Precocene II | CAS# 644-06-4 | Insecticide

MedKoo Cat#: 573467 | Name: Precocene II

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Description:

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

Precocene II is an antiallotropin compound capable of inhibiting juvenile hormone biosynthesis. Precocene II has antibacterial, antifungal, insecticidal, and antioxidant activities.

Chemical Structure

Precocene II

CAS#644-06-4

Theoretical Analysis

MedKoo Cat#: 573467

Name: Precocene II

CAS#: 644-06-4

Chemical Formula: C13H16O3

Exact Mass: 220.1099

Molecular Weight: 220.27

Elemental Analysis: C, 70.89; H, 7.32; O, 21.79

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 265.00
250mg	USD 415.00
500mg	USD 700.00
1g	USD 1,350.00

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Related CAS #

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Synonym

Ageratochromene; AI3-36847; BRN 0160683; Precocene II; Precocene-II; BRN0160683;

IUPAC/Chemical Name

2H-1-Benzopyran, 6,7-dimethoxy-2,2-dimethyl-

InChi Key

PTIDGSWTMLSGAH-UHFFFAOYSA-N

InChi Code

1S/C13H16O3/c1-13(2)6-5-9-7-11(14-3)12(15-4)8-10(9)16-13/h5-8H,1-4H3

SMILES Code

c12c(cc(OC)c(c1)OC)OC(C)(C)C=C2

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

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Precocene II is an antiallotropin compound capable of inhibiting juvenile hormone biosynthesis.

In vitro activity:

Precocene II increased the superoxide level in mitochondria as well as the amount of oxidized mitochondrial proteins. Ascorbic acid, glutathione, and α-tocopherol promoted trichothecene production by the fungus. These antioxidants compensated for the inhibitory activity of precocene II on trichothecene production. Reference: PLoS One. 2015 Aug 6;10(8):e0135031. https://pubmed.ncbi.nlm.nih.gov/26248339/

In vivo activity:

TBD

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	100.0	453.99

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 220.27 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.

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:

1. Furukawa T, Sakamoto N, Suzuki M, Kimura M, Nagasawa H, Sakuda S. Precocene II, a Trichothecene Production Inhibitor, Binds to Voltage-Dependent Anion Channel and Increases the Superoxide Level in Mitochondria of Fusarium graminearum. PLoS One. 2015 Aug 6;10(8):e0135031. doi: 10.1371/journal.pone.0135031. PMID: 26248339; PMCID: PMC4527739. 2. Hammond AH, Garle MJ, Fry JR. Mechanism of toxicity of precocene II in rat hepatocyte cultures. J Biochem Toxicol. 1995 Oct;10(5):265-273. doi: 10.1002/jbt.2570100507. PMID: 8847709. 1. Furukawa T, Sakamoto N, Suzuki M, Kimura M, Nagasawa H, Sakuda S. Precocene II, a Trichothecene Production Inhibitor, Binds to Voltage-Dependent Anion Channel and Increases the Superoxide Level in Mitochondria of Fusarium graminearum. PLoS One. 2015 Aug 6;10(8):e0135031. doi: 10.1371/journal.pone.0135031. PMID: 26248339; PMCID: PMC4527739. 2. Hammond AH, Garle MJ, Fry JR. Mechanism of toxicity of precocene II in rat hepatocyte cultures. J Biochem Toxicol. 1995 Oct;10(5):265-273. doi: 10.1002/jbt.2570100507. PMID: 8847709.

In vitro protocol:

In vivo protocol:

TBD

1: Ramadan KMA, El-Beltagi HS, Iqbal Z, Bendary ESA. The Synthesis, Fungicidal Activity, and in Silico Study of Alkoxy Analogues of Natural Precocenes I, II, and III. Molecules. 2022 Oct 24;27(21):7177. doi: 10.3390/molecules27217177. PMID: 36364004; PMCID: PMC9658145. 2: Sukmawan YP, Anggadiredja K, Adnyana IK. Anti-neuropathic Pain Mechanistic Study on A. conyzoides Essential Oil, Precocene II, Caryophyllene, or Longifolene as Single Agents and in Combination with Pregabalin. CNS Neurol Disord Drug Targets. 2023;22(6):924-931. doi: 10.2174/1871527321666220418121329. PMID: 35440325. 3: Kumar S, Sharma AK, Kumar B, Shakya M, Patel JA, Kumar B, Bisht N, Chigure GM, Singh K, Kumar R, Kumar S, Srivastava S, Rawat P, Ghosh S. Characterization of deltamethrin, cypermethrin, coumaphos and ivermectin resistance in populations of Rhipicephalus microplus in India and efficacy of an antitick natural formulation prepared from Ageratum conyzoides. Ticks Tick Borne Dis. 2021 Nov;12(6):101818. doi: 10.1016/j.ttbdis.2021.101818. Epub 2021 Sep 4. PMID: 34537543. 4: Pintong AR, Ampawong S, Komalamisra N, Sriwichai P, Popruk S, Ruangsittichai J. Insecticidal and Histopathological Effects of Ageratum conyzoides Weed Extracts against Dengue Vector, Aedes aegypti. Insects. 2020 Apr 3;11(4):224. doi: 10.3390/insects11040224. PMID: 32260093; PMCID: PMC7240669. 5: Huang J, Fang L, Wang S, Liu X, Chen Y, Chen Y, Tian H, Lin S, Tian S, Wei H, Gu X. Molecular cloning, expression profiling, and functional analysis of a broad-complex isoform 2/3 (Br-Z2/Z3) transcription factor in the diamondback moth, Plutella xylostella (L.). Arch Insect Biochem Physiol. 2019 Jun;101(2):e21549. doi: 10.1002/arch.21549. Epub 2019 Apr 3. PMID: 30941822. 6: Kumar KG, Tayade AB, Kumar R, Gupta S, Sharma AK, Nagar G, Tewari SS, Kumar B, Rawat AK, Srivastava S, Kumar S, Ghosh S. Chemo-profiling and bioassay of phytoextracts from Ageratum conyzoides for acaricidal properties against Rhipicephalus (Boophilus) microplus (Acari: Ixodidae) infesting cattle and buffaloes in India. Ticks Tick Borne Dis. 2016 Mar;7(2):342-9. doi: 10.1016/j.ttbdis.2015.12.005. Epub 2015 Dec 9. PMID: 26723275. 7: Sakuda S, Yoshinari T, Furukawa T, Jermnak U, Takagi K, Iimura K, Yamamoto T, Suzuki M, Nagasawa H. Search for aflatoxin and trichothecene production inhibitors and analysis of their modes of action. Biosci Biotechnol Biochem. 2016;80(1):43-54. doi: 10.1080/09168451.2015.1086261. Epub 2015 Sep 17. PMID: 26376763. 8: Furukawa T, Sakamoto N, Suzuki M, Kimura M, Nagasawa H, Sakuda S. Precocene II, a Trichothecene Production Inhibitor, Binds to Voltage-Dependent Anion Channel and Increases the Superoxide Level in Mitochondria of Fusarium graminearum. PLoS One. 2015 Aug 6;10(8):e0135031. doi: 10.1371/journal.pone.0135031. PMID: 26248339; PMCID: PMC4527739. 9: Kashima Y, Nakaya S, Miyazawa M. Volatile composition and sensory properties of Indian herbal medicine-Pavonia odorata-used in Ayurveda. J Oleo Sci. 2014;63(2):149-58. doi: 10.5650/jos.ess13125. Epub 2014 Jan 17. PMID: 24441709. 10: Sakamoto N, Tsuyuki R, Yoshinari T, Usuma J, Furukawa T, Nagasawa H, Sakuda S. Correlation of ATP citrate lyase and acetyl CoA levels with trichothecene production in Fusarium graminearum. Toxins (Basel). 2013 Nov 21;5(11):2258-69. doi: 10.3390/toxins5112258. PMID: 24284828; PMCID: PMC3847725. 11: Triseleva TA. [Antijuvenile influence of the precocene on the development of adult antennae in the apple surface eating tortricid Archips podana Scop. (Lepidoptera: Tortricidae)]. Izv Akad Nauk Ser Biol. 2012 Sep-Oct;(5):501-8. Russian. PMID: 23136738. 12: Adebayo AH, Jig CJ, Zhang YM, He WJ, Zeng GZ, Han HJ, Xu JJ, Akindahunsi AA, Tana NH. A new chromene isolated from Ageratum conyzoides. Nat Prod Commun. 2011 Sep;6(9):1263-5. PMID: 21941894. 13: Singh S, Kumar K. Sensitivity of last larval stadium of Chrysomya megacephala (Fabricius) to anti-allatin ageratochromene Precocene II. Indian J Exp Biol. 2011 Aug;49(8):600-8. PMID: 21870428. 14: Abdelkader MS, Lockwood GB. Volatile oils from the plant and hairy root cultures of Ageratum conyzoides L. Nat Prod Res. 2011 May;25(9):909-17. doi: 10.1080/14786419.2010.531724. PMID: 21547842. 15: Ribeiro VL, dos Santos JC, Martins JR, Schripsema J, Siqueira IR, von Poser GL, Apel MA. Acaricidal properties of the essential oil and precocene II obtained from Calea serrata (Asteraceae) on the cattle tick Rhipicephalus (Boophilus) microplus (Acari: Ixodidae). Vet Parasitol. 2011 Jun 30;179(1-3):195-8. doi: 10.1016/j.vetpar.2011.02.006. Epub 2011 Feb 15. PMID: 21402447. 16: Tsuyuki R, Yoshinari T, Sakamoto N, Nagasawa H, Sakuda S. Enhancement of trichothecene production in Fusarium graminearum by cobalt chloride. J Agric Food Chem. 2011 Mar 9;59(5):1760-6. doi: 10.1021/jf103969d. Epub 2011 Feb 7. PMID: 21299216. 17: Samaneh ET, Tayebeh R, Hassan E, Vahid N. Composition of essential oils in subterranean organs of three species of Valeriana L. Nat Prod Res. 2010 Nov;24(19):1834-42. doi: 10.1080/14786419.2010.482051. PMID: 21104529. 18: Kurade NP, Jaitak V, Kaul VK, Sharma OP. Chemical composition and antibacterial activity of essential oils of Lantana camara, Ageratum houstonianum and Eupatorium adenophorum. Pharm Biol. 2010 May;48(5):539-44. doi: 10.3109/13880200903193336. PMID: 20645797. 19: Ronderos JR. Changes in the corpora allata and epidermal proliferation along the fourth instar of the Chagas disease vector Triatoma infestans. Biocell. 2009 Dec;33(3):149-54. PMID: 20067030. 20: Nogueira JH, Gonçalez E, Galleti SR, Facanali R, Marques MO, Felício JD. Ageratum conyzoides essential oil as aflatoxin suppressor of Aspergillus flavus. Int J Food Microbiol. 2010 Jan 31;137(1):55-60. doi: 10.1016/j.ijfoodmicro.2009.10.017. Epub 2009 Oct 24. PMID: 19906457.