2'-O-Methylisoliquiritigenin can be extracted from Arachis and can upregulate the 5-HT, NE, DA and GABA signaling pathways, but has little effect on the NE pathway.

Physicochemical Properties

Molecular Formula	C16H14O4
Molecular Weight	270.28
Exact Mass	270.089
CAS #	51828-10-5
Related CAS #	3-Deoxysappanchalcone;112408-67-0
PubChem CID	5319688
Appearance	Light yellow to yellow solid powder
Density	1.3±0.1 g/cm3
Boiling Point	527.1±50.0 °C at 760 mmHg
Melting Point	210 - 212 °C
Flash Point	200.5±23.6 °C
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.658
LogP	2.96
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Heavy Atom Count	20
Complexity	344
Defined Atom Stereocenter Count	0
SMILES	COC1=C(C=CC(=C1)O)C(=O)/C=C/C2=CC=C(C=C2)O
InChi Key	PACBGANPVNHGNP-RUDMXATFSA-N
InChi Code	InChI=1S/C16H14O4/c1-20-16-10-13(18)7-8-14(16)15(19)9-4-11-2-5-12(17)6-3-11/h2-10,17-18H,1H3/b9-4+
Chemical Name	(E)-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms	3-Deoxysappanchalcone; 2'-O-Methylisoliquiritigenin; 112408-67-0; 4,4'-dihydroxy-2'-methoxychalcone; 2'-Methoxyisoliquiritigenin; CHEBI:519567; LHE9JFQ1U8; ...; 51828-10-5;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Natural flavone; 5-HT, NE, DA and GABA
ln Vitro	Results: Aqueous extract of PSL at a dose of 500 mg kg-1 (based on previous experience), along with different concentrations of the above four functional ingredients (189.86 µg kg-1 linalool, 114.75 mg kg-1 5-hydroxy-4',7-dimethoxyflavanone, 32.4mg kg-1 2'-O-methylisoliquiritigenin and 44.44 mg kg-1 ferulic acid), had a sedative-hypnotic effect by affecting neurotransmitter levels in mice. Conclusion: The data demonstrate that these four ingredients are the key functional factors for the sedative-hypnotic and anxiolytic effects of PSL aqueous extracts and that these effects occur via changes in neurotransmitter levels and pathways.
References	[1]. Sedative-hypnotic and Anxiolytic Effects and the Mechanism of Action of Aqueous Extracts of Peanut Stems and Leaves in Mice. J Sci Food Agric. 2018 Oct;98(13):4885-4894.
Additional Infomation	2'-O-methylisoliquiritigenin is a member of the class of chalcones that is isoliquiritigenin in which one of the hydroxy groups at position 2' is replaced by a methoxy group. It has a role as a metabolite. It is a member of chalcones, a monomethoxybenzene and a member of phenols. It is functionally related to an isoliquiritigenin. 2'-O-Methylisoliquiritigenin has been reported in Dracaena cochinchinensis, Dracaena cambodiana, and other organisms with data available. Peanut stems and leaves (PSL) have traditionally been used as both a special food and a herbal medicine in Asia. The sedative-hypnotic and anxiolytic effects of PSL have been recorded in classical traditional Chinese literature, and more recently by many other researchers. In a previous study, four sleep-related ingredients (linalool, 5-hydroxy-4',7-dimethoxyflavanone, 2'-O-methylisoliquiritigenin and ferulic acid), among which 5-hydroxy-4',7-dimethoxyflavanone and 2'-O-methylisoliquiritigenin were newly found in Arachis species, were screened by ultrahigh-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC/QTOF-MS). In the current study, quantitative examination of the above four ingredients was conducted. Serious fundamental functional studies were done in mice, including locomotor activity, direct sleep tests, pentobarbital-induced sleeping time tests, subthreshold dose of pentobarbital tests and barbital sodium sleep incubation period tests, to determine the material base for the sedative-hypnotic and anxiolytic effects of aqueous extracts of PSL. Furthermore, neurotransmitter levels in three brain regions (cerebrum, cerebellum and brain stem) were determined using UHPLC coupled with triple-quadrupole mass spectrometry (UHPLC/QQQ-MS) in order to elucidate the exact mechanism of action.[1]

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (369.99 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (9.25 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.6999 mL	18.4993 mL	36.9987 mL
	5 mM	0.7400 mL	3.6999 mL	7.3997 mL
	10 mM	0.3700 mL	1.8499 mL	3.6999 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.