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MedKoo Cat#: 592039 | Name: Chrysanthemic acid

Description:

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

Chrysanthemic acid is an insecticide.

Chemical Structure

Chrysanthemic acid
Chrysanthemic acid
CAS#10453-89-1

Theoretical Analysis

MedKoo Cat#: 592039

Name: Chrysanthemic acid

CAS#: 10453-89-1

Chemical Formula: C10H16O2

Exact Mass: 168.1150

Molecular Weight: 168.24

Elemental Analysis: C, 71.39; H, 9.59; O, 19.02

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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

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
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PubMed PMID: 29122986; PubMed Central PMCID: PMC5761793. 4: Tabata J, Ichiki RT. (1S,3R)-cis-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, Ferrisia virgata. J Chem Ecol. 2017 Aug;43(8):745-752. doi: 10.1007/s10886-017-0879-z. Epub 2017 Aug 19. PubMed PMID: 28823100. 5: Abe J, Nagahori H, Tarui H, Tomigahara Y, Isobe N. Metabolism of metofluthrin in rats: I. Identification of metabolites. Xenobiotica. 2018 Feb;48(2):157-169. doi: 10.1080/00498254.2017.1283718. Epub 2017 Feb 5. PubMed PMID: 28092216. 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.