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Tropolone Basic information Seven-carbon ring compound Uses Toxicity Product Name: Tropolone Synonyms: 2-Hydroxycyclohepta-2,4,6-trien-1-one;a-Tropolone;2-Hydroxycycloheptane-2,4,6-triene-1-one;Tropolone, 98% 1GR;Tropolone, 98% 5GR;TROPOLONE FOR SYNTHESIS 5 G;TROPOLONE FOR SYNTHESIS 1 G;TROPOLONE FOR SYNTHESIS 25 G CAS: 533-75-5 MF: C7H6O2 MW: 122.12 EINECS: 208-577-2 Product Categories: Tropolones;Tropolones & Azulenes;Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks Mol File: 533-75-5.mol   Tropolone Chemical Properties Melting point  50-52 °C (lit.) Boiling point  80-84 °C/0.1 mmHg (lit.) density  1.1483 (rough estimate) refractive index  1.5286 (estimate) Fp  >230 °F storage temp.  2-8°C solubility  40.9g/l (experimental) pka 6.7(at 25℃) form  Crystalline Powder color  Off-white to cream-beige Water Solubility  Soluble in water. Sensitive  Hygroscopic BRN  1904978 CAS DataBase Reference 533-75-5(CAS DataBase Reference) NIST Chemistry Reference 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-(533-75-5)   Safety Information Hazard Codes  Xi Risk Statements  22-36/37/38-37/38-41 Safety Statements  22-24/25-36/37/39-36-26 WGK Germany  3 RTECS  GU4075000 F  8-10-23 HS Code  29144090 MSDS Information Provider Language 2-Hydroxycyclohepta-2,4,6-trienone English SigmaAldrich English ACROS English ALFA English   Tropolone Usage And Synthesis 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. Uses Known as pyrrole pesticide, acaricide with new structure, it has been proved to have good biological control effect on boring, piercing-sucking and chewing insects and mites, better than cypermethrin and cypermethrin. Also its acaricidal activity is stronger than dicofol and tricyclic tin. This agent is characterized with the following: broad-spectrum pesticide and acaricide; both stomach poisoning and contact toxicity; no mutual resistance with other pesticides; moderate residual activity in crops; selective and systemic activity in nutrient solution absorbed by root system; moderate oral toxicity and lower dermal toxicity to mammalian life; low effective spray rate (100g active ingredient / hm2). Its significant insecticidal, acaricidal activity and unique chemical structure has received widespread attention and attention. 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) Chemical Properties White to light yellow crystalline Uses Reagent for the preparation of fused heterocycles1 and complexes of Ga(III) and In(III).2 Used as medicine and dye intermediates. Uses Tropolone is a sensitive reagent for reducing sugars. A non-benzenoid aromatic compound, Reagent for the preparation of fused heterocycles and complexes of Ga(III) and In(III). 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.]   Tropolone Preparation Products And Raw materials Raw materials Bicyclo[3.2.0]hept-2-ene, 6,6,7,7-tetrafluoro--->Cycloheptanone, 2-hydroxy--->1,3-Cycloheptadiene, 5,5,6,6-tetrafluoro--->1,4-Cycloheptadiene, 6,6,7,7-tetrafluoro--->Cycloheptatriene-->7,7-DICHLOROBICYCLO[3.2.0]HEPT-2-EN-6-ONE Preparation Products CYCLOHEPTENE   Product Name: Hinokitiol Synonyms: HINOKITIOL;BETA-THUJAPLICIN;BETA-THUJAPLICINE;B-THUJAPLICIN;2-HYDROXY-4-ISOPROPYLCYCLOHEPTA-2,4,6-TRIEN-1-ONE;2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIEN-1-ONE;2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIENE;2-hydroxy-6-isopropyl-cyclohepta-2,4,6-trien-1-one CAS: 499-44-5 MF: C10H12O2 MW: 164.2 EINECS: 207-880-7 Product Categories: Tropolones;Tropolones & Azulenes Mol File: 499-44-5.mol   Hinokitiol Chemical Properties Melting point  50-52 °C(lit.) Boiling point  140 °C10 mm Hg(lit.) density  1.0041 (rough estimate) refractive index  1.5190 (estimate) storage temp.  Sealed in dry,Room Temperature solubility  Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml). pka 7.06±0.30(Predicted) form  solid color  White Merck  14,9390 Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 4 months. CAS DataBase Reference 499-44-5(CAS DataBase Reference) NIST Chemistry Reference 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-(499-44-5) EPA Substance Registry System 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- (499-44-5)   Safety Information Hazard Codes  Xn Risk Statements  22 Safety Statements  36 WGK Germany  3 RTECS  GU4200000 MSDS Information   Hinokitiol Usage And Synthesis Chemical Properties Hinokitiol is a tropolone derivative containing an unsaturated seven-membered carbon ring. It is a monoterpenoid – cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. It is a enol and a cyclic ketone. It derives from a hydride of a cyclohepta-1,3,5-triene. Thujaplicins are soluble in organic solvents and aqueous buffers.Hinokitiol provides acetone on vigorous oxidation and gives the saturated monocyclic diol upon catalytic hydrogenation.It is stable to alkali and acids, forming salts or remaining unchanged, but does not convert to catechol derivatives. Hinokitiol, as other thujaplicins and tropolones, reversibly binds metal ions. It forms complex salts with metal ions. benefits Hinokitiol (β-thujaplicin) is a naturally occurring antioxidant, found in the heartwood of certain plants. It acts as a metal chelator and, also, enhances the activity of superoxide dismutase (Huang et al., 2015). It was found to be very protective in the assay. It has not been previously studied as a HC protectant. In addition to its antioxidant properties, hinokitiol has been shown to reduce inflammation via suppression of NFκB, and metalloproteinases, and to activate caspase 3. The former activities could contribute to its protective effect. Hinokitiol is a superpower ingredient that has anti-inflammatory, antioxidant, antibacterial, anti-fungal and anti-melanogenic properties. Best of all, hinokitiol is as gentle as it is powerful. Hinokitiol’s properties allow it to target the inflammatory redness and blemishes seen in rosacea and acne. Hinokitiol is effective against P. acnes bacteria, and there is no known acquired resistance to it, unlike other prescription antibiotics. Safety The safety of hinokitiol has been tested in rats and no carcinogenic effect to rats was found.In 2006, hinokitiol was categorized under the Domestic substances list (DSL) in Canada as non-persistent, non-bioaccumulative and non-toxic to aquatic organisms. Description Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins.Hinokitiol is used in oral and skin care products,and is a food additive used in Japan. Uses Antibacterial additive in foods, cosmetics, eye drops and toothpaste. Uses Hinokitiol is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol has inhibitory effects on Chlamydia trachomatis and may be clinically useful as a topical drug. Definition ChEBI: A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities. Anticancer Research Studied in xenograft tumors such lung adenocarcinoma cell, EGFR-TKI-resistantlines PC9-IR and H1975 in which the growth inhibition was observed, a novel antitumormechanism was hypothesized. In summary, the hinokitiol can induce DNAdamage and autophagy (Rodrigues et al. 2015). References 1) Ido et al (1999) Induction of apoptosis by hinokitiol, a potent iron chelator, in teratocarcinoma F9 cells is mediated through the activation of caspase-3; Cell Prolif., 32 63 2) Suzuki et al. (2000) Hinokitiol, a selective inhibitor of the platelet-type isozyme of arachidonate 12-lipoxygenase; Biochem. Biophys. Res. Commun., 275 885 3) Morita et al. (2007) The mechanism of the bactericidal activity of hinokitiol; Biocontrol Sci., 12 101 4) Liu and Yamauchi (2006) Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carcinoma cell lines; Biochem. Biophys. Res. Commun., 351 26 5) Lee et al. (2010) Hinokitiol activates the hypoxia-inducible factor (HIF) pathway through inhibition of HIF hydroxylases; Biochem. Biophys. Res. Commun., 396 370   Hinokitiol Preparation Products And Raw materials Raw materials 1,3-Cycloheptadiene,1-methoxy-6-(1-methylethyl)-(9CI)-->Boric acid, mono(1-methylethyl) ester-->2,4,6-Cycloheptatrien-1-one, 4-chloro-2-hydroxy--->beta-dolabrin-->3-Cycloheptene-1,2-dione,6-(1-methylethyl)-,(6S)-(9CI)-->2,4,6-Cycloheptatrien-1-one, 4-bromo-2-hydroxy--->2,4,6-Cycloheptatrien-1-one,2-amino-6-(1-methylethyl)-(9CI)-->Cycloheptanone, 3-(1-methylethyl)--->1,3,5-Cycloheptatriene, 1-methoxy-

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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research.  Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products.  Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation.  We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.

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