Matsuda K. Identification and characterization of a GDSL lipase-like protein that catalyzes the ester-forming reaction for pyrethrin biosynthesis in Tanacetum cinerariifolium- a new target for plant protection. Plant J. 2012 Jul;71(2):183-93. doi: 10.1111/j.1365-313X.2012.04980.x. Epub 2012 May 7. PubMed PMID: 22385412.

12: Elroby SA, Aziz SG. Understanding the decomposition reaction mechanism of chrysanthemic acid: a computational study. Chem Cent J. 2011 Oct 30;5:66. doi: 10.1186/1752-153X-5-66. PubMed PMID: 22035035; PubMed Central PMCID: PMC3247183.

13: Ujihara K, Mori T, Matsuo N. Recent advances of pyrethroids for household use. Top Curr Chem. 2012;314:31-48. doi: 10.1007/128_2011_253. Review. PubMed PMID: 22025062.

14: Nishizawa M, Yabusaki Y, Kanaoka M. Identification of the catalytic residues of carboxylesterase from Arthrobacter globiformis by diisopropyl fluorophosphate-labeling and site-directed mutagenesis. Biosci Biotechnol Biochem. 2011;75(1):89-94. PubMed PMID: 21266781.

15: Mitsukura K, Shimizu M, Matsushita K, Yoshida T, Nagasawa T. Characteristics and function of Alcaligenes sp. NBRC 14130 esterase catalysing the stereo-selective hydrolysis of ethyl chrysanthemate. J Appl Microbiol. 2010 Apr;108(4):1263-70. doi: 10.1111/j.1365-2672.2009.04522.x. Epub 2009 Sep 13. PubMed PMID: 19778353.

16: Krief A, Jeanmart S, Kremer A. Diastereoselective bromination of compounds bearing a cyclohex-3-enol moiety: application to the enantioselective synthesis of (1R)-cis-deltamethrinic acid. J Org Chem. 2008 Dec 19;73(24):9795-7. doi: 10.1021/jo8022507. PubMed PMID: 19007137.

17: Krief A, Gondal HY, Kremer A. Selected regiocontrolled transformations applied to the synthesis of (1S)-cis-chrysanthemic acid from (1S)-3,4-epoxy-2,2,5,5-tetramethylcyclohexanol. Chem Commun (Camb). 2008 Oct 21;(39):4753-5. doi: 10.1039/b808695h. Epub 2008 Aug 26. PubMed PMID: 18830482.

18: Rosini G, Borzatta V, Boschi F, Candido G, Marotta E, Righi P. The racemate cage. Influence of p(1),n(1) salt occurrence on enantiomer separation processes. The case of trans-chrysanthemic acid. Chem Commun (Camb). 2007 Jul 14;(26):2717-9. Epub 2007 Apr 19. PubMed PMID: 17594031.

19: Rosini G, Ayoub C, Borzatta V, Mazzanti A, Marotta E, Righi P. p1,n1 salts: Self-assembled supramolecular structures sequestering racemates. Diastereomeric separation and enantiomeric enrichment of trans-chrysanthemic acid. Chem Commun (Camb). 2006 Nov 4;(41):4294-6. Epub 2006 Aug 21. PubMed PMID: 17047845.

20: Paingankar M, Jain M, Deobagkar D. Biodegradation of allethrin, a pyrethroid insecticide, by an acidomonas sp. Biotechnol Lett. 2005 Dec;27(23-24):1909-13. PubMed PMID: 16328989.