Gummadiol - Misplaced Pages

Gummadiol
Names

Preferred IUPAC name (2R,3R,3aS,6S,6aR)-3,6-Di(2H-1,3-benzodioxol-5-yl)dihydro-1H,3H-furofuran-1,3a(4H)-diol
Other names 1,4-Dihydroxysesamin
Identifiers
CAS Number	57684-87-4
3D model (JSmol)	Interactive image
ChemSpider	10308017
PubChem CID	21722930
CompTox Dashboard (EPA)	DTXSID501045325
InChI InChI=1S/C20H18O8/c21-19-16-17(10-1-3-12-14(5-10)26-8-24-12)23-7-20(16,22)18(28-19)11-2-4-13-15(6-11)27-9-25-13/h1-6,16-19,21-22H,7-9H2/t16-,17+,18+,19+,20+/m0/s1Key: KCQXLVHWDSFFDF-OMQSBVIBSA-N
SMILES O5O(c1ccc2OCOc2c1)6(O)CO(c3ccc4OCOc4c3)56
Properties
Chemical formula	C₂₀H₁₈O₈
Molar mass	386.356 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Gummadiol is a lignan hemiacetal. It can be isolated from the heartwood of Gmelina arborea.

References

Anjaneyulu, A.S.R.; Rao, A.Madhusudhana; Rao, V.Kameswara; Row, L.Ramachandra; Pelter, Andrew; Ward, Robert S. (1975). "The structure of gummadiol - A lignan hemi-acetal". Tetrahedron Letters. 16 (22–23): 1803–1806. doi:10.1016/S0040-4039(00)75261-0.
Anjaneyulu, A.S.R.; Rao, A.Madhusudhana; Rao, V.Kameswara; Row, L.Ramachandra; Pelter, Andrew; Ward, Robert S. (1977). "Novel hydroxy lignans from the heartwood of gmelina arborea". Tetrahedron. 33: 133–143. doi:10.1016/0040-4020(77)80444-4.

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 (SDG)
Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol
Neolignans	Balanophonin Eusiderin Honokiol Interiotherin 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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