2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIEN-1-ONE
beta-thujaplicin
CAS: 499-44-5
Molecular Formula: C10H12O2
2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIEN-1-ONE - Names and Identifiers
| Name | beta-thujaplicin |
| Synonyms | Hinokitiol HINOKITIOL B-THUJAPLICIN BETA-THUJAPLICIN beta-thujaplicin BETA-THUJAPLICINE Beta-Thujaplicine 2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIENE 2-HYDROXY-4-ISOPROPYLCYCLOHEPTA-2,4,6-TRIEN-1-ONE 2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIEN-1-ONE 2-hydroxy-6-isopropyl-cyclohepta-2,4,6-trien-1-one 2-hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one |
| CAS | 499-44-5 |
| EINECS | 207-880-7 |
| InChI | InChI=1/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12) |
2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIEN-1-ONE - Physico-chemical Properties
| Molecular Formula | C10H12O2 |
| Molar Mass | 164.2 |
| Density | 1.0041 (rough estimate) |
| Melting Point | 50-52°C(lit.) |
| Boling Point | 140°C10mm Hg(lit.) |
| Flash Point | 128.1°C |
| Solubility | Insoluble in water |
| Vapor Presure | 8.98E-05mmHg at 25°C |
| Appearance | Colorless, prismatic crystals (recrystallized from anhydrous ethanol) |
| Color | White |
| Merck | 14,9390 |
| pKa | 7.06±0.30(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| 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. |
| Sensitive | Avoid contact with oxides |
| Refractive Index | 1.5190 (estimate) |
| MDL | MFCD00059582 |
| In vitro study | In U87MG and T98G glioma cell lines, hinokitiol demonstrates a dose-dependent decrease in viability, with IC 50 values of 316.5 ± 35.5 and 152.5 ± 25.3 µM, respectively. Hinokitiol represses ALDH activity and self-renewal ability in glioma stem cells, and inhibits in vitro oncogenicity. Hinokitiol also reduces Nrf2 expression in glioma stem cells in a dose-dependent manner. Hinokitiol (0-100 μM) inhibits colon cancer cell growth in a dose- and time-dependent manner. Hinokitiol (5, 10 μM) decreases DNMT1 and UHRF1 mRNA and protein expression, and increases TET1 expression via enhancement of 5hmC level in HCT-116 cells. Furthermore, hinokitiol reduces methylation status and restores mRNA expression of MGMT , CHST10 , and BTG4 genes. |
2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIEN-1-ONE - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | GU4200000 |
2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIEN-1-ONE - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | juniper alcohol, also known as cypress phenol, is a kind of monoterpenoid natural compound with phenolone skeleton extracted by Japanese scientists Anderson from the trunk of Taiwan cypress in 1948. it is a trophenolone compound, has good antibacterial properties, moisturizing properties and pest avoidance effects, and is a highly safe plant ingredient, it can be used as antibacterial and insect repellent. It is the main component of Taiwan Cypress essential oil. It has a wide range of biological activities and strong bactericidal ability. The minimum inhibitory concentration on general bacteria is 10-100ppm. The smell is fragrant and the effect is good. It can kill bacteria and microbacteria in the air, prevent pests from invading the human body, and inhibit human pathogenic bacteria. It has been used to produce shower gel, cosmetics, medicine and other products. Juniper alcohol has an amazing effect on inhibiting Staphylococcus aureus (MRSA). The bacteria often exist in the skin and respiratory tract of the human body, causing skin infections such as sepsis, peritonitis, food poisoning and furuncle abscess. |
| application of whitening agents | tyrosinase is a key enzyme for melanin formation. it can catalyze the conversion of light amino acid and dopa into excellent melanin and brown pigment through multiple ways in human body, thus causing the formation of freckles, chloasma and pregnancy spots. In vitro experiments showed that cypress alcohol had a strong inhibitory effect on tyrosinase bisphenol enzyme. With dopa as substrate, the cypress alcohol concentration (IC50) of 50% was 0.3umol/l. Its inhibitory effect is a reversible process, indicating that cypress alcohol only inhibits the activity of tyrosinase without causing permanent inactivation of the enzyme. The good regulatory mechanism of cypress alcohol on tyrosinase in melanocytes is closely related to its structure. Tyrosinase is a ketone-containing oxidoreductase. The 2-position meridian and 1-position ketone on cypress cycloheptatriene The structure can combine with the copper atom in the active center of tyrosinase to form a tight complex, which leads to a decrease in the catalytic activity of tyrosinase, which is the main way it inhibits the activity of tyrosinase; at the same time, the light group and ketone structure on cypress alcohol can also combine with tyrosinase-substrate complex (ES) to form a ternary complex to regulate the formation of melanin. |
| Preparation method | 1, from methoxycycloheptatriene via isopropyl cycloheptrienone and amino isopropyl cycloheptrienone synthesis. 2, cypress alcohol was synthesized from carvone through six-step reactions such as epoxidation and acetalization. 3, from isopropyl cyclohexanone or isopropyl cyclohexenone is converted into hydroxy nitrile, and isopropyl cycloheptanone is made in two steps, and then oxidized, bromination, and hydrogen bromide preparation. 4, brominated cycloheptadienone reacts with an organic substance, and then catalyzes hydrogenation synthesis. 5, from the addition of cyclopentadiene and a dichlorenone to isopropyl cyclopentadiene, and then solvent, the synthesis of cypress alcohol through a three-step reaction. The first four preparation methods have too many synthetic route steps or raw materials are difficult to obtain, and they cannot actually be produced industrially. Therefore, in recent years, it has mainly focused on the research of the fifth synthesis method. |
| biological activity | Hinokitiol is a volatile oil component isolated from Japanese cypress. it can reduce the expression of Nrf2, the mRNA and protein expression of DNMT1 and UHRF1, and has anti-infection, antioxidant and anti-tumor activities. |
Last Update：2024-04-09 21:54:55
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