| Identification | More | [Name]
N-Cbz-D-Alanine | [CAS]
26607-51-2 | [Synonyms]
BENZYLOXYCARBONYL-D-ALANINE
CBZ-D-ALANINE
CBZ-D-ALA-OH
N-ALPHA-BENZYLOXYCARBONYL-D-ALANINE
N-ALPHA-CARBOBENZOXY-D-ALANINE
N-ALPHA-CBZ-D-ALANINE
N-BENZYLOXYCARBONYL-D-ALANINE
N-CARBOBENZOXY-D-ALANINE
N-CBZ-D-ALANINE
Z-D-ALANINE
Z-D-ALA-OH
N-Benzyloxycarbonyl-D-alanine,98+%
N-CBZ-ALA-OH
n-carbobenzyloxy-d-aniline
CBZ-D-Ala-OH CBZ-D-Alanine
Z-D-ALA
N-Carbobenzyloxy-D-alanine
Z-D-ALANINE extrapure
carbobenzyloxy D-alanine
N-Cbz-D-alanine, Z-D-alanine | [EINECS(EC#)]
206-418-1 | [Molecular Formula]
C11H13NO4 | [MDL Number]
MFCD00063126 | [Molecular Weight]
223.23 | [MOL File]
26607-51-2.mol |
| Questions And Answer | Back Directory | [Preparation]
At 10°C, 10 mmol of D-alanine was dissolved in 4.0 ml of 8% sodium hydroxide (NaOH) aqueous solution to obtain a solution. While stirring, 14 mmol (1.8 ml) of benzyl chloroformate was added dropwise to the solution at a rate of 1 drop/9 seconds. The pH was maintained at 8 by adding 8% sodium hydroxide (NaOH) aqueous solution. After the addition was complete, the solution was placed at 28°C and stirred for 15 hours. Thin-layer chromatography was performed to confirm complete reaction. The solution was then washed three times with 5 ml of diethyl ether each time, and the ether was discarded, yielding the aqueous phase. The pH of the aqueous phase was adjusted to 3 with 30% hydrochloric acid, resulting in a milky white solid. The liquid after the appearance of a milky white solid was extracted three times with 5 ml of ethyl acetate each time. The extracts were combined and washed twice with 5 ml of distilled water each time and once with 5 ml of saturated brine each time. The liquid was then dried with anhydrous magnesium sulfate for 12 hours, filtered, and the filtrate was concentrated under reduced pressure to obtain a pale yellow oil. The oil was purified by column chromatography using a mixed solvent of ethyl acetate and petroleum ether in a volume ratio of 1:3 as the mobile phase to obtain N-Cbz-D-Alanine, with a yield of 71.8% and a melting point Mp of 86-87℃. |
| Chemical Properties | Back Directory | [Melting point ]
83-84°C | [Boiling point ]
422.1±38.0 °C(Predicted) | [density ]
1.246±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
almost transparency in Methanol | [form ]
Crystalline Powder | [pka]
4.00±0.10(Predicted) | [color ]
White to off-white | [Optical Rotation]
Consistent with structure | [Detection Methods]
T,NMR,Rotation | [BRN ]
2056163 | [InChI]
InChI=1S/C11H13NO4/c1-8(10(13)14)12-11(15)16-7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,12,15)(H,13,14)/t8-/m1/s1 | [InChIKey]
TYRGLVWXHJRKMT-MRVPVSSYSA-N | [SMILES]
C(O)(=O)[C@@H](C)NC(OCC1=CC=CC=C1)=O | [CAS DataBase Reference]
26607-51-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319-H335 | [Precautionary statements ]
P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29224999 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white solid | [Uses]
N-Cbz-D-alanine is the Cbz-protected form of D-Alanine (A480995). D-Alanine is an amino acid that is commonly found in bacteria, such as Streptococcus faecalis. It is essential for the biosynthesis of peptidoglycan crosslinking sub-units that are used for bacterial cell walls. D-Alanine is also known to cause cytotoxic oxidative stress in brain tumour cells. |
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