2-Hydroxycyclohepta-2,4,6-trien-1-one
Tropolone
CAS: 533-75-5
Molecular Formula: C7H6O2
2-Hydroxycyclohepta-2,4,6-trien-1-one - Names and Identifiers
| Name | Tropolone |
| Synonyms | Tropolone a-Tropolone TROPOLONE FOR SYNTHESIS 5 G TROPOLONE FOR SYNTHESIS 1 G TROPOLONE FOR SYNTHESIS 25 G 2-Hydroxy-2,4,6-cycloheptatrienone 2-Hydroxycyclohepta-2,4,6-trien-1-one 2-hydroxycyclohepta-2,4,6-trien-1-one 2-Hydroxy-2,4,6-cycloheptatrien-1-one 2-Hydroxycycloheptane-2,4,6-triene-1-one |
| CAS | 533-75-5 |
| EINECS | 208-577-2 |
| InChI | InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9) |
2-Hydroxycyclohepta-2,4,6-trien-1-one - Physico-chemical Properties
| Molecular Formula | C7H6O2 |
| Molar Mass | 122.12 |
| Density | 1.1483 (rough estimate) |
| Melting Point | 50-52 °C (lit.) |
| Boling Point | 80-84 °C/0.1 mmHg (lit.) |
| Flash Point | >230°F |
| Water Solubility | Soluble in water. |
| Solubility | 40.9g/l (experimental) |
| Vapor Presure | 3.4Pa at 25℃ |
| Appearance | Crystalline Powder |
| Color | Off-white to cream-beige |
| BRN | 1904978 |
| pKa | 6.7(at 25℃) |
| Storage Condition | 2-8°C |
| Sensitive | Hygroscopic |
| Refractive Index | 1.5286 (estimate) |
| MDL | MFCD00004158 |
| Use | Between pharmaceutical intermediates. |
2-Hydroxycyclohepta-2,4,6-trien-1-one - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | GU4075000 |
| FLUKA BRAND F CODES | 8-10-23 |
| HS Code | 29144090 |
2-Hydroxycyclohepta-2,4,6-trien-1-one - Reference
| Reference Show more | 1. [IF=4.952] Yulong Wei et al."Characterization of blueberry (Vaccinium corymbosum L.) catechol oxidases III binding mechanism in response to selected substrates and inhibitors."Lwt Food Sci Technol. 2022 Mar;158:113142 |
2-Hydroxycyclohepta-2,4,6-trien-1-one - Reference Information
| update date: | 2022/11/14 8:43:08 |
| LogP | 1.58 at 23℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| Seven-carbon cyclic compound | Cycloheptanenone is a seven-carbon cyclic compound, also known as trophenone, 2-hydroxyheptaenone, It is weakly acidic, has the characteristics of aromatic compounds, double bond and weak ketone. There are more than ten kinds of compounds known to contain seven-carbon rings in nature: 1, cypress alcohol (hinokitiol) exists as a red iron complex in Taiwan silk cypress wood. 2,α-and γ-garendonin (thujapricin,β-body is the same as cypress alcohol) exists in cypress and coniferous plants. It has antiseptic effect on wood as an antibacterial substance of the genus Queensway. 3,α-and β-bodies also exist in cypress essential oil. Dense penicillic acid (stipitatic acid, 6-hydroxyarylhepton-4-carboxylic acid) is formed as a metabolite of the genus Penicillium and has an antibacterial effect. 4, red purple gallin (purpurogallin) as a glycoside exists in the gall of the genus Fagaceae, can be used as a phenol oxidase test. 5, Nutka nootkatensis (nootkatin) and colchicine as an inhibitory substance in the heartwood of Cha- maecyparis cypress (Cha-) and its similar parabine alkaloids of the genus Colchicine (Colchicum). According to the properties of the above compounds, scientists speculate that tolophenone will play an important role in the metabolism of living ingredients. In 1936, the Japanese scientist Nozomi Tetsuo first began to pay attention to cycloheptanenone when studying Japanese cypress, while Europe and the United States began to study the structure of stipitatic acid and colchicine, and more in-depth research It was after 1950. |
| Biological activity | Tropolone are tropone derivatives with hydroxyl groups at position 2, and are precursors of many Azulene derivatives, such as 2-methylazulene-1-carboxylate. Tropolone is a potent mushroom tyrosinase inhibitor with an IC50 of 0.4 μM, and its inhibitory effect can be reversed by dialysis or excess CU2. |
| target | IC50: 0.4 μM (mushroom tyrosinase) |
| Use | Used as an intermediate in medicine and dyes |
Last Update：2024-04-09 19:05:12
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