Syringin is the main bioactive phenolic glycoside in Acanthopanax senticosus and has anti-osteoporotic effects. Syringin prevents pressure overload-induced cardiac hypertrophy by inhibiting autophagy.

Physicochemical Properties

Molecular Formula	C17H24O9
Molecular Weight	372.37
Exact Mass	372.142
CAS #	118-34-3
PubChem CID	5316860
Appearance	White to off-white solid powder
Density	1.4±0.1 g/cm3
Boiling Point	642.6±55.0 °C at 760 mmHg
Melting Point	192°C
Flash Point	342.4±31.5 °C
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.623
LogP	-1.94
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Heavy Atom Count	26
Complexity	432
Defined Atom Stereocenter Count	5
SMILES	COC1=CC(=CC(=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)OC)/C=C/CO
InChi Key	QJVXKWHHAMZTBY-GCPOEHJPSA-N
InChi Code	InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1
Chemical Name	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
Synonyms	NSC287441 Eleutheroside B NSC 287441Syringin NSC-287441
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

References

[1]. Syringin prevents bone loss in ovariectomized mice via TRAF6 mediated inhibition of NF-κB and stimulation of PI3K/AKT. Phytomedicine. 2018 Mar 15;42:43-50. [2]. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy. Int J Mol Med. 2017 Jan;39(1):199-207.

Additional Infomation

Syringin is a monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. It has a role as a hepatoprotective agent, a plant metabolite, an apoptosis inducer, an autophagy inducer, an anti-inflammatory agent, a neuroprotective agent and an antidepressant. It is a beta-D-glucoside, a monosaccharide derivative, a primary alcohol and a dimethoxybenzene. It is functionally related to a trans-sinapyl alcohol. Syringin has been reported in Acanthus ebracteatus, Jasminum mesnyi, and other organisms with data available. See also: Codonopsis pilosula root (part of).

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~268.55 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.71 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.71 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6855 mL	13.4275 mL	26.8550 mL
	5 mM	0.5371 mL	2.6855 mL	5.3710 mL
	10 mM	0.2686 mL	1.3428 mL	2.6855 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.