Pinoresinol - Misplaced Pages

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Pinoresinol
Names

IUPAC name 4-furan-3-yl]-2-methoxyphenol
Other names (+)-Pinoresinol
Identifiers
CAS Number	487-36-5
3D model (JSmol)	Interactive image
PubChem CID	73399
CompTox Dashboard (EPA)	DTXSID20964099
SMILES COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
Properties
Chemical formula	C₂₀H₂₂O₆
Molar mass	358.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Pinoresinol is a lignan found in Styrax sp. and in Forsythia suspensa. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.

In food, it is found in sesame seed and in Brassica vegetables.

References

Pastrorova et al. (1997)
On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Laurence B. Davin, Diana L. Bedgar, Takeshi Katayama and Norman G. Lewis, Phytochemistry, Volume 31, Issue 11, 1992, Pages 3869-3874, doi:10.1016/S0031-9422(00)97544-7
Pinoresinol: A lignol of plant origin serving for defense in a caterpillar. Frank C. Schroeder, Marta L. del Campo, Jacqualine B. Grant, Douglas B. Weibel, Scott R. Smedley, Kelly L. Bolton, Jerrold Meinwald and Thomas Eisner, PNAS October 17, 2006 vol. 103 no. 42 15497-15501, doi:10.1073/pnas.0605921103
Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Ivon E. J. Milder, Ilja C. W. Arts, Betty van de Putte, Dini P. Venema and Peter C. H. Hollman, British Journal of Nutrition (2005), 93: 393-402, doi:10.1079/BJN20051371

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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References