9,9'-epoxylignans

Description:

Lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group).

Ancestors:

Organic compounds ⮕ Lignans, neolignans and related compounds ⮕ Furanoid lignans ⮕ Tetrahydrofuran lignans ⮕ 9,9'-epoxylignans

Popular Products

Wikstromol
CAS: 61521-74-2 PubChem CID: 479756 Formula: C₂₀H₂₂O₇ Molecular Weight: 374.4

≥98%

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
Meridinol
CAS: 120051-54-9 PubChem CID: 11079164

Out of Stock Item #: M1022086

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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
Anhydrosecoisolariciresinol
CAS: 29388-33-8 Formula: C₂₀H₂₄O₅ Molecular Weight: 344.402

Powder ≥98%

Out of Stock Item #: A770601

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SMILES

COC1=C(C=CC(=C1)CC2COCC2CC3=CC(=C(C=C3)O)OC)O

InChIKey
ROGUIJKVZZROIQ-HOTGVXAUSA-N

InChI

1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
rac Enterolactone
CAS: 78473-71-9 PubChem CID: 10685477 Formula: C₁₈H₁₈O₄ Molecular Weight: 298.33

Solid ≥95%

Out of Stock Item #: R769244

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Technical Identifiers

IUPAC Name

(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

SMILES

C1C(C(C(=O)O1)CC2=CC(=CC=C2)O)CC3=CC(=CC=C3)O

InChIKey
HVDGDHBAMCBBLR-WMLDXEAASA-N

InChI

1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m0/s1
Dimethylmatairesinol
CAS: 25488-59-9 Formula: C₂₂H₂₆O₆ Molecular Weight: 386.44

Solid Moligand™ ? ≥98%

Out of Stock Item #: D697592

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Technical Identifiers

IUPAC Name

(3R,4R)-3,4-bis[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

SMILES

COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)OC)OC)OC

InChIKey
SNAOLIMFHAAIER-DLBZAZTESA-N

InChI

1S/C22H26O6/c1-24-18-7-5-14(11-20(18)26-3)9-16-13-28-22(23)17(16)10-15-6-8-19(25-2)21(12-15)27-4/h5-8,11-12,16-17H,9-10,13H2,1-4H3/t16-,17+/m0/s1
3,4-Divanillyltetrahydrofuran
CAS: 34730-78-4 PubChem CID: 182210 Formula: C₂₀H₂₄O₅ Molecular Weight: 344.4

Out of Stock Item #: D668121

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IUPAC Name

4-[[4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl]-2-methoxyphenol

SMILES

COC1=C(C=CC(=C1)CC2COCC2CC3=CC(=C(C=C3)O)OC)O

InChIKey
ROGUIJKVZZROIQ-UHFFFAOYSA-N

InChI

1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3

Synonyms
3,4-divanillyltetrahydrofuran | 4-[[4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl]-2-methoxyphenol | SCUTEL...
Hinokinin
CAS: 26543-89-5 PubChem CID: 442879 Formula: C₂₀H₁₈O₆ Molecular Weight: 354.35

≥99%

Out of Stock Item #: H648559

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Yatein
CAS: 40456-50-6 PubChem CID: 442835 Formula: C₂₂H₂₄O₇ Molecular Weight: 400.42

≥99%

Out of Stock Item #: Y650507

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SMILES

COC1=CC(=CC(=C1OC)OC)C[C@@H]2[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4
Trachelogenin
CAS: 34209-69-3 PubChem CID: 452855 Formula: C₂₁H₂₄O₇ Molecular Weight: 388.41

≥99%

Out of Stock Item #: T647299

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Technical Identifiers

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

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-/m0/s1

Synonyms
(-)-Trachelogenin | ACon1_002414 | DTXSID50187799 | 2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)DIHYDRO-3-HYDROXY-...
Nortrachelogenin
CAS: 34444-37-6 Formula: C₂₀H₂₂O₇ Molecular Weight: 374.38

≥98%

In Stock Item #: N413426

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Technical Identifiers

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

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/s1

Synonyms
Nortrachelogenin | SCHEMBL874637 | (-)-Wikstromol | CHEBI:7639 | Q27107549 | (3S,4S)-3-hydroxy-3,4-bis[(4-hydroxy-3-m...
(-)-Arctigenin
CAS: 7770-78-7 Formula: C₂₁H₂₄O₆ Molecular Weight: 372.41

10mM in DMSO

In Stock Item #: A425916

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Technical Identifiers

IUPAC Name

(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

SMILES

COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC

InChIKey
NQWVSMVXKMHKTF-JKSUJKDBSA-N

InChI

1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1

Synonyms
Arctigenin|(-)-Arctigenin|7770-78-7|(+/-)-Arctigenin|Arctigenin, (+/-)-|UNII-U76MR9VS6M|U76MR9VS6M|Arctigenin, trans-...
(-)-Arctigenin
CAS: 7770-78-7 Formula: C₂₁H₂₄O₆ Molecular Weight: 372.41

≥98%(HPLC)

In Stock Item #: A109807

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Technical Identifiers

IUPAC Name

(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

SMILES

COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC

InChIKey
NQWVSMVXKMHKTF-JKSUJKDBSA-N

InChI

1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1

Synonyms
2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R-trans)- | SCHEMBL3...

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