Name | D-Valine |
Synonyms | D-VAL D-Valine D-VALINE H-D-Val-OH Valine, D- H-D-VAL-OH D-2-AMINOISOVALERIC ACID ALPHA-AMINO-ISOVALERIANIC ACID D-2-Amino-3-methylbutanoic acid (R)-α-Aminoisovaleric acid, D-2-Amino-3-methylbutanoic acid |
CAS | 640-68-6 |
EINECS | 211-368-9 |
InChI | InChI=1/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m1/s1 |
InChIKey | KZSNJWFQEVHDMF-SCSAIBSYSA-N |
Molecular Formula | C5H11NO2 |
Molar Mass | 117.15 |
Density | 1.2000 (estimate) |
Melting Point | >295°C (subl.)(lit.) |
Boling Point | 213.6±23.0 °C(Predicted) |
Specific Rotation(α) | -27.5 º (c=5, 5N HCl) |
Flash Point | 83°C |
Water Solubility | 56 g/L (20 ºC) |
Solubility | Soluble in water (56 mg/ml at 20° C), Aqueous Acid, and 3N HCI. Insoluble in ethanol |
Vapor Presure | 0.0633mmHg at 25°C |
Appearance | White crystal |
Color | White to off-white |
BRN | 1721135 |
pKa | 2.37±0.10(Predicted) |
Storage Condition | room temp |
Refractive Index | -27 ° (C=8, 6mol/L H |
MDL | MFCD00064219 |
Physical and Chemical Properties | melting point 302-303°C |
Use | Used as raw materials and pharmaceutical intermediates, also for the synthesis of Alatan sweetener |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. 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 | YV9360000 |
TSCA | Yes |
HS Code | 29224995 |
Reference Show more | 1. [IF=7.1] Haiyan Fu et al."Rational design of an “on-off-on” fluorescent assay for chiral amino acids based on quantum dots and nanoporphyrin."Sensor Actuat B-Chem. 2019 May;287:1 2. [IF=7.79] Ye Lu et al."Enhancing hydrogel-based long-lasting chemiluminescence by a platinum-metal organic framework and its application in array detection of pesticides and D-amino acids."Nanoscale. 2020 Feb;12(8):4959-4967 3. [IF=4.759] Lixia Chen et al."Theoretical electronic circular dichroism investigations of chiral amino acids and development of separation and identification methods independent of standards."J Chromatogr A. 2021 Sep;1654:462446 |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
valine | valine is an essential amino acid for human body, and the requirement of adult men is 10mg/(kg · d). (FAO/WHO 1973). If the lack of this product, can cause neurological disorders, reduced development, anemia and so on. valine is one of the 20 kinds of amino acids that make up the protein, the chemical name is 2-amino -3-methyl butyric acid, belongs to the branched chain amino acid, is also the necessary 8 kinds of amino acids and sugar amino acids, it works with two other high-concentration amino acids (isoleucine and leucine) to promote normal growth of the body, repair tissues, regulate blood sugar, and provide the required energy. When engaged in intense physical activity, valine can provide the muscles with additional energy to produce glucose to prevent muscle weakness. It also helps remove excess nitrogen (a potential toxin) from the liver and transports the nitrogen the body needs to various parts. valine is an essential amino acid, which means that the body itself cannot produce and must be supplemented by dietary sources. Its natural food sources include cereals, dairy products, mushrooms, mushrooms, peanuts, soy protein, and meat. D-valine is also present in some actinomycin (e. G., jirimycin). Although most people get enough from their diet, cases of valine deficiency are common. When valine is insufficient, The central nervous system function of rats will be disturbed, ataxia and limb tremor. Through the anatomical section of brain tissue, it is found that there is degeneration of Red nuclear cells. Patients with advanced liver cirrhosis are easy to form hyperinsulinemia due to liver function damage, resulting in a decrease in branched chain amino acids in blood, the ratio of branched-chain amino acids to aromatic amino acids is reduced from 3.0 to 3.5 in normal people to 1.0 to 1.5. Therefore, injections of branched-chain amino acids such as valine are commonly used to treat liver failure and damage to these organs caused by alcoholism and drug abuse. |
application field | D-valine due to its own biochemical properties, it can be used for the synthesis of new efficient pesticides pyrethroid and fenvalerate, and the valine insecticidal pyrethroid prepared from it is a kind of broad-spectrum and promising insecticidal and acaricidal agent, it can inhibit the activity of insect enzyme system and play the role of killing and stomach poison. It can effectively control the main pests of cotton, fruit trees, vegetables and other crops, including Lepidoptera and Diptera. D-valine is also widely used in biomedical research, such as inhibiting the growth of fibroblasts, and affecting the morphology and function of pulmonary artery endothelial cells. D-valine is also an important chiral drug raw material, such as can be used in the synthesis of anti-tumor drugs and anti-diabetes and its complications. With the expansion of D-valine application field and the expansion of market demand, the preparation of D-valine will become one of the hot spots in amino acid research. D-valine is an important organic chiral source, which is mainly used in the fields of chiral drugs, chiral additives, chiral auxiliaries and so on. As an optically active organic acid, it plays an irreplaceable role in the asymmetric synthesis of some chiral compounds. At present, it is mainly used to produce new broad-spectrum antibiotics, valine protectant for polypeptide synthesis. |
Use | D-valine is an intermediate of cyhalofluthrin. used as raw materials and pharmaceutical intermediates, also used in the synthesis of Alatan sweetener used in biochemical research. used in cell culture as a selective inhibitor of cell proliferation to inhibit cells lacking D-amino acid oxidase |
production method | with acetyl-DL-valine as raw material, D-valine crystals were separated by acylase and acidified with hydrochloric acid, the product was refined by recrystallization. The preparation method is to react ethyl 2-isopropylacetoacetate with benzene diazonium salt to generate the corresponding hydrazine compound, and then reduce it to valine in zinc-ethanol solution, and then carry out chemical or biological resolution. |