ChemicalBook > Product Catalog >Biochemical Engineering >Amino Acids and Derivatives >Proline derivatives >L-Hydroxyproline

L-Hydroxyproline

L-Hydroxyproline Structure
CAS No.
51-35-4
Chemical Name:
L-Hydroxyproline
Synonyms
TRANS-4-HYDROXY-L-PROLINE;HYDROXYPROLINE;(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;Hyp;4-Hydroxyproline;4-HYDROXY-L-PROLINE;H-HYP-OH;4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;HYDROXY-L-PROLINE;4R-4-hydroxyproline
CBNumber:
CB8357870
Molecular Formula:
C5H9NO3
Molecular Weight:
131.13
MOL File:
51-35-4.mol
MSDS File:
SDS
Modify Date:
2024/11/19 23:02:33

L-Hydroxyproline Properties

Melting point 273 °C (dec.)(lit.)
alpha -75.5 º (c=5, H2O)
Boiling point 242.42°C (rough estimate)
Density 1.3121 (rough estimate)
vapor density 4.5 (vs air)
refractive index -75.5 ° (C=4, H2O)
storage temp. Store below +30°C.
solubility H2O: 50 mg/mL
form Crystals or Crystalline Powder
pka 1.82, 9.66(at 25℃)
color White
PH 5.5-6.5 (50g/l, H2O, 20℃)
Odor Odorless
optical activity [α]25/D 75.6°, c = 1 in H2O
Water Solubility 357.8 g/L (20 º C)
Merck 14,4840
BRN 471933
InChIKey PMMYEEVYMWASQN-DMTCNVIQSA-N
LogP -0.350 (est)
CAS DataBase Reference 51-35-4(CAS DataBase Reference)
NIST Chemistry Reference Hydroxyproline(51-35-4)
EPA Substance Registry System trans-4-Hydroxy-L-proline (51-35-4)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P271-P280
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-22
Safety Statements  24/25-36/37/39-27-26
WGK Germany  3
RTECS  TW3586500
TSCA  Yes
HazardClass  IRRITANT
HS Code  29339990
NFPA 704
1
0 0

L-Hydroxyproline price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) H5534 trans-4-Hydroxy-L-proline BioReagent, suitable for cell culture, ≥98.5% 51-35-4 10MG ₹2955.23 2022-06-14 Buy
Sigma-Aldrich(India) H5534 trans-4-Hydroxy-L-proline BioReagent, suitable for cell culture, ≥98.5% 51-35-4 25G ₹23522.73 2022-06-14 Buy
Sigma-Aldrich(India) H5534 trans-4-Hydroxy-L-proline BioReagent, suitable for cell culture, ≥98.5% 51-35-4 100G ₹63066.45 2022-06-14 Buy
Sigma-Aldrich(India) PHR1939 Hydroxyproline Pharmaceutical Secondary Standard; Certified Reference Material 51-35-4 500MG ₹15826.15 2022-06-14 Buy
Sigma-Aldrich(India) H5534 trans-4-Hydroxy-L-proline BioReagent, suitable for cell culture, ≥98.5% 51-35-4 1KG ₹319705.55 2022-06-14 Buy
Product number Packaging Price Buy
H5534 10MG ₹2955.23 Buy
H5534 25G ₹23522.73 Buy
H5534 100G ₹63066.45 Buy
PHR1939 500MG ₹15826.15 Buy
H5534 1KG ₹319705.55 Buy

L-Hydroxyproline Chemical Properties,Uses,Production

Description

A non-essential amino acid. Can be isolated from gelatin. Hydroxyproline has not been reported as added to food in any of the NAS surveys.

Chemical Properties

White crystalline powder

Uses

A natural constituent of animal structural proteins such as collagen and elastin. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline.

Production Methods

In the past L-Hydroxyproline was isolated by hydrolysis of animal collagen, e. g. gelatine or collagen, of which it is a major constituent. L-Hydroxyproline is an unnatural amino acid which is made in the body by hydroxylation of L-Proline. The presence of L-Hydroxyproline and proline are key to maintaining the stability of the tight collagen helix.
Today L-Hydroxyproline is manufactured by bio-catalysed hydroxylation of proline in bacteria. Together with its other isomers, L-Hydroxyproline is also used as an inter mediate for a range of pharmaceutical active ingredients.
Produced by hydroxylation of L-proline after protein synthesis. It is contained rich in collagen and elastin. Known to stabilization of triple-helix structure of collagen. Widely used as an intermediate for medicines.

Definition

ChEBI: An optically active form of 4-hydroxyproline having L-trans-configuration.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Purification Methods

Crystallise it from MeOH/EtOH (1:1). Separation from normal allo-isomer can be achieved by crystallisation of the copper salts [see Levine Biochemical Preparations 8 114 1961]. Separation from proline is achieved via the crystalline picrate, CdCl2, or acid ammonium rhodanate salts [see Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2182 1961, Kapfhammer & Mohn Z Physiol Chem 306 76 1956]. [Beilstein 22/5 V 7.]

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