Norbergenin is an ortho-desmethyl analogue of bergenin with moderate anti-oxidant effect (IC50 for scavenging DPPH free radicals is 13 μM; scavenging superoxide anion is 32 μM).

Physicochemical Properties

Molecular Formula	C13H14O9
Molecular Weight	314.246
Exact Mass	314.064
Elemental Analysis	C, 49.69; H, 4.49; O, 45.82
CAS #	79595-97-4
PubChem CID	90476206
Appearance	White to yellow solid powder
LogP	-1.3
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	1
Heavy Atom Count	22
Complexity	443
Defined Atom Stereocenter Count	5
SMILES	OC1C(O)=C(O)C=C2C=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC2=O
InChi Key	GDYGAIKPBLFCKR-OIPGZRGRSA-N
InChi Code	InChI=1S/C13H14O9/c14-2-5-8(17)10(19)12-11(21-5)6-3(13(20)22-12)1-4(15)7(16)9(6)18/h1,5,8,10-12,14-19H,2H2/t5-,8-,10+,11+,12-/m1/s1
Chemical Name	Pyrano(3,2-c)(2)benzopyran-6(2H)-one, 3,4,4a,10b-tetrahydro-3,4,8,9,10-pentahydroxy-2-(hydroxymethyl)-, (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-
Synonyms	Demethylbergenin;Norbergenin
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

ln Vitro	Norbergenin, which is the O-demethyl derivative of bergenin, the main component of Mallotus japonicus, has been found to show moderate antioxidant activity (IC(50) 13 microM in DPPH radical scavenging; 32 microM in superoxide anion scavenging). Modification of sugar part on norbergenin by coupling with a variety of fatty acids was employed for increasing its antioxidant activity. Selective esterification of hydroxyl groups on the sugar part enhanced greatly antioxidant activity.
ln Vivo	Norbergenin 11-hexanoate not only exhibited stronger antioxidant activity than catechins, but also prevented neuronal death in primary cultures of rat cortical neurons at a concentration of 10 microM in DMEM supplemented with N2.
References	[1]. Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity. Bioorg Med Chem. 2003;11(8):1781-1788.
Additional Infomation	Norbergenin has been reported in Peltophorum africanum, Mallotus japonicus, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~125 mg/mL (~397.79 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (6.62 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 20.8 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: ≥ 2.08 mg/mL (6.62 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 20.8 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: ≥ 2.08 mg/mL (6.62 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 20.8 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	3.1822 mL	15.9109 mL	31.8218 mL
	5 mM	0.6364 mL	3.1822 mL	6.3644 mL
	10 mM	0.3182 mL	1.5911 mL	3.1822 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.