| Identification | More | [Name]
cis-4-Hydroxy-D-proline | [CAS]
2584-71-6 | [Synonyms]
(2R,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID
(2R,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
(4R,2R)-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID
CIS-4-HYDROXY-D-PROLINE
CIS-D-4-HYDROXYPROLINE
CIS-D-HYDROXYPROLINE
D-ALLO-4-HYDROXY-2-PYRROLIDINE-CARBOXYLIC ACID
D-ALLO-HYDROXYPROLINE
D-CIS-4-HYDROXYPROLINE
D-CIS-HYDROXYPROLINE
H-D-CIS-HYP-OH
HYDROXY-D-PROLINE [ALLO]
D-trans-Hydroxyproline
cis-4-D-Hydroxyproline
(2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid
D-ALLO-4-HYDROXYPROLINE
D-Proline, 4-hydroxy-, (4R)-
(2R,4R)-(-)-4-Hydroxypyrrolidin-2-ylcarboxylic acid
D-CIS-HYDROXYPROLINE, (2R,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID
(2R,4R)-4-HYDROXY-D-PROLINE | [EINECS(EC#)]
219-963-5 | [Molecular Formula]
C5H9NO3 | [MDL Number]
MFCD00005252 | [Molecular Weight]
131.13 | [MOL File]
2584-71-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white powder | [Melting point ]
243 °C (dec.)(lit.)
| [alpha ]
58 º (c=2, water 24 ºC) | [Boiling point ]
242.42°C (rough estimate) | [density ]
1.3121 (rough estimate) | [refractive index ]
1.4300 (estimate) | [storage temp. ]
Store at RT. | [solubility ]
Water (Slightly) | [form ]
Powder | [pka]
2.14±0.40(Predicted) | [color ]
White | [Optical Rotation]
56.1°(C=0.93 g/100ml H2O) | [Water Solubility ]
5 g/100 mL | [BRN ]
81439 | [InChI]
1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m1/s1 | [InChIKey]
PMMYEEVYMWASQN-QWWZWVQMSA-N | [SMILES]
O[C@H]1CN[C@H](C1)C(O)=O | [LogP]
-1.840 (est) | [CAS DataBase Reference]
2584-71-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P271-P280 | [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 .
S22:Do not breathe dust .
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
| [F ]
10 | [HS Code ]
29339900 | [Storage Class]
13 - Non Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
white powder | [Uses]
cis-4-Hydroxy-D-proline (cas# 2584-71-6) is a compound useful in organic synthesis. | [Definition]
ChEBI: D-proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (R-configuration). | [Biochem/physiol Actions]
Cis-4-Hydroxy-D-proline may be used as a starting material for the 13-step synthesis of new conformationally restricted PNA adenine monomer and the synthesis of N-Benzyl pyrrolidinyl sordaricin derivatives. Cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase. Cis-4-Hydroxy-D-proline may be used to analyze the substrate specificity of amino acid transporter PAT1. | [Synthesis]
General procedure for the synthesis of cis-4-hydroxy-D-proline using L-hydroxyproline as starting material: a synthetic route has been successfully developed for the other two stereoisomers in the pro4 monomer class. A controlled differential isomerization strategy [34] was employed to convert 30 g of trans-4-hydroxy-(L)-proline 5 into its diastereoisomer cis-4-hydroxy-(D)-proline 14 in 57% isolated yield. Further processing of the intermediate by the synthetic method described in Scheme 1 allowed the synthesis of two additional enantiomers of the pro4 structural unit class 3, pro4(2R,4R) and pro4(2R,4S) (see Scheme 3 for details). | [References]
[1] Tetrahedron Asymmetry, 2003, vol. 14, # 20, p. 3141 - 3152
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 2, p. 197 - 201
[3] Tetrahedron, 2009, vol. 65, # 4, p. 862 - 876
[4] Patent: US2004/77879, 2004, A1. Location in patent: Page 13
[5] Patent: WO2018/13867, 2018, A1. Location in patent: Paragraph 339 |
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