D-Proline Chemical Properties

Melting point:

223 °C (dec.) (lit.)

alpha 

84.75 º (c=4, H2O)

Boiling point:

215.41°C (rough estimate)

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

InChIKey

ONIBWKKTOPOVIA-SCSAIBSYSA-N

LogP

-0.060 (est)

CAS DataBase Reference

344-25-2(CAS DataBase Reference)

EPA Substance Registry System

D-Proline (344-25-2)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-24/25-36/37/39-26

WGK Germany 

3

F 

3-10

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29339990

MSDS

• Language:English Provider:D-Pyrrolidine-2-carboxylic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

D-Proline Usage And Synthesis

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.

Uses

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.

Uses

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

Uses

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

D-Proline(344-25-2)Related Product Information

• D-Tartaric acid
• D-Alanine
• D-Proline
• trans-4-Hydroxy-D-proline
• N-Benzyloxycarbonyl-D-proline
• cis-4-Hydroxy-D-proline
• Fmoc-D-proline
• BOC-D-PRO-OSU
• AC-D-PRO-OH
• (3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid
• Z-D-PYR-OH
• Methyl pyrrolidine-2-carboxylate hydrochloride
• D-Pyroglutamic acid
• Ethyl D-(-)-pyroglutamate
• Oxaceprol
• trans-4-Cyclohexyl-L-proline
• 1-(4-HYDROXY-PHENYL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID,1-(4-HYDROXY-PHENYL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID
• H-D-PRO-OTBU