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

(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Cas Number: 127882-73-9 Compound CID: 148091

Formula: C₂₇H₂₄N₂O₉ Molecular Weight: 520.5

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

SMILES: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)NC6=CC=C(C=C6)[N+](=O)[O-]

InChIKey: DLROLUIVVKTFPW-LVEBQJTPSA-N

InChI: InChI=1S/C27H24N2O9/c1-34-21-7-13(8-22(35-2)26(21)30)23-16-9-19-20(38-12-37-19)10-17(16)25(18-11-36-27(31)24(18)23)28-14-3-5-15(6-4-14)29(32)33/h3-10,show more

Synonyms: GL-331 | NSC-628679 | 0I81858VSZ | GL331 | NSC628672 | (5R,5aR,8aS,9S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-nitrop...

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2-Phenoxy-1-phenylpropane-1,3-diol
- ≥97%
Cas Number: 70110-65-5 Compound CID: 66898687

Formula: C₁₅H₁₆O₃ Molecular Weight: 244.28

IUPAC Name: 2-phenoxy-1-phenylpropane-1,3-diol

SMILES: C1=CC=C(C=C1)C(C(CO)OC2=CC=CC=C2)O

InChIKey: POAUKTKCUURWJL-UHFFFAOYSA-N

InChI: InChI=1S/C15H16O3/c16-11-14(18-13-9-5-2-6-10-13)15(17)12-7-3-1-4-8-12/h1-10,14-17H,11H2
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meso-dihydroguaiaretic acid
- ≥98%
Cas Number: 66322-34-7 Compound CID: 476856

IUPAC Name: 4-[(2S,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol

SMILES: CC(CC1=CC(=C(C=C1)O)OC)C(C)CC2=CC(=C(C=C2)O)OC

InChIKey: ADFOLUXMYYCTRR-OKILXGFUSA-N

InChI: InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14+
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Schineolignin B
- ≥98%
Cas Number: 1352185-26-2 Compound CID: 49871581

IUPAC Name: 5-[4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol

SMILES: CC(CC1=CC(=C(C=C1)OC)OC)C(C)CC2=CC(=C(C(=C2)OC)OC)O

InChIKey: ITXTZJSELNILSN-UHFFFAOYSA-N

InChI: InChI=1S/C22H30O5/c1-14(9-16-7-8-19(24-3)20(12-16)25-4)15(2)10-17-11-18(23)22(27-6)21(13-17)26-5/h7-8,11-15,23H,9-10H2,1-6H3
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Syringaresinol
- ≥98%
Cas Number: 1177-14-6 EC Number: 866-825-0 Compound CID: 100067

IUPAC Name: 4-[6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol

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

InChIKey: KOWMJRJXZMEZLD-UHFFFAOYSA-N

InChI: InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3
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Isolariciresinol
- ≥98%
Cas Number: 548-29-8 Compound CID: 160521

IUPAC Name: (6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol

SMILES: COC1=C(C=C2C(C(C(CC2=C1)CO)CO)C3=CC(=C(C=C3)O)OC)O

InChIKey: OGFXBIXJCWAUCH-KPHUOKFYSA-N

InChI: InChI=1S/C20H24O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-4,6-8,13,15,20-24H,5,9-10H2,1-2H3/t13-,15-,20-/m0/show more
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Lariciresinol
- ≥98%
Cas Number: 83327-19-9

IUPAC Name: 4-[[(3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol

SMILES: COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)O)OC)O

InChIKey: MHXCIKYXNYCMHY-SXGZJXTBSA-N

InChI: InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m1show more
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Eleutheroside E1
- ≥98%
Cas Number: 7374-79-0 Compound CID: 443024

IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenoxy]-6-(hydroxshow more

SMILES: COC1=CC(=CC(=C1O)OC)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC5C(C(C(C(O5)CO)O)O)O)OC

InChIKey: WEKCEGQSIIQPAQ-IRBNZIFYSA-N

InChI: InChI=1S/C28H36O13/c1-34-16-5-12(6-17(35-2)21(16)30)25-14-10-39-26(15(14)11-38-25)13-7-18(36-3)27(19(8-13)37-4)41-28-24(33)23(32)22(31)20(9-29)40-28/hshow more
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epipinoresinol-4-O-glucopyranoside
- ≥98%
Cas Number: 24404-49-7 Compound CID: 5351523

IUPAC Name: 2-[4-[3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

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

InChIKey: QLJNETOQFQXTLI-UHFFFAOYSA-N

InChI: InChI=1S/C26H32O11/c1-32-18-7-12(3-5-16(18)28)24-14-10-35-25(15(14)11-34-24)13-4-6-17(19(8-13)33-2)36-26-23(31)22(30)21(29)20(9-27)37-26/h3-8,14-15,20show more
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daphneticin,
- ≥98%
Cas Number: 83327-22-4 Compound CID: 158341

IUPAC Name: (2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

SMILES: COC1=CC(=CC(=C1O)OC)C2C(OC3=C(O2)C=CC4=C3OC(=O)C=C4)CO

InChIKey: QLFQDIADUIVNRF-CRAIPNDOSA-N

InChI: InChI=1S/C20H18O8/c1-24-13-7-11(8-14(25-2)17(13)23)18-15(9-21)27-20-12(26-18)5-3-10-4-6-16(22)28-19(10)20/h3-8,15,18,21,23H,9H2,1-2H3/t15-,18-/m1/s1
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Salvadoraside
- ≥95%
Cas Number: 143522-30-9 Compound CID: 162343330

IUPAC Name: 2-[4-[[5-[3,5-dimethoxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-4-(hydroxymethyl)oxolan-3-yl]methyl]-2,6-dimethoxyphenoxy]-6-(hydroxshow more

SMILES: COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)CC3COC(C3CO)C4=CC(=C(C(=C4)OC)OC5C(C(C(C(O5)CO)O)O)O)OC

InChIKey: JJHDIHQKWJEDDR-UHFFFAOYSA-N

InChI: InChI=1S/C34H48O18/c1-44-18-6-14(7-19(45-2)31(18)51-33-28(42)26(40)24(38)22(11-36)49-33)5-16-13-48-30(17(16)10-35)15-8-20(46-3)32(21(9-15)47-4)52-34-2show more
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Matairesinoside
- ≥96%
Cas Number: 23202-85-9 EC Number: 882-545-1 Compound CID: 486612

IUPAC Name: (3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-show more

SMILES: COC1=C(C=CC(=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)O

InChIKey: AAGCATAPYOEULE-LHHMAMHXSA-N

InChI: InChI=1S/C26H32O11/c1-33-19-9-13(3-5-17(19)28)7-15-12-35-25(32)16(15)8-14-4-6-18(20(10-14)34-2)36-26-24(31)23(30)22(29)21(11-27)37-26/h3-6,9-10,15-16,show more
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