N-Benzoyl-3-phenylisoserine, (2R,3S)-

HCID 2762289CAS 132201-33-3

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Grundinformationen

Standard-SMILES: O=C(N[C@@H](c1ccccc1)[C@@H](O)C(=O)O)c1ccccc1
InChIKey: HYJVYOWKYPNSTK-UONOGXRCSA-N
Summenformel: C16H15NO4
Durchschnittliche Molmasse: 285,29 g/mol
Monoisotopische Masse: 285,10010796

Namen und Bezeichner

Bevorzugter Name: N-Benzoyl-3-phenylisoserine, (2R,3S)-
IUPAC: (2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoic acid
Englischer Name: (2R,3S)-N-Benzoyl-3-phenyl Isoserine
Summenformel: C16H15NO4
Molmasse: 285.3

Namen und Synonyme

132201-33-3(2R,3S)-N-Benzoyl-3-phenylisoserineN-Benzoyl-3-phenylisoserine, (2R,3S)-D998Q2WJCMUNII-D998Q2WJCMBenzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (alphaR,betaS)-DTXSID10157433BENZENEPROPANOIC ACID, .BETA.-(BENZOYLAMINO)-.ALPHA.-HYDROXY-, (.ALPHA.R,.BETA.S)-RefChem:162890DTXCID0079924N-Benzoyl-(2R,3S)-3-phenylisoserine(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoic acid

Weitere Namen anzeigen

taxol side chainTAXOL(R) SIDE CHAINPaclitaxel Impurity 30Paclitaxel Impurity N1Taxol side chain alcoholTAXOL SIDE CHAIN ACID(SH)SIDE CHAINS OF PACLITAXEL--4(2R,3S)-3-Benzoylamino-2-Hydro(2R,3S)-N-Benzoylphenylisoserine

(2R,3S)-N-Benzoyl-3-phenyl IsoserineMFCD00274633188003-77-2(2R,3S)-rel-3-Benzamido-2-hydroxy-3-phenylpropanoic acid(2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropanoic Acid ((2R,3S)-N-Benzoyl-3-phenylisoserine)(2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropionic acid; (2R,3S)-N-Benzoyl-3-phenylisoserine; N-Benzoyl-(2R,3S)-3-phenylisoserine; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (alphaR,betaS)-; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, [R-(R*,S*)]-; Taxol side chain acidTaxol Side Chain AcidN-Benzoyl-(2R,3S,)-3-phenylisoserine

Datenbank-Bezeichner

CAS: 132201-33-3
PubChem CID: 2762289
DTXSID: DTXSID10157433
ChEMBL: CHEMBL134943
UNII: D998Q2WJCM
EC Number: 631-348-7
Nikkaji: J391.951J

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,7
Polarare Oberfläche (TPSA): 86,6 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 5
Schwere Atome: 21
Formalladung: 0
Komplexität: 359

Physikochemische Eigenschaften

Schmelzpunkt: 169 · 169-172 °C (lit.)
Siedepunkt: 580.7 · 580.7±50.0 °C(Predicted)
Dichte: 1.316 · 1.316±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
Löslichkeit: Acetonitrile (Slightly), DMSO (Slightly), Ethanol (Slightly)
Aggregatzustand: Solid
pka: 3.4 · 3.40±0.17(Predicted)
Farbe: White to Off-White
Major Application: peptide synthesis
InChI: 1S/C16H15NO4/c18-14(16(20)21)13(11-7-3-1-4-8-11)17-15(19)12-9-5-2-6-10-12/h1-10,13-14,18H,(H,17,19)(H,20,21)/t13-,14+/m0/s1
InChIKey: HYJVYOWKYPNSTK-UONOGXRCSA-N
SMILES: O[C@H]([C@@H](NC(=O)c1ccccc1)c2ccccc2)C(O)=O
CAS Datenbank: 132201 · 132201-33-3(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract 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 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；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

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (100%)

Sicherheitsdaten

wgk: 3
hs_code: 29242990
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Anwendungen · 1 Eintrag

Verwenden(2R,3S)-N-Benzoyl-3-phenylisoserine is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-N-Benzoyl-3-phenylisoserine shows cytotoxic, antiviral and immunomodulatory activity.