Lariciresinol

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
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	360.406 g·mol−1
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

Lariciresinol is a lignan, i.e., a type of phenylpropanoids. It is the precursor to enterolignans by the action of gut microflora.

Occurrence

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

See also

• List of phytochemicals in food

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.