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

Medioresinol
- ≥93%
Cas Number: 40957-99-1 Compound CID: 181681

IUPAC Name: 4-[(3S,3aR,6S,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenol

SMILES: COC1=CC(=CC(=C1O)OC)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC

InChIKey: VJOBNGRIBLNUKN-BMHXQBNDSA-N

InChI: InChI=1S/C21H24O7/c1-24-16-6-11(4-5-15(16)22)20-13-9-28-21(14(13)10-27-20)12-7-17(25-2)19(23)18(8-12)26-3/h4-8,13-14,20-23H,9-10H2,1-3H3/t13-,14-,20+,show more
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(+)-Pinoresinol monomethyl ether 4-O-β-D-glucoside
- ≥98%
Cas Number: 74957-57-6 Compound CID: 21722933

IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-show more

SMILES: COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)OC

InChIKey: KFFCKOBAHMGTMW-UZAJXFTPSA-N

InChI: InChI=1S/C27H34O11/c1-32-17-6-4-13(8-19(17)33-2)25-15-11-36-26(16(15)12-35-25)14-5-7-18(20(9-14)34-3)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,15-16show more
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Deoxypodophyllotoxin
- ≥99%
Cas Number: 19186-35-7 Compound CID: 345501

Formula: C₂₂H₂₂O₇ Molecular Weight: 398.41

IUPAC Name: (5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one

SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(CC4=CC5=C(C=C24)OCO5)COC3=O

InChIKey: ZGLXUQQMLLIKAN-SVIJTADQSA-N

InChI: InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3/t13-,19+show more

Synonyms: AC-34638 | Anthricin | F82121 | (5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3...
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Rabdosiin
- ≥99%
Cas Number: 263397-69-9 Compound CID: 101064233

Formula: C₃₆H₃₀O₁₆ Molecular Weight: 718.61

IUPAC Name: (2S)-2-[(1S,2R)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-3show more

SMILES: C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C2C(C3=CC(=C(C=C3C=C2C(=O)OC(CC4=CC(=C(C=C4)O)O)C(=O)O)O)O)C5=CC(=C(C=C5)O)O)O)O

InChIKey: VKWZFIDWHLCPHJ-ZLESDFJESA-N

InChI: InChI=1S/C36H30O16/c37-21-4-1-15(7-24(21)40)9-29(33(45)46)51-35(49)20-11-18-13-27(43)28(44)14-19(18)31(17-3-6-23(39)26(42)12-17)32(20)36(50)52-30(34(4show more
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(-)-Epipodophyllotoxin
- ≥99%
Cas Number: 4375-07-9 Compound CID: 105111

Formula: C₂₂H₂₂O₈ Molecular Weight: 414.41

SMILES: COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O
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Hinokinin
- ≥99%
Cas Number: 26543-89-5 Compound CID: 442879

Formula: C₂₀H₁₈O₆ Molecular Weight: 354.35

SMILES: C1[C@@H]([C@H](C(=O)O1)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
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Diphyllin
- ≥99%
Cas Number: 22055-22-7

Formula: C₂₁H₁₆O₇ Molecular Weight: 380.35

IUPAC Name: 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one

SMILES: COC1=C(C=C2C(=C1)C(=C3C(=C2O)COC3=O)C4=CC5=C(C=C4)OCO5)OC

InChIKey: VMEJANRODATDOF-UHFFFAOYSA-N

InChI: InChI=1S/C21H16O7/c1-24-15-6-11-12(7-16(15)25-2)20(22)13-8-26-21(23)19(13)18(11)10-3-4-14-17(5-10)28-9-27-14/h3-7,22H,8-9H2,1-2H3

Synonyms: NSC 309691 | 9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-naphtho[2,3-c]furan-1(3H)-one
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Xanthocillin X permethyl ether
- ≥99%
Cas Number: 4464-33-9 Compound CID: 6444453

Formula: C₂₀H₁₆N₂O₂ Molecular Weight: 316.35

SMILES: COC1=CC=C(C=C1)/C=C(\[N+]#[C-])/C(=C/C2=CC=C(C=C2)OC)/[N+]#[C-]
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Cleistanthin B
- ≥99%
Cas Number: 30021-77-3 Compound CID: 119458

Formula: C₂₇H₂₆O₁₂ Molecular Weight: 542.49

IUPAC Name: 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one

SMILES: COC1=C(C=C2C(=C1)C(=C3C(=C2OC4C(C(C(C(O4)CO)O)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC

InChIKey: BJGIWVGXMRUMNA-WBYCZGBQSA-N

InChI: InChI=1S/C27H26O12/c1-33-16-6-12-13(7-17(16)34-2)25(39-27-24(31)23(30)22(29)19(8-28)38-27)14-9-35-26(32)21(14)20(12)11-3-4-15-18(5-11)37-10-36-15/h3-7show more

Synonyms: Naphtho(2,3-c)furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxy- | 9-(1,3-benzodio...
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Secoisolariciresinol diglucoside
- ≥99%
Cas Number: 257930-74-8 Compound CID: 72189390

Formula: C₃₂H₄₆O₁₆ Molecular Weight: 686.70

IUPAC Name: (2R,3R,4S,5S,6R)-2-[(2S,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutoxy]-6-(hshow more

SMILES: COC1=C(C=CC(=C1)CC(COC2C(C(C(C(O2)CO)O)O)O)C(CC3=CC(=C(C=C3)O)OC)COC4C(C(C(C(O4)CO)O)O)O)O

InChIKey: SBVBJPHMDABKJV-NNSPVXBOSA-N

InChI: InChI=1S/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(3show more
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(-)-Zuonin A
- ≥99%
Cas Number: 84709-25-1 Compound CID: 234441

Formula: C₂₀H₂₀O₅ Molecular Weight: 340.37

IUPAC Name: 5-[5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-1,3-benzodioxole

SMILES: CC1C(C(OC1C2=CC3=C(C=C2)OCO3)C4=CC5=C(C=C4)OCO5)C

InChIKey: QFUXQRHAJWXPGP-UHFFFAOYSA-N

InChI: InChI=1S/C20H20O5/c1-11-12(2)20(14-4-6-16-18(8-14)24-10-22-16)25-19(11)13-3-5-15-17(7-13)23-9-21-15/h3-8,11-12,19-20H,9-10H2,1-2H3
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Guaiacin
- ≥99%
Cas Number: 36531-08-5 Compound CID: 11724027

Formula: C₂₀H₂₄O₄ Molecular Weight: 328.40

SMILES: C[C@@H]1CC2=CC(=C(C=C2[C@@H]([C@H]1C)C3=CC(=C(C=C3)O)OC)O)OC
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