Lariciresinol

Lariciresinol is a lignan, i.e., a type of phenylpropanoids. It is the precursor to enterolignans by the action of gut microflora. Enterolignans are of interest because they are speculated to exhibit beneficial medicinal properties.

Lariciresinol
Chemical structure of lariciresinol
Names
IUPAC name
4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.222.965
KEGG
UNII
  • InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1 ☒N
    Key: MHXCIKYXNYCMHY-AUSJPIAWSA-N ☒N
  • InChI=1/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
    Key: MHXCIKYXNYCMHY-AUSJPIAWBV
  • COc1cc(ccc1O)C[C@H]2CO[C@@H]([C@H]2CO)c3ccc(c(c3)OC)O
Properties
C20H24O6
Molar mass 360.40 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Occurrence

In food, it is found in sesame seeds and in Brassica vegetables.[1] It is also found in the bark and wood of white fir (Abies alba).[2]

See also

References
  1. Milder, Ivon E. J; Arts, Ilja C. W; Putte, Betty van de; Venema, Dini P; Hollman, Peter C. H (2007). "Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". British Journal of Nutrition. 93 (3): 393–402. doi:10.1079/BJN20051371. PMID 15877880.
  2. Benković, Eva Tavčar; Grohar, Tina; Žigon, Dušan; Švajger, Urban; Janeš, Damjan; Kreft, Samo; Štrukelj, Borut (2014). "Chemical composition of the silver fir (Abies alba) bark extract Abigenol® and its antioxidant activity". Industrial Crops and Products. 52: 23–28. doi:10.1016/j.indcrop.2013.10.005.


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