Neohesperidin (Hesperetin 7-O-neohesperidoside), a naturally occuring flavanone glycoside found in citrus fruits, is an antioxidant agent, also has neuroprotective properties. Unlike other citrus flavanones, it does not inhibit oral carcinogenesis in a rat model.

Physicochemical Properties

Molecular Formula	C28H34O15
Molecular Weight	610.56
Exact Mass	610.189
CAS #	13241-33-3
Related CAS #	Neohesperidin dihydrochalcone;20702-77-6
PubChem CID	232990
Appearance	White to off-white solid powder
Density	1.7±0.1 g/cm3
Boiling Point	933.7±65.0 °C at 760 mmHg
Melting Point	239-243ºC
Flash Point	306.7±27.8 °C
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.695
LogP	2.44
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	7
Heavy Atom Count	43
Complexity	940
Defined Atom Stereocenter Count	0
SMILES	O([C@@]1([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C([H])([H])[H])O1)O[H])O[H])O[H])[C@@]1([H])[C@]([H])(OC2=C([H])C(=C3C(C([H])([H])[C@]([H])(C4C([H])=C([H])C(=C(C=4[H])O[H])OC([H])([H])[H])OC3=C2[H])=O)O[H])O[C@]([H])(C([H])([H])O[H])[C@]([H])([C@]1([H])O[H])O[H]
InChi Key	ARGKVCXINMKCAZ-UZRWAPQLSA-N
InChi Code	InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
Chemical Name	(S)-7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one
Synonyms	NSC-31048; NSC31048;NSC 31048;Hesperetin 7-Neohesperidoside;
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	Neohesperidin causes MDA-MB-231 human breast cancer cells to undergo apoptosis. Neohesperidin's IC50 values were 32.5±1.8 μM and 47.4±2.6 μM at 24 and 48 hours, respectively. In cells treated with neohesperidin, there was a considerable up-regulation of P53 and Bax expression and a down-regulation of Bcl-2 expression [1]. In the DPPH free radical scavenging experiment, neohesperidin demonstrates antioxidant activity (IC50=22.31 μg/mL) [2].
ln Vivo	The stomach damage brought on by a 55.0% HCl/ethanol mixture was dramatically reduced by neohesperidin (50 mg/kg). Neohesperidin (50 mg/kg) markedly decreased gastric production and acid excretion in pyloric ligated rats while also raising pH [1]. Treatment with neohesperidin dramatically lowered mice's serum glucose, fasting blood glucose, and glycosylated serum protein (GSP). In diabetic rats, it greatly enhances insulin sensitivity and oral glucose tolerance while lowering insulin resistance. Neohesperidin dramatically lowered the liver index, leptin levels, total cholesterol, and serum triglycerides in mice [3].
References	[1]. Lee JH, et al. Protective effects of neohesperidin and poncirin isolated from the fruits of Poncirus trifoliata on potential gastric disease. Phytother Res. 2009 Dec;23(12):1748-53. [2]. Xu F, et al. Neohesperidin induces cellular apoptosis in human breast adenocarcinoma MDA-MB-231 cells via activating the Bcl-2/Bax-mediated signaling pathway. Nat Prod Commun. 2012 Nov;7(11):1475-8. [3]. Jia S, et al. Hypoglycemic and hypolipidemic effects of neohesperidin derived from Citrus aurantium L. in diabetic KK-A(y) mice. Food Funct. 2015 Mar;6(3):878-86
Additional Infomation	Hesperetin 7-neohesperidoside is a glycoside and a member of flavonoids. Neohesperidin has been reported in Citrus reticulata, Citrus deliciosa, and other organisms with data available. See also: Neohesperidin (annotation moved to).

Solubility Data

Solubility (In Vitro)

DMSO:> 10 mM Water: N/A Ethanol: N/A

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.09 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 (4.09 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 (4.09 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. Solubility in Formulation 4: 5 mg/mL (8.19 mM) in 0.5% CMC-Na/saline water (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.6378 mL	8.1892 mL	16.3784 mL
	5 mM	0.3276 mL	1.6378 mL	3.2757 mL
	10 mM	0.1638 mL	0.8189 mL	1.6378 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.