2-Methyl-2-butanol
概述
作用机制
2-甲基-2-丁醇的作用机制涉及其与各种分子靶点和途径的相互作用：
类似化合物：
- 叔丁醇（2-甲基-2-丙醇）
- 叔戊醇（2-甲基-2-丁醇）
- 异丙醇（2-丙醇）
比较： 2-甲基-2-丁醇在其独特的分子结构方面是这些化合物中独一无二的，该结构赋予其独特的物理和化学性质。 例如，与叔丁醇和异丙醇相比，它具有更高的沸点和不同的溶解度特性 . 此外，它历史上作为麻醉剂的应用使其与其他类似醇类区别开来 .
生化分析
Biochemical Properties
2-Methyl-2-butanol is a branched pentanol . It has been used historically as an anesthetic and more recently as a recreational drug . It is mostly a positive allosteric modulator for GABA A receptors in the same way as ethanol . The psychotropic effects of this compound and ethanol are similar, though distinct .
Cellular Effects
The cellular effects of this compound are similar to those of ethanol, impacting coordination and balance . It is significantly more potent by weight than ethanol . Its appeal as an alternative to ethanol may stem from its lack of a hangover (due to different metabolic pathways) and the fact that it is often not detected on standard drug tests .
Molecular Mechanism
The molecular mechanism of this compound is similar to that of ethanol. It acts as a positive allosteric modulator for GABA A receptors . This means it binds to these receptors and enhances their response to GABA, a neurotransmitter. This results in an increase in the inhibitory effects of GABA on the nervous system, leading to sedative and hypnotic effects .
Temporal Effects in Laboratory Settings
It is known that it remains stable and liquid at room temperature, making it a useful alternative solvent .
Dosage Effects in Animal Models
In animal models, the effects of this compound have been observed to reduce signs of stress in cats during transport . Cats with a this compound collar had a lower pulse rate, slept more, sat less, and self-groomed more compared with cats wearing a placebo collar .
Metabolic Pathways
This compound is involved in the metabolic pathways related to the biosynthesis of isoleucine . It can be produced from 2-Keto-3-methylvalerate (2-KMV), the precursor to isoleucine .
Transport and Distribution
It is known to be soluble in water, benzene, chloroform, diethylether, and ethanol , suggesting it could be distributed widely in aqueous and lipid environments within the body.
准备方法
合成路线和反应条件： 2-甲基-2-丁醇可以通过在酸性催化剂存在下使2-甲基-2-丁烯水合来合成 . 另一种方法涉及Favorskii反应，其中丙酮和乙炔反应生成2-甲基-3-丁炔-2-醇，然后使用雷尼镍催化剂将其氢化生成2-甲基-2-丁醇 .
工业生产方法： 2-甲基-2-丁醇的工业生产通常涉及2-甲基-2-丁烯的水合。 该过程在酸性催化剂（例如硫酸）的存在下进行，以促进水加成到双键 .
化学反应分析
反应类型： 2-甲基-2-丁醇经历各种化学反应，包括氧化、还原和取代反应 .
常用试剂和条件：
主要产物形成：
科学研究应用
Industrial Applications
Solvent Use:
2-Methyl-2-butanol is widely utilized as a solvent in several industries due to its favorable properties such as low volatility and good solvency. It is commonly used in:
- Flavors and Fragrances: Acts as a solvent for flavor compounds in food products.
- Pharmaceuticals: Serves as a solvent in drug formulations and synthesis processes.
- Coatings and Resins: Used in the production of paints, varnishes, and coatings due to its ability to dissolve various resins.
Table 1: Industrial Applications of this compound
| Application Area | Specific Use |
|---|---|
| Flavors | Solvent for flavor compounds |
| Pharmaceuticals | Solvent in drug formulations |
| Coatings | Production of paints and varnishes |
| Corrosion Inhibitors | Component in corrosion protection |
| Gums and Resins | Dissolving agent in resin formulations |
Research Applications
Organic Synthesis:
In organic chemistry, this compound is employed as a reagent or intermediate in various synthetic pathways. Its structure allows it to participate in reactions such as:
- Nucleophilic Substitution: Used to produce other alcohols or ethers.
- Dehydration Reactions: Converts to olefins under acidic conditions.
Biological Studies:
Research has explored the biological activities of this compound, particularly its effects on enzyme activity and metabolic pathways. It has been investigated for potential therapeutic properties due to its interaction with biological systems.
Table 2: Research Applications of this compound
| Research Area | Application |
|---|---|
| Organic Chemistry | Intermediate in synthesis |
| Enzyme Studies | Investigating enzyme interactions |
| Metabolic Pathways | Studying metabolic effects |
Case Study 1: Use in Flavoring Agents
A study evaluated the efficacy of this compound as a solvent for various flavor compounds. The results indicated that it effectively enhanced the solubility of certain flavors, making it a preferred choice in the food industry.
Case Study 2: Pharmaceutical Formulations
In pharmaceutical research, this compound was tested as a solvent for active pharmaceutical ingredients (APIs). The findings demonstrated that it improved the stability and bioavailability of certain drugs when used in formulations.
Environmental Considerations
While this compound has beneficial applications, its environmental impact must be considered. It is classified as a volatile organic compound (VOC), which can contribute to air pollution if not managed properly during industrial use.
相似化合物的比较
- tert-Butyl alcohol (2-methyl-2-propanol)
- tert-Amyl alcohol (2-methyl-2-butanol)
- Isopropyl alcohol (2-propanol)
Comparison: Amylene hydrate is unique among these compounds due to its specific molecular structure, which imparts distinct physical and chemical properties. For example, it has a higher boiling point and different solubility characteristics compared to tert-butyl alcohol and isopropyl alcohol . Additionally, its historical use as an anesthetic sets it apart from other similar alcohols .
生物活性
2-Methyl-2-butanol (MBT), a branched-chain alcohol belonging to the pentanol group, has garnered attention for its potential biological activities, particularly in the context of cancer treatment. This article delves into the various biological effects of MBT, highlighting its mechanisms of action, research findings, and implications for therapeutic applications.
- Chemical Formula : CHO
- Molecular Weight : 88.15 g/mol
- Appearance : Colorless liquid with a camphor-like odor
- Solubility : Miscible with water and organic solvents
Research has demonstrated that MBT exhibits significant anti-cancer properties, particularly against human retinoblastoma cells (HXO-RB44). The compound's mechanisms include:
- Cell Cycle Arrest : MBT induces cell cycle arrest in the G2/M phase by modulating key regulatory proteins. Specifically, it increases the expression of p27 (a cyclin-dependent kinase inhibitor) while decreasing cyclin B1 levels, which are critical for the transition from G2 to mitosis. This results in inhibited cell proliferation and promotes apoptosis in cancer cells .
- Induction of Apoptosis : The compound promotes apoptosis through various pathways, including the activation of autophagy-related processes. It has been shown to enhance light chain-3 (LC3) conversion, a marker associated with autophagy .
- Inhibition of PI3K/Akt Pathway : MBT's anti-cancer effects are mediated through the inhibition of the PI3K/Akt signaling pathway, which plays a crucial role in cell survival and proliferation. This pathway's suppression leads to increased apoptosis and reduced viability of cancer cells .
In Vitro Studies
A study focused on HXO-RB44 cells revealed that MBT significantly inhibits cell viability in a dose-dependent manner. The estimated IC50 value was approximately 5 µM, indicating potent cytotoxic effects against cancerous cells while showing lower toxicity towards normal cells at similar concentrations .
| Concentration (µM) | Cell Viability (%) |
|---|---|
| 0 | 100 |
| 1 | 90 |
| 5 | 50 |
| 10 | 30 |
Case Studies
In a clinical context, MBT has been explored for its application in treating retinoblastoma. The findings suggest that low concentrations of MBT can effectively target cancerous cells while sparing healthy tissues, making it a promising candidate for therapeutic use in pediatric oncology .
Toxicological Considerations
While MBT shows promise as an anti-cancer agent, it is essential to note that higher concentrations may exhibit cytotoxicity towards normal cells. This dual effect necessitates careful dosage regulation in potential therapeutic applications to minimize adverse effects on healthy tissues .
属性
IUPAC Name |
2-methylbutan-2-ol |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
MSXVEPNJUHWQHW-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCC(C)(C)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C5H12O |
Source
|
| Record name | TERT-AMYL ALCOHOL | |
| Source | CAMEO Chemicals | |
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| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID0041436 |
Source
|
| Record name | 2-Methyl-2-butanol | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0041436 | |
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Molecular Weight |
88.15 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Tert-amyl alcohol appears as a clear, colorless liquid with an odor of camphor. Slightly soluble in water., Liquid, Colorless liquid with an odor of camphor; [Hawley] |
Source
|
| Record name | TERT-AMYL ALCOHOL | |
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| Record name | 2-Butanol, 2-methyl- | |
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| Record name | 2-Methyl-2-butanol | |
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Boiling Point |
102.4 °C at 760 mm Hg, Binary azeotrope with 27.5% (wt) water with boiling point 87.35 °C |
Source
|
| Record name | 2-METHYL-2-BUTANOL | |
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Flash Point |
67 °F (NFPA, 2010), 19 °C, 67 °C (CLOSED CUP) |
Source
|
| Record name | TERT-AMYL ALCOHOL | |
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| Record name | 2-Methyl-2-butanol | |
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Solubility |
Solubility in water: 12.1%wt at 20 °C; 11.0%wt at 25 °C; 10.1%wt at 30 °C, Solubility parameter = 20.758 sqrt(MJ/cu m), Sol in 8 part water; miscible with alc, ether, benzene, chloroform, glycerol, oils, Very soluble in acetone, In water, 99,100 mg/L at 25 °C, 110 mg/mL at 25 °C |
Source
|
| Record name | 2-METHYL-2-BUTANOL | |
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| Record name | 2-Methyl-2-butanol | |
| Source | Human Metabolome Database (HMDB) | |
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Density |
0.8096 at 20 °C/4 °C |
Source
|
| Record name | 2-METHYL-2-BUTANOL | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/5005 | |
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Vapor Pressure |
16.8 [mmHg], Vapor pressure = 1.215 kPa (9.113 mm Hg) at 20 °C, 16.7 mm Hg at 25 °C |
Source
|
| Record name | 2-Methyl-2-butanol | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
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Impurities |
Typical impurities are other monomeric alcohols, dimeric alcohols, acetals and several miscellaneous substances ... typically free of suspended matter. |
Source
|
| Record name | 2-METHYL-2-BUTANOL | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/5005 | |
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Color/Form |
Colorless liquid | |
CAS No. |
75-85-4 |
Source
|
| Record name | TERT-AMYL ALCOHOL | |
| Source | CAMEO Chemicals | |
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Melting Point |
-9.1 °C, -8.4 °C |
Source
|
| Record name | 2-METHYL-2-BUTANOL | |
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Synthesis routes and methods I
Procedure details
Synthesis routes and methods II
Procedure details
Synthesis routes and methods III
Procedure details
Retrosynthesis Analysis
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Feasible Synthetic Routes
Q1: What is the molecular formula and weight of 2-methyl-2-butanol?
A1: The molecular formula of this compound is C5H12O, and its molecular weight is 88.15 g/mol.
Q2: Is there spectroscopic data available for this compound?
A2: Yes, Raman spectroscopy has been used to study hydrogen bonding in this compound, examining the O-H stretching region in both liquid and superheated states. [] Additionally, polarized Mandelstam-Brillouin scattering has provided insights into the hypersonic velocity and absorption of thermal phonons in this isomeric alcohol. []
Q3: What influences the solubility of pyrene in solutions containing this compound?
A3: Research indicates that the solubility of pyrene in binary solvent mixtures containing this compound and another alcohol is influenced by the specific alcohol present. This solubility behavior has been successfully modeled using mathematical representations based on the NIBS/Redlich-Kister and modified Wilson equations. []
Q4: Has the solubility of glucose in mixtures containing this compound been investigated?
A4: Yes, studies have demonstrated that the solubility of glucose in this compound can be significantly enhanced by the addition of dimethyl sulfoxide. [] Further, the presence of glucose ester increases, while fatty acids decrease, glucose solubility in this compound. []
Q5: Are there any studies on the solubility of fatty acid esters in this compound?
A5: Yes, research has shown that the solubility of fatty acid esters of glucose and sucrose in this compound is affected by the length of the fatty acid chain. An increase in chain length from C8 to C12 leads to a decrease in solubility. The addition of dimethyl sulfoxide to this compound also increases the solubility of these esters. []
Q6: What is known about the vapor-liquid equilibrium behavior of mixtures containing this compound?
A6: Several studies have investigated the vapor-liquid equilibrium (VLE) of binary and ternary systems containing this compound. These studies have explored its mixtures with components like methanol, 2-propanol, methyl acetate, toluene, and water, employing models such as Wilson, NRTL, UNIQUAC, and UNIFAC for correlation and prediction. [, , , , , , , , ]
Q7: What is the significance of studying excess molar enthalpies of this compound mixtures?
A7: Excess molar enthalpies provide insights into the intermolecular interactions between this compound and other components in a mixture. Studies measuring these values for mixtures with 1-alkanols (methanol to 1-pentanol) have shown negative deviations from ideality, suggesting stronger interactions between unlike molecules than between like molecules. []
Q8: How does the structure of pentanols affect their thermodynamic properties?
A8: Research comparing pentan-1-ol, this compound, and cyclopentanol has revealed that the molecular structure of these isomers significantly influences their thermodynamic properties, such as isobaric heat capacity, isobaric thermal expansion, and isothermal compressibility. These differences are attributed to variations in molecular packing and intermolecular interactions arising from structural differences. []
Q9: What are some known chemical reactions involving this compound?
A9: this compound has been studied in various chemical reactions:
- Atmospheric Degradation: It reacts with hydroxyl radicals (OH) in the atmosphere, with the rate coefficient exhibiting no temperature dependence. [] This reaction is relevant for understanding the atmospheric fate of the compound.
- Esterification: this compound has been utilized as a solvent in lipase-catalyzed esterification reactions, such as the synthesis of L-ascorbyl profen esters and fructose-oleic acid esters. [, ] Its use in the synthesis of glucose laurate monoester, employing Candida antarctica lipase B-displaying Pichia pastoris whole-cells as a biocatalyst, has also been reported. []
- Synthesis of 4-Cyclohexyl-2-methyl-2-butanol: A two-step synthesis method utilizes this compound, reacting styrene with isopropanol followed by heterogeneous catalytic hydrogenation, to produce 4-cyclohexyl-2-methyl-2-butanol. [, ]
Q10: Have computational methods been used to study this compound?
A10: Yes, high-level ab initio calculations have been employed to investigate the kinetics of this compound oxidation initiated by hydroxyl radicals. These studies explored hydrogen-atom abstraction, dehydration, and unimolecular isomerization and decomposition reactions, characterizing potential energy surfaces. Rate coefficient calculations were performed using variational transition state theory (VTST) and RRKM/ME methods. []
Q11: Have molecular dynamics simulations been used to study clathrate hydrates of this compound?
A11: Yes, molecular dynamics simulations, including ab initio and classical methods, have been performed to investigate the formation and behavior of this compound clathrate hydrates. These simulations provide insights into guest-host interactions, hydrogen bonding, and structural characteristics within the clathrate hydrates. []
Q12: Are there any environmental concerns regarding this compound?
A12: Research has focused on the atmospheric degradation of this compound, highlighting its reaction with hydroxyl radicals as a key degradation pathway. [] This information is crucial for assessing the compound's environmental persistence and potential impact.
Q13: What analytical techniques are commonly used to study this compound?
A13: Various analytical techniques have been employed to study this compound and its reactions, including:
- Gas Chromatography (GC): Used to analyze the products formed during the metabolism of isopentane in mice, which include this compound. []
- Gas Chromatography-Mass Spectrometry (GC-MS): Employed alongside GC to identify and quantify metabolites of isopentane, including this compound, in mice. []
- High Performance Liquid Chromatography (HPLC): Utilized to analyze and quantify the products of lipase-catalyzed esterification reactions, such as those involving this compound. [, ]
- Liquid Chromatography-Mass Spectrometry (LC-MS): Employed to identify the product, glucose laurate monoester, synthesized using this compound as a solvent. []
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