하이드록시프롤린
하이드록시프롤린 · 4-하이드록시프롤린 · Hyp · TRANS-4-HYDROXY-L-PROLINE · HYDROXYPROLINE · (2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID · 4-HYDROXY-L-PROLINE · 4-Hydroxyproline
식별자 및 물리적 특성
| CAS No. | 51-35-4 |
|---|---|
| 분자식 | C5H9NO3 |
| 평균 분자량 | 131.13 g/mol |
| 단동위원소 질량 | 131.05824315 g/mol |
| SMILES | O=C(O)[C@@H]1C[C@@H](O)CN1 |
| InChIKey | PMMYEEVYMWASQN-DMTCNVIQSA-N |
| PubChem CID | 5810 |
| ChEMBL | CHEMBL352418 |
| ChEBI | CHEBI:18095 |
| EC No. | 200-091-9 |
| DTXSID | DTXSID10883225 |
| 현지명 | 하이드록시프롤린 |
화학 및 물리적 성질
| XLogP | -3.3 |
|---|---|
| 극성 표면적 | 69.6 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 9 |
| 형식 전하 | 0 |
| 복잡도 | 125 |
| 물질 분류 | Biological Agents -> Amino Acids and Derivatives |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| 화장품 | Skin conditioningSurfactantAntistaticHair conditioning |
| LogP(분배 계수) | -3.17 |
| 식품 첨가물 | Use unspecified -> FDA Substance added to food |
| 용해도 | Soluble in water at 0, 25, 50, and 60 °C361 mg/mL at 25 °CH2O: 50 mg/mL |
| 끓는 점 | Decomposes242.42°C (rough estimate) |
| 녹는점 | 274°C274 - 275 °C273 °C (dec.)(lit.) |
| Physical Description | Solid[Merck Index] White crystalline powder[Alfa Aesar MSDS] |
| Dissociation Constants | pK1′ 1.82 and pK2′ 9.65 |
| Collision Cross Section | 130.23 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]139.3 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]122 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]128.1 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]127.9 Ų [M+H]+ |
| 밀도 | 1.3121 (rough estimate) |
| 증기 밀도 | 4.5 (vs air) |
| 굴절률 | -75.5 ° (C=4, H2O) |
| 저장 조건 | Store below +30°C. |
| 물리적 상태 | 결정 또는 결정성 분말 |
| pKa(산도 계수) | 1.82, 9.66(at 25℃) |
| 색상 | 하얀색 |
| 냄새 | 냄새 없는 |
| pH | 5.5-6.5 (50g/l, H2O, 20℃) |
| 용해도 | 357.8g/L(20℃) |
| Merck | 14,4840 |
| BRN | 471933 |
| 화장품 원료 기능 | 헤어 컨디셔닝대전방지제계면활성제 - 세정피부 컨디셔닝 |
| InChI | 1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1 |
| InChIKey | PMMYEEVYMWASQN-DMTCNVIQSA-N |
| SMILES | O[C@H]1CN[C@@H](C1)C(O)=O |
| LogP(분배 계수) | -0.350 (est) |
| NIST | Hydroxyproline(51-35-4) |
| EPA | trans-4-Hydroxy-L-proline (51-35-4) |
화학적 성질
White crystalline powder
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 89.3% (25 of 28) of all reports.WarningH315 (10.7%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, 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 28 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: L-Proline, 4-hydroxy-, (4R)-Status: Active Update: 27-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21207L-Proline, 4-hydroxy-, (4R)-: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | IMAP assessments - L-Proline, 4-hydroxy-, trans-: Environment tier I assessment |
| 유해성 요약 | May cause irritation[Alfa Aesar MSDS] See L-Proline. |
| Hazard Classes and Categories | Skin Irrit. 2 (10.7%) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | TW3586500 |
| 관세 코드 | 29339990 |
| 위험 문구(R) | 36/37/38-22 |
| 위험 표시 | Xi,Xn |
| 안전 문구(S) | 24/25-36/37/39-27-26 |
| 위험 등급 | IRRITANT |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
A non-essential amino acid. Can be isolated from gelatin. Hydroxyproline has not been reported as added to food in any of the NAS surveys.
용도
A natural constituent of animal structural proteins such as collagen and elastin. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline.
일반 설명
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
제조 및 합성 방법
생산 방법
In the past L-Hydroxyproline was isolated by hydrolysis of animal collagen, e. g. gelatine or collagen, of which it is a major constituent. L-Hydroxyproline is an unnatural amino acid which is made in the body by hydroxylation of L-Proline. The presence of L-Hydroxyproline and proline are key to maintaining the stability of the tight collagen helix. Today L-Hydroxyproline is manufactured by bio-catalysed hydroxylation of proline in bacteria. Together with its other isomers, L-Hydroxyproline is also used as an inter mediate for a range of pharmaceutical active ingredients. Produced by hydroxylation of L-proline after protein synthesis. It is contained rich in collagen and elastin. Known to stabilization of triple-helix structure of collagen. Widely used as an intermediate for medicines.