51-35-4

Basic information

• Product Name: L-Hydroxyproline
• Synonyms: H-HYP-OH;H-HYP-OH (TRANS);H-L-HYDROXYPROLINE;H-L-HYP-OH;H-TRANS-HYP-OH;HYDROXYPROLINE;HYDROXY-L-PROLINE;HYDROXY-L-PROLINE, TRANS-4-
• CAS NO: 51-35-4
• Molecular Formula: C₅H₉NO₃
• Molecular Weight: 131.13
• EINECS: 200-091-9
• Product Categories: Nitrogen cyclic compounds;PHARMACEUTICALS;Amino Acids;Pyrrole&Pyrrolidine&Pyrroline;Hydroxyproline [Hyp];Unusual Amino Acids;Biochemistry;Biological-modified Amino Acids;L-Amino Acids;Amino Acids;Amino Acids & Derivatives;Chiral Reagents;Heterocycles
• Mol File: 51-35-4.mol
• Article Data: 68

Chemical Properties

• Melting Point: 273 °C (dec.)(lit.)
• Boiling Point: 242.42°C (rough estimate)
• Flash Point: 168.6 °C
• Appearance: White/Crystals or Crystalline Powder
• Density: 1.3121 (rough estimate)
• Vapor Density: 4.5 (vs air)
• Refractive Index: -75.5 ° (C=4, H2O)
• Storage Temp.: Store at RT.
• Solubility: H2O: 50 mg/mL
• PKA: 1.82, 9.66(at 25℃)
• Water Solubility: 357.8 g/L (20 º C)
• Merck: 14,4840
• BRN: 471933
• CAS DataBase Reference: L-Hydroxyproline(CAS DataBase Reference)
• NIST Chemistry Reference: L-Hydroxyproline(51-35-4)
• EPA Substance Registry System: L-Hydroxyproline(51-35-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 24/25-36/37/39-27-26
• WGK Germany: 3
• RTECS: TW3586500
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 51-35-4(Hazardous Substances Data)

Usage

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.

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.

Definition

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

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.

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.]

InChI:InChI:1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)

Upstream product

• 9000-71-9 Casein 
• 146317-23-9 Α-PROTEIN 
• 9000-70-8 Gelatin 

Downstream Products

• 104706-47-0 (R)-(-)-3-Pyrrolidinol hydrochloride 
• 61478-28-2 (2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine 
• 102195-79-9 N-Boc-cis-4-Hydroxy-L-proline methyl ester 

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