533-75-5 Usage
Description
Tropolone, also known as pyrrole pesticide, is a unique chemical compound with a non-benzenoid aromatic structure. It has gained significant attention due to its broad-spectrum pesticidal and acaricidal properties, as well as its potential applications in various industries.
Uses
Used in Pesticides and Acaricides Industry:
Tropolone is used as a broad-spectrum pesticide and acaricide for controlling boring, piercing-sucking, and chewing insects, as well as mites. It demonstrates better effectiveness than cypermethrin and dicofol, with strong stomach poisoning and contact toxicity. It also lacks mutual resistance with other pesticides, making it a valuable addition to integrated pest management strategies.
Used in Pharmaceutical Industry:
Tropolone serves as a medicine and dye intermediate, contributing to the development of new pharmaceutical products and dyes.
Used in Chemical Synthesis:
As a reagent, tropolone is utilized in the preparation of fused heterocycles and complexes of Ga(III) and In(III), which are essential in various chemical and material science applications.
Used in Analytical Chemistry:
Tropolone acts as a sensitive reagent for detecting reducing sugars, making it a valuable tool in analytical chemistry for identifying and quantifying these sugars in various samples.
Seven-carbon ring compound
Tropolone, also known as tohenone and 2-hydroxygenone, is a kind of seven-carbon ring compound, which is weakly acidic and has the properties of aromatic compounds, double bond and weak ketone. There are more than ten kinds of compounds known in nature containing seven-carbon rings:
Hinokitiol, as a red iron complex, is found in cypress wood in Taiwan.
Alpha- and gamma-thujapricin (β-body is the same as hinokitiol) are found in cypress and coniferous plants. It acts as an antibacterial agent to the wood for anticorrosion
α- body and β-body also exist in the cypress essential oil. Stipitatic acid (6- hydroxyaryl heptanone-4-carboxylic acid) is the metabolite of penicillium, and has an antibacterial effect.
Purpurogallin, as glycoside, is found in the galls of mistletoe plants and can be used as a phenol oxidase test.
As nootkatin of the nootka heartwood and subalkaloids of colchicine and the like of colchicum used as inhibitor.
According to the properties of the compounds above, the scientists speculate that tocophenone plays an important role in the metabolic process of living components. It wss Japanese scientists Tetsuo Nozoe who first paid attention to tropolone in 1936 when he was researching hinokitiol, while the work in Europe and the United States started from the structure of stipitatic acid and colchicine, going further after 1950.
Toxicity
The acute oral toxicity LD50 in rats was 459 mg / kg (female) , 223 mg / kg (male) and (662 mg / kg, rat). The acute dermal toxicity LD(50) in rabbit was no less than 2000mg/kg. There was mild irritation to the eye of rabbits. LC50 in Japanese carp is 0.5mg / L (48h) . An improved test and hamster ovary test, done by Ames, showed no mutations had been caused. Japanese carp LC50 is 0.5mg / L (48h)
Flammability and Explosibility
Notclassified
Synthesis
To a mixture of sodium hydroxide (33 g) with glacial acetic acid (270 ml) was added dropwise via funnel 7,7-dichlorobicyclo[3,2,0]hepta-2-ene-6-ketone (33.5 g) under nitrogen, and the mixture was heated to reflux for 8 hours. After PH was adjusted to 1 with hydrochloric acid (50 ml), the mixture was filtered and extracted with benzene (3 × 90ml). The combined extracts were concentrated in vacuo to give brownish black oil.Fraction of reduced pressure distillation at 100 °C/67 Pa was collected to give gross product as a pale yellow solid. Recrystallization from mixture of dichloromethane and pentane (1/4, V/V) gave analytically pure product Tropolone(17.8 g,77%) as a white needle crystal, m.p. 50~51 °C.
Purification Methods
Crystallise tropolone from hexane or pet ether and sublime it at 40o/4mm. Also distil it at high vacuum. [Beilstein 8 IV 159.]
Check Digit Verification of cas no
The CAS Registry Mumber 533-75-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 3 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 533-75:
(5*5)+(4*3)+(3*3)+(2*7)+(1*5)=65
65 % 10 = 5
So 533-75-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
533-75-5Relevant articles and documents
Plymale, D. L.,Smith, W. H.
, p. 2267 - 2269 (1968)
Chiroptical switching behavior of heteroleptic ruthenium complexes bearing acetylacetonato and tropolonato ligands
Sato, Hisako,Tateyama, Kazunori,Yamazaki, Kana,Yoshida, Jun,Yuge, Hidetaka
, p. 14611 - 14617 (2021/11/04)
Four types of tris-chelate ruthenium complexes bearing acetylacetonato (acac) and tropolonato (trop) ligands were synthesized and optically resolved into Δ and Λ isomers: [Ru(acac)3] (Ru-0), [Ru(acac)2(trop)] (Ru-1), [Ru(acac)(trop)2] (Ru-2), and [Ru(trop)3] (Ru-3). Chiral HPLC chromatograms, electronic circular dichroism (ECD), and vibrational circular dichroism (VCD) of the four ruthenium complexes were systematically investigated. As a result, the absolute configurations of the newly prepared enantiomeric complexes Ru-2 and Ru-3 were determined. For the case of Ru-2, its absolute configuration was also confirmed by single crystal X-ray diffraction analysis. The ECD changes upon chemical oxidation were further investigated for the four complexes. An ECD change in enantiomeric Ru-1 was observed upon oxidation, but the oxidized species soon returned to the neutral state within a few minutes. Enantiomers of Ru-3 also showed explicit ECD changes upon oxidation. Further, the lifetime of the oxidized state was the longest among the four investigated complexes, whereas they racemized in solution at room temperature. In contrast, the enantiomers of heteroleptic complexes (Ru-1 and Ru-2) concurrently exhibited ECD changes, relatively long lifetime of the oxidized state, and nil or quite slow racemization behavior. The coexistence of acac and trop ligands was key to making the competing factors compatible in the resultant ruthenium complexes.
Investigation of self-immolative linkers in the design of hydrogen peroxide activated metalloprotein inhibitors
Jourden, Jody L. Major,Daniel, Kevin B.,Cohen, Seth M.
supporting information; experimental part, p. 7968 - 7970 (2011/08/07)
A series of self-immolative boronic ester protected methyl salicylates and metal-binding groups with various linking strategies have been investigated for their use in the design of matrix metalloproteinase proinhibitors.
Evidence from mechanistic probes for distinct hydroperoxide rearrangement mechanisms in the intradiol and extradiol catechol dioxygenases
Xin, Meite,Bugg, Timothy D. H.
experimental part, p. 10422 - 10430 (2009/02/04)
Three mechanistic probes were used to investigate whether the Criegee rearrangement step of catechol 1,2-dioxygenase (CatA) from Acinetobacter sp. proceeds via a direct 1,2-acyl migration, via homolytic O-O cleavage, or via a benzene oxide-oxepin rearrangement. Incubation of CatA with 3- chloroperoxybenzoic acid led to the formation of a 9:1 mixture of 2-chlorophenol and 3-chlorophenol, via a mechanism involving O-O homolytic cleavage. Incubation of CatA with 2-hydroperoxy-2-methylcyclohexanone led to formation of 5,6-diketoheptan-1-ol, also consistent with an O-O homolytic cleavage mechanism, and not consistent with a direct 1,2-acyl migration. No reaction product was isolated from incubation of CatA with 6-hydroxymethyl-6-methylcyclohexa-2,4- dienone, an analogue that is able to undergo the benzene oxide-oxepin rearrangement, but not able to undergo O-O homolytic cleavage. In contrast, incubation of extradiol dioxygenase MhpB from Escherichia coli with 6-hydroxymethyl-6-methylcyclohexa2,4-dienone led to the formation of a 2-tropolone ring expansion product, consistent with a direct 1,2-alkenyl migration for extradiol cleavage. Taken together, the results imply different mechanisms for the Criegee rearrangement steps of intradiol and extradiol catechol dioxygenases: a direct 1,2-alkenyl migration for extradiol cleavage and an O-O homolytic cleavage mechanism for intradiol cleavage.