| Identification | More | [Name]
L-Hydroxyproline | [CAS]
51-35-4 | [Synonyms]
(2S,4R)-(-)-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID
(2S,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID
(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
[2S,4S]-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID
4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID
4-HYDROXY-L-PROLINE
4-HYDROXY-L-PROLINE TRANS ISOMER
4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
H-HYP-OH
H-HYP-OH (TRANS)
H-L-HYDROXYPROLINE
H-L-HYP-OH
H-TRANS-HYP-OH
HYDROXY-L-PROLINE
HYDROXY-L-PROLINE, TRANS-4-
HYDROXYPROLINE
HYDROXYPROLINE, L-
L4-4-HYDROXY-2-PYRROLIDINE-CARBOXYLIC ACID TRANS ISOMER
L-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID
L-4-HYDROXY-2-PYRROLIDINE-CARBOXYLIC ACID TRANS-ISOMER | [EINECS(EC#)]
200-091-9 | [Molecular Formula]
C5H9NO3 | [MDL Number]
MFCD00064320 | [Molecular Weight]
131.13 | [MOL File]
51-35-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystalline powder | [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 at RT. | [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) | [Detection Methods]
NMR,Rotation | [Merck ]
14,4840 | [BRN ]
471933 | [InChIKey]
PMMYEEVYMWASQN-DMTCNVIQSA-N | [LogP]
-0.350 (est) | [Uses]
hydroxyproline is a skin-conditioning amino acid. It is a component of collagen. | [CAS DataBase Reference]
51-35-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Hydroxyproline(51-35-4) | [EPA Substance Registry System]
51-35-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
TW3586500
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29339990 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Α-PROTEIN-->Casein-->Gelatin-->Soy bean Isoflavone Isoflavone 10-40%-->Bone glue | [Preparation Products]
(R)-(-)-3-Pyrrolidinol hydrochloride-->N-Boc-cis-4-Hydroxy-L-proline methyl ester-->(2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine-->tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride-->N-Boc-4-oxo-L-Proline methyl ester-->Fmoc-L-hydroxyproline-->3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid-->1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-4-methyl-, 1,1-dimethylethyl ester, (2S,4S)--->2-PyrrolidineMethanol, 4-hydroxy-, hydrochloride (1:1), (2S,4R)--->BETONICINE-->TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE-->N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER-->1-BENZYLPYRROLE-->1-PHENYLPYRROLE |
| Hazard Information | Back Directory | [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 | [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.] |
|
|