Grundinformationen
- CAS
618-27-9- Standard-SMILES
O=C(O)[C@@H]1C[C@H](O)CN1- InChIKey
PMMYEEVYMWASQN-IMJSIDKUSA-N- Summenformel
- C5H9NO3
- Durchschnittliche Molmasse
- 131,13 g/mol
- Monoisotopische Masse
- 131,05824315
Namen und Bezeichner
- Bevorzugter Name
- Cis-4-Hydroxy-L-Proline
- IUPAC
- (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid
- Lokaler Name
- cis-4-Hydroxy-L-prolin
- Englischer Name
- cis-4-Hydroxy-L-proline
- Summenformel
- C5H9NO3
- Molmasse
- 131.13
Namen und Synonyme
cis-4-Hydroxy-L-proline(4S)-4-hydroxy-L-prolineL-Proline, 4-hydroxy-, (4S)-Hydroxyproline, cis-L-allo-hydroxyprolineallo-4-HydroxyprolineHydroxyproline cis-form4-cis-L-hydroxyprolinecis-HydroxyprolineProline, 4-allo-hydroxy-, L-allo-hydroxy-L-Proline43V78B6A3B
Weitere Namen anzeigen
(2S,4S)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACIDH-CIS-HYP-OHCIS-4-HYDROXYPROLINECIS-HYP-OH(4S)-4-hydroxypyrrolidine-2-carboxylic acidCHYPcis Lcis-L-Hyp-OH
EINECS 210-542-1CIS-L-4-HYDROXYPROLINENSC 206274cis-hydroxy-L-prolineL-Proline, allo-hydroxy-CHEBI:28397DTXSID20883473(2S,4S)-4-hydroxy-2-pyrrolidinecarboxylic acid
Datenbank-Bezeichner
- CAS
618-27-9- PubChem CID
- 440015
- DTXSID
DTXSID20883473- ChEMBL
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -3,3
- Polarare Oberfläche (TPSA)
- 69,6 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 125
Experimentelle und physikochemische Eigenschaften
Physical DescriptionWhite powder; [Sigma-Aldrich MSDS]
Physikochemische Eigenschaften
- Schmelzpunkt
- 257 °C · 257 °C (dec.) (lit.)
- Siedepunkt
- 242.42 °C · 242.42°C (rough estimate)
- Dichte
- 1.3121 · 1.3121 (rough estimate)
- Brechungsindex
- -59 ° · -59 ° (C=2, H2O)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- soluble
- Aggregatzustand
- Powder
- pka
- 2.14 · 2.14±0.40(Predicted)
- Farbe
- White to beige
- Wasserlöslichkeit
- soluble
- Merck
- 14 · 14,4840
- BRN
- 81440 · 81440
- Major Application
- peptide synthesis
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (2 of 6) of reports.
Warning
H302 (16.7%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (16.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (16.7%): Harmful if inhaled [Warning Acute toxicity, inhalation]；H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 2 of 6 reports by companies.；There are 4 notifications provided by 4 of 6 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.
Gefahrenhinweise
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (16.7%)；Acute Tox. 4 (16.7%)；Skin Irrit. 2 (50%)；Eye Irrit. 2A (50%)；Acute Tox. 4 (16.7%)；STOT SE 3 (50%)
Sicherheitsdaten
Chemie und Industrie
Verwendung und Herstellung
UsesNon-essential amino acid analog present in collagen; [Merck Index]
General Manufacturing InformationL-Proline, 4-hydroxy-, (4S)-: ACTIVE
Anwendungen
Verwendencis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line3 and rat pancreatic carcinoma cell line DSL6A. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Zugehörige Reaktionen
4
Notizen zur Verbindung
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