Gmelanone

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Gmelanone

IUPAC name (1R,2S,5S)-2,5-Bis(1,3-benzodioxol-5-yl)-3,6-dioxabicyclo[3.2.1]octan-8-one
Identifiers
	ChemSpider	10308036
Jmol-3D images	{{#if:O=C4[C@@H]1CO[C@]4(CO[C@@H]1c2ccc3OCOc3c2)c5ccc6OCOc6c5\|Image 1
SMILES O=C4[C@@H]1CO[C@]4(CO[C@@H]1c2ccc3OCOc3c2)c5ccc6OCOc6c5
Properties
Molecular formula	C₂₀H₁₆O₇
Molar mass	368.33 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Gmelanone is a lignan found in the heartwood of Gmelina arborea.^[1]

Arboreol can be transformed by acid catalysis into gmelanone.^[2]

References

↑ Novel hydroxy lignans from the heartwood of gmelina arborea. A.S.R. Anjaneyulu, A.Madhusudhana rao, V.Kameswara Rao and L.Ramachandra Row, Tetrahedron, 1977, Volume 33, Issue 1, Pages 133–143, doi:10.1016/0040-4020(77)80444-4
↑ Acid catalysed rearrangements of arboreol: A biomimetic synthesis of gmelanone. L. Ramachandra Row and Reveru Ventkateswarlu, Tetrahedron Letters, 1980, Volume 21, Issue 30, Pages 2919–2922, doi:10.1016/S0040-4039(00)78645-X

v t e Types of lignans

Lignans	Arboreol Arctigenin Chamaecypanone A and B Eudesmin Globoidnan A Gmelanone Gmelinol Gummadiol Isootobanone Lyoniresinol Macelignan Matairesinol Obtulignolide Pinoresinol Pluviatilol Podophyllotoxin Secoisolariciresinol Sesamin Sesamolin Steganacin

Lignan glycosides	Arctiin Aviculin (isolariciresinol-9'-rhamnopyranoside) Secoisolariciresinol diglucoside

Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol

Neolignans	Balanophonin Eusiderin Honokiol Linderin A Magnolol Megaphone 4-O-Methylhonokiol Rhaphidecursinol A Rhaphidecursinol B

Flavonolignans	Cinchonain-Ib Dehydrosilybin Deoxysilycistin Deoxysilydianin Hydnocarpin Hydnowightin Neosilyhermin Palstatin Rhodiolin Salcolin A Salcolin B Scutellaprostin A, B, C, D, E and F Silandrin Silyamandin Silibinin Silybinome Silicristin Silydianin Silyhermin Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether

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