Chemistry:Arctiin

Arctiin

Names
IUPAC name (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-{[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl}oxolan-2-one
Identifiers
CAS Number	20362-31-6 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL388452 Y
ChemSpider	90827 Y
KEGG	C16915 Y
MeSH	arctigenin
PubChem CID	100528
UNII	TM5RQ949K7 Y
InChI InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1 Y Key: XOJVHLIYNSOZOO-SWOBOCGESA-N Y InChI=1/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1 Key: XOJVHLIYNSOZOO-SWOBOCGEBY
SMILES O=C2OC[C@H](Cc1ccc(OC)c(OC)c1)[C@H]2Cc4ccc(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO)c(OC)c4
Properties
Chemical formula	C27H34O11
Molar mass	534.558 g·mol−1
Melting point	110 to 112 °C (230 to 234 °F; 383 to 385 K)
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

Tracking categories (test):

• SizeSet

Arctiin is a lignan found in many plants of the family Asteraceae, particularly the greater burdock (Arctium lappa) and Centaurea imperialis, and in Trachelospermum asiaticum, Saussurea heteromalla, and Forsythia viridissima. It is the glucoside of arctigenin.

Arctiin and arctigenin have shown anticancer effects in animal research. They have been found to act as agonists of the adiponectin receptor 1.

External links

• Arctiin entry in the public domain NCI Dictionary of Cancer Terms

 This article incorporates public domain material from the U.S. National Cancer Institute document "Dictionary of Cancer Terms".