Pinocembrin (DL-0108), the racemate of Pinocembrin, is a potent androgen receptor ligand with the potential for the treatment of acute stroke. Pinocembrin [(+)-Pinocoembrin; Dihydrochrysin; Galangin flavanone] is a naturally occurring flavonoid that is present in fingerroot, propolis, damiana, and honey. It has strong antimicrobial, anti-inflammatory, and gastrointestinal protective properties. It is a potent anti-allergic agent that functions as a competitive inhibitor of histidine decarboxylase.

Physicochemical Properties

Molecular Formula	C15H12O4
Molecular Weight	256.25
Exact Mass	256.074
Elemental Analysis	C, 70.31; H, 4.72; O, 24.97
CAS #	68745-38-0
Related CAS #	68745-38-0
PubChem CID	238782
Appearance	White to off-white solid powder
Density	1.386g/cm3
Boiling Point	520.6ºC at 760 mmHg
Melting Point	202-203ºC
Flash Point	203.3ºC
Vapour Pressure	1.85E-11mmHg at 25°C
Index of Refraction	1.661
LogP	2.804
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Heavy Atom Count	19
Complexity	337
Defined Atom Stereocenter Count	0
SMILES	Oc1cc(O)c2C(=O)CC(Oc2c1)c1ccccc1
InChi Key	URFCJEUYXNAHFI-UHFFFAOYSA-N
InChi Code	InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2
Chemical Name	5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms	DL-0108; DL0108; DL 0108; Pinocembrin
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

ln Vitro	Pinocembrin (5,7-dihydroxyflavanone) is one of the main flavonoids that have been isolated and purified using different chromatographic techniques from a variety of plants, primarily from Sparattosperma leucanthum, Eucalyptus, Populus, and Pinus heartwood, among other diverse flora. Numerous pharmacological properties, such as antimicrobial, anti-inflammatory, antioxidant, and anticancer properties, have been thoroughly studied[1]. In primary cortical neurons exposed to oxygen-glucose deprivation/reoxygenation (OGD/R), pinocembrin has been demonstrated to increase neuronal viability, decrease lactate dehydrogenase release, inhibit the production of NO and ROS, increase glutathione levels, and downregulate the expression of neuronal NO synthase (nNOS) and iNOS[2].
ln Vivo	Pinocembrin has a broad therapeutic time window for its neuroprotective effects against cerebral ischemia injury, which may be related to its antiexcitotoxic properties[1]. It can control apoptosis, modify mitochondrial function, shield the blood-brain barrier, and lower reactive oxygen species (ROS). Astrocytic end-feet edema, neuronal apoptosis, deformation of endothelial cells and capillaries, and brain swelling may all be ameliorated by pinocembrin (10 mg/kg, i.v.). Pinocembrin inhibits ER stress and apoptosis in MCAO rats by lowering the expression of caspase-12 and C/EBP homologous protein (CHOP)/GADD153 through the PERK-elF2α-ATF4 signaling pathway. In mice, the lethal dose of intravenous pinocembrin (LD50) exceeds 700 mg/kg.
Cell Assay	SH-SY5Y cells are cultured at 37°C in a humidified environment with 5% CO2 in DMEM supplemented with 10% FBS, 100 units/mL penicillin, and 100 µg/mL streptomycin. Trypsinization is used to pass cells every three to five days. Subsequently, a 96-well plate is seeded with 1 × 104 cells per well, and the plate is incubated for 24 hours at 37 °C in a humidified atmosphere that contains 5% CO2. After one of the compounds is pretreated for one hour, the entire medium is replaced with fresh medium containing 1% FBS. Either 30 nM staurosporine or 2.0 µg/mL tunicamycin is then added. Assays for nuclear staining are conducted 24 hours after the initial incubation. Cell death is evaluated.
Animal Protocol	male Sprague-Dawley rats 22.5 or 67.5 mg/kg i.v.
References	[1]. Biomed Res Int . 2013:2013:379850. [2]. Mol Neurobiol . 2016 Apr;53(3):1794-1801. [3]. J Pharm Biomed Anal . 2009 Jul 12;49(5):1277-81. [4]. J Agric Food Chem . 2008 Oct 8;56(19):8944-53.
Additional Infomation	5,7-Dihydroxyflavanone has been reported in Apis, Boesenbergia rotunda, and other organisms with data available. See also: Pinostrobin (annotation moved to).

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.9024 mL	19.5122 mL	39.0244 mL
	5 mM	0.7805 mL	3.9024 mL	7.8049 mL
	10 mM	0.3902 mL	1.9512 mL	3.9024 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.