L-ピログルタミン酸
L-ピログルタミン酸 · 2-ケト-ピロリジン-5-カルボン酸 · 5-オキソ-2-ピロリジンカルボン酸 · (2S)-5-オキソピロリジン-2α-カルボン酸 · (S)-ピログルタミン酸 · L-グルチミニン酸 · L-グルタミン酸ラクタム · (2S)-5-オキソピロリジン-2-カルボン酸
識別子と物理属性
| CAS No. | 98-79-3 |
|---|---|
| 分子式 | C5H7NO3 |
| 平均分子量 | 129.11 g/mol |
| 単同位体質量 | 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 |
| 現地名 | L-ピログルタミン酸 |
化学・物理的性質
| XLogP | -0.8 |
|---|---|
| 極性表面積 | 66.4 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 1 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 154 |
| 溶解度 | 476000476.0 mg/mL at 13 °C>19.4 [ug/mL] (The mean of the results at pH 7.4)H2O: 1M at20℃、透明、無色10～15g/100mL（20℃） |
| 融点 | 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]- |
| 比旋光度 | -27.5 º (c=10, 1 N NaOH) |
| 沸点 | 239.15°C (rough estimate) |
| 密度 | 1.3816 (rough estimate) |
| 蒸気圧 | 0.002Pa at 25℃ |
| 屈折率 | -10 ° (C=5, H2O) |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | 3.32(at 25℃) |
| 外観・状態 | 結晶性粉末 |
| 色 | ホワイトからオフホワイト |
| pH | 1.7 (50g/l, H2O, 20℃) |
| 臭い | 白色の結晶、無臭、わずかに酸味がある |
| Merck | 14,8001 |
| BRN | 82132 |
| 安定性 | 安定。塩基、酸、強力な酸化剤とは相容れない。 |
| 主な用途 | ペプチド合成 |
| 化粧品成分の機能 | 保湿剤保湿 |
| 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（分配係数） | -1.233 at 20℃ |
| CAS データベース | 98-79-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Pidolic acid(98-79-3) |
| EPAの化学物質情報 | 5-Oxo-L-proline (98-79-3) |
化学的特性
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.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| その他の安全情報 | IMAP assessments - L-Proline, 5-oxo-: Environment tier I assessmentEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| 有害性の概要 | An irritant that may cause serious eye injury |
用途
解説
L-ピログルタミン酸，ピログルタミンサン，5-oxo-L-proline．C5H7NO3(129.12)．L-グルタミン酸を100 ℃ で加熱脱水すると得られる．野菜，果物中に含まれ，タンパク質のN末端に存在することもある．融点162～163 ℃．[α]D25－11.3°(水)．pK1 3.32．水，エタノール，アセトン，氷酢酸に可溶，酢酸エチルに難溶，エーテルに不溶．強酸やアルカリで開環し，グルタミン酸となる．免疫グロブリン，ガストリン，α1-酸性糖タンパク質など，多くの生体物質に含まれている．
使用
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.
製法・合成法
純化方法
Crystallise S-pyroglutamic acid by dissolving it in boiling EtOH (20g in 100mL), cooling and after a few minutes additing pet ether (b 40-60o, 120mL), then after 5 minutes adding a further 120mL, and coThis has m 155.5-157.5o and [] D -11.4o (c 4.4, H2O) [Hardy Synthesis 290 1978, Pellegata et al. Synthesis 614 1978]. The NH4 salt has m 184-186o (from EtOH). [Beilstein 22/6 V 7.]