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N-Cbz-Hydroxy-L-proline

CAS No.
13504-85-3
Chemical Name:
N-Cbz-Hydroxy-L-proline
Synonyms
CBZ-L-HYDROXYPROLINE;(2S,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;Z-HYP-OH;CBZ-HYP-OH;Z-Hyp;Z-L-HYP-OH;CBZ-L-HYP-OH;-4-hydroxy-L;Z-HYP(BZL)-OH;Z-HYDROXYPROLINE
CBNumber:
CB5148552
Molecular Formula:
C13H15NO5
Molecular Weight:
265.26
MDL Number:
MFCD00037329
MOL File:
13504-85-3.mol
MSDS File:
SDS
Last updated:2026-01-13 11:20:29
Product description Number Pack Size Price
Z-Hyp-OH ≥99.0% (T) 96310 25g $99.4
Z-Hyp-OH ≥99.0% (T) 96310 5g $79
trans-N-Carbobenzoxy-4-hydroxy-L-proline >98.0%(HPLC)(T) C2506 5g $24
trans-N-Carbobenzoxy-4-hydroxy-L-proline >98.0%(HPLC)(T) C2506 25g $123
(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylicAcid1-BenzylEster H953385 5g $70
More product size

N-Cbz-Hydroxy-L-proline Properties

Melting point 104-107 °C
Boiling point 486.9±45.0 °C(Predicted)
Density 1.416±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Dichloromethane, Ethyl Acetate
pka 3.78±0.40(Predicted)
form Oil
color White to off-white
optical activity [α]20/D 54±1°, c = 2% in ethanol
Water Solubility Slightly soluble in water.
BRN 90295
Major Application peptide synthesis
InChI 1S/C13H15NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,10-11,15H,6-8H2,(H,16,17)/t10-,11+/m1/s1
InChIKey WWVCWLBEARZMAH-MNOVXSKESA-N
SMILES O[C@@H]1C[C@H](N(C1)C(=O)OCc2ccccc2)C(O)=O
CAS DataBase Reference 13504-85-3(CAS DataBase Reference)
UNSPSC Code 12352209
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
PPE Eyeshields, Gloves, type N95 (US)
WGK Germany  3
HS Code  29339900
Storage Class 11 - Combustible Solids
NFPA 704
1
0 0

N-Cbz-Hydroxy-L-proline price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 96310 Z-Hyp-OH ≥99.0% (T) 13504-85-3 25g $99.4 2025-07-31 Buy
Sigma-Aldrich 96310 Z-Hyp-OH ≥99.0% (T) 13504-85-3 5g $79 2023-06-20 Buy
TCI Chemical C2506 trans-N-Carbobenzoxy-4-hydroxy-L-proline >98.0%(HPLC)(T) 13504-85-3 5g $24 2025-07-31 Buy
TCI Chemical C2506 trans-N-Carbobenzoxy-4-hydroxy-L-proline >98.0%(HPLC)(T) 13504-85-3 25g $123 2025-07-31 Buy
TRC H953385 (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylicAcid1-BenzylEster 13504-85-3 5g $70 2021-12-16 Buy
Product number Packaging Price Buy
96310 25g $99.4 Buy
96310 5g $79 Buy
C2506 5g $24 Buy
C2506 25g $123 Buy
H953385 5g $70 Buy

N-Cbz-Hydroxy-L-proline Chemical Properties,Uses,Production

Chemical Properties

Viscous Oil

Uses

A competitive inhibitor of porcine kidney prolidase.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Benzyl chloroformate

501-53-1

L-Hydroxyproline

51-35-4

N-Cbz-Hydroxy-L-proline

13504-85-3

GENERAL METHOD: To a solution of L-hydroxyproline (78.7 g, 600 mmol) and sodium bicarbonate (126 g, 1.5 mol) in water (900 mL), a solution of benzyl chloroformate (89.6 mL, 630 mmol) in dioxane (90 mL) was slowly added. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction (monitored by thin-layer chromatography), the reaction mixture was cooled to 0 °C in an ice bath and acidified to pH 2 with 12 M hydrochloric acid (about 75 mL was required). Subsequently, the aqueous phase was extracted with ethyl acetate (3 × 500 mL), the organic phases were combined and washed with saturated brine (3 × 200 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a colorless viscous oil. The yield was quantitative, and the product could be directly used in the next reaction without further purification.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1845 - 1847
[2] Angewandte Chemie - International Edition, 2007, vol. 46, # 47, p. 9073 - 9077
[3] Patent: EP1193270, 2002, A2. Location in patent: Page 14, 35-36, 105
[4] Tetrahedron Letters, 2016, vol. 57, # 44, p. 4882 - 4884
[5] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 5, p. 575 - 580

501-53-1
2584-71-6
13504-85-3
Synthesis of N-Cbz-Hydroxy-L-proline from Benzyl chloroformate and cis-4-Hydroxy-D-proline
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View Lastest Price from N-Cbz-Hydroxy-L-proline manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
N-Cbz-Hydroxy-L-proline pictures 2026-01-30 N-Cbz-Hydroxy-L-proline
13504-85-3
US $10.00 / KG 1KG 99% 5tons Hebei Chuanghai Biotechnology Co., Ltd
Z-Hyp-OH pictures 2024-04-28 Z-Hyp-OH
13504-85-3
US $5.00 / kg 1kg 99.92% 50000tons Ouhuang Engineering Materials (Hubei) Co., Ltd
Z-Hyp-oh pictures 2022-01-26 Z-Hyp-oh
13504-85-3
US $0.00 / KG 1KG 98.3% 100 tons Honest Joy Holdings Limited
  • Z-Hyp-OH pictures
  • Z-Hyp-OH
    13504-85-3
  • US $5.00 / kg
  • 99.92%
  • Ouhuang Engineering Materials (Hubei) Co., Ltd
  • Z-Hyp-oh pictures
  • Z-Hyp-oh
    13504-85-3
  • US $0.00 / KG
  • 98.3%
  • Honest Joy Holdings Limited

N-Cbz-Hydroxy-L-proline Spectrum

(2S,4R)-N-Cbz-trans-4-hydroxy-L-proline Z-L-HYP-OH Z-L-4-HYDROXYPROLINE Z-L-4-TRANS-HYDROXYPROLINE TRANS-N-ALPHA-BENZYLOXYCARBONYL-L-HYDROXYPROLINE BENZYLOXYCARBONYL-L-4-HYDROXYPROLINE CBZ-HYP-OH CBZ-L-HYDROXYPROLINE CBZ-L-HYP-OH N-Carbobenzyloxy-4-hydroxy-L-proline (trans) N-Z-4-hydroxy-L-proline (trans) 1-benzyl hydrogen (2S-trans)-4-hydroxypyrrolidine-1,2-dicarboxylate Z-trans-4-hydroxy-L-proline N-Cbz-cis-4-hydroxy-D-proline (2R,4R)-N-CBZ-4-HYDROXY-D-PROLINE Cbz-L-4- Hydroxyproline N-Benzyloxycarbonyl-4-hydroxy-L-proline N-Benzyloxycarbonyl-L-Hydroproline N-CARBOBENZYLOXY-TRANS-4-HYDROXY-L-PROLINE N-CBZ-CIS-4-HYDROXY-L-PROLINE CBZ-TRANS-4-HYDROXY-L-PROLINE Z-L-HYDROXYPROLINE extrapure N-carbobenzyloxy-hydroxy-L-proline N-Cbz-Hydroxy-L-proline, Z-L-4-Hydroxyproline (2S)-1-(Benzyloxycarbonyl)-4β-hydroxypyrrolidine-2α-carboxylic acid (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid hydrogen 1-(phenylmethyl) ester (4R)-1-(Benzyloxycarbonyl)-4-hydroxy-L-proline (4R)-N-(Benzyloxycarbonyl)-4-hydroxy-L-proline 1-(Benzyloxycarbonyl)-trans-4-hydroxy-L-proline N-(Benzyloxycarbonyl)-trans-4-hydroxy-L-proline Z-Hyp (2R)-2-hydroxy-1-phenylmethoxycarbonyl-2-pyrrolidinecarboxylic acid N-ALPHA-CARBOBENZOXY-L-HYDROXYPROLINE N-ALPHA-CARBOBENZOXY-O-BENZYL-TRANS-4-HYDROXY-L-PROLINE N-ALPHA-CBZ-L-4-TRANS-HYDROXYPROLINE N-ALPHA-BENZYLOXYCARBONYL-TRANS-L-HYDROXYPROLINE N-ALPHA-CARBOBENZOXY-(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID N-CARBOBENZOXY-L-HYDROXYPROLINE N-CBZ-HYDROXY-L-PROLINE Z-4-HYDROXY-L-PROLINE Z-HYP(BZL)-OH Z-HYP-OH Z-HYDROXYPROLINE Z-L-HYDROXYPROLINE N-carbobenzyloxy-4-hydroxy-l-proline 1-(benzyloxycarbonyl)-4-hydroxy-proline 4-hydroxy-1-(phenylmethoxycarbonyl)pyrrolidine-2-carboxylic acid N-Cbz-Hydroxy-L-prol (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, N-CBZ protected trans-4-Hydroxy-L-proline, N-CBZ protected 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(phenylMethyl) ester, (2S,4R)- trans-N-Carbobenzoxy-4-hydroxy-L-proline trans-N-Cbz-4-hydroxy-L-proline Z-Hyp-OH (2S,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic Acid 1-Benzyl Ester N-CBZ-4-hydroxy-L-proline Z-Hyp-OH >=99.0% (T) Z-L-4-trans-hydroxyproline≥ 98% (HPLC)