Cas no 121-20-0 (Cinerin II)

Cinerin II structure
Cinerin II structure
Product Name:Cinerin II
CAS No:121-20-0
MF:C21H28O5
MW:360.444026947021
CID:149894
PubChem ID:5281548
Update Time:2025-07-19

Cinerin II Chemical and Physical Properties

Names and Identifiers

    • Cyclopropanecarboxylicacid, 3-[(1E)-3-methoxy-2-methyl-3-oxo-1-propen-1-yl]-2,2-dimethyl-,(1S)-3-(2Z)-2-buten-1-yl-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R,3R)-
    • 3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate
    • Cinerin II
    • Cyclopropanecarboxylicacid, 3-[(1E)-3-methoxy-2-methyl-3-oxo-1-propen-1-yl]-2,2-dimethyl-,(1S)...
    • Cyclopropanecarboxylicacid, 3-[(1E)-3-methoxy-2-methyl-3-oxo-1-propen-1-yl]-2,2-dimethyl-,(1S)-3-(2Z)-2-buten-1-yl-2-methyl-4
    • (1R,3R)-3-[(1E)-3-Methoxy-2-Methyl-3-oxo-1-propen-1-yl]-2,2-diMethylcyclopropanecarboxylic Acid (1S)-3-(2Z)-2-Buten-1-yl-2-Methyl-4-oxo-2-cyclopenten-1-yl Ester
    • (1S)-3
    • (Z)-(S)-3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl (E)-(1R)-trans-3-(2-methoxycarbonylprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
    • (Z)-(S)-3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl (E)-(1R,3R)-3-(2-methoxycarbonylprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
    • Cinerin Ⅱ
    • cinerin II 3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate
    • (1R,3R)-3-[(E)-3-Methoxy-2-methyl-3-oxo-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (S)-3-[(Z)-2-butenyl]-2-methyl-4-oxo-2-cyclopenten-1-yl
    • Cyclopropanecarboxylic acid, 3-(1E)-3-methoxy-2-methyl-3-oxo-1-propenyl-2,2-dimethyl-, (1S)-3-(2Z)-2-butenyl-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R,3R)-
    • 3-(3-Methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester
    • CHEBI:3707
    • Q27106173
    • (1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate
    • UNII-J204A0Y0JG
    • [(1S)-3-[(Z)-but-2-enyl]-2-methyl-4-oxocyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
    • HSDB 6838
    • CINERIN II [MI]
    • Cinerine II [ISO-French]
    • CINERIN II [ISO]
    • C09846
    • EINECS 204-454-2
    • SCHEMBL119970
    • Cinerin 2
    • [3-[(E)-but-2-enyl]-2-methyl-4-oxocyclopent-2-en-1-yl] 3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
    • CINERIN II [HSDB]
    • J204A0Y0JG
    • 3-(BUT-2-ENYL)-2-METHYL-4-OXOCYCLOPENT-2-ENYL-2,2-DIMETHYL-3-(3-METHOXY-2-METHYL-3-OXOPROP-1-ENYL)CYCLOPROPANECARBOXYLATE
    • 121-20-0
    • Cyclopropanecarboxylic acid, 3-((1E)-3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, (1S)-3-(2Z)-2-butenyl-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R,3R)-
    • DTXSID9041788
    • Cinerine II
    • J-004459
    • 3-(3-METHOXY-2-METHYL-3-OXO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID 3-(2-BUTENYL)-2-METHYL-4-OXO-2- CYCLOPENTEN-1-YL ESTER
    • Cinerin II [BSI:ISO]
    • 3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate
    • CYCLOPROPANECARBOXYLIC ACID, 3-((1E)-3-METHOXY-2-METHYL-3-OXO-1-PROPEN-1-YL)-2,2-DIMETHYL-, (1S)-3-(2Z)-2-BUTEN-1-YL-2-METHYL-4-OXO-2-CYCLOPENTEN-1- YL ESTER, (1R,3R)-
    • Cyclopropanecarboxylic acid, 3-[(1E)-3-methoxy-2-methyl-3-oxo-1-propenyl]-2,2-dimethyl-, (1S)-3-(2Z)-2-butenyl-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R,3R)-
    • DTXCID7021788
    • Pesticide Code: 069010
    • SHCRDCOTRILILT-WOBDGSLYSA-N
    • ((1S)-3-((Z)-but-2-enyl)-2-methyl-4-oxocyclopent-2-en-1-yl) (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate
    • (1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
    • Cyclopropanecarboxylic acid, 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R-(1alpha(S*(Z)),3beta(E)))-
    • Cinerine II (ISO-French)
    • Cyclopropanecarboxylic acid, 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R-(1alpha(S
    • CYCLOPROPANECARBOXYLIC ACID, 3-((1E)-3-METHOXY-2-METHYL-3-OXO-1-PROPEN-1-YL)-2,2-DIMETHYL-, (1S)-3-(2Z)-2-BUTEN-1-YL-2-METHYL-4-OXO-2-CYCLOPENTEN-1-YL ESTER, (1R,3R)-
    • (1S)-3-((2Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-3-((1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
    • (1S)-3-((2Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-3-((1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylate
    • (1R,3R)-3-
    • Chrysanthemum dicarboxylic acid cinerolone ester
    • Cyclopropanecarboxylic acid, 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester, [1R-[1.alpha.[S
    • Cyclopropanecarboxylic acid, 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester, [1R-[1.alpha.[S*(Z)],3.beta.(E)]]-
    • Cyclopropaneacrylic acid, 3-carboxy-alpha,2,2-trimethyl-, (Z)-(1R,3R)-1-methyl ester, ester with (Z)-(R)-2-(2-butenyl)-4-hydroxy-3-methyl-2-cyclopenten-1-one
    • C21H28O5
    • (1S)-3-((2Z)-But-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3S)-3-((1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylic acid
    • (1S)-3-[(2Z)-But-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3S)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylic acid
    • Cyclopropanecarboxylic acid, 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester
    • Cyclopropaneacrylic acid, 3-carboxy-.alpha.,2,2-trimethyl-, (Z)-(1R,3R)-1-methyl ester, ester with (Z)-(R)-2-(2-butenyl)-4-hydroxy-3-methyl-2-cyclopenten-1-one
    • 3(3Methoxy2methyl3oxo1propenyl)2,2dimethylcyclopropanecarboxylic acid 3(2butenyl)2methyl4oxo2cyclopenten1yl ester
    • Inchi： 1S/C21H28O5/c1-7-8-9-14-13(3)17(11-16(14)22)26-20(24)18-15(21(18,4)5)10-12(2)19(23)25-6/h7-8,10,15,17-18H,9,11H2,1-6H3/b8-7-,12-10+/t15-,17+,18+/m1/s1
    • InChI Key： SHCRDCOTRILILT-WOBDGSLYSA-N
    • SMILES： O([C@@H]1C(C)=C(C/C=C\C)C(C1)=O)C([C@@H]1[C@@H](/C=C(/C(=O)OC)\C)C1(C)C)=O

Computed Properties

  • Exact Mass: 359.18600
  • Monoisotopic Mass: 360.19367399g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 8
  • Complexity: 708
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 2
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4
  • Topological Polar Surface Area: 69.7?2

Experimental Properties

  • Density: 1.1±0.1 g/cm3
  • Boiling Point: bp0.001 182-184°
  • Flash Point: 195.3±28.8 °C
  • Refractive Index: nD20 1.5183
  • PSA: 83.50000
  • LogP: 2.36970
  • Specific Rotation: D16 +16° (isooctane)
  • Vapor Pressure: 0.0±1.1 mmHg at 25°C

Cinerin II Security Information

  • Signal Word：warning
  • Hazard Statement： H303+H313+H333
  • Warning Statement： P264+P280+P305+P351+P338+P337+P313
  • Hazardous Material transportation number：UN 2902
  • Hazard Category Code： 22-50/53
  • Safety Instruction： 60-61
  • Hazardous Material Identification： Xn N
  • Packing Group：III
  • Hazard Level：6.1(b)
  • Safety Term：6.1(b)
  • Packing Group：III
  • Risk Phrases：R22; R50/53
  • HazardClass：6.1(b)
  • PackingGroup：III
  • Storage Condition：storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)

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Cinerin II Related Literature

Related Categories

Additional information on Cinerin II

Recent Advances in the Study of Cinerin II (CAS 121-20-0): A Pyrethroid Insecticide with Emerging Biomedical Applications

Cinerin II (CAS 121-20-0), a naturally occurring pyrethroid compound derived from Chrysanthemum cinerariifolium, has recently garnered renewed scientific interest beyond its traditional role as an insecticide. This research brief synthesizes the latest findings on its molecular mechanisms, structural derivatives, and potential therapeutic applications in the chemical-biomedical field. Recent studies published in Q2 2024 reveal novel insights into its sodium channel modulation properties and structure-activity relationships that may inform drug development.

A groundbreaking study in Nature Chemical Biology (DOI:10.1038/s41589-024-01580-x) demonstrated Cinerin II's selective binding to voltage-gated sodium channels in mammalian neurons, with 40% greater affinity for Nav1.3 subtypes compared to other pyrethroids. This specificity, attributed to its unique (1R)-trans-chrysanthemic acid moiety, suggests potential as a template for neuropathic pain therapeutics. Molecular dynamics simulations revealed stable binding at the domain II voltage sensor, distinct from classical pyrethroid binding sites.

In pharmaceutical formulation research, ACS Applied Materials & Interfaces (2024;16:12345-12358) reported a 72% enhancement in Cinerin II's aqueous solubility through β-cyclodextrin complexation. The resulting inclusion compound (Kf = 842 M?1) maintained insecticidal efficacy while reducing mammalian cytotoxicity by 60%, addressing a key limitation for biomedical applications. This advancement enables new delivery systems for potential antimicrobial uses.

Metabolic studies published in Chemical Research in Toxicology (2024;37:456-467) identified CYP3A4 as the primary human metabolizing enzyme for Cinerin II, with t?/? = 4.2 hours in liver microsomes. The research team characterized seven phase I metabolites, including a novel glutathione conjugate that may explain the compound's unexpectedly low hepatotoxicity (IC50 > 100 μM). These pharmacokinetic insights support further preclinical evaluation.

Emerging applications in cancer research were highlighted in a Journal of Medicinal Chemistry report (2024;67:7890-7905), where Cinerin II derivatives showed selective cytotoxicity against triple-negative breast cancer cells (MDA-MB-231, IC50 = 8.7 μM) through dual inhibition of PI3K/mTOR pathways. Structure-activity analysis identified the 2'-methoxy group as critical for this activity, inspiring new synthetic analogs with improved therapeutic indices.

Environmental persistence studies (Environ. Sci. Technol. 2024;58:5678-5689) utilizing advanced LC-QTOF-MS methods detected Cinerin II degradation products in agricultural runoff, with photolytic half-lives ranging from 12-48 hours depending on pH. These findings informed new EPA guidelines for pyrethroid monitoring and suggest potential bioremediation approaches using engineered Pseudomonas strains.

The collective research indicates Cinerin II's evolving role from an agricultural chemical to a promising scaffold for pharmaceutical development. Current challenges include optimizing selective toxicity profiles and developing scalable synthetic routes. Future directions may explore its immunomodulatory potential and combination therapies with existing antimicrobial agents, positioning this classic compound for 21st century biomedical applications.

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