EN
0
Home > Products > Natural Products & Standards > Botanical Reference Standards > (-)-Arctigenin
(-)-Arctigenin structure, CAS 7770-78-7

(-)-Arctigenin

CAS Number7770-78-7

SynonymsArctigenin; (2S)-2-[(2S,12bS)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]but-3-en-1-ol; 2-(1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-but-3-en-1-ol; MFCD00870597; (-)-Arctigenin; (-)-arctigenine; (3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one; l-Arctigenin; (3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanone; (-)-antirhine

Molecular FormulaC21H24O6

Molecular Weight372.41

Purity≥95 (LC/MS-ELSD)%

Density1.2±0.1 g/cm3

Boiling Point567.0±45.0 °C at 760 mmHg

Melting Point100 °C

Flash Point

Appearancesolid

EINECS

MSDSChineseEnglish

SymbolTransport

Signal WordWarning

Cat. No.: 2A-9008920 Purity: ≥95 (LC/MS-ELSD)%
Change View

Please Login or Create an Account to: See VlP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

Inquiry

Quality Control of [ 7770-78-7 ] Purity: ≥95 (LC/MS-ELSD)% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number7770-78-7
Catalog No.2A-9008920
Chinese Name牛蒡子苷元
SynonymsArctigenin; (2S)-2-[(2S,12bS)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]but-3-en-1-ol; 2-(1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-but-3-en-1-ol; MFCD00870597; (-)-Arctigenin; (-)-arctigenine; (3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one; l-Arctigenin; (3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanone; (-)-antirhine
Molecular FormulaC21H24O6
Molecular Weight372.41
Purity≥95 (LC/MS-ELSD)
Density1.2±0.1 g/cm3
Boiling Point567.0±45.0 °C at 760 mmHg
Melting Point100 °C
Appearancesolid
Water SolubilityDMSO: 34 mg/mL with heating and sonicating, solubl
Storage Condition−20°C
ApplicationArctigenin is a lignan found in some Asteraceae plants and has antiviral and anticancer activities.
PubChem ID329824754
MDL NumberMFCD00870597
SMILESCOc1cc(C[C@@H]2[C@H](COC2=O)Cc3ccc(OC)c(OC)c3)ccc1O
InChI1S/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
InChI KeyNQWVSMVXKMHKTF-JKSUJKDBSA-N
NACRES CodeNA.25
UNSPSC12352205
Hazard SymbolsTransport
MSDSmsds/8920_1_7770_78_7.pdf
BioactivityArctigenin is a lignan found in certain plants of the Asteraceae; it has shown antiviral and anticancer effects in glass; it is the aglycone of arctiin.IC50 value: Target: anticancer agentArctiin and its aglucone, arctigenin from the fruits of Arctium lappa L. showed potent in vitro antiviral activities against influenza A virus (A/NWS/33, H1N1) (IFV). Based on the data from time-of-addition experiments and on release tests of progeny viruses, arctigenin was assumed to interfere with early event(s) of viral replication after viral penetration into cells, and to suppress the release of progeny viruses from the host cells [1]. arctigenin treatment reduced viability of bladder cancer T24 cells in a dose- and time-dependent manner after treatment with arctigenin (10, 20, 40, 80, and 100 μmol/L) for 24 hr and 48 hr. Arctigenin treatment clearly arrested tumor cells in the G1 phase of the cell cycle. At the molecular level, arctigenin treatment decreased cyclin D1 expression, whereas CDK4 and CDK6 expression levels were unaffected. Moreover, arctigenin selectively altered the phosphorylation of members of the MAPK superfamily, decreasing phosphorylation of ERK1/2 and activated phosphorylation of p38 significantly in a dose-dependent manner [2]. The use of arctigenin has been shown to be effective in a mouse model of Japanese encephalitis [3]. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> MMP Research Areas >> Cancer Natural Products >> Phenylpropanoids References [1]. Hayashi K, et al. Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza A virus. Biol Pharm Bull. 2010;33(7):1199-205. [2]. Yang S, et al. Arctigenin anti-tumor activity in bladder cancer T24 cell line through induction of cell-cycle arrest and apoptosis. Anat Rec (Hoboken). 2012 Aug;295(8):1260-6. [3]. Swarup V, et al. Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan. J Antimicrob Chemother. 2008 Mar;61(3):679-88. Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 567.0±45.0 °C at 760 mmHg Melting Point 100 °C Molecular Formula C21H24O6 Molecular Weight 372.412 Flash Point 198.8±22.2 °C Exact Mass 372.157288 PSA 74.22000 LogP 2.47 Appearance of Characters solid Vapour Pressure 0.0±1.6 mmHg at 25°C Index of Refraction 1.576 InChIKey NQWVSMVXKMHKTF-JKSUJKDBSA-N SMILES COc1cc(CC2C(=O)OCC2Cc2ccc(OC)c(OC)c2)ccc1O Storage condition −20°C Water Solubility DMSO: 34 mg/mL with heating and sonicating, soluble
Use ofProperties Name (-)-Arctigenin Synonym More Synonyms Arctigenin Biological Activity Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> MMP Research Areas >> Cancer Natural Products >> Phenylpropanoids References [1]. Hayashi K, et al. Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza A virus. Biol Pharm Bull. 2010;33(7):1199-205. [3]. Swarup V, et al. Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan. J Antimicrob Chemother. 2008 Mar;61(3):679-88. Chemical & Physical Properties Molecular Formula C21H24O6 Exact Mass 372.157288 PSA 74.22000 Appearance of Characters solid Index of Refraction 1.576 InChIKey NQWVSMVXKMHKTF-JKSUJKDBSA-N
Transport InfoShipping Name: UN
MSDS Transport InfoModule 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available
Related Products in Botanical Reference Standards
Sterol;cholesterin,cholest-5-en-3beta-ol57-88-52A-9008757
Stilbene dicarboxylic acid chloride2A-1087582A-9008758
Tanshinone I568-73-02A-9008772
Tanshinone IIB2A-1087732A-9008773
Tectochrysin520-28-52A-9008774
(-)-Fisetinidol490-49-32A-9008922
3'-Methoxypuerarin2A-3000672A-9008984
6-Hydroxyluteolin-7-O-sambubioside2A-3000912A-9009008
6-Shogaol555-66-82A-9009010
8-Gingerol23513-08-82A-9009018
Browse all Botanical Reference Standards products »
Contact Us

Phone:

630-322-8886

630-322-8887

Email:

[email protected]

Office Locations:

Chicago, IL, USA

San Francisco, CA, USA