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Lignans, neolignans and related compounds

Description:

Plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Ancestors:

Organic compounds ⮕ Lignans, neolignans and related compounds
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Items 97-108 of 247

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  1. Phillygenin
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 487-39-8        Compound CID:  3083590
    Formula:  C21H24O6        Molecular Weight: 372.41
    IUPAC Name:  4-[(3S,3aR,6R,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
    SMILES:  COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)OC
    InChIKey: CPJKKWDCUOOTEW-YJPXFSGGSA-N
    InChI:  InChI=1S/C21H24O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-26-20(14(15)10-27-21)12-4-6-16(22)18(8-12)24-2/h4-9,14-15,20-22H,10-11H2,1-3H3/t14-,15-,20+,21show more
    Synonyms: Epipinoresinol methyl ether | 4-((1S,3aR,4R,6aR)-4-(3,4-Dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl)-2-met...
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  2. Phillygenin
      Grade & Purity: 
    • ≥98%
    Cas Number: 487-39-8        Compound CID:  3083590
    Formula:  C21H24O6        Molecular Weight: 372.41
    IUPAC Name:  4-[(3S,3aR,6R,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
    SMILES:  COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)OC
    InChIKey: CPJKKWDCUOOTEW-YJPXFSGGSA-N
    InChI:  InChI=1S/C21H24O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-26-20(14(15)10-27-21)12-4-6-16(22)18(8-12)24-2/h4-9,14-15,20-22H,10-11H2,1-3H3/t14-,15-,20+,21show more
    Synonyms: Epipinoresinol methyl ether | 4-((1S,3aR,4R,6aR)-4-(3,4-Dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl)-2-met...
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  3. Paulownin
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 13040-46-5        Compound CID:  3084131
    Formula:  C20H18O7        Molecular Weight: 370.35
    IUPAC Name:  (3R,3aS,6S,6aR)-3,6-bis(1,3-benzodioxol-5-yl)-3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3a-ol
    SMILES:  C1C2C(OCC2(C(O1)C3=CC4=C(C=C3)OCO4)O)C5=CC6=C(C=C5)OCO6
    InChIKey: CAQZFLPWHBKTTR-WNISUXOKSA-N
    InChI:  InChI=1S/C20H18O7/c21-20-8-23-18(11-1-3-14-16(5-11)26-9-24-14)13(20)7-22-19(20)12-2-4-15-17(6-12)27-10-25-15/h1-6,13,18-19,21H,7-10H2/t13-,18-,19-,20-show more
    Synonyms: MS-25951 | CCG-268295 | AC-33983 | s9013 | Paulownin | 1H,3H-Furo(3,4-c)furan-3a(4H)-ol, 1,4-bis(1,3-benzodioxol-5-yl...
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  4. PS210
      Grade & Purity: 
    • ≥98%
    Cas Number: 1221962-86-2        Compound CID:  66760004
    Formula:  C15H9N3O        Molecular Weight: 247.25
    IUPAC Name:  2-[3-oxo-1-phenyl-3-[4-(trifluoromethyl)phenyl]propyl]propanedioic acid
    SMILES:  C1=CC=C(C=C1)C(CC(=O)C2=CC=C(C=C2)C(F)(F)F)C(C(=O)O)C(=O)O
    InChIKey: MLJPLHGJBUWCBA-UHFFFAOYSA-N
    InChI:  InChI=1S/C19H15F3O5/c20-19(21,22)13-8-6-12(7-9-13)15(23)10-14(11-4-2-1-3-5-11)16(17(24)25)18(26)27/h1-9,14,16H,10H2,(H,24,25)(H,26,27)
    Synonyms: 2-[3-Oxo-1-phenyl-3-[4-(trifluoromethyl)phenyl]propyl]-propanedioic acid
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  5. Nortrachelogenin
      Grade & Purity: 
    • ≥98%
    Cas Number: 34444-37-6
    Formula:  C20H22O7        Molecular Weight: 374.38
    IUPAC Name:  (3S,4S)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
    SMILES:  COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)O
    InChIKey: ZITBJWXLODLDRH-XOBRGWDASA-N
    InChI:  InChI=1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20-/m0/show more
    Synonyms: Nortrachelogenin|34444-37-6|Pinopalustrin|(-)-Wikstromol|(-)-Wikstromol; NSC 271296|NSC698802|(3S,4S)-3-hydroxy-3,4-b...
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  6. Nordihydroguaiaretic Acid
    Cas Number: 500-38-9
    Formula:  C18H22O4        Molecular Weight: 302.37
    IUPAC Name:  4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
    SMILES:  CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O
    InChIKey: HCZKYJDFEPMADG-UHFFFAOYSA-N
    InChI:  InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3
    Synonyms: NORDIHYDROGUAIARETIC ACID|500-38-9|NDGA|Dihydronorguaiaretic acid|Actinex|4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbuty...
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  7. Myrislignan
      Grade & Purity: 
    • ≥98%
    Cas Number: 171485-39-5
    Formula:  C21H26O6        Molecular Weight: 374.43
    IUPAC Name:  4-[(1R,2S)-2-(2,6-dimethoxy-4-prop-2-enylphenoxy)-1-hydroxypropyl]-2-methoxyphenol
    SMILES:  CC(C(C1=CC(=C(C=C1)O)OC)O)OC2=C(C=C(C=C2OC)CC=C)OC
    InChIKey: ULZFTGWWPHYLGI-RBZFPXEDSA-N
    InChI:  InChI=1S/C21H26O6/c1-6-7-14-10-18(25-4)21(19(11-14)26-5)27-13(2)20(23)15-8-9-16(22)17(12-15)24-3/h6,8-13,20,22-23H,1,7H2,2-5H3/t13-,20-/m0/s1
    Synonyms: Q-100206 | 4-((1R,2S)-2-(4-Allyl-2,6-dimethoxyphenoxy)-1-hydroxypropyl)-2-methoxyphenol | AC-34668 | FT-0688337 | HY-...
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  8. Myrislignan
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 171485-39-5
    Formula:  C21H26O6        Molecular Weight: 374.43
    IUPAC Name:  4-[(1R,2S)-2-(2,6-dimethoxy-4-prop-2-enylphenoxy)-1-hydroxypropyl]-2-methoxyphenol
    SMILES:  CC(C(C1=CC(=C(C=C1)O)OC)O)OC2=C(C=C(C=C2OC)CC=C)OC
    InChIKey: ULZFTGWWPHYLGI-RBZFPXEDSA-N
    InChI:  InChI=1S/C21H26O6/c1-6-7-14-10-18(25-4)21(19(11-14)26-5)27-13(2)20(23)15-8-9-16(22)17(12-15)24-3/h6,8-13,20,22-23H,1,7H2,2-5H3/t13-,20-/m0/s1
    Synonyms: Myrislignan|171485-39-5|CHEMBL4085435|(aR)-alpha-[(1S)-1-[2,6-Dimethoxy-4-(2-propen-1-yl)phenoxy]ethyl]-4-hydroxy-3-m...
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  9. Magnolin
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 31008-18-1
    Formula:  C23H28O7        Molecular Weight: 416.46
    IUPAC Name:  (3S,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
    SMILES:  COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC)OC)OC
    InChIKey: MFIHSKBTNZNJIK-RZTYQLBFSA-N
    InChI:  InChI=1S/C23H28O7/c1-24-17-7-6-13(8-18(17)25-2)21-15-11-30-22(16(15)12-29-21)14-9-19(26-3)23(28-5)20(10-14)27-4/h6-10,15-16,21-22H,11-12H2,1-5H3/t15-,show more
    Synonyms: Magnolin|31008-18-1|(+)-magnolin|(+/-)-Magnolin|1275595-33-9|95DA2NWV8P|(1s,3ar,4s,6ar)-1-(3,4-dimethoxyphenyl)-4-(3,...
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  10. Macelignan
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 107534-93-0
    Formula:  C20H24O4        Molecular Weight: 328.4
    IUPAC Name:  4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
    SMILES:  CC(CC1=CC2=C(C=C1)OCO2)C(C)CC3=CC(=C(C=C3)O)OC
    InChIKey: QDDILOVMGWUNGD-UONOGXRCSA-N
    InChI:  InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1
    Synonyms: (+)-Anwulignan;Anwuligan | AKOS037645016 | (+)-Anwulignan | 4-((2S,3R)-4-(benzo[d][1,3]dioxol-5-yl)-2,3-dimethylbutyl...
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  11. Isotetrandrine
      Grade & Purity: 
    • ≥98%
    Cas Number: 477-57-6
    Formula:  C38H42N2O6        Molecular Weight: 622.75
    IUPAC Name:  (1S,14R)-9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,show more
    SMILES:  CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)OC)OC
    InChIKey: WVTKBKWTSCPRNU-XZWHSSHBSA-N
    InChI:  InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5show more
    Synonyms: AKOS030497625 | UNII-C7WJK43784 | (11S,31R)-16,36,37,54-tetramethoxy-12,32-dimethyl-11,12,13,14,31,32,33,34-octahydro...
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  12. Isosilybin
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 72581-71-6
    Formula:  C25H22O10        Molecular Weight: 482.44
    IUPAC Name:  (2R,3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
    SMILES:  COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
    InChIKey: FDQAOULAVFHKBX-DBMPWETRSA-N
    InChI:  InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,1show more
    Synonyms: Isosilybin|72581-71-6|Isosilybinin|CHEMBL5204643|(2R,3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxy...
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