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ChemicalBook--->CAS DataBase List--->51-35-4

51-35-4

51-35-4 Structure

51-35-4 Structure
IdentificationMore
[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 PropertiesBack 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)
[bulk density]

610kg/m3
[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 DataBack 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 ProductsBack 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
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

(2S,4R)-(-)-4-Hydroxy-2-pyrrolinecarboxylic acid(51-35-4).msds
Hazard InformationBack 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
[reaction suitability]

reaction type: solution phase peptide synthesis
[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.]
Spectrum DetailBack Directory
[Spectrum Detail]

L-Hydroxyproline(51-35-4)MS
L-Hydroxyproline(51-35-4)1HNMR
L-Hydroxyproline(51-35-4)13CNMR
L-Hydroxyproline(51-35-4)IR1
L-Hydroxyproline(51-35-4)IR2
L-Hydroxyproline(51-35-4)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

trans-4-Hydroxy-L-proline, 99+%(51-35-4)
[Alfa Aesar]

trans-4-Hydroxy-L-proline, 99+%(51-35-4)
[Sigma Aldrich]

51-35-4(sigmaaldrich)
[TCI AMERICA]

trans-4-Hydroxy-L-proline,>99.0%(T)(51-35-4)
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