Pyroglutamic acid is 5-oxyproline. It is produced by the dehydration in between the α-NH2 group along with the γ-hydroxyl group of glutamic acid to form an intramolecular amide bond; it can in addition be generated by shedding the amido group in the glutamine bit. If glutathione synthetase deficiency, can create pyroglutamic acidemia, a collection of clinical signs and symptoms. Pyroglutamateemia is a condition of natural acid metabolism triggered by the deficiency of glutathione synthetase. Medical indications consist of beginning within 12 to 24-hour of birth, dynamic hemolysis, jaundice, chronic metabolic acidosis, mental retardation, and so on; pee consists of pyroglutamic acid, lactic acid, and also α-deoxy-4-glycotolactone. Therapy, symptomatic, focus on diet plan modification after one years of age.
L-Pyroglutamic Acid Property
Melting point
160-163 °C(lit.)
alpha
-27.5 º (c=10, 1 N NaOH)
Boiling point
239.15°C (rough estimate)
density
1.3816 (rough estimate)
vapor pressure
0.002Pa at 25℃
refractive index
-10 ° (C=5, H2O)
storage temp.
2-8°C
solubility
H2O: 1 M at 20 °C, clear, colorless
form
Crystalline Powder
pka
3.32(at 25℃)
color
White to off-white
PH
1.7 (50g/l, H2O, 20℃)
Odor
wh. crystal, odorless, sl. acidic taste
optical activity
[α]20/D 10.5±1°, c = 5% in H2O
Water Solubility
10-15 g/100 mL (20 ºC)
L-Pyroglutamic Acid Uses
L-pyroglutamic acid is among one of the most vital chemical intermediates, which are widely used in the fields of medicine as well as health and wellness, food, cosmetics as well as agriculture. Researches have revealed that the human mind as well as cerebrospinal liquid contain a large quantity of pyroglutamic acid, which can reinforce the details exchange in between the left and appropriate hemispheres of the brain as well as assistance improve memory. L-pyroglutamate has inhibitory activity versus pains, BCHE, and Bacel enzymes that minimize cholinergic neurotransmission that plays a crucial duty in cognitive disability associated with Alzheimer’s disease, Therefore, L-pyroglutamic acid has the effect of protecting against Alzheimer’s illness.
L-pyroglutamic acid can be utilized to synthesize lots of essential crooked materials (such as: alkaloids and amino acids) or natural intermediates. Recently, numerous alkaloid chiral substances have actually been synthesized making use of L pyroglutamic acid as a chiral resource. For instance: Ueno as well as Oppolzer synthesized kainic acid with solid transmission activity in the nerves. Keusenkothen et al. used asymmetric free radical cyclization to precisely manufacture pyrrolizidine by-products. In 1922, Fleurant et al. reported the discerning synthesis of Indolizidine alkaloids using L-pyroglutamic acid as a chiral resource. In 1989, Ikota initially asymmetrically synthesized piperidine alkaloids utilizing L-pyroglutamic acid as a chiral resource. In addition, Jain et al. manufactured bicyclic piperazines with constricted conformations. Pryrolidine alkaloid synthesized from L-pyroglutamic acid exists in plants, as well as its medicinal residential properties include hepatotoxic results, mutagenesis and carcinogenesis. In 1979, Saijo reported the synthesis of 4 diastereoisomers of 11-deoxy-8-azaprostaglandin E1 using L-pyroglutamic acid as a chiral resource. 11-deoxy-8-aza PEG1 has Hinders the organic activity of gastric acid secretion as well as bronchodilation.
By-products of L-pyroglutamic acid are additionally important industrial products. Sodium L-pyroglutamate is a biomimetic substance, which is comparable in framework to the substance that controls the skin’s dampness secretion. It is a fundamental part of the natural moisturizing aspect (NMF) of human skin, and also its moisturizing capacity is higher than that of commonly used moisturizers such as glycerin., Propylene Glycol as well as Sorbitol etc. Due to its excellent physical activity, skin compatibility as well as security, and additionally has particular whitening and anti-wrinkle effects, it is additionally commonly made use of in the cosmetics sector. A collection of substances can be manufactured by utilizing L-pyroglutamic acid derivatives as chiral complementary agents. For example, Zhao Gang et al. have more established the 5-hydroxymethyl 2-pyrrolidone developed by decrease of L pyroglutamic acid esterification as chiral auxiliary agents. The biomimetic pesticide optically active dichloropyrethroid acid was synthesized. In 1984, Ikota et al. made use of L pyroglutamic acid as a basic material to get methoxymethanol ether through esterification, decrease, as well as etherification, and manufactured cis and trans β-lactams with this as a chiral source, and also additional gotten Optically pure phenylalanine derivative. In 2006, Guo Fucheng as well as others utilized L-pyroglutamic acid as well as anhydrous ethylamine as resources as well as pyridine as a homogeneous system to manufacture L-theanine.
The Preparation Method of L-Pyroglutamic Acid
L-pyroglutamic acid is created by eliminating a particle of water from the L-glutamic acid molecule. Its prep work procedure is simple, and also the crucial actions are the control of temperature and dehydration time. ( 1) Add 100 g of L-glutamic acid right into a 500 ml beaker, warm the beaker with an oil bathroom, and when the temperature rises to 145-150 ° C, maintain it warm for 45 mins to execute dehydration reaction. The dehydrated remedy was brown in color. ( 2) After the dehydration reaction is ended up, the solution is poured into boiling water with a volume of concerning 350 milliliters, and also the service is entirely dissolved in water. After cooling down to 40-50 ° C, include an ideal quantity of turned on carbon for decolorization (repeated two times). A colorless and clear service was acquired. ( 3) When the colorless clear option prepared symphonious (2) is straight heated, evaporated as well as concentrated till the volume is lowered to regarding half, then moved to a water bathroom as well as remained to concentrate till the quantity has to do with 1/3, after that the heating can be stopped, as well as the Allow to cool in a water bathroom to slowly crystallize. Anemic prismatic crystals can be obtained after 10 to 20 hours. The amount of L-pyroglutamic acid made use of in cosmetics depends upon the formula. This product can also be utilized in cosmetics in the form of 50% concentrated remedy.
Production Process of L-Pyroglutamic Acid
L-pyroglutamic acid has a wide range of uses and high commercial value, and has become a research hotspot in recent years. There are many methods for synthesizing L-pyroglutamic acid reported at home and abroad, but the output of L-glutamic acid/L-sodium glutamate in my country is relatively large and the price is low, so the method for synthesizing L-pyroglutamic acid is mostly based on L -Glutamic acid or sodium L glutamate as raw material. Its process route is as follows:
Microbial Fermentation Yinxin uses L-glutamic acid as raw material to obtain L-pyroglutamic acid through the catalytic condensation of microbial alcaligenes. At a temperature of 50°C and a pH of 7.4, 0.2 The g/L powdered alcaligenesin reacted with 5×10~5mol/L zinc chloride solution for 60 min, and the conversion rate reached 95%. In addition, a pyroglutaminase was isolated from various Alcaligenes and Pseudomonas cultures, and this enzyme has dual activities on the dehydration cyclization of glutamic acid and the ring-opening hydrolysis of pyroglutamic acid. Microbial fermentation can prepare L-pyroglutamic acid with higher purity by changing the reaction conditions (such as the purity of alcaligenesin).
wet pyrolysis Wet pyrolysis is to add an appropriate amount of glutamic acid or sodium glutamate to a certain amount of distilled water at a certain temperature, and stir for a period of time to generate L-pyroglutamic acid. Cui Zhimin et al. used sodium glutamate as a raw material, first dissolved it in an aqueous solution, and reacted at a constant temperature of 180°C for 2 hours to obtain a light yellow melt; then dissolved it in water, filtered it while it was hot, evaporated, and dried to obtain L-pyroglutamic acid Sodium, the yield can reach 87.5% under the optimal conditions. Yang Xiaoling et al. used sodium glutamate as a raw material, in the presence of silicone oil and a catalyst, dehydration and cyclization reaction at 180°C for 2.5 hours, and then dissolved in water to obtain a mixed solution of oil and water. The product of L-sodium pyroglutamate aqueous solution was in the lower layer. The conversion rate of sodium glutamate was 96.7%, and the yield of L-pyroglutamic acid after acidification was 83.5%. The L-glutamic acid aqueous solution was heated and refluxed overnight to obtain a L-pyroglutamic acid solution (85%-86% conversion rate), and the anion exchange resin was used to remove the L-glutamic acid that did not participate in the reaction.
dry pyrolysis L-glutamic acid is directly heated and melted, decomposed at 150°C to generate L-pyroglutamic acid, and the reactant is dissolved in water to obtain an aqueous solution of L-pyroglutamic acid, which is evaporated and concentrated to obtain a colorless prismatic crystal. Li Qun et al. used dry heat method to prepare sodium L-pyroglutamate with L-sodium glutamate as raw material. At the same time, the process conditions of the synthesis were optimized, and the best conversion rate reached 96%. Mao Yunping and others used L-sodium glutamate as raw material to prepare L-sodium pyroglutamate, and slowly cooled and crystallized under the protection of nitrogen, with a yield of up to 95%.
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