(-)-Pinoresinol 4-O-glucoside ((-)-Pinoresinol 4-O-β-D-glucopyranoside) is a potent and orally bioactive α-glucosidase inhibitor (antagonist) with IC50 of 48.13 µM. (-)-Pinoresinol 4-O-glucoside increases cell migration and early differentiation of preosteoblasts. (-)-Pinoresinol 4-O-glucoside increases the protein levels of BMP2, p-Smad1/5/8, and RUNX2. (-)-Pinoresinol 4-O-glucoside reduces oxidative stress, hyperglycemia, and hepatotoxicity. (-)-Pinoresinol 4-O-glucoside may be used for studying osteoporosis and periodontal disease.

Physicochemical Properties

Molecular Formula	C26H32O11
Molecular Weight	520.53
Exact Mass	520.194
CAS #	41607-20-9
PubChem CID	11168362
Appearance	Typically exists as solid at room temperature
Density	1.4±0.1 g/cm3
Boiling Point	752.5±60.0 °C at 760 mmHg
Flash Point	408.9±32.9 °C
Vapour Pressure	0.0±2.6 mmHg at 25°C
Index of Refraction	1.619
LogP	-0.69
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	7
Heavy Atom Count	37
Complexity	741
Defined Atom Stereocenter Count	9
SMILES	COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)O
InChi Key	QLJNETOQFQXTLI-JKUDBEEXSA-N
InChi Code	InChI=1S/C26H32O11/c1-32-18-7-12(3-5-16(18)28)24-14-10-35-25(15(14)11-34-24)13-4-6-17(19(8-13)33-2)36-26-23(31)22(30)21(29)20(9-27)37-26/h3-8,14-15,20-31H,9-11H2,1-2H3/t14-,15-,20-,21-,22+,23-,24+,25+,26-/m1/s1
Chemical Name	(2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6R,6aS)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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
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	IC50: 48.13 µM (α-Glucosidase)[1]
ln Vitro	In osteogenic supplemented media (OS) containing 50 µg/mL, (-)-Pinoresinol 4-O-glucoside (0, 10, 30 µM; 24 hours) enhances cell migration during preosteoblast differentiation [1]< /sup>. (-)-Pinoresinol 4-O-glucoside (10, 30 µM; 7 days) promotes the development of mineralized nodules during preosteoblast differentiation and accelerates early differentiation [1]. Preosteoblasts treated with (10, 30 µM; 3 days) (-)-Pinoresinol 4-O-glucoside exhibit increased BMP2, ALP, and OCN mRNA expression [1]. BMP2,p-Smad1/5/8, and RUNX2 all have higher levels of protein expression when exposed to (-)-Pinoresinol 4-O-glucoside (10, 30 µM; 3 days) [1].
ln Vivo	(-)-Pinoresinol 4-O-glucoside (50 mg/kg; oral; 20 days) lowers the hepatotoxicity, hyperglycemia, and oxidative stress in mice[2].
Animal Protocol	Animal/Disease Models: 27-30 g, Male Swiss albino mice[2] Doses: 50 mg/kg Route of Administration: Po; twenty days Experimental Results: demonstrated a hepatoprotective activity in vivo as it lowered AST and ALT levels, caused a prominent decline in serum glucose level by 37.83% in streptozotocin-treated mice with promising elevation in insulin level of 25.37%.
References	[1]. Effects of PIN on Osteoblast Differentiation and Matrix Mineralization through Runt-Related Transcription Factor. Int J Mol Sci. 2020 Dec 16;21(24):9579. [2]. Pinoresinol-4-O-β-D-glucopyranoside: a lignan from prunes (Prunus domestica) attenuates oxidative stress, hyperglycaemia and hepatic toxicity in vitro and in vivo. J Pharm Pharmacol. 2020 Dec;72(12):1830-1839.
Additional Infomation	(-)-Pinoresinol glucoside is a glycoside and a lignan. (-)-Pinoresinol glucoside has been reported in Acer truncatum, Tinospora sinensis, and other organisms with data available.

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	1.9211 mL	9.6056 mL	19.2112 mL
	5 mM	0.3842 mL	1.9211 mL	3.8422 mL
	10 mM	0.1921 mL	0.9606 mL	1.9211 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.