- Email: [email protected]
Chromatographic data
Dzz3
CWROMATOGRAPNIC DATA (1972) TABLE
530
TLC nz;l
VALUES
(R. L.
MITAI
AND
OF
SOME
S. K.
TRZPHENODIOXAZINII;S
JAIN,
AND
ANALOGUES
J. C&m. Sec. C, (1971) 1877)
I
Thin layer: Silica Gel G (Merck). Solvents : S, = Benzene-nitrobonzeno (95 : 5). 9,’ S, = Hexone-pyridine (4: I), (I 7 : 3), Ss!.+ ‘.. % -e Benzonc-n-butanol Detection: All spots are coloured and the colour chan8cs after spraying with COW. sulphuric acid.
_
Compound X
RF Y
Sl
%I
SLl
H ti Cl
0.74 0.67 o-Q3 0.55 0.88 0.84 0.84 0.75 0.68 0.62 0.74 0.61 0.81 0.74 0857 0.53 0.43 0037
0.70 0.66 0.81 0.77 0.80 o-74 0.72 0.67 0.64 o.Go a.69 0.60 0.75 0.63 o*49 o-37 0.41 0.33
o,6g
Cl
E : CH,
CI-l,
OCH, GCH, GCZH, OCaHe H z,g-d&Cl 1-E2,9-di-Cl H 2,g-dinitro H 2,g-dinitro
o,G2
o*77 o&7 0173 o.G2 0.68 0.61 o-57 0.49 0.67 0.55 0.72 o&g 0133 o-24 0*34 0.2g
Spot colotcr bcfovej after spraying
red/blue redjbluc red/blue red/blue red/blue red/blue red/blue red/blue red/blue red/blue red/blue red/ blue red/blue red/blue brown/violet brown/bluish brown/green brown/green
green
I.
.,
Dzr14
CNROMATOGRAPHIC DATA(I972)
TABLE
531
TLC
VALUES OF SOME 5-AMINO-IMLDAZOLES,-PYRAZOLES AND -TRIAzOLES
Rp
(N. J. CUSACIC, G. SHAW AND G. J. LITCHFXELD,J. Ckcm. S’dc. C, (1971) 1503) Thin layer: Whatman CC 4I cellulose. Solvents : S, = n-Butanol-acetic acid-tvatcr (12 : 3: 5). (sp. gr. 0.880)~water (4: 3 : I : 2). Sa = tort.-Butanol-butan-2-one-ammonia Detection: D, = UV light. Da = Ammonium molybdate. D, = Bratton-Marshall reagent according to G. SHAW AND D. V. WILSON, J, Cltem. SO&, (1962) 2937. Compound
g-Aminoimidazolc 5-Aminoimiclazole-4-carboxylic acid g-Aminopyrazole 5-Aminopyrazole-4-carboxylic acid J-Amino- I ,2,3-triazolo 5-Amino-I,2,3-triazoIc-$-carboxylic acid J-Amino- I -cyclohexylimidazole 5-Amino-I-cyclohcxylimidazole-4-carboxylic acid 5-Amino-I-cyclohcxylpyrazole g-Amino-I-cyclohexylpyrazole-4-carboxylic acid 5-Amino-I-cyclohcxyl-I,2,3-triazole 5-Amino-I-cyclohoxyl-r,2,3-triazole-4-carboxylic acid 5-Amino-I-p-o-ribofuranosylimidazole 5-Amino-I-~-D-ribofuranosylimidazole-4~carboxylic acid 5-Amino-I-B-D-ribofuranosylimidazole 5’-phosphate 5-Amino-I-#&p-ribofuranosylimidazole-4-carboxylic acid 5’.phosphate 5-Amino-I-cyclohcxyl-2-methylimiclazole 5-Amino-r-cyclohexyl-2-imidazole-4-carboxylic acid
RF %
%
0.48 0,48
o&7 0.36 0.74 0.35 0.45
0.44 0.67 0.59 0.55 0.63 0.72 OS5 0.90 0.91 0.90 0.42 0.40
0019 0.19 0.75 0.73
0.15 0.94 0.63 o-99 0.63 0.97 0.73 0.62 0.30 0.14 0.06 0.94 0.70
“,:*1;
!Lwlj
CHROMATOGRAPHIC TABLE
DATA
(1972)
532
PC RF VALUES
ELPHO
AND
(Cw. DIZGANLAND
MORILITIES OF SORIE SUGAR
PHOSPHATES
M. HALMANN,J. C/rem, Sec. C, (1971) 1460)
chvomalogvaplby Paper : Schleichcr and Scht\ll No. zo45a. ‘Solvent : Methanol-formic acid-water ( I 6 : 3 : I). Detection: Aniline hydrogen phthalatc and ammonium Paper
molybclate.
Papev eleclvoplbovesis Paper : Whatman No. I. Operating conditions : Savant Instrument Co. Model LF ZOAclcctrophoresis tank, voltage gradient 40-Go V/cm. Electrolyte : Buffer pH 3.5 (6.6 ml of pyriclinc and 66 ml of acetic acicl diluted with water to 3 1). Compound D-Glucose IX-D-Glucose I-phosphate p-~-Glucose r-phosphate Glucose 6-phosphate D-Arabinose Arabinofuranose I-phosphate Arabinopyranose I-phosphate Maltose phosphate Cellobiose phosphate Lactose phosphate Melibiose phosphate
0.87 0.68 0.84
0.14 0.68 0.68 0.68 0.14 0.73 0.73 0.53 0.53 0.53 0.53
0.89 o.sg 0.57 0.57
TABLE 533’ Cc SEPARATION OF SUBSTITUTIZD PHENOLS (J. J. KIRKLAND, J, Citvowzato~v.Sci., g (1971) 214) Column : Sorbcnt : Eluent : Operating conditions: Detection : Note :
I m x 0.083 in.1.D. 0.88 o/obondccl ether phase on Zipax (Du Pont). 2.5 O/O methanol in cyclopentane. Flow rate, I ml/min; column inlet pressure, 250 p.s.i. Amount loaded 20 141 of 0.25 mg/ml p- and nt-cresol, 0.125 mg/ml each of phenol, 2,62,3-, 3,4- and 3,5 di-methylphenol. By IR recording. 3 = p-cresol; 4 = 3,g-dimcthylphenol; 5 = 1 = phenol ; 2 = m-cresol; 3,4-climethylphenol; 6 = 2,3-dimcthylphcnol; 7 = 2,6-climethylphenol. 7
0.005
.
22.5
As
I
15 Time
(mA
0
CWKOMATOGKAPN~C
UuIItY
TABLE
534
TLC &
VALUES
(J.
W.
MATHIESON
OF
SPINOCHROMES
AND
R.
I-3. THOMSON,
J. CAem. Sm. C, (1971)
IGO)
Thin layer: Cellulose MN 300 plates. go y0 formic acid. Solvent : Detection : Visible and UV light.
%
44
R3
OH OMe OH OH OH OH OH
AC
H 1% Et AC
:z OH OH
OH
OH OMo OH %I OH OH H OH
%I Et 1-I H OH OH I II
%
43
z OH OH H OH E OH H OH
Colouv
RF
purple pink pink red yellow red orange orange red yellow orange red red
0,sz 0.82 0.s2
0.73 0.70 0.67 0x93 0.61 O.GI
oe5.5 0,4c 0.4G 0.28
DATA
[ &g7:
CRROMATOGRAPNIC
TABLE cc
DATA
D1z7
(1972)
535
SEPARATION
OF PHBNYL.ENBDZhMINB
lSOMBRS
(J* J. IQRICLAND, J. Ckvomalogv. SC&, 9 (1971) 214) I m x 0.083 in. I.D. Column : Sorbent : 0.88 o/obonded ether phase on Zipnx (Du Pout), surface porosity below 3714, 5 y. methnnol in cyclopentsne. .:,--Buff cr : 27O. ~~,$per~ting conditions : Flow rate I ml/min. column inlet pressure 2Go p.s.i., temperature Sample loaclecl: G ~1 of 0.05 mg of each isomer in the cluting solvent. By RI recording. Detection :
UNKNOWN
J ,
8I TABLE _
6
2 4 TIME, MINUTES
536
ELL>H,O OF CHOLINE, ACETYLCHOLINE AND RELATED COMPOUNDS (W. D. RAID, D. R. HAUBRICH AND G. KRISI-INA, Anal, Biochem.., 42 (rgp) 394) Whatmann No. 3MM paper Sorbcnt : 0.3 M pyricline, which was simultanecksly ,o.G61M with respect to formic Buffer: acid, pH 4.6. Operating conditions: 1,500 V/cm; running time, 2.5 h; room temperature. The spots were visuslizocl by applying iodine vnpours. Detection: Migvatiolzrate (cm/z,5k)
Compotcnd Choline N-Dimethylaminocthanol N-Methylnminoothsmol Ethanolamine ,. Acetylcholine Propionylcl~olinc Butyrylcholine Benzoyloholine Succinylcholine Acotyl-/3 methylcholine CDP-cholme Phosphorylcholine / Carnitine Acetylcarnitino ‘/
,,’ ,:,.
,. ,
,...
0
,
:” .
..’.
,“,‘,
”
335 330 3900 42,o 3215 30#0 27.0 24,o 3&o 3040 -300 -I,0 30 5’14
DILB
CAROMATOGRAPNLC
TABLE
DATA
(X972)
537
cc SIIPARATION OF THIOLHYDROXAMATES (J. J. KIRKLAND, ,I. Chvtmatogr. SC;., g (197x) .zog) I m x 0.083 in. I.D. Zipax (Du Pont) with 0.88 % ether phase (for details see J. J. KIRKLAND AND J. J. DESTEPANO, J. Clwovnatogr. Sci., 8 (1970) 309). Controlled poros- ‘:~~,, -1 ity surface below 37 /L. i#V IO o/odioxane in isooctane. Go “, : Flow rate, o.YG ml/min; column inlet pressure Igo p.s.i.; temperature By I.R recording.
Column : Sorbont:
Elucnt : Operating Detection
conditions
:
..
y+J
?T
(CH3)2-
51’;’
N-C-0-N-O-C-N-Cl-l3
6
6
4
2
0
Time (min) TABLE
538
cc SEPARATION OF ANILINE DERIVATIVES, n-TRIDECANE~AND TETRAHYDROCHINALDINE (G. DEININGER AND I. HAL&Z, J. Chromatop. Sci., g (1971) gr) 20 cm long, 2 mm I.D. .’ Non-porous glass bead of sieve fraction o.og-o.ro mm. Stationary phase: brush with 3-hydroxypropionitrile bristles, sieve fraction 0.05o-o.060 mm. It-Hoptane : Column inlet pressure, 1.20 atm; flow rate, 0.62 ml/min. By IR recording. 3 = tatrahydrocbinaldinet;’ T k uc-tridecano ; 2 P N,N’;dimethylaniline; 4 = 2,6-dimothylaniline.
Column : Sorbont :
Eluent : Operating Detection
conditions
:
Noto : 3
.
CWROMATOGRAPRIC TABLE CC
DATA
539
SEPARATION
OF
(C. G. VAN TEELIN~, Column : Sorbent :
Bu ffcrs :
Operating
conditions:
ANTHOCYANINS
2.0 r
:
ON
P. E. CANSFIELD
COLUMNS OF POLYVINYLPYRROLIDONE AND
R. A. GALLOP, J. C/mmdog~.
Sci., g (1971) 508)
rg x 150 nm or alternatively IS x 70 mm. Hydrated insoluble polyvinylpyrroliclonc, Polycar A. T. (Gcncml Anilirrc and Film Corporation). The column was devclopccl with 0.25 N MCI in water until the pigment moved halfway down the column. The solvent was then changed to 0.5 N HCl in 500/ mclhnnol and elution continued until all the bands had left the column. Bcforc analysis the column wns washed with 150 ml of 0.25 N I-ICI in water. Flow rates were within 30-40 ml/h, flow unclcr gravity. 1.8 or IO ml fractions
Detection
Dmg
(1972)
By optical
were collcctcd as indicatccl. clcnsit)? reading in visible
Cyanldin 3.Rutlnoside 520nm
Fraction
number
ia
Cyaniclln 3-Rutlnoside
Pelargonidln
3.blucoside
light.
‘D120
CWROMXTOGRAPWIC
Peonidln 3~Galactoside Peonidin 3mArabinaside 3- Qalactosldc
Cyanidin
I
I
4
6
I
I
,,I
I
3-Arabinoside
I,,
8 10 12 14 16 15 20 22 24 Ractlon number
u3ml fmctionsY.JOml
DATA
(1972
CWROMATOGRAPNIC DATA (1972) TABLE
530
TLC nz;l
VALUES
(R. L.
MITAI
AND
OF
SOME
S. K.
TRZPHENODIOXAZINII;S
JAIN,
AND
ANALOGUES
J. C&m. Sec. C, (1971) 1877)
I
Thin layer: Silica Gel G (Merck). Solvents : S, = Benzene-nitrobonzeno (95 : 5). 9,’ S, = Hexone-pyridine (4: I), (I 7 : 3), Ss!.+ ‘.. % -e Benzonc-n-butanol Detection: All spots are coloured and the colour chan8cs after spraying with COW. sulphuric acid.
_
Compound X
RF Y
Sl
%I
SLl
H ti Cl
0.74 0.67 o-Q3 0.55 0.88 0.84 0.84 0.75 0.68 0.62 0.74 0.61 0.81 0.74 0857 0.53 0.43 0037
0.70 0.66 0.81 0.77 0.80 o-74 0.72 0.67 0.64 o.Go a.69 0.60 0.75 0.63 o*49 o-37 0.41 0.33
o,6g
Cl
E : CH,
CI-l,
OCH, GCH, GCZH, OCaHe H z,g-d&Cl 1-E2,9-di-Cl H 2,g-dinitro H 2,g-dinitro
o,G2
o*77 o&7 0173 o.G2 0.68 0.61 o-57 0.49 0.67 0.55 0.72 o&g 0133 o-24 0*34 0.2g
Spot colotcr bcfovej after spraying
red/blue redjbluc red/blue red/blue red/blue red/blue red/blue red/blue red/blue red/blue red/blue red/ blue red/blue red/blue brown/violet brown/bluish brown/green brown/green
green
I.
.,
Dzr14
CNROMATOGRAPHIC DATA(I972)
TABLE
531
TLC
VALUES OF SOME 5-AMINO-IMLDAZOLES,-PYRAZOLES AND -TRIAzOLES
Rp
(N. J. CUSACIC, G. SHAW AND G. J. LITCHFXELD,J. Ckcm. S’dc. C, (1971) 1503) Thin layer: Whatman CC 4I cellulose. Solvents : S, = n-Butanol-acetic acid-tvatcr (12 : 3: 5). (sp. gr. 0.880)~water (4: 3 : I : 2). Sa = tort.-Butanol-butan-2-one-ammonia Detection: D, = UV light. Da = Ammonium molybdate. D, = Bratton-Marshall reagent according to G. SHAW AND D. V. WILSON, J, Cltem. SO&, (1962) 2937. Compound
g-Aminoimidazolc 5-Aminoimiclazole-4-carboxylic acid g-Aminopyrazole 5-Aminopyrazole-4-carboxylic acid J-Amino- I ,2,3-triazolo 5-Amino-I,2,3-triazoIc-$-carboxylic acid J-Amino- I -cyclohexylimidazole 5-Amino-I-cyclohcxylimidazole-4-carboxylic acid 5-Amino-I-cyclohcxylpyrazole g-Amino-I-cyclohexylpyrazole-4-carboxylic acid 5-Amino-I-cyclohcxyl-I,2,3-triazole 5-Amino-I-cyclohoxyl-r,2,3-triazole-4-carboxylic acid 5-Amino-I-p-o-ribofuranosylimidazole 5-Amino-I-~-D-ribofuranosylimidazole-4~carboxylic acid 5-Amino-I-B-D-ribofuranosylimidazole 5’-phosphate 5-Amino-I-#&p-ribofuranosylimidazole-4-carboxylic acid 5’.phosphate 5-Amino-I-cyclohcxyl-2-methylimiclazole 5-Amino-r-cyclohexyl-2-imidazole-4-carboxylic acid
RF %
%
0.48 0,48
o&7 0.36 0.74 0.35 0.45
0.44 0.67 0.59 0.55 0.63 0.72 OS5 0.90 0.91 0.90 0.42 0.40
0019 0.19 0.75 0.73
0.15 0.94 0.63 o-99 0.63 0.97 0.73 0.62 0.30 0.14 0.06 0.94 0.70
“,:*1;
!Lwlj
CHROMATOGRAPHIC TABLE
DATA
(1972)
532
PC RF VALUES
ELPHO
AND
(Cw. DIZGANLAND
MORILITIES OF SORIE SUGAR
PHOSPHATES
M. HALMANN,J. C/rem, Sec. C, (1971) 1460)
chvomalogvaplby Paper : Schleichcr and Scht\ll No. zo45a. ‘Solvent : Methanol-formic acid-water ( I 6 : 3 : I). Detection: Aniline hydrogen phthalatc and ammonium Paper
molybclate.
Papev eleclvoplbovesis Paper : Whatman No. I. Operating conditions : Savant Instrument Co. Model LF ZOAclcctrophoresis tank, voltage gradient 40-Go V/cm. Electrolyte : Buffer pH 3.5 (6.6 ml of pyriclinc and 66 ml of acetic acicl diluted with water to 3 1). Compound D-Glucose IX-D-Glucose I-phosphate p-~-Glucose r-phosphate Glucose 6-phosphate D-Arabinose Arabinofuranose I-phosphate Arabinopyranose I-phosphate Maltose phosphate Cellobiose phosphate Lactose phosphate Melibiose phosphate
0.87 0.68 0.84
0.14 0.68 0.68 0.68 0.14 0.73 0.73 0.53 0.53 0.53 0.53
0.89 o.sg 0.57 0.57
TABLE 533’ Cc SEPARATION OF SUBSTITUTIZD PHENOLS (J. J. KIRKLAND, J, Citvowzato~v.Sci., g (1971) 214) Column : Sorbcnt : Eluent : Operating conditions: Detection : Note :
I m x 0.083 in.1.D. 0.88 o/obondccl ether phase on Zipax (Du Pont). 2.5 O/O methanol in cyclopentane. Flow rate, I ml/min; column inlet pressure, 250 p.s.i. Amount loaded 20 141 of 0.25 mg/ml p- and nt-cresol, 0.125 mg/ml each of phenol, 2,62,3-, 3,4- and 3,5 di-methylphenol. By IR recording. 3 = p-cresol; 4 = 3,g-dimcthylphenol; 5 = 1 = phenol ; 2 = m-cresol; 3,4-climethylphenol; 6 = 2,3-dimcthylphcnol; 7 = 2,6-climethylphenol. 7
0.005
.
22.5
As
I
15 Time
(mA
0
CWKOMATOGKAPN~C
UuIItY
TABLE
534
TLC &
VALUES
(J.
W.
MATHIESON
OF
SPINOCHROMES
AND
R.
I-3. THOMSON,
J. CAem. Sm. C, (1971)
IGO)
Thin layer: Cellulose MN 300 plates. go y0 formic acid. Solvent : Detection : Visible and UV light.
%
44
R3
OH OMe OH OH OH OH OH
AC
H 1% Et AC
:z OH OH
OH
OH OMo OH %I OH OH H OH
%I Et 1-I H OH OH I II
%
43
z OH OH H OH E OH H OH
Colouv
RF
purple pink pink red yellow red orange orange red yellow orange red red
0,sz 0.82 0.s2
0.73 0.70 0.67 0x93 0.61 O.GI
oe5.5 0,4c 0.4G 0.28
DATA
[ &g7:
CRROMATOGRAPNIC
TABLE cc
DATA
D1z7
(1972)
535
SEPARATION
OF PHBNYL.ENBDZhMINB
lSOMBRS
(J* J. IQRICLAND, J. Ckvomalogv. SC&, 9 (1971) 214) I m x 0.083 in. I.D. Column : Sorbent : 0.88 o/obonded ether phase on Zipnx (Du Pout), surface porosity below 3714, 5 y. methnnol in cyclopentsne. .:,--Buff cr : 27O. ~~,$per~ting conditions : Flow rate I ml/min. column inlet pressure 2Go p.s.i., temperature Sample loaclecl: G ~1 of 0.05 mg of each isomer in the cluting solvent. By RI recording. Detection :
UNKNOWN
J ,
8I TABLE _
6
2 4 TIME, MINUTES
536
ELL>H,O OF CHOLINE, ACETYLCHOLINE AND RELATED COMPOUNDS (W. D. RAID, D. R. HAUBRICH AND G. KRISI-INA, Anal, Biochem.., 42 (rgp) 394) Whatmann No. 3MM paper Sorbcnt : 0.3 M pyricline, which was simultanecksly ,o.G61M with respect to formic Buffer: acid, pH 4.6. Operating conditions: 1,500 V/cm; running time, 2.5 h; room temperature. The spots were visuslizocl by applying iodine vnpours. Detection: Migvatiolzrate (cm/z,5k)
Compotcnd Choline N-Dimethylaminocthanol N-Methylnminoothsmol Ethanolamine ,. Acetylcholine Propionylcl~olinc Butyrylcholine Benzoyloholine Succinylcholine Acotyl-/3 methylcholine CDP-cholme Phosphorylcholine / Carnitine Acetylcarnitino ‘/
,,’ ,:,.
,. ,
,...
0
,
:” .
..’.
,“,‘,
”
335 330 3900 42,o 3215 30#0 27.0 24,o 3&o 3040 -300 -I,0 30 5’14
DILB
CAROMATOGRAPNLC
TABLE
DATA
(X972)
537
cc SIIPARATION OF THIOLHYDROXAMATES (J. J. KIRKLAND, ,I. Chvtmatogr. SC;., g (197x) .zog) I m x 0.083 in. I.D. Zipax (Du Pont) with 0.88 % ether phase (for details see J. J. KIRKLAND AND J. J. DESTEPANO, J. Clwovnatogr. Sci., 8 (1970) 309). Controlled poros- ‘:~~,, -1 ity surface below 37 /L. i#V IO o/odioxane in isooctane. Go “, : Flow rate, o.YG ml/min; column inlet pressure Igo p.s.i.; temperature By I.R recording.
Column : Sorbont:
Elucnt : Operating Detection
conditions
:
..
y+J
?T
(CH3)2-
51’;’
N-C-0-N-O-C-N-Cl-l3
6
6
4
2
0
Time (min) TABLE
538
cc SEPARATION OF ANILINE DERIVATIVES, n-TRIDECANE~AND TETRAHYDROCHINALDINE (G. DEININGER AND I. HAL&Z, J. Chromatop. Sci., g (1971) gr) 20 cm long, 2 mm I.D. .’ Non-porous glass bead of sieve fraction o.og-o.ro mm. Stationary phase: brush with 3-hydroxypropionitrile bristles, sieve fraction 0.05o-o.060 mm. It-Hoptane : Column inlet pressure, 1.20 atm; flow rate, 0.62 ml/min. By IR recording. 3 = tatrahydrocbinaldinet;’ T k uc-tridecano ; 2 P N,N’;dimethylaniline; 4 = 2,6-dimothylaniline.
Column : Sorbont :
Eluent : Operating Detection
conditions
:
Noto : 3
.
CWROMATOGRAPRIC TABLE CC
DATA
539
SEPARATION
OF
(C. G. VAN TEELIN~, Column : Sorbent :
Bu ffcrs :
Operating
conditions:
ANTHOCYANINS
2.0 r
:
ON
P. E. CANSFIELD
COLUMNS OF POLYVINYLPYRROLIDONE AND
R. A. GALLOP, J. C/mmdog~.
Sci., g (1971) 508)
rg x 150 nm or alternatively IS x 70 mm. Hydrated insoluble polyvinylpyrroliclonc, Polycar A. T. (Gcncml Anilirrc and Film Corporation). The column was devclopccl with 0.25 N MCI in water until the pigment moved halfway down the column. The solvent was then changed to 0.5 N HCl in 500/ mclhnnol and elution continued until all the bands had left the column. Bcforc analysis the column wns washed with 150 ml of 0.25 N I-ICI in water. Flow rates were within 30-40 ml/h, flow unclcr gravity. 1.8 or IO ml fractions
Detection
Dmg
(1972)
By optical
were collcctcd as indicatccl. clcnsit)? reading in visible
Cyanldin 3.Rutlnoside 520nm
Fraction
number
ia
Cyaniclln 3-Rutlnoside
Pelargonidln
3.blucoside
light.
‘D120
CWROMXTOGRAPWIC
Peonidln 3~Galactoside Peonidin 3mArabinaside 3- Qalactosldc
Cyanidin
I
I
4
6
I
I
,,I
I
3-Arabinoside
I,,
8 10 12 14 16 15 20 22 24 Ractlon number
u3ml fmctionsY.JOml
DATA
(1972