L-Hydroxyproline Chemical 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

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 Information

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

MSDS

• Language:English Provider:(2S,4R)-(-)-4-Hydroxy-2-pyrrolinecarboxylic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

L-Hydroxyproline Usage And Synthesis

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.]

L-Hydroxyproline(51-35-4)Related Product Information

• D-Proline
• trans-4-Hydroxy-D-proline
• trans,trans-2,4-Undecadienal
• N-Acetyl-L-Hydroxyproline
• L-Proline
• CHLOROPHOSPHONAZO III
• L-PROLINE-(4-3H(N))
• trans-4-Hydroxy-L-proline methyl ester hydrochloride
• L-(+)-Prolinol
• L-Leucine
• Methyl L-leucinate hydrochloride
• cis-4-Hydroxy-D-proline
• Boc-Hyp-OH
• cis-4-Hydroxy-L-proline
• BETONICINE
• (2S,4R)-BOC 4-HYDROXYPROLINE METHYL ESTER,(2S,4R)-BOC 4-HYDROXYPROLINE METHYL ESTER,(2S,4R)-BOC 4-HYDROXYPROLINE METHYL ESTER
• BOC-HYP(BZL)-OH
• Fmoc-Hyp(tBu)-OH