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.

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  1. Helioxanthin 8-1
    CAS: 840529-13-7 Formula: C20H12N2O6 Molecular Weight: 376.300
    Out of Stock Item #: H1020122
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    IUPAC Name
    11-(1,3-benzodioxol-5-yl)-8,9-dihydro-[1,3]benzodioxolo[7,6-g]phthalazine-7,10-dione
    SMILES
    C1OC2=C(O1)C=C(C=C2)C3=C4C(=CC5=C3C(=O)NNC5=O)C=CC6=C4OCO6
    InChIKey
    PXSPEYYAEFFUMN-UHFFFAOYSA-N
    InChI
    1S/C20H12N2O6/c23-19-11-5-9-2-4-13-18(28-8-26-13)16(9)15(17(11)20(24)22-21-19)10-1-3-12-14(6-10)27-7-25-12/h1-6H,7-8H2,(H,21,23)(H,22,24)
  2. Helioxanthin
    CAS: 18920-47-3 Formula: C20H12O6 Molecular Weight: 348.3
    Out of Stock Item #: H1359791
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    IUPAC Name
    10-(1,3-benzodioxol-5-yl)-9H-[2]benzofuro[6,5-g][1,3]benzodioxol-7-one
    SMILES
    C1C2=C(C=C3C=CC4=C(C3=C2C5=CC6=C(C=C5)OCO6)OCO4)C(=O)O1
    InChIKey
    JUBRYHUFFFYTGR-UHFFFAOYSA-N
    InChI
    1S/C20H12O6/c21-20-12-5-10-2-4-15-19(26-9-24-15)18(10)17(13(12)7-22-20)11-1-3-14-16(6-11)25-8-23-14/h1-6H,7-9H2
  3. Clemastanin B
    CAS: 112747-98-5 PubChem CID: 10009802 Formula: C32H44O16 Molecular Weight: 684.68
    Out of Stock Item #: C1005252
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    IUPAC Name
    (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[[(3R,4R,5S)-4-(hydroxymethyl)-5-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxshow more
    SMILES
    COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)OC5C(C(C(C(O5)CO)O)O)O
    InChIKey
    PBLWZMSRSJTRHJ-NCIRKIHRSA-N
    InChI
    1S/C32H44O16/c1-42-20-8-14(3-5-18(20)45-31-28(40)26(38)24(36)22(11-34)47-31)7-16-13-44-30(17(16)10-33)15-4-6-19(21(9-15)43-2)46-32-29(41)27(39)25(37)2show more
  4. Epimagnolin A
    CAS: 41689-51-4 Formula: C23H28O7 Molecular Weight: 416.46
    Solid Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. ≥98%
    Out of Stock Item #: D1292927
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    IUPAC Name
    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-UHFFFAOYSA-N
    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
    Synonyms
    (1S,3aR,4R,6aR)-1-(3,4-Dimethoxyphenyl)-4-(3,4,5-trimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan | 3-(3,4-Dimethox...
  5. Nyasol
    CAS: 96895-25-9 PubChem CID: 6438674 Formula: C17H16O2 Molecular Weight: 252.31
    Out of Stock Item #: N1329194
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    IUPAC Name
    4-[(1E,3R)-3-(4-hydroxyphenyl)penta-1,4-dienyl]phenol
    SMILES
    C=CC(C=CC1=CC=C(C=C1)O)C2=CC=C(C=C2)O
    InChIKey
    VEAUNWQYYMXIRB-BOTMBNHJSA-N
    InChI
    1S/C17H16O2/c1-2-14(15-7-11-17(19)12-8-15)6-3-13-4-9-16(18)10-5-13/h2-12,14,18-19H,1H2/b6-3+/t14-/m1/s1
  6. Justicidin B
    CAS: 17951-19-8 Formula: C21H16O6 Molecular Weight: 364.3
    Out of Stock Item #: J1354005
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    IUPAC Name
    4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1H-benzo[f][2]benzofuran-3-one
    SMILES
    COC1=CC2=CC3=C(C(=C2C=C1OC)C4=CC5=C(C=C4)OCO5)C(=O)OC3
    InChIKey
    RTDRYYULUYRTAN-UHFFFAOYSA-N
    InChI
    1S/C21H16O6/c1-23-16-7-12-5-13-9-25-21(22)20(13)19(14(12)8-17(16)24-2)11-3-4-15-18(6-11)27-10-26-15/h3-8H,9-10H2,1-2H3
  7. Justicidin A
    CAS: 25001-57-4 Formula: C22H18O7 Molecular Weight: 394.4
    Out of Stock Item #: J1343595
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    IUPAC Name
    9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-3H-benzo[f][2]benzofuran-1-one
    SMILES
    COC1=C(C=C2C(=C1)C(=C3C(=C2OC)COC3=O)C4=CC5=C(C=C4)OCO5)OC
    InChIKey
    ANFSXHKDCKWWDB-UHFFFAOYSA-N
    InChI
    1S/C22H18O7/c1-24-16-7-12-13(8-17(16)25-2)21(26-3)14-9-27-22(23)20(14)19(12)11-4-5-15-18(6-11)29-10-28-15/h4-8H,9-10H2,1-3H3
  8. Dehydrosilybin
    CAS: 25166-14-7 Formula: C25H20O10 Molecular Weight: 480.4
    Out of Stock Item #: D1298253
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    IUPAC Name
    3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
    SMILES
    COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
    InChIKey
    BVKQRAYKLBRNIK-UHFFFAOYSA-N
    InChI
    1S/C25H20O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,24,26-29,31H,10H2show more
  9. Chicanin
    CAS: 78919-28-5 Formula: C20H22O5 Molecular Weight: 342.39
    Solid Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. ≥99%
    Out of Stock Item #: C1310066
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    IUPAC Name
    4-[(2R,3S,4R,5R)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
    SMILES
    CC1C(C(OC1C2=CC3=C(C=C2)OCO3)C4=CC(=C(C=C4)O)OC)C
    InChIKey
    JPDORDSJPIKURD-OCBHBYCGSA-N
    InChI
    1S/C20H22O5/c1-11-12(2)20(14-5-7-16-18(9-14)24-10-23-16)25-19(11)13-4-6-15(21)17(8-13)22-3/h4-9,11-12,19-21H,10H2,1-3H3/t11-,12+,19+,20+/m0/s1
    Synonyms
    Chicanine
  10. Wikstromol
    CAS: 61521-74-2 PubChem CID: 479756 Formula: C20H22O7 Molecular Weight: 374.4
    Out of Stock Item #: W1045838
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    Technical Identifiers
    IUPAC Name
    (3R,4R)-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-JLTOFOAXSA-N
    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-/m1/s1
  11. Picropodopyllotoxone
    CAS: 477-48-5 PubChem CID: 3083574
    Out of Stock Item #: P1033305
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    Technical Identifiers
    IUPAC Name
    (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione
    SMILES
    COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(=O)C4=CC5=C(C=C24)OCO5
    InChIKey
    ISCQYPPCSYRZOT-MJXNMMHHSA-N
    InChI
    1S/C22H20O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19+/mshow more
  12. Meridinol
    CAS: 120051-54-9 PubChem CID: 11079164
    Out of Stock Item #: M1022086
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    Technical Identifiers
    IUPAC Name
    (3S,4S)-3,4-bis(1,3-benzodioxol-5-ylmethyl)-3-hydroxyoxolan-2-one
    SMILES
    C1C(C(C(=O)O1)(CC2=CC3=C(C=C2)OCO3)O)CC4=CC5=C(C=C4)OCO5
    InChIKey
    OTWLSQPCSOEBAY-XOBRGWDASA-N
    InChI
    1S/C20H18O7/c21-19-20(22,8-13-2-4-16-18(7-13)27-11-25-16)14(9-23-19)5-12-1-3-15-17(6-12)26-10-24-15/h1-4,6-7,14,22H,5,8-11H2/t14-,20-/m0/s1
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