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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

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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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Shengrong Sun et al.
Planta medica, 77(2), 141-145 (2010-08-19)
The involvement of unfolded protein response (UPR) activation in tumor survival and resistance to chemotherapies suggests a new anticancer strategy targeting UPR pathway. Arctigenin, a natural product, has been recently identified for its antitumor activity with selective toxicity against cancer
Ji Yun Lee et al.
Archives of pharmacal research, 33(6), 947-957 (2010-07-08)
We previously reported that arctigenin, a phenylpropanoid dibenzylbutyrolactone lignan isolated from Forsythia koreana, exhibits anti-inflammatory, antioxidant, and analgesic effects in animal models. In addition, arctigenin inhibited eosinophil peroxidase and activated myeloperoxidase in inflamed tissues. In this study, we tested the
Vivek Swarup et al.
The Journal of antimicrobial chemotherapy, 61(3), 679-688 (2008-01-31)
OBJECTIVES; To evaluate therapeutic efficacy of arctigenin in an experimental model of Japanese encephalitis (JE). Four- to 5-week-old BALB/c mice of either sex were infected intravenously with lethal dose of 3 x 10(5) pfu of Japanese encephalitis virus (JEV). By
Suresh Awale et al.
Cancer research, 66(3), 1751-1757 (2006-02-03)
Tumor cells generally proliferate rapidly and the demand for essential nutrients as well as oxygen always exceeds the supply due to the unregulated growth and the insufficient and inappropriate vascular supply. However, cancer cells show an inherent ability to tolerate
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
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