D(+)-Phenylalaninol Chemical Properties

Melting point:

93-95 °C(lit.)

Boiling point:

122 °C / 4mmHg

alpha 

23 º (c=1.2, 1 N HCl 22 ºC)

Density 

1.0406 (rough estimate)

refractive index 

23.5 ° (C=1.2, 1mol/L HCl)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in Dichloromethane, Ethyl Acetate, Methanol.

form 

Crystalline Powder and Chunks

pka

12.85±0.10(Predicted)

color 

White to yellow

optical activity

[α]/D +22.8°, c = 1.2 in 1 M HCl

Sensitive 

Air Sensitive

BRN 

4665408

InChI

InChI=1/C9H13NO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-5,9,11H,6-7,10H2/t9-/s3

InChIKey

STVVMTBJNDTZBF-DJEYLCQNNA-N

SMILES

C(C1C=CC=CC=1)[C@@H](N)CO |&1:7,r|

CAS DataBase Reference

5267-64-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34

Safety Statements 

26-36/37/39-45-27

RIDADR 

UN 3259 8/PG 3

WGK Germany 

3

F 

10-23

HazardClass 

IRRITANT

HazardClass 

8

PackingGroup 

III

HS Code 

29221990

MSDS

• Language:English Provider:D(+)-Phenylalaninol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

D(+)-Phenylalaninol Usage And Synthesis

Detected method

Phenomena, including gelation and fluorescence, are used as easily detected sensors of chiral recognition. Qin et al. have developed a new type of isomerized diphenylalanine-based supramolecular gel (LFDF), which showed the visible enantiomeric discrimination of phenylalaninol enantiomers via fluorescence and gelation measurements. The addition of L- or D-phenylalaninol to the peptide gel led to complete collapse within one minute after adding the L-form, which was not observed in D-phenylalaninol. Meanwhile, by doping with the fluorescent dye thioflavin T (ThT), the prepared ThT-LFDF gel system can sensitively detect the L/D-phenylalanine enantiomer through fluorescence quenching, which has the advantages of visualization, easy manipulation, and high detection sensitivity.

Description

D-phenylalanine is the D-enantiomer of phenylalanine. It is a conjugate base of a D-phenylalaninium and an enantiomer of a L-phenylalanine. D-Phenylalanine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). It may be light-sensitive. This compound reacts with strong oxidizing agents, acids and bases. It acts as a weak acid in solution.

Chemical Properties

white to light yellow crystal powde

Uses

D-Phenylalaninol is used as a chiral auxiliary for asymmetric Michael reactions. It is an enantiomer of L-Phenylalaninol, an inhibitor of intestinal Phenylalanine absorption. It acts as an inhibiting agent to the enzymes which are responsible for the breakdown of endorphins.

Purification Methods

It can be recrystallised from Et2O, *C6H6/pet ether (b 40-60o) or toluene and distilled in a vacuum. It has been purified by dissolving in Et2O, drying over K2CO3, filtering, evaporating to a small volume, cooling in ice and collecting the plates. Store them in the presence of KOH (i.e. CO2—free atm). [Karrer & Ehrhardt Helv Chim Acta 34 3203 1951, Oeda Bull Chem Soc Jpn 13 465 1938.] The picrate has m 141-141.5o (from EtOH/pet ether). The hydrogen oxalate has m 177o, 161-162o [Hunt & McHale J Chem Soc 2073 1957]. The racemate has m 87-88o from *C6H6/pet ether (75-77o from Et2O), and the hydrochloride has m 139-141o [Fodor et al. J Chem Soc 1858 1951]. [Beilstein 13 IV 1920.]

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