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HomeProduct name listD-Proline

D-Proline

Synonym(s):(R)-Pyrrolidine-2-carboxylic acid;(S)-Pyrrolidine-2-carboxylic acid;L-Proline

  • CAS NO.:344-25-2
  • Empirical Formula: C5H9NO2
  • Molecular Weight: 115.13
  • MDL number: MFCD00064317
  • EINECS: 206-452-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 08:26:49
D-Proline Structural

What is D-Proline?

Chemical properties

White to off-white powder

Occurrence

D-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva. These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity.

The Uses of D-Proline

Labelled D-Proline Lasubine II and (+)-Cermizine C.

The Uses of D-Proline

Used in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C.

The Uses of D-Proline

proline is a skin-conditioning agent. An amino acid found in the collagen molecule.

Definition

ChEBI: D-proline is the D-enantiomer of proline. It has a role as a mouse metabolite. It is a D-alpha-amino acid and a proline. It is a conjugate base of a D-prolinium. It is a conjugate acid of a D-prolinate. It is an enantiomer of a L-proline. It is a tautomer of a D-proline zwitterion.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 2818, 1949 DOI: 10.1021/ja01176a065
Tetrahedron Letters, 28, p. 6469, 1987 DOI: 10.1016/S0040-4039(00)96890-4

Properties of D-Proline

Melting point: 223 °C (dec.) (lit.)
Boiling point: 215.41°C (rough estimate)
alpha  84.75 º (c=4, H2O)
Density  1.36
refractive index  85 ° (C=4, H2O)
storage temp.  Inert atmosphere,Room Temperature
solubility  Methanol (Slightly), Water (Sparingly)
pka 1.952(at 25℃)
form  Powder
color  White to yellow to pale brown
optical activity [α]22/D +85.0°, c = 4 in H2O
Water Solubility  soluble >1000 g/L (20 ºC)
Sensitive  Hygroscopic
BRN  80811
CAS DataBase Reference 344-25-2(CAS DataBase Reference)
EPA Substance Registry System D-Proline (344-25-2)

Safety information for D-Proline

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for D-Proline

InChIKey ONIBWKKTOPOVIA-SCSAIBSYSA-N

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