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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
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12 Items

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  1. Anhydrosecoisolariciresinol
      Grade & Purity: 
    • ≥98%
    Cas Number: 29388-33-8
    Formula:  C20H24O5        Molecular Weight: 344.402
    SMILES:  COC1=C(C=CC(=C1)CC2COCC2CC3=CC(=C(C=C3)O)OC)O
    InChIKey: ROGUIJKVZZROIQ-HOTGVXAUSA-N
    InChI:  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
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  2. rac Enterolactone
      Grade & Purity: 
    • ≥95%
    Cas Number: 78473-71-9        Compound CID:  10685477
    Formula:  C18H18O4        Molecular Weight: 298.33
    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:  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
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  3. Dimethylmatairesinol
      Grade & Purity: 
    • ≥98%
    Cas Number: 25488-59-9        Compound CID:  384877
    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:  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/sshow more
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  4. 3,4-Divanillyltetrahydrofuran
    Cas Number: 34730-78-4        Compound CID:  182210
    Formula:  C20H24O5        Molecular Weight: 344.4
    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:  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...
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  5. Details
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  6. Details
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  7. Trachelogenin
      Grade & Purity: 
    • ≥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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  8. Nortrachelogenin
      Grade & Purity: 
    • ≥98%
    Cas Number: 34444-37-6
    Formula:  C20H22O7        Molecular Weight: 374.38
    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:  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/show more
    Synonyms: Nortrachelogenin|34444-37-6|Pinopalustrin|(-)-Wikstromol|(-)-Wikstromol; NSC 271296|NSC698802|(3S,4S)-3-hydroxy-3,4-b...
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  9. (-)-Arctigenin
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 7770-78-7
    Formula:  C21H24O6        Molecular Weight: 372.41
    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:  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-...
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  10. (-)-Arctigenin
      Grade & Purity: 
    • ≥98%(HPLC)
    Cas Number: 7770-78-7
    Formula:  C21H24O6        Molecular Weight: 372.41
    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:  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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  11. (-)-Arctigenin
    Cas Number: 7770-78-7
    Formula:  C21H24O6        Molecular Weight: 372.41
    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:  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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  12. Matairesinol
      Grade & Purity: 
    • ≥98%
    Cas Number: 580-72-3
    Formula:  C20H22O6        Molecular Weight: 358.39
    IUPAC Name:  (3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
    SMILES:  COC1=C(C=CC(=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)O
    InChIKey: MATGKVZWFZHCLI-LSDHHAIUSA-N
    InChI:  InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1
    Synonyms: AKOS000283004 | Matairesinol, >=85% (HPLC) | A831721 | Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3...
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