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51-35-4
???:
????????
???(??):
????????;4-????????
???:
L-Hydroxyproline
???(??):
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
???:
C5H9NO3
??? ??:
131.13
MOL ??:
51-35-4.mol
MSDS ??:
SDS

???????? ??

???
273 °C (dec.)(lit.)
??
-75.5 º (c=5, H2O)
?? ?
242.42°C (rough estimate)
??
1.3121 (rough estimate)
?? ??
610kg/m3
?? ??
4.5 (vs air)
???
-75.5 ° (C=4, H2O)
?? ??
Store below +30°C.
???
H2O: 50 mg/mL
??? ??
?? ?? ??? ??
?? ?? (pKa)
1.82, 9.66(at 25℃)
??
???
??
?? ??
??????(pH)
5.5-6.5 (50g/l, H2O, 20℃)
optical activity
[α]25/D 75.6°, c = 1 in H2O
???
357.8g/L(20℃)
Merck
14,4840
BRN
471933
InChIKey
PMMYEEVYMWASQN-DMTCNVIQSA-N
LogP
-0.350 (est)
CAS ??????
51-35-4(CAS DataBase Reference)
NIST
Hydroxyproline(51-35-4)
EPA
trans-4-Hydroxy-L-proline (51-35-4)
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  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xi,Xn
?? ???? ?? 36/37/38-22
????? 24/25-36/37/39-27-26
WGK ?? 3
RTECS ?? TW3586500
TSCA Yes
?? ?? IRRITANT
HS ?? 29339990
????(GHS): GHS hazard pictograms
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ?? GHS hazard pictograms
??????:
P261 ??·?·??·???·??·...·????? ??? ????.
P271 ?? ?? ??? ? ?? ???? ?????.
P280 ????/???/???/?????? ?????.
NFPA 704
1
0 0

???????? MSDS


(2S,4R)-(-)-4-Hydroxy-2-pyrrolinecarboxylic acid

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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.

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White crystalline powder

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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.

??

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

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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.

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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

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.]

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