1-Hydroxy-cyclobutanecarboxylic acid is an organic compound with a chemical formula of C5H8O3, a molecular weight of 116.12 g/mol, and CAS 41248-13-9. It is a white crystal, usually showing Cubic or hexagonal structure. The solubility in water is low, and only 0.41 g of 1-hydroxycyclobutanecarboxylic acid can be dissolved in 100 mL of water at most. It can be dissolved in organic solvents such as ethanol, methanol and methylene chloride. is a chiral molecule that contains a chiral center. Therefore, it is optically active, deflecting polarized light passing through it. Different enantiomers have different optical rotations. It can also be used to prepare solvents, dyes, lubricants, etc. In addition, it can also be used to study new catalysts, optoelectronic materials and functional molecules, etc.
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1-Hydroxy-cyclobutanecarboxylic acid is an organic compound that has many uses.
1. Pharmaceutical industry:
It is an important intermediate and raw material, which can be used to synthesize a variety of drug molecules. For example, it can prepare anticancer drug 5-fluorouracil (5-Fluorouracil) through derivatization reaction, which is widely used in the treatment of colorectal cancer, gastric cancer and head and neck cancer; Precursor to the depression drug probenecid (Bupropion). In addition, it can also be used as a synthetic intermediate of heparin-based blood anticoagulant Fondaparinux, which is clinically used to prevent deep vein thrombosis and pulmonary embolism and other diseases. At present, the United States, Europe, Japan and other places have relatively advanced pharmaceutical industries, so these regions are likely to use it.
2. Cosmetics industry:
It contains hydroxyl and carboxyl functional groups and can be used as an additive in the cosmetic industry. For example, it can be added to certain toothpastes and mouthwashes to clean teeth and kill bacteria. In addition, it can also be used to synthesize emulsifiers and stabilizers, making certain cosmetics more stable and durable. At present, the United States, Europe, Japan and other places have relatively advanced pharmaceutical industries, so these regions are likely to use it.
3. Material industry:
It is soluble and biologically active, and can be used in the fields of coatings, plastics and fibers. For example, it can react with monomers such as acrylic acid to form copolymer materials for the preparation of highly transparent and flexible molecular materials. In addition, it can also be used in the synthesis of fluorescent dyes, pigments and photochromic agents, which can be used in displays, laser printers and safety marks.
4. Food industry:
It is also widely used in the food industry. For example, it can be used as sour agent, pickle and condiment, etc., and plays an important role in seasoning and food additives. At the same time, due to its bactericidal and antioxidant properties, it is also used in the production of preservatives and plays a role in keeping food fresh. The agricultural technology in North America, Europe, Oceania and other developed countries is relatively mature, so the substance may be widely used in these areas.
1-Hydroxy-cyclobutanecarboxylic acid is an organic compound with the chemical formula C5H8O3. Several synthetic methods of 1-hydroxycyclobutanecarboxylic acid will be presented.
1-Hydroxycyclobutanecarboxylic acid can be prepared by oxidation of cyclobutanedione. First, cyclobutanedione is oxidized with oxygen in the presence of a basic catalyst to generate the transition state of 1,2-cyclobutanedione, which is then hydrolyzed to 1-hydroxycyclobutanecarboxylic acid. The commonly used basic catalysts are sodium hydroxide and potassium hydroxide. Concrete reaction formula is as follows:
-C4H4O2 + O2 → transition state (intermediate)
-transition state (intermediate) + H2O → C5H8O3
The advantage of this method is that the reaction conditions are mild, the yield is high, and it is easy to operate, but oxygen is needed as an oxidant, and safety equipment needs to be used. At the same time, the choice and amount of catalyst used will also affect the yield.
1-Hydroxycyclobutanecarboxylic acid can also be prepared by alkylation of cyclopentanone and formaldehyde. First, cyclopentanone is reacted with formaldehyde using an acid catalyst to produce hydroxyketones. Hydroxyketone is then hydrolyzed under basic conditions to give 1-hydroxycyclobutanecarboxylic acid. Concrete reaction formula is as follows:
- C5H8O + CH2O → Hydroxyketone
- Hydroxyketone + NaOH → C5H8O3
This method does not require oxygen, and is simple and easy to control, but the yield is low, and the selection and usage amount of the acid catalyst need to be considered.
1-Hydroxycyclobutanecarboxylic acid can also be prepared by Diels-Alder reaction. Combine dicarbonyl tetrahydrofuran (2,3-Dihydrofuran-2,3-dione) with butadiene as a substrate, and heat it to about 100°C to react to produce a cyclobutanedione intermediate. Alkaline hydrolysis is then used to obtain 1-hydroxycyclobutanecarboxylic acid. The reaction conditions of the Diels-Alder reaction are relatively mild and have a wide range of applications, but the synthesis method has high requirements for the selection and operation of raw materials.
- C11H13BF4FeO3 + C16H14 → intermediate (C4H4O2)
- intermediate (C4H4O2) + NaOH → C5H8O3
1-Hydroxycyclobutanecarboxylic acid can also be prepared by the lactam initiator method. First, acrylic acid is reacted with a monohydric alcohol to form a lactone, and then an ammoniating agent (such as sodium hydroxide) is added to hydrolyze it into a lactam. Finally, the lactam undergoes alcoholysis reaction to generate 1-hydroxycyclobutanecarboxylic acid. Concrete reaction formula is as follows:
-C3H4O2+monohydric alcohol → lactone
-lactone + ammoniating agent → lactam
-lactam + base → hydroxy acid
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Chemical Formula |
C5H8O3 |
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Exact Mass |
116 |
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Molecular Weight |
116 |
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m/z |
116 (100.0%), 117 (5.4%) |
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Elemental Analysis |
C, 51.72; H, 6.94; O, 41.34 |
It also known as 1-Hydroxycyclobutane-1-carboxylic acid, has a molecular formula of C5H8O3 and a molecular weight of 116.12 g/mol. Its structural formula is as follows:
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It can be seen that the 1-Hydroxy-cyclobutanecarboxylic acid molecule consists of two parts: a cyclic four-membered ring (cyclobutane) and a hydroxyl and carboxyl functional group. There is a covalent bond between each carbon atom on the four-membered ring and two adjacent carbon atoms, and the two pairs of two bonds formed by two mutually perpendicular bonds are axial bonds (axial); and the other two A one-to-one bond composed of perpendicular bonds is called a flat bond (equatorial). At the same time, due to the contraction of the four-membered ring, the plane bond of 1-Hydroxy-cyclobutanecarboxylic acid is slightly biased towards the center of the four-membered ring.
In the three-dimensional configuration analysis of product, the spatial orientation of axial bonds and planar bonds is very important. Axial bonds are more stable because the hydrogen atoms above and below are more repulsive; planar bonds are less stable because they interact with other molecules on the four-membered ring. Specifically, axial bonds are bonds located at two opposite corner positions of a tetrahedron, while planar bonds are bonds located at the other two opposite face corner positions.
Since the spatial configuration of it is relatively complex, it needs to be analyzed by different technical means, such as NMR spectroscopy and X-ray crystallography. Among them, nuclear magnetic resonance (Nuclear Magnetic Resonance, NMR) technology can provide information about chemical bonds in molecules, including chemical shift, coupling constant, radius of rotation, degree of freedom of rotation, chemical ring formation, chemical interaction, etc. -A very important method of the structure of cyclobutanecarboxylic acid.
In the NMR spectrum analysis of product, its structure can be determined by observing the chemical shift value of the carboxyl proton. Specifically, the carboxyl protons of this compound can appear in the range of 3.9 to 4.2 ppm, which is due to the different resonance environment of the carboxyl group. At the same time, it also has a hydroxyl group, the proton of which can appear in the range of 1.3 to 2.0 ppm, due to the difference in the interaction between the hydroxyl group and other atoms on the four-membered ring. In addition, it also showed two signals in the NMR spectrum, that is, the peaks corresponding to the two hydrogen atoms on the axial bond and the two hydrogen atoms on the planar bond. The chemical shifts of two hydrogen atoms on an axial bond are usually higher, around 2 to 2.5 ppm, while those on a planar bond are lower, usually around 1 to 1.5 ppm.
In addition to NMR techniques, X-ray crystallography is also a commonly used method for structural analysis. This method can determine its precise structure by configuring it molecules in the crystal and using the X-ray scattering law. In X-ray crystallography analysis, it is necessary to observe the changes of the crystal by keeping the crystal in a flowing atmosphere. At the same time, special software and computer programs are required to simulate and process data to obtain more accurate results.
Adverse reactions
1-Hydroxy-cyclobutanecarboxylic acid is an organic compound containing a cyclobutane ring and functional groups of hydroxyl and carboxyl. Its unique chemical structure makes it have certain potential application value in fields such as organic synthesis, drug research and development, and chemical production.
Skin Contact
When 1-hydroxycyclobutanecarboxylic acid comes into direct contact with the skin, it may cause a series of adverse reactions. Due to the fact that the skin is the largest organ in the human body and has barrier function, certain chemicals can penetrate the skin barrier and enter the body. The polarity of 1-hydroxycyclobutane carboxylic acid allows it to dissolve to a certain extent in the oil and water on the surface of the skin, thereby increasing its likelihood of penetrating the skin.
Local stimulus response
In the early stages of contact, there may be skin irritation symptoms such as redness, itching, and stinging. This is because when the compound comes into contact with skin cells, it may interfere with the normal metabolic processes of cells, disrupt the structure and function of cell membranes, and lead to the release of inflammatory mediators such as histamine and prostaglandins, thereby triggering local inflammatory reactions. With prolonged exposure time or increased exposure dose, irritation symptoms may worsen, leading to serious injuries such as skin swelling, blisters, and even ulcers.
Allergic reactions
Some individuals may have an allergic constitution to 1-hydroxycyclobutane carboxylic acid. At first contact, the body's immune system may recognize it as a foreign antigen and produce specific antibodies. When exposed again, antigens bind to antibodies, activating the immune system and triggering allergic reactions. The symptoms of allergic reactions are diverse. Mild cases may present with skin urticaria, rash, etc., while severe cases may result in systemic allergic reactions such as anaphylactic shock, characterized by a sharp drop in blood pressure, difficulty breathing, loss of consciousness, etc., posing a serious threat to life and health.
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