L-Hydroxyproline Property

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

Odor

Odorless

PH

5.5-6.5 (50g/l, H2O, 20℃)

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

L-Hydroxyproline Chemical Properties,Usage,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 versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins.

Uses

hydroxyproline is a skin-conditioning amino acid. It is a component of collagen.

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

Biochem/physiol Actions

Trans-4-Hydroxy-L-proline is used in the organic synthesis of depsilairdin analogues, noncompetitive peptidomimetic inhibitors of multidrug resistance P-glycoprotein and 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analogues.

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.]