Pinoresinol

Pinoresinol
IUPAC name 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
Other names (+)-Pinoresinol
Identifiers
CAS number	487-36-5 Y=
PubChem	73399
ChEMBL	CHEMBL487611 N
Jmol-3D images	Image 1
SMILES COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
Properties
Molecular formula	C20H22O6
Molar mass	358.38 g/mol
Exact mass	358.141638 u
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pinoresinol is a lignan found in Styrax sp.^[1] and in Forsythia suspensa.^[2] It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.^[3]

In food, it is found in sesame seed and in Brassica vegetables.^[4]

See also

• List of phytochemicals in food

References

1. ^ Pastrorova et al. (1997)
2. ^ 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
3. ^ 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
4. ^ 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

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