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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
Molecular Weight:
131.13
MDL Number:
MFCD00064320
MOL File:
51-35-4.mol
MSDS File:
SDS
Last updated:2024-11-19 23:02:33

L-Hydroxyproline 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
PH 5.5-6.5 (50g/l, H2O, 20℃)
Odor Odorless
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)
Substances Added to Food (formerly EAFUS) L-HYDROXYPROLINE
CAS DataBase Reference 51-35-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII RMB44WO89X
NIST Chemistry Reference Hydroxyproline(51-35-4)
EPA Substance Registry System trans-4-Hydroxy-L-proline (51-35-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P271-P280
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
NFPA 704
1
0 0

L-Hydroxyproline price More Price(83)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich H54409 trans-4-Hydroxy-L-proline ≥99% 51-35-4 2.5g $39.2 2024-03-01 Buy
Sigma-Aldrich 41875 trans-4-Hydroxy-L-proline analytical standard 51-35-4 100mg $72.7 2024-03-01 Buy
Sigma-Aldrich PHR1939 Hydroxyproline Pharmaceutical Secondary Standard; Certified Reference Material 51-35-4 500MG $151 2022-05-15 Buy
TCI Chemical H0296 trans-4-Hydroxy-L-proline >99.0%(HPLC)(T) 51-35-4 5g $28 2024-03-01 Buy
TCI Chemical H0296 trans-4-Hydroxy-L-proline >99.0%(HPLC)(T) 51-35-4 25g $68 2024-03-01 Buy
Product number Packaging Price Buy
H54409 2.5g $39.2 Buy
41875 100mg $72.7 Buy
PHR1939 500MG $151 Buy
H0296 5g $28 Buy
H0296 25g $68 Buy

L-Hydroxyproline Chemical Properties,Uses,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 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

hydroxyproline is a skin-conditioning amino acid. It is a component of collagen.

Uses

A versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins.

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.]

147-85-3
51-35-4
Synthesis of L-Hydroxyproline from L-Proline
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View Lastest Price from L-Hydroxyproline manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
L-Hydroxyproline pictures 2024-11-25 L-Hydroxyproline
51-35-4
US $10.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
L-Hydroxyproline pictures 2024-11-25 L-Hydroxyproline
51-35-4
US $6.00 / kg 1kg 99% 2000KG/Month HebeiShuoshengImportandExportco.,Ltd
L-Hydroxyproline pictures 2024-11-25 L-Hydroxyproline
51-35-4
US $6.00 / kg 1kg More than 99% 2000KG/Month Hebei Longbang Technology Co., Ltd
  • L-Hydroxyproline pictures
  • L-Hydroxyproline
    51-35-4
  • US $10.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
  • L-Hydroxyproline pictures
  • L-Hydroxyproline
    51-35-4
  • US $6.00 / kg
  • More than 99%
  • Hebei Longbang Technology Co., Ltd
(S)-(-)-TRANS-4-HYDROXYPROLINE FOR SYNTH trans-4-Hydroxy-L-proline, 99+% 10GR trans-4-Hydroxy-L-proline, 99+% 25GR trans-4-Hydroxy-L-proline Microbial, cell culture tested 4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID 4-HYDROXY-L-PROLINE TRANS ISOMER (S)-(-)-TRANS-4-HYDROXYPROLINE RARECHEM EM WB 0135 TRANS-L-HYDROXYPROLINE TRANS-L-(-)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID 4-L-Hydroxyproline delta-Hydroxyproline L-Proline, 4-hydroxy-, trans- L-Proline,4-hydroxy-,trans Ls-Hydroxyproline Proline, 4-hydroxy- Proline, 4-hydroxy-, L- trans-Hydroxyproline (-)-(2S,4R)-4-Hydroxyproline L-Hypro (4R)-4-Hydroxy-L-proline (4R)-4β-Hydroxy-L-proline 2-Hydroxy-L-proline 2-Hydroxyproline L-Hydroxyproline 〔trans-4-Hydroxy-L-proline〕 L-Hydroxyproline 〔trans-4-Hydroxy-L-proline〕, Animal-Free trans-L-4-Hydroxyproline≥ 99% (Titration) trans-L-4-HydroxyprolineNon-animal Japanese origin99.0-101.0% (Assay, dry basis) trans-4-Hydroxy-L-proline,99%e.e. TRANS-4-HYDROXY-L-PROLINE BIOXTRA, > (S)-(-)-trans-4-Hydroxyproline for synthesis [2S,4S]-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID (2S,4R)-(-)-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID (2S,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID H-HYP-OH (TRANS) H-L-HYDROXYPROLINE H-L-HYP-OH H-TRANS-HYP-OH HYDROXY-L-PROLINE, TRANS-4- HYDROXYPROLINE, L- L-(-)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID L-4-TRANS-HYDROXYPROLINE L-4-HYDROXY-2-PYRROLIDINECARBOXYLIC ACID L-4-HYDROXY-2-PYRROLIDINE-CARBOXYLIC ACID TRANS-ISOMER L4-4-HYDROXY-2-PYRROLIDINE-CARBOXYLIC ACID TRANS ISOMER L-TRANS-4-HYDROXYPROLINE L-HYDROXYPROLINE (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acidHyp 4-hydroxy-L-proline (trans) TRANS-4-HYDROXY-L-PROLINE, 99+% L-HydroxyprolineForBiochemistry L-Hydroxyproline99+% L-HYDROXYPROLINE ( AKA ) TRANS 4 HYDROXY L PROLINE TRANS 4 HYDROXY L PROLINE (HYPRO) TRANS-L-HYDROXYPROLINE, (2S,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID L-HYDROXY PROLINE/TRANS-L-4-HYDROXYPROLINE L-HYDROXYPROLINE51-35-4 HYDROXY-L-PROLINE, trans-4-(RG)