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Mycotoxin
Phomoxanthone B
Другие языки:

    Phomoxanthone B

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    Phomoxanthone B
    Phomoxanthone B structure.svg
    Names
    Preferred IUPAC name
    (5R,5′R,6R,6′R,10aR,10′aR)-10a,10′a-Bis[(acetyloxy)methyl]-1,1′,8,8′-tetrahydroxy-6,6′-dimethyl-9,9′-dioxo-5,5′,6,6′,7,7′,10a,10′a-octahydro-9H,9′H-[2,4′-bixanthene]-5,5′-diyl diacetate
    Other names
    PXB
    Identifiers
    3D model (JSmol)
    ChEBI
    ChEMBL
    ChemSpider
    PubChem CID
    • InChI=1S/C38H38O16/c1-15-11-25(45)30-33(48)28-26(53-37(30,13-49-17(3)39)35(15)51-19(5)41)10-8-21(31(28)46)22-7-9-23(43)27-32(47)29-24(44)12-16(2)36(52-20(6)42)38(29,54-34(22)27)14-50-18(4)40/h7-10,15-16,35-36,43,46-48H,11-14H2,1-6H3/t15-,16-,35-,36-,37+,38+/m1/s1
      Key: RWPGIQJRECCQEK-ACMZUNAXSA-N
    • CC1CC(=O)C2=C(C3=C(C=CC(=C3O)C4=C5C(=C(C=C4)O)C(=C6C(=O)CC(C(C6(O5)COC(=O)C)OC(=O)C)C)O)OC2(C1OC(=O)C)COC(=O)C)O
    • [C@H]1(CC(=C2[C@@]([C@@H]1OC(=O)C)(Oc1c(C2=O)c(ccc1c1c(c2C(=O)C3=C(C[C@H]([C@H]([C@]3(Oc2cc1)COC(=O)C)OC(=O)C)C)O)O)O)COC(=O)C)O)C
    • C[C@@H]1CC(=O)C2=C(C3=C(C=CC(=C3O)C4=C5C(=C(C=C4)O)C(=C6C(=O)C[C@H]([C@H]([C@]6(O5)COC(=O)C)OC(=O)C)C)O)O[C@@]2([C@@H]1OC(=O)C)COC(=O)C)O
    Properties
    C38H38O16
    Molar mass 750.70 g/mol
    not soluble
    Solubility in DMSO good
    Solubility in EtOH moderate
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    The mycotoxin phomoxanthone B, or PXB for short, is a toxic natural product. It is a less toxic isomer of phomoxanthone A and one of the two founding members of the class of phomoxanthone compounds. The phomoxanthones are named after the fungus Phomopsis, from which they were first isolated, and after their xanthonoid structure. Chemically, they are dimers of two tetrahydroxanthones that are covalently linked to each other. PXB itself is a homodimer of two identical diacetylated tetrahydroxanthones. The position of the link between the two tetrahydroxanthones is the only structural difference between PXB and its isomers PXA and dicerandrol C: In PXA, the two xanthonoid monomers are symmetrically linked at C-4,4’, while in PXB, they are asymmetrically linked at C-2,4’, and in dicerandrol C, they are symmetrically linked at C-2,2’.

    Wikimedia Commons has media related to Phomoxanthone.

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