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Phenylpropanoids and polyketides

Phenylpropaniods are organic compounds characterized by having an aromatic ring and a three-carbon propene tail. Polyketides are compounds characterized by having two or more carbonyl functional groups connected with a single carbon atom.
Cinnamic acids and derivatives (267)
Coumarins and derivatives (263)
Flavonoids (174)
Phenylpropanoic acids (166)
Linear 1 3-diarylpropanoids (140)
Depsides and depsidones (69)
Stilbenes (60)
Cinnamaldehydes (42)
Isoflavonoids (41)
Isocoumarins and derivatives (18)
Cinnamyl alcohols (16)
Tetracyclines (10)
Anthracyclines (7)
Dihydrocoumarins (5)
Macrolide lactams (4)
Macrolactams (3)
Macrolides and analogues (2)
Neoflavonoids (2)
Angucyclines (1)
Ochratoxins and related substances (1)

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1

Tyrphostin B46, 98+%, Thermo Scientific Chemicals

CAS: 133550-34-2 Molecular Formula: C19H18N2O3 Molecular Weight (g/mol): 322.364 MDL Number: MFCD00209865 InChI Key: GSQOBTOAOGXIFL-WJDWOHSUSA-N Synonym: tyrphostin b46,z-2-cyano-3-3,4-dihydroxyphenyl-n-3-phenylpropyl prop-2-enamide,n-3 inverted exclamation marka-phenylpropyl-3,4-dihydroxybenzylidenecyanoacetamide PubChem CID: 5353390 IUPAC Name: (Z)-2-cyano-3-(3,4-dihydroxyphenyl)-N-(3-phenylpropyl)prop-2-enamide SMILES: C1=CC=C(C=C1)CCCNC(=O)C(=CC2=CC(=C(C=C2)O)O)C#N

PubChem CID 5353390
CAS 133550-34-2
Molecular Weight (g/mol) 322.364
MDL Number MFCD00209865
SMILES C1=CC=C(C=C1)CCCNC(=O)C(=CC2=CC(=C(C=C2)O)O)C#N
Synonym tyrphostin b46,z-2-cyano-3-3,4-dihydroxyphenyl-n-3-phenylpropyl prop-2-enamide,n-3 inverted exclamation marka-phenylpropyl-3,4-dihydroxybenzylidenecyanoacetamide
IUPAC Name (Z)-2-cyano-3-(3,4-dihydroxyphenyl)-N-(3-phenylpropyl)prop-2-enamide
InChI Key GSQOBTOAOGXIFL-WJDWOHSUSA-N
Molecular Formula C19H18N2O3
2

(E)-3,4-Dihydroxybenzylideneacetone, 97%

CAS: 123694-03-1 Molecular Formula: C10H10O3 Molecular Weight (g/mol): 178.187 MDL Number: MFCD00916691 InChI Key: YIFZKRGUGKLILR-UHFFFAOYSA-N Synonym: 3-buten-2-one,4-3,4-dihydroxyphenyl-, 3e,3,4-dihydroxybenzalacetone,acmc-20dpit PubChem CID: 53446072 IUPAC Name: 4-(3,4-dihydroxyphenyl)but-3-en-2-one SMILES: CC(=O)C=CC1=CC(=C(C=C1)O)O

PubChem CID 53446072
CAS 123694-03-1
Molecular Weight (g/mol) 178.187
MDL Number MFCD00916691
SMILES CC(=O)C=CC1=CC(=C(C=C1)O)O
Synonym 3-buten-2-one,4-3,4-dihydroxyphenyl-, 3e,3,4-dihydroxybenzalacetone,acmc-20dpit
IUPAC Name 4-(3,4-dihydroxyphenyl)but-3-en-2-one
InChI Key YIFZKRGUGKLILR-UHFFFAOYSA-N
Molecular Formula C10H10O3
3

4-Hydroxy-3-methoxycinnamic acid, 99%

CAS: 1135-24-6 Molecular Formula: C10H10O4 Molecular Weight (g/mol): 194.19 MDL Number: MFCD00004400 InChI Key: KSEBMYQBYZTDHS-HWKANZROSA-N Synonym: ferulic acid,trans-ferulic acid,4-hydroxy-3-methoxycinnamic acid,trans-4-hydroxy-3-methoxycinnamic acid,3-4-hydroxy-3-methoxyphenyl acrylic acid,e-ferulic acid,coniferic acid,ferulate,ferulic acid, trans,2-propenoic acid, 3-4-hydroxy-3-methoxyphenyl PubChem CID: 445858 ChEBI: CHEBI:17620 IUPAC Name: (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid SMILES: COC1=C(C=CC(=C1)C=CC(=O)O)O

PubChem CID 445858
CAS 1135-24-6
Molecular Weight (g/mol) 194.19
ChEBI CHEBI:17620
MDL Number MFCD00004400
SMILES COC1=C(C=CC(=C1)C=CC(=O)O)O
Synonym ferulic acid,trans-ferulic acid,4-hydroxy-3-methoxycinnamic acid,trans-4-hydroxy-3-methoxycinnamic acid,3-4-hydroxy-3-methoxyphenyl acrylic acid,e-ferulic acid,coniferic acid,ferulate,ferulic acid, trans,2-propenoic acid, 3-4-hydroxy-3-methoxyphenyl
IUPAC Name (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
InChI Key KSEBMYQBYZTDHS-HWKANZROSA-N
Molecular Formula C10H10O4
4

p-Hydroxycinnamic acid, 98%, predominantly trans

CAS: 501-98-4 Molecular Formula: C9H8O3 Molecular Weight (g/mol): 164.16 MDL Number: MFCD00004399 InChI Key: NGSWKAQJJWESNS-ZZXKWVIFSA-N Synonym: p-coumaric acid,4-hydroxycinnamic acid,p-hydroxycinnamic acid,4-coumaric acid,trans-4-hydroxycinnamic acid,trans-p-coumaric acid,p-cumaric acid,3-4-hydroxyphenyl acrylic acid,para-coumaric acid,hydroxycinnamic acid PubChem CID: 637542 ChEBI: CHEBI:32374 IUPAC Name: (E)-3-(4-hydroxyphenyl)prop-2-enoic acid SMILES: C1=CC(=CC=C1C=CC(=O)O)O

PubChem CID 637542
CAS 501-98-4
Molecular Weight (g/mol) 164.16
ChEBI CHEBI:32374
MDL Number MFCD00004399
SMILES C1=CC(=CC=C1C=CC(=O)O)O
Synonym p-coumaric acid,4-hydroxycinnamic acid,p-hydroxycinnamic acid,4-coumaric acid,trans-4-hydroxycinnamic acid,trans-p-coumaric acid,p-cumaric acid,3-4-hydroxyphenyl acrylic acid,para-coumaric acid,hydroxycinnamic acid
IUPAC Name (E)-3-(4-hydroxyphenyl)prop-2-enoic acid
InChI Key NGSWKAQJJWESNS-ZZXKWVIFSA-N
Molecular Formula C9H8O3
5

4-Hydroxy-3-methoxycinnamic acid, Mixture of isomers, ≥99.0% (HPLC), MilliporeSigma™ Supelco™

4-Hydroxy-3-methoxycinnamic acid is a ubiquitous plant constituent primarily occurring in seeds and leaves. It arises from the metabolism of phenylalanine and tyrosine.

6

4-Fluorocinnamic acid, 98+%

CAS: 459-32-5 Molecular Formula: C9H7FO2 Molecular Weight (g/mol): 166.151 MDL Number: MFCD00004395 InChI Key: ISMMYAZSUSYVQG-ZZXKWVIFSA-N Synonym: 4-fluorocinnamic acid,e-3-4-fluorophenyl acrylic acid,2e-3-4-fluorophenyl prop-2-enoic acid,p-fluorocinnamic acid,3-4-fluorophenyl acrylic acid,e-p-fluorocinnamic acid,trans-4-fluorocinnamic acid,p-fluoro cinnamic acid,3-4-fluorophenyl prop-2-enoic acid,2-propenoic acid, 3-4-fluorophenyl-, 2e PubChem CID: 1530234 IUPAC Name: (E)-3-(4-fluorophenyl)prop-2-enoic acid SMILES: C1=CC(=CC=C1C=CC(=O)O)F

PubChem CID 1530234
CAS 459-32-5
Molecular Weight (g/mol) 166.151
MDL Number MFCD00004395
SMILES C1=CC(=CC=C1C=CC(=O)O)F
Synonym 4-fluorocinnamic acid,e-3-4-fluorophenyl acrylic acid,2e-3-4-fluorophenyl prop-2-enoic acid,p-fluorocinnamic acid,3-4-fluorophenyl acrylic acid,e-p-fluorocinnamic acid,trans-4-fluorocinnamic acid,p-fluoro cinnamic acid,3-4-fluorophenyl prop-2-enoic acid,2-propenoic acid, 3-4-fluorophenyl-, 2e
IUPAC Name (E)-3-(4-fluorophenyl)prop-2-enoic acid
InChI Key ISMMYAZSUSYVQG-ZZXKWVIFSA-N
Molecular Formula C9H7FO2
7

3-Chlorocinnamic acid, predominantly trans, 98+%

CAS: 1866-38-2 Molecular Formula: C9H7ClO2 Molecular Weight (g/mol): 182.603 MDL Number: MFCD00004384 InChI Key: FFKGOJWPSXRALK-SNAWJCMRSA-N Synonym: 3-chlorocinnamic acid,3-3-chlorophenyl acrylic acid,m-chlorocinnamic acid,e-3-3-chlorophenyl acrylic acid,2e-3-3-chlorophenyl acrylic acid,trans-3-chlorocinnamic acid,e-3-chlorocinnamic acid,2e-3-3-chlorophenyl prop-2-enoic acid,2-propenoic acid, 3-3-chlorophenyl,rarechem bk hc t320 PubChem CID: 735250 IUPAC Name: (E)-3-(3-chlorophenyl)prop-2-enoic acid SMILES: C1=CC(=CC(=C1)Cl)C=CC(=O)O

PubChem CID 735250
CAS 1866-38-2
Molecular Weight (g/mol) 182.603
MDL Number MFCD00004384
SMILES C1=CC(=CC(=C1)Cl)C=CC(=O)O
Synonym 3-chlorocinnamic acid,3-3-chlorophenyl acrylic acid,m-chlorocinnamic acid,e-3-3-chlorophenyl acrylic acid,2e-3-3-chlorophenyl acrylic acid,trans-3-chlorocinnamic acid,e-3-chlorocinnamic acid,2e-3-3-chlorophenyl prop-2-enoic acid,2-propenoic acid, 3-3-chlorophenyl,rarechem bk hc t320
IUPAC Name (E)-3-(3-chlorophenyl)prop-2-enoic acid
InChI Key FFKGOJWPSXRALK-SNAWJCMRSA-N
Molecular Formula C9H7ClO2
8

4-Acetoxy-3-methoxycinnamic acid, 98+%

CAS: 2596-47-6 Molecular Formula: C12H12O5 Molecular Weight (g/mol): 236.223 MDL Number: MFCD00014378 InChI Key: IHKNVZISLLDMOR-GQCTYLIASA-N Synonym: acetylferulic acid,4-acetoxy-3-methoxycinnamic acid,3-methoxy-4-acetoxycinnamic acid,3-4-acetoxy-3-methoxyphenyl acrylic acid,cinnamic acid, 4-acetoxy-3-methoxy,acetylated ferulic acid,cinnamic acid, 4-hydroxy-3-methoxy-, acetate,2-propenoic acid, 3-4-acetyloxy-3-methoxyphenyl,2e-3-4-acetyloxy-3-methoxyphenyl prop-2-enoic acid PubChem CID: 5354677 ChEBI: CHEBI:86582 IUPAC Name: (E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoic acid SMILES: CC(=O)OC1=C(C=C(C=C1)C=CC(=O)O)OC

PubChem CID 5354677
CAS 2596-47-6
Molecular Weight (g/mol) 236.223
ChEBI CHEBI:86582
MDL Number MFCD00014378
SMILES CC(=O)OC1=C(C=C(C=C1)C=CC(=O)O)OC
Synonym acetylferulic acid,4-acetoxy-3-methoxycinnamic acid,3-methoxy-4-acetoxycinnamic acid,3-4-acetoxy-3-methoxyphenyl acrylic acid,cinnamic acid, 4-acetoxy-3-methoxy,acetylated ferulic acid,cinnamic acid, 4-hydroxy-3-methoxy-, acetate,2-propenoic acid, 3-4-acetyloxy-3-methoxyphenyl,2e-3-4-acetyloxy-3-methoxyphenyl prop-2-enoic acid
IUPAC Name (E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoic acid
InChI Key IHKNVZISLLDMOR-GQCTYLIASA-N
Molecular Formula C12H12O5
9

3-Hydroxy-4-methoxycinnamic acid, predominantly trans, 98+%

CAS: 537-73-5 Molecular Formula: C10H10O4 Molecular Weight (g/mol): 194.186 MDL Number: MFCD00004391 InChI Key: QURCVMIEKCOAJU-HWKANZROSA-N Synonym: isoferulic acid,3-hydroxy-4-methoxycinnamic acid,hesperetic acid,3-3-hydroxy-4-methoxyphenyl acrylic acid,2e-3-3-hydroxy-4-methoxyphenyl prop-2-enoic acid,isoferulate,2-propenoic acid, 3-3-hydroxy-4-methoxyphenyl,e-3-3-hydroxy-4-methoxyphenyl acrylic acid,3-3-hydroxy-4-methoxyphenyl prop-2-enoic acid,3-hydroxy-4-methoxy-cinnamic acid PubChem CID: 736186 ChEBI: CHEBI:27794 IUPAC Name: (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid SMILES: COC1=C(C=C(C=C1)C=CC(=O)O)O

PubChem CID 736186
CAS 537-73-5
Molecular Weight (g/mol) 194.186
ChEBI CHEBI:27794
MDL Number MFCD00004391
SMILES COC1=C(C=C(C=C1)C=CC(=O)O)O
Synonym isoferulic acid,3-hydroxy-4-methoxycinnamic acid,hesperetic acid,3-3-hydroxy-4-methoxyphenyl acrylic acid,2e-3-3-hydroxy-4-methoxyphenyl prop-2-enoic acid,isoferulate,2-propenoic acid, 3-3-hydroxy-4-methoxyphenyl,e-3-3-hydroxy-4-methoxyphenyl acrylic acid,3-3-hydroxy-4-methoxyphenyl prop-2-enoic acid,3-hydroxy-4-methoxy-cinnamic acid
IUPAC Name (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
InChI Key QURCVMIEKCOAJU-HWKANZROSA-N
Molecular Formula C10H10O4
10

trans-4-(Trifluoromethyl)cinnamic acid, 98%

CAS: 16642-92-5 Molecular Formula: C10H6F3O2 Molecular Weight (g/mol): 215.15 MDL Number: MFCD00002696 InChI Key: ANRMAUMHJREENI-ZZXKWVIFSA-M Synonym: 4-trifluoromethyl cinnamic acid,trans-4-trifluoromethyl cinnamic acid,p-trifluoromethyl cinnamic acid,e-3-4-trifluoromethyl phenyl acrylic acid,2e-3-4-trifluoromethyl phenyl prop-2-enoic acid,4-trifluoromethylcinnamic acid,2-propenoic acid, 3-4-trifluoromethyl phenyl,3-4-trifluoromethyl-phenyl-acrylic acid,ptf-cna,trans-4-trifluoromethylcinnamic acid PubChem CID: 688070 ChEBI: CHEBI:60705 IUPAC Name: (E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoic acid SMILES: [O-]C(=O)\C=C\C1=CC=C(C=C1)C(F)(F)F

PubChem CID 688070
CAS 16642-92-5
Molecular Weight (g/mol) 215.15
ChEBI CHEBI:60705
MDL Number MFCD00002696
SMILES [O-]C(=O)\C=C\C1=CC=C(C=C1)C(F)(F)F
Synonym 4-trifluoromethyl cinnamic acid,trans-4-trifluoromethyl cinnamic acid,p-trifluoromethyl cinnamic acid,e-3-4-trifluoromethyl phenyl acrylic acid,2e-3-4-trifluoromethyl phenyl prop-2-enoic acid,4-trifluoromethylcinnamic acid,2-propenoic acid, 3-4-trifluoromethyl phenyl,3-4-trifluoromethyl-phenyl-acrylic acid,ptf-cna,trans-4-trifluoromethylcinnamic acid
IUPAC Name (E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoic acid
InChI Key ANRMAUMHJREENI-ZZXKWVIFSA-M
Molecular Formula C10H6F3O2
11

4-Acetamidocinnamic acid, predominantly trans, 98%

CAS: 1918352 MDL Number: MFCD00016846 ChEBI: CHEBI:16388

CAS 1918352
ChEBI CHEBI:16388
MDL Number MFCD00016846
12

4-Isopropylcinnamic acid, predominantly trans, 98+%

CAS: 3368-21-6 Molecular Formula: C12H14O2 Molecular Weight (g/mol): 190.24 MDL Number: MFCD00016544 InChI Key: SJDOOXOUSJDYFE-VMPITWQZSA-N Synonym: 4-isopropylcinnamic acid,3-4-isopropylphenyl acrylic acid,p-isopropylcinnamic acid,2e-3-4-isopropylphenyl acrylic acid,cinnamic acid, p-isopropyl,2-propenoic acid, 3-4-1-methylethyl phenyl,2e-3-4-propan-2-yl phenyl prop-2-enoic acid,e-3-4-isopropylphenyl acrylic acid,e-3-4-isopropyl-phenyl-acrylic acid,2e-3-4-isopropylphenyl prop-2-enoic acid PubChem CID: 719753 IUPAC Name: (E)-3-(4-propan-2-ylphenyl)prop-2-enoic acid SMILES: CC(C)C1=CC=C(\C=C\C(O)=O)C=C1

PubChem CID 719753
CAS 3368-21-6
Molecular Weight (g/mol) 190.24
MDL Number MFCD00016544
SMILES CC(C)C1=CC=C(\C=C\C(O)=O)C=C1
Synonym 4-isopropylcinnamic acid,3-4-isopropylphenyl acrylic acid,p-isopropylcinnamic acid,2e-3-4-isopropylphenyl acrylic acid,cinnamic acid, p-isopropyl,2-propenoic acid, 3-4-1-methylethyl phenyl,2e-3-4-propan-2-yl phenyl prop-2-enoic acid,e-3-4-isopropylphenyl acrylic acid,e-3-4-isopropyl-phenyl-acrylic acid,2e-3-4-isopropylphenyl prop-2-enoic acid
IUPAC Name (E)-3-(4-propan-2-ylphenyl)prop-2-enoic acid
InChI Key SJDOOXOUSJDYFE-VMPITWQZSA-N
Molecular Formula C12H14O2
13

trans-Cinnamic Acid, Analytical Standard, ≥98.0% (HPLC), MilliporeSigma™ Supelco™

trans-Cinnamic acid occurs in plants, formed via deamination of L-phenylalanine in the presence of enzymatic catalyst, L-phenylalanine ammonia-lyase.

14

trans-4-Nitrocinnamic acid, 98+%

CAS: 882-06-4 Molecular Formula: C9H7NO4 Molecular Weight (g/mol): 193.158 MDL Number: MFCD00007381 InChI Key: XMMRNCHTDONGRJ-ZZXKWVIFSA-N Synonym: 4-nitrocinnamic acid,3-4-nitrophenyl acrylic acid,p-nitrocinnamic acid,cinnamic acid, p-nitro,2-propenoic acid, 3-4-nitrophenyl,e-3-4-nitrophenyl acrylic acid,3-4-nitrophenyl propenoic acid,trans-4-nitrocinnamic acid,ccris 1665,2e-3-4-nitrophenyl prop-2-enoic acid PubChem CID: 737157 SMILES: C1=CC(=CC=C1C=CC(=O)O)[N+](=O)[O-]

PubChem CID 737157
CAS 882-06-4
Molecular Weight (g/mol) 193.158
MDL Number MFCD00007381
SMILES C1=CC(=CC=C1C=CC(=O)O)[N+](=O)[O-]
Synonym 4-nitrocinnamic acid,3-4-nitrophenyl acrylic acid,p-nitrocinnamic acid,cinnamic acid, p-nitro,2-propenoic acid, 3-4-nitrophenyl,e-3-4-nitrophenyl acrylic acid,3-4-nitrophenyl propenoic acid,trans-4-nitrocinnamic acid,ccris 1665,2e-3-4-nitrophenyl prop-2-enoic acid
InChI Key XMMRNCHTDONGRJ-ZZXKWVIFSA-N
Molecular Formula C9H7NO4
15

3,4,5-Trimethoxycinnamic acid, predominantly trans, 99%

CAS: 90-50-6 Molecular Formula: C12H14O5 Molecular Weight (g/mol): 238.239 MDL Number: MFCD00004388 InChI Key: YTFVRYKNXDADBI-SNAWJCMRSA-N Synonym: 3,4,5-trimethoxycinnamic acid,o-methylsinapic acid,3,4,5-trimethoxyphenylacrylic acid,3-3,4,5-trimethoxyphenyl acrylic acid,3-3,4,5-trimethoxyphenyl-2-propenoic acid,3,4,5-trimethoxy cinnamic acid,sinapic acid methyl ether,e-3-3,4,5-trimethoxyphenyl acrylic acid,cinnamic acid, 3,4,5-trimethoxy,2e-3-3,4,5-trimethoxyphenyl acrylic acid PubChem CID: 735755 IUPAC Name: (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid SMILES: COC1=CC(=CC(=C1OC)OC)C=CC(=O)O

PubChem CID 735755
CAS 90-50-6
Molecular Weight (g/mol) 238.239
MDL Number MFCD00004388
SMILES COC1=CC(=CC(=C1OC)OC)C=CC(=O)O
Synonym 3,4,5-trimethoxycinnamic acid,o-methylsinapic acid,3,4,5-trimethoxyphenylacrylic acid,3-3,4,5-trimethoxyphenyl acrylic acid,3-3,4,5-trimethoxyphenyl-2-propenoic acid,3,4,5-trimethoxy cinnamic acid,sinapic acid methyl ether,e-3-3,4,5-trimethoxyphenyl acrylic acid,cinnamic acid, 3,4,5-trimethoxy,2e-3-3,4,5-trimethoxyphenyl acrylic acid
IUPAC Name (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
InChI Key YTFVRYKNXDADBI-SNAWJCMRSA-N
Molecular Formula C12H14O5