Phenylpropanoids & Flavonoids

Both phenylpropanoids and flavonoids are natural organic compounds of plant origin biosynthesized via the shikimic acid pathway. Phenylalanine and tyrosine are their precursors (Fig. 1).1)
Phenylpropanoids are classified to the group of compounds in which side chains with three carbons are attached to a benzene ring. They are ingredients of essential oils obtained from anis, cinnamon bark, and clove and are used for fragrances and aromatherapy.
Flavonoids are, in general, a group of compounds in which carbon chains are extended with malonyl-CoA to form a carbon skeleton of C6-C3-C6. Chalcone, flavonoid and isoflavonoid belong to these types of compounds. Most of them have phenolic hydroxy groups and they show anti-oxidative activity. Some of them show physiologic activities towards plants, such as phytoalexins, with the budding of seeds and adjusting of growth. Isoflavonoid is a unique compound group: they are biosynthesized via the phenyl group migration from flavonoid. To date, they are found only in the Leguminosae/Fabacaeae plant family. This distinct biosynthesis triggered researchers to investigate detailed biosynthetic mechanisms.2)

■Solubility
They are generally soluble in many organic solvents. They can be rather difficult to dissolve in less polar solvents such as hexane but dissolve well in high polar solvents such as chloroform, methanol and DMSO. Compounds with carboxyl or phenolic hydroxy groups are soluble in aqueous alkaline solutions. Since they are easily oxidized in the liquid state, we suggest you to use them within a short period of time after preparation.

■Storage Precautions
As long as no special remark is mentioned in the catalogues or labels, they can be stored at room temperature. Solids can be stored longer than liquid compounds or solutions. Note should be taken that compounds with phenolic hydroxy groups are labile to oxidation and can gradually change color from brown to black while being stored. Compounds with aldehyde groups are also apt to be oxidized to carboxylic acids. After unsealing these labile reagents, they should be stored refrigerated or frozen under an inert gas such as nitrogen/argon.

Phenylpropanoids

Flavonoids

Phenylpropanoids

Cinnamic Acids & Esters

A0014 A0014 A2413 A2413 C0878 C0878
A0691 A0691 A0971 A0971 C0358 C0358
B1690 B1690 B1943 B1943 B1961 B1961
C0002 C0002 C0149 C0149 C0974 C0974
C0975 C0975 C2200 C2200 C0181 C0181
C1205 C1205 C1206 C1206 C0617 C0617
C0536 C0536 C0353 C0353 C0636 C0636
A0901 A0901 C0960 C0960 C0393 C0393
C0394 C0394 C0655 C0655 C0447 C0447
C1768 C1768 D2588 D2588 D3794 D3794
D2343 D2343 D4115 D4115 D1728 D1728
D1972 D1972 D2326 D2326 D2364 D2364
D1765 D1765 D2932 D2932 D0648 D0648
E0856 E0856 C0359 C0359 C0448 C0448
E0677 E0677 M1082 M1082 E0739 E0739
M1204 M1204 N0598 N0598 H0267 H0267
F0244 F0244 F0248 F0248 F0264 F0264
C0918 C0918 H0685 H0685 H0524 H0524
C1779 C1779 M0444 M0444 M0449 M0449
M0576 M0576 M0761 M0761 C1672 C1672
C0360 C0360 M0715 M0715 M1295 M1295
M1298 M1298 M1336 M1336 M0634 M0634
N0354 N0354 N0355 N0355 N0356 N0356
P1300 P1300 P1898 P1898 T1323 T1323
T1780 T1780 T1547 T1547 T2499 T2499
T2608 T2608 T1104 T1104 T1393 T1393
T2016 T2016 C0899 C0899
A0014 alpha-Acetamidocinnamic Acid
A2413 2-Acetoxycinnamic Acid
C0878 Allyl Cinnamate (stabilized with TBC)
A0691 4-Aminocinnamic Acid
A0971 4-Azidocinnamaldehyde
C0358 Benzyl Cinnamate
B1690 4-Bromocinnamic Acid
B1943 2-Bromocinnamic Acid
B1961 trans-3-Bromocinnamic Acid
C0002 Caffeic Acid
C0149 4-Chlorocinnamic Acid
C0974 2-Chlorocinnamic Acid
C0975 3-Chlorocinnamic Acid
C2200 4-Chloro-2-fluorocinnamic Acid
C0181 Chlorogenic Acid Hydrate
C1205 4-Chloro-3-nitrocinnamic Acid
C1206 2-Chloro-5-nitrocinnamic Acid
C0617 Cholesterol trans-Cinnamate
C0536 trans-Cinnamamide
C0353 trans-Cinnamic Acid
C0636 trans-Cinnamic Acid Zone Refined (number of passes:40)
A0901 Cinnamyl Acetate
C0960 Cinnamyl Cinnamate
C0393 trans-p-Coumaric Acid
C0394 trans-o-Coumaric Acid
C0655 trans-m-Coumaric Acid
C0447 alpha-Cyanocinnamic Acid
C1768 alpha-Cyano-4-hydroxycinnamic Acid
D2588 trans-2,4-Dichlorocinnamic Acid
D3794 trans-2,5-Dichlorocinnamic Acid
D2343 2,4-Difluorocinnamic Acid
D4115 trans-2,6-Difluorocinnamic Acid
D1728 3,4-Dimethoxycinnamic Acid
D1972 2,5-Dimethoxycinnamic Acid
D2326 trans-2,3-Dimethoxycinnamic Acid
D2364 2,4-Dimethoxycinnamic Acid
D1765 3,5-Dimethoxy-4-hydroxycinnamic Acid
D2932 3,5-Dimethoxy-4-hydroxycinnamic Acid [Matrix for MALDI-TOF/MS]
D0648 4-Dimethylaminocinnamaldehyde
E0856 4-Ethoxycinnamic Acid
C0359 Ethyl Cinnamate
C0448 Ethyl alpha-Cyanocinnamate
E0677 Ethyl 4-Cyanocinnamate
M1082 2-Ethylhexyl 4-Methoxycinnamate
E0739 Ethyl 4-Hydroxy-3-methoxycinnamate
M1204 Ethyl 4-Methoxycinnamate
N0598 Ethyl 4-Nitrocinnamate
H0267 trans-Ferulic Acid
F0244 4-Fluorocinnamic Acid
F0248 2-Fluorocinnamic Acid
F0264 3-Fluorocinnamic Acid
C0918 cis-3-Hexen-1-yl Cinnamate
H0685 alpha-Hexylcinnamaldehyde
H0524 3-Hydroxy-4-methoxycinnamic Acid
C1779 Isopropyl Cinnamate
M0444 3-Methoxycinnamic Acid
M0449 trans-2-Methoxycinnamic Acid
M0576 4-Methoxycinnamic Acid
M0761 cis-2-Methoxycinnamic Acid
C1672 Methyl 4-Chlorocinnamate
C0360 Methyl Cinnamate
M0715 4-Methylcinnamic Acid
M1295 2-Methylcinnamic Acid
M1298 3-Methylcinnamic Acid
M1336 alpha-Methylcinnamic Acid
M0634 3,4-Methylenedioxycinnamic Acid
N0354 3-Nitrocinnamic Acid
N0355 4-Nitrocinnamic Acid
N0356 2-Nitrocinnamic Acid
O0172 gamma-Oryzanol
P1300 alpha-Phenylcinnamic Acid
P1898 4-Propoxycinnamic Acid
T1323 Sodium 3,4,5-Trimethoxycinnamate
T1780 3-(Trifluoromethoxy)cinnamic Acid
T1547 3-(Trifluoromethyl)cinnamic Acid
T2499 4-(Trifluoromethyl)cinnamic Acid
T2608 2-(Trifluoromethyl)cinnamic Acid
T1104 3,4,5-Trimethoxycinnamic Acid
T1393 2,4,5-Trimethoxycinnamic Acid
T2016 2,3,4-Trimethoxycinnamic Acid
C0899 Vinyl Cinnamate (stabilized with MEHQ)
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Cinnamaldehydes

B1253 B1253 C0352 C0352 F0722 F0722
H0952 H0952 M1012 M1012 N0541 N0541
N0611 N0611
B1253 alpha-Bromocinnamaldehyde
C0352 trans-Cinnamaldehyde
F0722 4-Fluorocinnamaldehyde
H0952 2-Hydroxycinnamaldehyde
M1012 4-Methoxycinnamaldehyde
N0541 4-Nitrocinnamaldehyde
N0611 2-Nitrocinnamaldehyde
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Cinnamic Acid Derivatives

P0133 P0133 C0362 C0362 C1109 C1109
C1235 C1235 D1953 D1953 N0690 N0690
P0133 Cinnamoyl Chloride
C0362 Cinnamyl Alcohol
C1109 Cinnamyl Bromide
C1235 Cinnamyl Chloride
D1953 3-(3,4-Dimethoxyphenyl)propionic Acid
N0690 4-Nitrocinnamyl Alcohol
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Phenylpropenes

A1184 A1184 A0702 A0702 D1360 D1360
P0494 P0494 B1441 B1441 B1366 B1366
E0804 E0804 A0232 A0232 E0210 E0210
H1309 H1309 I0132 I0132 M1174 M1174
M1175 M1175 P0495 P0495 P1103 P1103
A1184 1-Acetoxy-2-methoxy-4-(1-propenyl)benzene
A0702 4-Allylanisole
D1360 4-Allyl-1,2-dimethoxybenzene
P0494 trans-Anethole
B1441 1-Benzyloxy-2-methoxy-4-(1-propenyl)benzene
B1366 3,4-Bis(4-acetoxyphenyl)-2,4-hexadiene
E0804 2-Ethoxy-5-(1-propenyl)phenol
A0232 Eugenol
E0210 Eugenol Acetate
H1309 Honokiol
I0132 Isoeugenol (cis- and trans- mixture)
M1174 cis-beta-Methylstyrene (stabilized with TBC)
M1175 trans-beta-Methylstyrene
P0495 beta-Methylstyrene (cis- and trans- mixture) (stabilized with TBC)
P1103 4-(1-Propenyl)-1,2-dimethoxybenzene
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Coumarins

A0979 A0979 A1527 A1527 A2200 A2200
A1848 A1848 M0760 M0760 B2111 B2111
B2088 B2088 B2840 B2840 A5551 A5551
A5570 A5570 U0001 U0001 C1196 C1196
C2297 C2297 C1691 C1691 C0395 C0395
C2267 C2267 C2268 C2268 D4001 D4001
M0216 M0216 M0631 M0631 D3355 D3355
D3356 D3356 E0375 E0375 E0386 E0386
E0024 E0024 E0538 E0538 E0545 E0545
E0491 E0491 E0733 E0733 E0642 E0642
E0783 E0783 H1145 H1145 H0235 H0235
H1327 H1327 H1005 H1005 M1723 M1723
M2233 M2233 M1862 M1862 M1393 M1393
M1398 M1398 M0825 M0825 M0189 M0189
M1236 M1236 M0879 M0879 M0881 M0881
M0766 M0766 M0971 M0971 M2093 M2093
M0453 M0453 P1060 P1060 S0367 S0367
T2267 T2267 H0236 H0236 W0005 W0005
X0009 X0009
A0979 7-Acetoxy-4-bromomethylcoumarin [for HPLC Labeling]
A1527 7-Acetoxy-4-methylcoumarin
A2200 3-Acetylcoumarin
A1848 8-Acetyl-7-hydroxy-4-methylcoumarin
M0760 7-Amino-4-methylcoumarin [for HPLC Labeling]
B2111 3-(2-Benzimidazolyl)-7-(diethylamino)coumarin
B2088 3-(2-Benzothiazolyl)-7-(diethylamino)coumarin
B2840 Bergapten
A5551 Br-Mmc (=4-Bromomethyl-7-methoxycoumarin) [for HPLC Labeling]
A5570 4-Bromomethyl-6,7-dimethoxycoumarin [for HPLC Labeling]
U0001 Calcein Blue
C1196 4-Carboxymethyl-6,7-methylenedioxycoumarin
C2297 3-Chlorocoumarin
C1691 4-Chloro-3-nitrocoumarin
C0395 Coumarin
C2267 Coumarin 102
C2268 Coumarin 314
D4001 Daphnetin
M0216 Dicoumarol
M0631 7-Diethylamino-4-methylcoumarin
D3355 7-(Dimethylamino)-4-methylcoumarin
D3356 7-(Dimethylamino)-4-(trifluoromethyl)coumarin
E0375 Ellagic Acid Dihydrate
E0386 Esculetin
E0024 Esculin Sesquihydrate
E0538 7-Ethoxycoumarin
E0545 4-Ethoxycoumarin
E0491 7-Ethoxy-4-methylcoumarin
E0733 Ethyl 6-Bromocoumarin-3-carboxylate
E0642 Ethyl 7-(Diethylamino)coumarin-3-carboxylate
E0783 Ethyl 6-[4-(Diphenylamino)phenyl]coumarin-3-carboxylate
H1145 Hexyl 7-(Diethylamino)coumarin-3-carboxylate
H0235 4-Hydroxycoumarin
H1327 6-Hydroxycoumarin
H1005 6-Hydroxy-4-methylcoumarin
M1723 7-Methoxycoumarin
M2233 7-Methoxycoumarin-3-carboxylic Acid
M1862 8-Methoxy-4-methylbenzo[g]coumarin
M1393 7-Methoxy-4-methylcoumarin
M1398 6-Methoxy-4-methylcoumarin
M0825 Methyl Calcein Blue Hydrate [Indicator for complexometry Copper]
M0189 6-Methylcoumarin
M1236 7-Methylcoumarin
M0879 6,7-Methylenedioxy-4-isocyanatomethylcoumarin [for HPLC Labeling]
M0881 6,7-Methylenedioxy-4-methyl-3-maleimidocoumarin [for HPLC Labeling]
M0766 4-Methylesculetin
M0971 4-Methyl-6,7-methylenedioxycoumarin
M2093 6-Methyl-4-phenyl-2-chromanone
M0453 4-Methylumbelliferone
P1060 4-Methylumbelliferyl Phosphate
S0367 Scopoletin
T2267 Trioxsalen
H0236 Umbelliferone
W0005 Warfarin Sodium (contains Isopropyl Alcohol)
X0009 Xanthotoxin
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Flavonoids

Chalcones

C0071 C0071 D2884 D2884 D2808 D2808
F0425 F0425 F0459 F0459 F0460 F0460
H0234 H0234 H0385 H0385 H0945 H0945
H0955 H0955 I0822 I0822 M1409 M1409
N0675 N0675 N0839 N0839 P0248 P0248
C0071 Chalcone
D2884 4,4'-Difluorochalcone
D2808 trans-1,3-Diphenyl-2-propen-1-ol
F0425 4'-Fluorochalcone
F0459 4-Fluorochalcone
F0460 4-Fluoro-4'-methylchalcone
H0234 2-Hydroxychalcone
H0385 2'-Hydroxychalcone
H0945 4'-Hydroxychalcone
H0955 4-Hydroxychalcone
I0822 Isoliquiritigenin
M1409 4-Methoxychalcone
N0675 Neohesperidin Dihydrochalcone Hydrate
N0839 4-Nitrochalcone
P0248 Phlorizin Hydrate
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Flavonoids

A1514 A1514 T2721 T2721 B2835 B2835
C0705 C0705 C0958 C0958 C1652 C1652
D1916 D1916 D3908 D3908 E0890 E0890
E0694 E0694 T0121 T0121 F0255 F0255
F0015 F0015 H0721 H0721 H0049 H0049
H1006 H1006 H1024 H1024 H1025 H1025
H1026 H1026 H1027 H1027 H0379 H0379
H0851 H0851 H0852 H0852 H1238 H1238
K0018 K0018 M1403 M1403 M1346 M1346
M1423 M1423 M0338 M0338 P0041 P0041
M2131 M2131 N0072 N0072 N0073 N0073
N0871 N0871 P0042 P0042 R0035 R0035
S0508 S0508 T2708 T2708 T2682 T2682
A1514 Apigenin
T2721 Baicalein
B2835 Baicalin
C0705 (+)-Catechin Hydrate
C0958 Catechin Hydrate
C1652 Chrysin
D1916 7,8-Dihydroxyflavone
D3908 Diosmin
E0890 (-)-Epicatechin Gallate
E0694 (-)-Epigallocatechin Gallate Hydrate
T0121 Fisetin
F0255 Flavanone
F0015 Flavone
H0721 Hesperetin
H0049 Hesperidin
H1006 7-Hydroxyflavanone
H1024 2'-Hydroxyflavanone
H1025 3'-Hydroxyflavanone
H1026 4'-Hydroxyflavanone
H1027 6-Hydroxyflavanone
H0379 3-Hydroxyflavone
H0851 6-Hydroxyflavone
H0852 7-Hydroxyflavone
H1238 5-Hydroxyflavone
K0018 Kaempferol Hydrate
M1403 6-Methoxyflavanone
M1346 6-Methoxyflavone
M1423 7-Methoxyflavone
M0338 Methyl Hesperidine
P0041 Morin Hydrate
M2131 Myricetin
N0072 Naringenin
N0073 Naringin Hydrate
N0871 Nobiletin
P0042 Quercetin Hydrate
R0035 Rutin Trihydrate
S0508 Silybin (mixture of Silybin A and Silybin B)
T2708 Tangeretin
T2682 3',4',5,7-Tetrahydroxyflavone
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Isoflavonoids

D2668 D2668 G0272 G0272 I0669 I0669
P1886 P1886
D2668 Daidzein
G0272 Genistein
I0669 Ipriflavone
P1886 Puerarin
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Literature

1) P. M. Dewick, in Medicinal Natural Products, 3rd ed., John Wiley & Sons Ltd, Chichester, 2009, p. 137.
2) T. Akashi, T. Aoki, S. Ayabe, Plant Physiol. 2005, 137, 882 [DOI].

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