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

Yatein
- ≥99%
Cas Number: 40456-50-6 Compound CID: 442835

Formula: C₂₂H₂₄O₇ Molecular Weight: 400.42

SMILES: COC1=CC(=CC(=C1OC)OC)C[C@@H]2[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4
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Cleomiscosin A
- ≥99%
Cas Number: 76948-72-6 Compound CID: 442510

Formula: C₂₀H₁₈O₈ Molecular Weight: 386.35

SMILES: COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C4C(=CC(=C3O2)OC)C=CC(=O)O4)CO)O
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(+)-Syringaresinol
- ≥99%
Cas Number: 21453-69-0 Compound CID: 443023

Formula: C₂₂H₂₆O₈ Molecular Weight: 418.44

IUPAC Name: 4-[(3S,3aR,6S,6aR)-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-HCIHMXRSSA-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/t13-,14show more

Synonyms: 6YWP8N8R9S | 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxy-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-...
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Hypophyllanthin
- ≥98%
Cas Number: 33676-00-5 EC Number: 803-418-9 Compound CID: 182140

Formula: C₂₄H₃₀O₇ Molecular Weight: 430.49

IUPAC Name: (7R,8R,9S)-9-(3,4-dimethoxyphenyl)-4-methoxy-7,8-bis(methoxymethyl)-6,7,8,9-tetrahydrobenzo[g][1,3]benzodioxole

SMILES: COCC1CC2=CC(=C3C(=C2C(C1COC)C4=CC(=C(C=C4)OC)OC)OCO3)OC

InChIKey: LBJCUHLNHSKZBW-XGHQBKJUSA-N

InChI: InChI=1S/C24H30O7/c1-25-11-16-8-15-10-20(29-5)23-24(31-13-30-23)22(15)21(17(16)12-26-2)14-6-7-18(27-3)19(9-14)28-4/h6-7,9-10,16-17,21H,8,11-13H2,1-5H3show more

Synonyms: NSC-619044 | Naphtho(1,2-d)-1,3-dioxole, 9-(3,4-dimethoxyphenyl)-6,7,8,9-tetrahydro-4-methoxy-7,8-bis(methoxymethyl)-...
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Episyringaresinol 4'-O-β-D-glncopyranoside
- ≥99%
Cas Number: 137038-13-2 Compound CID: 45482321

Formula: C₂₈H₃₆O₁₃ Molecular Weight: 580.58

IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6R,6aS)-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-FKLBZQFOSA-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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Rhodiolin
- ≥98%
Cas Number: 86831-53-0 Compound CID: 14778358

Formula: C₂₅H₂₀O₁₀ Molecular Weight: 480.42

IUPAC Name: (2R,3R)-6,8-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-9-(4-hydroxyphenyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-7-one

SMILES: COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C4=C3OC(=C(C4=O)O)C5=CC=C(C=C5)O)O)CO)O

InChIKey: POVCYOFRCMBMKD-XMSQKQJNSA-N

InChI: InChI=1S/C25H20O10/c1-32-16-8-12(4-7-14(16)28)22-18(10-26)34-24-17(33-22)9-15(29)19-20(30)21(31)23(35-25(19)24)11-2-5-13(27)6-3-11/h2-9,18,22,26-29,31show more
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Masoprocol
- ≥98%
Cas Number: 27686-84-6 EC Number: 248-606-6

Formula: C₁₈H₂₂O₄ Molecular Weight: 302.36

IUPAC Name: 4-[(2S,3R)-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-TXEJJXNPSA-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/t11-,12+

Synonyms: meso-Nordihydroguaiaretic acid | meso-NDGA
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Trachelogenin
- ≥99%
Cas Number: 34209-69-3 Compound CID: 452855

Formula: C₂₁H₂₄O₇ Molecular Weight: 388.41

IUPAC Name: (3S,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

SMILES: COC1=C(C=C(C=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)OC

InChIKey: YFVZKLQNMNKWSB-BTYIYWSLSA-N

InChI: InChI=1S/C21H24O7/c1-25-17-7-5-13(9-19(17)27-3)8-15-12-28-20(23)21(15,24)11-14-4-6-16(22)18(10-14)26-2/h4-7,9-10,15,22,24H,8,11-12H2,1-3H3/t15-,21-/m0show more

Synonyms: (-)-Trachelogenin | ACon1_002414 | DTXSID50187799 | 2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)DIHYDRO-3-HYDROXY-...
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Kobusin
Cas Number: 36150-23-9

Formula: C₂₁H₂₂O₆ Molecular Weight: 370.4

IUPAC Name: 5-[(3S,3aR,6S,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole

SMILES: COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC5=C(C=C4)OCO5)OC

InChIKey: AWOGQCSIVCQXBT-VUEDXXQZSA-N

InChI: InChI=1S/C21H22O6/c1-22-16-5-3-12(7-18(16)23-2)20-14-9-25-21(15(14)10-24-20)13-4-6-17-19(8-13)27-11-26-17/h3-8,14-15,20-21H,9-11H2,1-2H3/t14-,15-,20+,show more

Synonyms: (+)-Spinescin | ACon1_001273 | kobusin | Methylpiperitol | (3abeta,6abeta)-1beta-(3,4-Dimethoxyphenyl)-4beta-(1,3-ben...

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J-104123
IUPAC Name: (3R)-4-{[(2S,3S,4E)-3-[(3,4-dichlorophenyl)methyl]-5-(naphthalen-2-yl)pent-4-en-2-yl]carbamoyl}-3-methylbutanoic acid

SMILES: C[C@@H](CC(=O)O)CC(=O)N[C@H]([C@@H](Cc1ccc(c(c1)Cl)Cl)/C=C/c1ccc2c(c1)cccc2)C

InChIKey: LVRZMZFXRFKCCY-KSYFVSBMSA-N

InChI: InChI=1S/C28H29Cl2NO3/c1-18(14-28(33)34)13-27(32)31-19(2)23(16-21-9-12-25(29)26(30)17-21)11-8-20-7-10-22-5-3-4-6-24(22)15-20/h3-12,15,17-19,23H,13-14,show more
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Berbamine dihydrochloride
- 10mM in DMSO
Cas Number: 6078-17-7(DMSO) Compound CID: 16217067

Formula: C₃₇H₄₀N₂O₆ ·2HCl Molecular Weight: 681.65

IUPAC Name: (1S,14R)-20,21,25-trimethoxy-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),8,10,1show more

SMILES: CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)O)OC.Cl.Cl

InChIKey: USRXDYNDPPUBSG-KKXMJGKMSA-N

InChI: InChI=1S/C37H40N2O6.2ClH/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-31-18-23(8-11-30(31)40)17-29-35-25(13-15-39(29)2)20-34(42show more

Synonyms: Berbamine dihydrochloride|6078-17-7|Berbamine (dihydrochloride)|K44OC6U989|berbamine hydrochloride|Berbenine|(1S,14R)...
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(−)-Asarinin
- ≥98%(HPLC)
Cas Number: 133-05-1

Formula: C₂₀H₁₈O₆ Molecular Weight: 354.35

IUPAC Name: 5-[(3R,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole

SMILES: C1C2C(COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6

InChIKey: PEYUIKBAABKQKQ-WZBLMQSHSA-N

InChI: InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19-,20+/m0/show more

Synonyms: Asarinin | ASARININ (-) | HMS3266O08 | HY-B1091 | SDCCGMLS-0066831.P001 | Spectrum4_001725 | UNII-C3RVX72NMG | ASARIN...
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