Guidechem | China Chemical Manufacturers,suppliers,B2B Marketplace
Encyclop..
  • Products
  • Encyclopedia
  • Buy offers
  • Suppliers
Home> Encyclopedia >Organic Acid>Pharmaceutical Intermediates>Organic Intermediate
N-Benzyloxycarbonyl-L-proline structure
N-Benzyloxycarbonyl-L-proline structure

N-Benzyloxycarbonyl-L-proline

Iupac Name:(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
CAS No.: 1148-11-4
Molecular Weight:249.26
Modify Date.: 2023-03-06 09:40
Introduction: Used in the synthesis of biochemical reagents, oxytocin, vasopressin and other peptides. View more+
1. Names and Identifiers
1.1 Name
N-Benzyloxycarbonyl-L-proline
1.2 Synonyms

(2S)-1-[(Benzyloxy)carbonyl]-2-pyrrolidinecarboxylate (2S)-1-[(Phenylmethoxy)carbonyl]pyrrolidine-2-carboxylic acid (2S)-1-Phenylmethoxycarbonylpyrrolidine-2-carboxylicacid (S)-1-(benzyloxycarbonyl)-pyrrolidine-2-carboxylic acid (S)-1-carbobenzoxypyrrolidine-2-carboxylic acid (S)-N-(benzyloxycarbonyl)-proline (S)-N-CBZ-pyrrolidine-2-carboxylic acid 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (2S)- 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- (9CI) 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, ion(1-), (2S)- 1,2-Pyrrolidinedicarboxylic acid, 1-benzyl ester, L- 1-[(Benzyloxy)carbonyl]-L-proline Benzyloxycarbonyl-L-proline Boc-Ile-OH.1/2H2O Carbobenzoxy-L-proline carbobenzoxyproline Carbobenzyloxy-L-proline Cbz-L-proline CBZ-L-Pro-OH EINECS 214-557-4 MFCD00003170 MFCD00020830 N-[(phenyl-methoxy)carbonyl]-L-proline N-benzyloxycarbonyl-(S)-proline N-Benzyloxycarbonyl-L-proline~Z-Pro-OH n-benzyloxycarbonylproline N-Carbobenzoxy-L-proline N-Carbobenzyloxy-L-proline N-Cbz-L-proline N-cbz-L-proline crystalline N-CBZ-L-Proline N-Carbobenzyloxy-L-proline N-Cbz-L-Pro-OH Z-L-Proline Z-Pro-OH

1.3 CAS No.
1148-11-4
1.4 CID
101987
1.5 EINECS(EC#)
214-557-4
1.6 Molecular Formula
C13H15NO4 (isomer)
1.7 Inchi
InChI=1S/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m0/s1
1.8 InChkey
JXGVXCZADZNAMJ-NSHDSACASA-N
1.9 Canonical Smiles
C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)O
1.10 Isomers Smiles
C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)C(=O)O
2. Properties
2.1 Density
1.1952 (rough estimate)
2.1 Melting point
75-77 °C
2.1 Boiling point
392.36°C (rough estimate)
2.1 Refractive index
-40 ° (C=2, EtOH)
2.1 Flash Point
215.3 oC
2.1 Precise Quality
249.100113
2.1 PSA
66.84000
2.1 logP
1.81010
2.1 Solubility
Solubility in methanol, almost transparency.
2.2 Appearance
white to light yellow crystal powder
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
white to light yellow crystal powder
2.5 Color/Form
White to Yellow Solid
2.6 pKa
3.99±0.20(Predicted)
2.7 Water Solubility
Appearance:white to off-white crystalline powder
Hazard Symbols:Not regulated
particular:particular
2.8 Stability
Stable under normal temperatures and pressures.
2.9 StorageTemp
Sealed in dry,Room Temperature
3. Use and Manufacturing
3.1 Usage

An inhibitor of prolidase.

4. Safety and Handling
4.1 Hazard Codes
Xn
4.1 Risk Statements
62-36/37/38-20/21/22
4.1 Safety Statements
22-24/25-36-26
4.1 Hazard Class
IRRITANT
4.1 RIDADR
NONH for all modes of transport
4.1 WGK Germany
3
4.1 RTECS
UY0745000
4.1 Specification

The?IUPAC name of?N-Carbobenzoxy-L-proline is 1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid . With the?CAS registry number 1148-11-4, it is also named as?1-(Benzyloxycarbonyl)proline ; Benzyloxycarbonyl-L-proline ; Benzyloxycarbonylproline ; Carbobenzoxy-L-proline ; Carbobenzoxy-S-proline?;?L-1,2-Pyrrolidinedicarboxylic acid 1-benzyl ester ; 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- (9CI) .

The?N-Carbobenzoxy-L-proline is white to light yellow crystal powder?which should be stored at the?temperature of?2-8 °C. It is harmful by inhalation, in contact with skin and if swallowed.?And it is irritating to eyes, respiratory system and skin.?Risk of impaired fertility.?So people should?not breathe dust and avoid contact with skin and eyes.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable protective clothing.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 1.17 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -0.35 ; (4)ACD/LogD (pH 7.4): -2.07 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 3.13 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 5 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 4 ; (12)Index of Refraction: 1.582 ; (13)Molar Refractivity: 63.55 cm3 ; (14)Molar Volume: 190.3 cm3 ; (15)Polarizability: 25.19×10-24 cm3 ; (16)Surface Tension: 58.5 dyne/cm ; (17)Enthalpy of Vaporization: 72.53 kJ/mol ; (18)Vapour Pressure: 3.06E-08 mmHg at 25°C ; (19)Rotatable Bond Count: 4 ; (20)Exact Mass: 249.100108 ; (21)MonoIsotopic Mass: 249.100108 ; (22)Topological Polar Surface Area: 66.8 ; (23)Heavy Atom Count: 18.

People can use the following data to convert to the molecule structure.?SMILES: O=C(O)[C@@H]2N(C(=O)OCc1ccccc1)CCC2;?InChI: InChI=1/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m1/s1.

The following is the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravaginal > 1gm/kg (1000mg/kg) ? Journal of Pharmaceutical Sciences. Vol. 68, Pg. 696, 1979.

4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UY0745000
CHEMICAL NAME :
1,2-Pyrrolidinedicarboxylic acid, 1-benzyl ester, L-
CAS REGISTRY NUMBER :
1148-11-4
LAST UPDATED :
199406
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C13-H15-N-O4
MOLECULAR WEIGHT :
249.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravaginal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
280 mg/kg
SEX/DURATION :
female 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravaginal
DOSE :
280 ug/kg
SEX/DURATION :
female 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H318 Causes serious eye damage

Precautionary statement(s)
Prevention

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P310 Immediately call a POISON CENTER/doctor/\u2026

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
N-(Benzyloxycarbonyl)-L-proline is a potent in vitro and in vivo inhibitor of prolidase; a specific peptidase that cleaves dipeptides with a C-terminal prolyl and hydroxylprolyl residue. It is also used in the synthesis of N-(L-Prolyl)-β-alanine which is a derivative of the naturally occurring beta amino acid β-Alanine.
9.1 Uses
N-(Benzyloxycarbonyl)-L-proline is a potent in vitro and in vivo inhibitor of prolidase; a specific peptidase that cleaves dipeptides with a C-terminal prolyl and hydroxylprolyl residue. It is also used in the synthesis of N-(L-Prolyl)-β-alanine which is a derivative of the naturally occurring beta amino acid β-Alanine.
9.2 Preparation
Caution! All procedures must be carried out in an efficient fume cupboard, wearing latex gloves and chemical-proof safety goggles. ι-Proline (10.0 g, 8.7 mmol) was dissolved in 2 m sodium hydroxide solution (40 mL), and the solution was cooled to ice-water temperature. Z-Cl (20.5 g, 12 mmol) was added portionwise, with vigorous stirring or occasional shaking, over a period of 30 min at 0–5 °C to the solution of l-proline. The ice bath was then removed and stirring or occasional shaking was continued for 30 min while the reaction mixture warmed to room temperature. The mixture was then acidified to Congo red by the gradual addition of concentrated hydrochloric acid, and the oil was extracted into ethyl acetate. The extract was dried over magnesium sulfate, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was extracted/triturated with warm tetrachloromethane. The washings were decanted and the residue was further purified by recrystallization from ethyl acetate/petroleum ether.
9.3 用途

Carbobenzoxyproline is an inhibitor of prolidase.
9.4 BRN
88579
9.5 Chemical Properties
white to light yellow crystal powder
10. Computational chemical data
  • Molecular Weight: 249.26g/mol
  • Molecular Formula: C13H15NO4
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 249.10010796
  • Monoisotopic Mass: 249.10010796
  • Complexity: 312
  • Rotatable Bond Count: 4
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 66.8
  • Heavy Atom Count: 18
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccByOAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAAABAAAAHgAACAAADCjhmAYwCIMABgCIAiDSGAACAAAgAAAIiAGICIgKJjKAsTiMcAAkxgGYqAeY0SIOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Recommended Suppliers
Global222SuppliersView all >>
  • Products:Division I, the main production Lead acetate phenylacetamide Cyromazine quality is very good!
  • Tel:86-185-31123677
  • Email:xing@yan-xi.com
N-Benzyloxycarbonyl-L-proline
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1 USD/kilogram
  • Time: 2023/05/11
Inquire
  • Products:Manufacture & Supply Biopharm Chemical, Specialty Chemical, PetroChemical.
  • Tel:86-592-8883942
  • Email:sale@amitychem.com
Factory Supply N-Carbobenzyloxy-L-proline
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 0.1 USD/kilogram
  • Time: 2023/03/01
Inquire
  • Products:Chemical products
  • Tel:86-571-88938639
  • Email:sales-gc@dycnchem.com
N-Carbobenzoxy-L-proline
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1 USD/kilogram
  • Time: 2023/06/02
Inquire
  • Products:Cosmetic Raw Materials,solvents,etc.
  • Tel:86-311-66562153
  • Email:spring@crovellbio.com
Cbz-L-Proline CAS 1148-11-4
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 10 USD/kilogram
  • Time: 2023/06/06
Inquire
  • Products:We ZERchem, facing global High-tech pharmaceutical raw materials, high value-added new type intermediates fine chemicals custom synthesis, scale-up production and rare chemicals trade.
  • Tel:+86-571-82512721
  • Email:sales@zeerrui.com
N-Benzyloxycarbonyl-L-proline
  • Purity:99%Packing: 200kg/bag FOB
  • Price:  
  • Time: 2023/06/06
Inquire
12. Realated Product Infomation