Lariciresinol : Occurrence Wikipedia, the free encyclopedia

Lariciresinol

Lariciresinol
Names

IUPAC name 4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol
Identifiers
CAS Number	27003-73-2^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL518421^N
ChemSpider	294521^N
ECHA InfoCard	100.222.965
KEGG	C10646^Y
PubChem CID	332427
UNII	73XCE5OZB0^Y
CompTox Dashboard (EPA)	DTXSID30318362
InChI 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
SMILES COc1cc(ccc1O)C[C@H]2CO[C@@H]([C@H]2CO)c3ccc(c(c3)OC)O
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references

Chemical compound

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.

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]

References

^ 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.
^ 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.