Chiral Compounds

Propanolol which is a beta-blockerwas analyzed using an alkaline eluent using ORpak CDB-453 HQ (a column for chiral separation).

Sample : Propranolol

Column       : Shodex ORpak CDB-453 HQ (4.6mmID*150mm)
Eluent       : 1.4% CH3COOH + 3.4% Triethylamine + 0.2M NaCl(pH8.2)
Flow rate    : 0.2mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Chlorphenylamine which is an antihistaminic was analyzed using ORpak CDB-453 HQ (a column for chiral separation) with an alkaline eluent.

Sample : Chlorpheniramine

Column       : Shodex ORpak CDB-453 HQ (4.6mmID*150mm)
Eluent       : 1.0% CH3COOH + 2.3% Triethylamine + 0.2M NaCl(pH8.2)
Flow rate    : 0.2mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Tolperisone which is a muscle relaxant was analyzed using ORpak CDB-453 HQ (a column for chiral separation) with an alkaline eluent.

Sample : Tolperisone

Column       : Shodex ORpak CDB-453 HQ (4.6mmID*150mm)
Eluent       : 1.4% CH3COOH + 3.4% Triethylamine + 0.2M NaCl(pH8.2)
Flow rate    : 0.2mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Optical rotation of each peak can be monitored by using a combination of an optical rotation detector (ORD) and ORpak CDB-453 HQ (a column for chiral separation). A positive peak shows dextrorotation, while a negative peak shows levorotation. The analysis of methionine-beta-naphthylamide, an amino acid using a UV detector and an optical rotation detector is shown.

Sample : Methionine-beta-naphthylamide

Column       : Shodex ORpak CDB-453 HQ (4.6mmID*150mm)
Eluent       : [1.4% CH3COOH + 0.7% Triethylamine + 0.1M NaCl (pH3.9)]/CH3CN=80/20
Flow rate    : 0.2mL/min
Detector     : UV(300nm), ORD
Column temp. : 20deg-C

Optical rotation of each peak can be monitored by using a combination of an optical rotation detector (ORD) and ORpak CDB-453 HQ (a column for chiral separation). A positive peak shows dextrorotation, while a negative peak shows levorotation. The results of the analysis of chlorthalidone, a diuretic, using a UV detector and an optical rotation detector is shown.

Sample : Chlorthalidone

Column       : Shodex ORpak CDB-453 HQ (4.6mmID*150mm)
Eluent       : (1.1% CH3COOH + 0.2M NaCl)/CH3CN=90/10
Flow rate    : 0.2mL/min
Detector     : UV(300nm), ORD
Column temp. : 10deg-C

Chiral compounds were analyzed using ORpak CDB-453 HQ (a column for chiral separation).

Sample :
2-(4-Hydroxyphenoxy)propionic acid
2-Phenoxypropionic acid
2-Phenylbutyric acid

Chiral compounds were analyzed using ORpak CDA-453 HQ, CDB-453 HQ and CDC-453 HQ (columns for chiral separation).

Sample :
6-Fluorotryptophan
Alanine-beta-naphthylamide
DNS-Leucine
MTH-Phenylalanine

Chiral compounds were analyzed using ORpak CDB-453 HQ( a column for chiral separation ).

Sample :
Benzoin
Brompheniramine
Homatropine
Terbutaline

Chiral compounds were analyzed using ORpak CDB-453 HQ (a column for chiral separation).

Sample :
5-(4-Methylphenyl)-5-phenyl hydantoin
Efaroxan
Indapamide
Laudanosoline

Chiral compounds were analyzed using AFpak ABA-894 and ORpak CRX-853 (columns for chiral separation).

Sample :
4-(1-Oxo-2-cyclohezylmethyl)-benzoic acid
DNS-Valine
Mandelic acid
Phenylalanine

Chlorpheniramine and methaboric intermediates were analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample :
1. Chlorpheniramine
2. Monodesmethyl-chlorpheniramine
3. Didesmethyl-chlorpheniramine

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 10% CH3CN 90% (1.0% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 30deg-C

Courtesy of Dr. Sakurai, Tohoku Cllage of Pharmacy

The chiral compounds listed below were separated using ORpak CDBS-453.
We think that chiral compounds of which chemical structure is similar to one of the components listed below can probably be separated using ORpak CDBS-435.

Epinephrine Terbutaline Norphenylephrine
alpha=1.15, Rs=2.1
Eluent: A		 alpha=1.14, Rs=2.2
Eluent: D		 alpha=1.11, Rs=1.9
Eluent: D
Oxyphencyclimine Trihexyphenidyl Promethazine
alpha=1.11, Rs=1.6
Eluent: C		 alpha=1.14, Rs=1.8
Eluent: C		 alpha=1.08, Rs=1.2
Eluent: E
Trimipramine Brompheniramine Homatropine
alpha=1.13, Rs=1.9
Eluent: E		 alpha=1.35, Rs=4.2
Eluent: B		 alpha=1.14, Rs=1.7
Eluent: E
Benzoin Zopiclone Nefopam
alpha=1.15, Rs=1.8
Eluent: E		 alpha=1.22, Rs=1.8
Eluent: B		 alpha=1.35, Rs=4.9
Eluent: E
Oxazepam Hexobarbital Norlaudanosoline
alpha=1.20, Rs=2.4
Eluent: B		 alpha=1.18, Rs=2.1
Eluent: A		 alpha=1.24, Rs=2.1
Eluent: B
Chlortharidone Indapamide Efaroxan
alpha=1.29, Rs=3.8
Eluent: B		 alpha=1.18, Rs=2.2
Eluent: D		 alpha=1.11, Rs=1.8
Eluent: E
2-Phenoxypropionic acid Propranolol
alpha=1.15, Rs=2.4
Eluent: B		 alpha=1.11, Rs=1.5
Eluent: E		 
Eluent A :1% CH3CN + 99% (0.05% CH3COOH + 0.2M NaCl) in H2O
Eluent B :10% CH3CN + 90% (1.1% CH3COOH + 0.2M NaCl) in H2O
Eluent C :30% CH3CN + 70% (1.1% CH3COOH + 0.2M NaCl) in H2O
Eluent D :10% CH3CN + 90% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Eluent E :25% CH3CN + 75% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O

Epinephrine was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Epinephrine

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 1% CH3CN + 99%(0.05% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Zopiclone was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Zopiclone

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 10% CH3CN + 90% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

2-Phenoxypropionic acid was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample :
2-Phenoxypropionic acid

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 10% CH3CN + 90% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Indapamide was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Indapamide

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 10% CH3CN + 90% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Terbutaline was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Terbutaline

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 10% CH3CN + 90% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Norlaudanosoline was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Norlaudanosoline

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 10% CH3CN + 90% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Chlortharidone was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Chlortharidone

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 10% CH3CN + 90% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Valethamate was analyzed using ORpak CDBS-453 ( a column for chiral separation ).

Sample : Valethamate

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 30% CH3CN+ 70% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Trihexyphenidyl was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Trihexyphenidyl

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 30% CH3CN + 70% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Carprofen was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Carprofen

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 30% CH3CN + 70% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Procyclidine was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Procyclidine

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 30% CH3CN + 70% (1.1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Norphenylephrine was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Norphenylephrine

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 10% CH3CN + 90% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Trimipramine was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Trimipramine

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 25% CH3CN + 75% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Propranolol was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Propanolol

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 25% CH3CN + 75% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Homatropine was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Homatropine

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 25% CH3CN + 75% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Benzoine was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Benzoin

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 25% CH3CN + 75% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Efaroxan was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Efaroxan

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 25% CH3CN + 75% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Nefopam was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Nefopam

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 25% CH3CN + 75% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Laudanosoline was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Laudanosoline

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 25% CH3CN + 75% (1.4% CH3COOH + 0.7% (C2H5)3N + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 10deg-C

Warfarin was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Warfarin

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 20% CH3CN + 80%(1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.4mL/min
Column temp. : 16.5deg-C

Lorazepam was analyzed using ORpak CDBS-453 (a column for chiral separation).

Sample : Lorazepam

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 20% CH3CN + 80%(1% CH3COOH + 0.2M NaCl) in H2O
Flow rate    : 0.5mL/min
Detector     : UV(254nm)
Column temp. : 15deg-C

Bromoisovalerylurea was analyzed using ORpak CDBS-453 (a column for chiral separation). Detection was done using both a UV detector and an optical rotation detector (ORD).

Sample : 2-Bromoisovalerylurea

Column       : Shodex ORpak CDBS-453 (4.6mmID*150mm)
Eluent       : 0.02M Potassium phosphate in 0.1M Sodium chloride(pH 4.4)
Flow rate    : 1.0mL/min
Detector     : UV (220nm)
               ORD
Column temp. : 15deg-C

Abe et al., Analytical Sciences, 15 (1999) 397.

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