Astringin (trans-Astringin) is a natural glycoside found in spruce (Picea sitchensis) and Norway spruce (Picea abies), grape (Vitis vinifera) cell cultures and wine. Astringin has potent antioxidant capacity and cancer chemopreventive activity.

Physicochemical Properties

Molecular Formula	C20H22O9
Molecular Weight	406.3833
Exact Mass	406.126
CAS #	29884-49-9
PubChem CID	5281712
Appearance	White to yellow solid powder
Density	1.593±0.06 g/cm3(Predicted)
Boiling Point	756.1±60.0 °C(Predicted)
Melting Point	218-220 °C
Vapour Pressure	5.06E-24mmHg at 25°C
LogP	0.152
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Heavy Atom Count	29
Complexity	544
Defined Atom Stereocenter Count	5
SMILES	C1=CC(=C(C=C1/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
InChi Key	PERPNFLGJXUDDW-CUYWLFDKSA-N
InChi Code	InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
Chemical Name	(2S,3R,4S,5S,6R)-2-[3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-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

References

[1]. Highly regioselective hydroxylation of polydatin, a resveratrol glucoside, for one-step synthesis of astringin, a piceatannol glucoside, by P450 BM3. Enzyme Microb Technol. 2017 Feb;97:34-42.

Additional Infomation

Trans-astringin is a stilbenoid that is piceatannol substituted at position 3 by a beta-D-glucosyl residue. It has a role as a metabolite, an antioxidant and an antineoplastic agent. It is a polyphenol, a stilbenoid, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a piceatannol. Astringin has been reported in Abies nephrolepis, Picea abies, and other organisms with data available. Astringin is a metabolite found in or produced by Saccharomyces cerevisiae.

Solubility Data

Solubility (In Vitro)

DMSO : ~125 mg/mL (~307.59 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 1.25 mg/mL (3.08 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 12.5 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: ≥ 1.25 mg/mL (3.08 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 12.5 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	2.4608 mL	12.3038 mL	24.6075 mL
	5 mM	0.4922 mL	2.4608 mL	4.9215 mL
	10 mM	0.2461 mL	1.2304 mL	2.4608 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.