ChemicalBook > CAS DataBase List > L-Hydroxyproline

L-Hydroxyproline

Product Name
L-Hydroxyproline
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
Formula Weight
131.13
MOL File
51-35-4.mol
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H54409
Product name
trans-4-Hydroxy-L-proline
Purity
≥99%
Packaging
2.5g
Price
$39.2
Updated
2024/03/01
Sigma-Aldrich
Product number
41875
Product name
trans-4-Hydroxy-L-proline
Purity
analytical standard
Packaging
100mg
Price
$72.7
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR1939
Product name
Hydroxyproline
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
500MG
Price
$151
Updated
2022/05/15
TCI Chemical
Product number
H0296
Product name
trans-4-Hydroxy-L-proline
Purity
>99.0%(HPLC)(T)
Packaging
5g
Price
$28
Updated
2024/03/01
TCI Chemical
Product number
H0296
Product name
trans-4-Hydroxy-L-proline
Purity
>99.0%(HPLC)(T)
Packaging
25g
Price
$68
Updated
2024/03/01
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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.]

L-Hydroxyproline Preparation Products And Raw materials

Raw materials

Soy bean Isoflavone Isoflavone 10-40% Α-protein Bone glue Casein Gelatin

Preparation Products

N-Boc-cis-4-Hydroxy-L-proline methyl ester (R)-(-)-3-Pyrrolidinol hydrochloride (2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine
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L-Hydroxyproline Suppliers

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View Lastest Price from L-Hydroxyproline manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
L-Hydroxyproline 51-35-4
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-24
HebeiShuoshengImportandExportco.,Ltd
Product
L-Hydroxyproline 51-35-4
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-08
WUHAN FORTUNA CHEMICAL CO., LTD
Product
L-Hydroxyproline 51-35-4
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98.5%-101.0%; AJI92
Supply Ability
10 TONS
Release date
2021-07-27

51-35-4, L-HydroxyprolineRelated Search:

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

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