CAS 132201-33-3 N-Benzoyl-3-phenylisoserine, (2R,3S)- (HCID 2762289)

Names & identifiers

Preferred name: N-Benzoyl-3-phenylisoserine, (2R,3S)-
IUPAC: (2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoic acid
English name: (2R,3S)-N-Benzoyl-3-phenyl Isoserine
Molecular formula: C16H15NO4
Molecular weight: 285.3

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 86.6 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 5
Heavy atoms: 21
Formal charge: 0
Complexity: 359

Physicochemical properties

Melting point: 169 · 169-172 °C (lit.)
Boiling point: 580.7 · 580.7±50.0 °C(Predicted)
Density: 1.316 · 1.316±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: Acetonitrile (Slightly), DMSO (Slightly), Ethanol (Slightly)
form: Solid
pka: 3.4 · 3.40±0.17(Predicted)
color: White to Off-White
optical activity: 20 · [α]20/D 40°, c = 1.0 in ethanol
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 DataBase Reference: 132201 · 132201-33-3(CAS DataBase Reference)
FDA UNII: 998 Q2WJCM · D998Q2WJCM
UNSPSC Code: 12352209 · 12352209
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
HS Code: 29242990 · 29242990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

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

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29242990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses(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.

UsesThe presence of this chiral side chain has proven to be essential for the biological activity of taxol, one of the most promising anticancer agents being investigated. The challenging synthesis of taxol has stimulated interest in the attachment of the C-13 side chain to naturally derived taxanes like baccatin III.