Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
L-피로글루탐 산
L-피로글루탐산 · 피씨에이 · L피로글루탐산 · PYROGLUTAMIC ACID · H-PYR-OH · (S)-5-OXOPYRROLIDINE-2-CARBOXYLIC ACID · L-5-OXOPROLINE · 5-oxoproline
식별자 및 물리적 특성
| CAS No. | 98-79-3 |
|---|---|
| 분자식 | C5H7NO3 |
| 평균 분자량 | 129.11 g/mol |
| 단동위원소 질량 | 129.04259309 g/mol |
| SMILES | O=C1CC[C@@H](C(=O)O)N1 |
| InChIKey | ODHCTXKNWHHXJC-VKHMYHEASA-N |
| PubChem CID | 7405 |
| ChEMBL | CHEMBL397976 |
| ChEBI | CHEBI:18183 |
| EC No. | 202-700-3 |
| DTXSID | DTXSID6046260 |
| 현지명 | L-피로글루탐 산 |
화학 및 물리적 성질
| XLogP | -0.8 |
|---|---|
| 극성 표면적 | 66.4 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 9 |
| 형식 전하 | 0 |
| 복잡도 | 154 |
| 용해도 | 476000476.0 mg/mL at 13 °C>19.4 [ug/mL] (The mean of the results at pH 7.4)H2O: 1 M at 20 °C, 투명, 무색 |
| 녹는점 | 184.7160-163 °C(lit.) |
| Physical Description | Solid[Merck Index] White crystalline powder[Alfa Aesar MSDS] |
| Collision Cross Section | 121 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]130.6 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]130.3 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]124.1 Ų [M-H]- [CCS Type: DT130.1 Ų [M+H]+ [CCS Type: DT124.6 Ų [M-H]- |
| 끓는 점 | 239.15°C (rough estimate) |
| 밀도 | 1.3816 (rough estimate) |
| 증기압 | 0.002Pa at 25℃ |
| 굴절률 | -10 ° (C=5, H2O) |
| 저장 조건 | 2-8°C |
| pKa(산도 계수) | 3.32(at 25℃) |
| 물리적 상태 | 결정성 분말 |
| 색상 | 흰색에서 황백색까지 |
| pH | 1.7 (50g/l, H2O, 20℃) |
| 냄새 | 백색 결정, 무취, 약간 신맛 |
| 용해도 | 10-15 g/100 mL (20 ºC) |
| Merck | 14,8001 |
| BRN | 82132 |
| 안정성 | 안정적인. 염기, 산, 강산화제와 호환되지 않습니다. |
| 주요 응용 | 펩타이드 합성 |
| 화장품 원료 기능 | 보습제보습 |
| InChI | 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 |
| InChIKey | ODHCTXKNWHHXJC-VKHMYHEASA-N |
| SMILES | OC(=O)[C@@H]1CCC(=O)N1 |
| LogP(분배 계수) | -1.233 at 20℃ |
| NIST | Pidolic acid(98-79-3) |
| EPA | 5-Oxo-L-proline (98-79-3) |
화학적 성질
L-pyroglutamic acid has its scientific name being L-2-pyrrolidone-5-carboxylic acid. Precipitation from ethanol and petroleum ether mixture were colorless orthorhombic bipyramid crystals with the melting temperature being 162~163 °C. It is soluble in water, alcohol, acetone and acetic acid, slightly soluble in ethyl acetate, and insoluble in ether. Specific rotation-11.9 ° (c = 2, H2O). It is produced from 42% aqueous solution of glutamic acid which subjects to heating dehydration, concentration, crystallization, washing and drying to obtain L-pyroglutamic acid.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 1.5% (5 of 343) of reports.DangerH315 (21.9%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (78.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (20.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (21.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 343 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 5 of 343 reports by companies.There are 15 notifications provided by 338 of 343 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 규제 정보 | Chemical: L-Proline, 5-oxo-L-Proline, 5-oxo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of L-Proline, 5-oxo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 25-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24879Status: Active Update: 17-06-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18035L-Proline, 5-oxo-: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | IMAP assessments - L-Proline, 5-oxo-: Environment tier I assessmentEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| 유해성 요약 | An irritant that may cause serious eye injury[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (21.9%)Eye Dam. 1 (78.1%)Eye Irrit. 2A (20.4%)STOT SE 3 (21.6%) |
| Treatment | Glutathione Synthetase Deficiency: The clinical management of GS deficient patients is aimed at correction of acidosis, prevention of haemolytic crises and support of endogenous defence against reactive oxygen species (ROS). In the neonatal period, correction of metabolic acidosis, electrolyte imbalances, treatment of anaemia and excessive hyperbilirubinaemia are of crucial importance. Correction of acidosis can be reached through bicarbonate, citrate or tris-hydroxymethyl aminomethane (THAM). Doses of up to 10 mmol/kg/day, or even higher in episodes of acute infections, may be required. Repeated blood transfusions may be necessary in patients with massive haemolysis. Drugs and foods known to precipitate haemolytic crises in patients with glucose- 6-phosphatase dehydrogenase deficiency should be avoided. Successful treatment with erythropoietin has been reported in one patient. Early supplementation with vitamin E and vitamin C are thought to replenish the lack of GSH as a scavenger of free radicals. Recommended doses are 10 mg/kg/day for vitamin E and 100 mg/kg/day for vitamin C. A longterm follow-up study of 28 patients suggested that early supplementation with both vitamins may prevent CNS damage and improve the long-term clinical outcome in GS-deficient patients. The value of N-acetylcysteine, which is known to protect cells from oxidative stress in vitro, in the treatment of GS deficiency is controversial. It was suggested that the low intracellular GSH concentrations and cysteine availabilty might be increased by N-acetylcysteine. However, supplementation with N-acetylcysteine should not be recommended, because it was shown at least in cultured fibroblasts that patients with GS deficiency accumulate cysteine, which is known to be neurotoxic in excessive amounts. A therapeutic trial with orally administered GSH showed no lasting benefit in two patients with GS deficiency. GSH esters, lipid-soluble preparations which are easily transported into cells where they |
| 건강 영향 | Chronically high levels of pyroglutamic acid are associated with at least 5 inborn errors of metabolism including: 5-Oxoprolinuria, 5-oxoprolinase deficiency, Glutathione Synthetase Deficiency, Hawkinsinuria and Propionic acidemia. |
| 독성 요약 | 5-Oxoprolinuria develops in moderate to severe cases of glutathione synthetase deficiency. The deficiency in glutathione synthetase leads to the accumulation of γ-glutamylcysteine, which is converted into 5-oxoproline by the action of γ-glutamyl cyclotransferase. The excessive formation of 5-oxoproline exceeds the capacity of 5-oxoprolinase, leading to accumulation of 5-oxoproline in body fluids causing metabolic acidosis and 5-oxoprolinuria. 5-Oxoproline accumulation is thought to be the cause of metabolic acidosis in Hawkinsinuria. 5-Oxoprolinase deficiency also leads to decreased conversion of 5-oxoproline to glutamate, resulting in elevated levels of 5-oxoproline in body fluids. 5-Oxoprolinuria has also been described in patients with urea cycle defects, such as ornithine transcarbamoylase deficiency or homocystinuria. In nephropathic cystinosis 5-oxoprolinuria may occur because of secondary impairment of the γ-glutamyl cycle resulting from decreased availability of free cysteine and can be corrected through cysteamine therapy. Transient 5-oxoprolinuria of unknown cause has been reported in very preterm infants. Limited availability of glycine in malnutrition and pregnancy as well as increased turnover of collagen, fibrinogen and other proteins containing considerable amounts of 5-oxoproline in patients with severe burns or Stevens-Johnson syndrome may lead to 5-oxoprolinuria. In addition, certain drugs, such as paracetamol, vigabatrin or some antibiotics (flucloxacillin, netimicin), are known to induce 5-oxoprolinuria, probably through interaction with the γ-glutamyl cycle. Particular infant formulas and tomato juice may contain modified proteins with increased content of 5-oxoproline. (T527) |
| Signs and Symptoms | Patients with the moderate variant of glutathione synthetase deficiency usually present during the neonatal period with severe and chronic metabolic acidosis, mild to moderate haemolytic anaemia, jaundice and 5-oxoprolinuria. After the neonatal period, the condition usually stabilises, but patients may become critically ill during infections owing to pronounced acidosis and electrolyte imbalances. Several patients have died during such episodes. In addition to the symptoms mentioned above, patients with severe GS deficiency develop progressive CNS symptoms, e.g. mental retardation, seizures, spasticity, ataxia and intention tremor. In addition, some patients suffer from recurrent severe bacterial infections, which is probably due to defective granulocyte function. Hawkinsinuria is characterised by failure to thrive and metabolic acidosis in infancy. After the 1st year of life the condition appears to be asymptomatic. Early weaning from breastfeeding seems to precipitate the diseasethe condition may be asymptomatic in breastfed infants. 5-Oxoprolinase Deficiency: Up to now, eight patients in six different families have been described. The clinical symptoms are inconstant and very heterogeneous, including renal stone formation, enterocolitis, neonatal hypoglycaemia, microcytic anaemia, microcephaly and mental retardation. It remains to be established wheter symptoms in identified patients are merely a coincidence. (T527) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | TW3710000 |
| 관세 코드 | 29337900 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-36-37/39 |
| 위험 등급 | IRRITANTAquatic Chronic 3Eye Dam. 1 |
| 기존화학 물질 | KE-29979 |
| F 고인화성물질 | 21 |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
L-Pyroglutamic acid is an amino acid that is used in the synthesis of peptides. It has also been observed to convert when placed at the N-terminus in vivo to create IgG2 antibodies.