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Merck
CN

SMB00075

(−)-Arctigenin

Synonym(s):

2(3H)-Furanone, (3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone

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About This Item

Empirical Formula (Hill Notation):
C21H24O6
CAS Number:
7770-78-7
Molecular Weight:
372.41
NACRES:
NA.25
PubChem Substance ID:
329824754
UNSPSC Code:
12352205
MDL number:
MFCD00870597

Key Documents

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InChI

1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1

SMILES string

COc1cc(C[C@@H]2[C@H](COC2=O)Cc3ccc(OC)c(OC)c3)ccc1O

InChI key

NQWVSMVXKMHKTF-JKSUJKDBSA-N

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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General description

Arctigenin is a lignan found in the root of Arctium lappa L. It has been used in pharmacologic, as well as cosmetic, research and has demonstrated several antiviral and anticancer effects.

Biochem/physiol Actions

Dibenzylbutyrolactone ligand, natural product, viral integrase and topoisomerase II inhibitor, antioxidant, antiviral, anti-inflammatory, immunomodulator.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
12222867V
122228-67V

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Jong-Sik Jin et al.
Biological & pharmaceutical bulletin, 30(5), 904-911 (2007-05-03)
Plant lignans, such as pinoresinol diglucoside, secoisolariciresinol diglucoside and arctiin, are metabolized to mammalian lignans, enterolactone or enterodiol, by human intestinal bacteria. Their metabolic processes include deglucosylation, ring cleavage, demethylation, dehydroxylation and oxidation. Here we isolated an intestinal bacterium capable
Ju-Young Kim et al.
Journal of cellular physiology, 224(1), 33-40 (2010-03-17)
Cancer cells in poorly vascularized solid tumors are constantly or intermittently exposed to stressful microenvironments, including glucose deprivation, hypoxia, and other forms of nutrient starvation. These tumor-specific conditions, especially glucose deprivation, activate a signaling pathway called the unfolded protein response
Min Kyung Cho et al.
International immunopharmacology, 4(10-11), 1419-1429 (2004-08-18)
Arctigenin, naturally occurring in Bardanae fructus, Saussurea medusa, Arctium lappa L., Torreya nucifera and Ipomea cairica, is a phenylpropanoid dibenzylbutyrolactone lignan with antioxidant and anti-inflammatory activities. Previously, we showed that arctigenin potently inhibited the induction of nitric oxide synthase (iNOS)
Shiming Liu et al.
Phytochemical analysis : PCA, 16(2), 86-89 (2005-05-11)
A simple method involving polyamide column chromatography in combination with HPLC-PAD and HPLC-ESI/MS for isolating and identifying two kinds of lignans, arctiin and arctigenin, in the leaves of burdock (Arctium lappa L.) has been established. After extraction of burdock leaves
Xiangyang Yao et al.
Journal of cellular biochemistry, 112(10), 2837-2849 (2011-05-25)
Arctigenin is a dibenzylbutyrolactone lignan isolated from Bardanae fructus, Arctium lappa L, Saussureamedusa, Torreya nucifera, and Ipomea cairica. It has been reported to exhibit anti-inflammatory activities, which is mainly mediated through its inhibitory effect on nuclear transcription factor-kappaB (NF-κB). But
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