Geniposidic acid is an iridoid glucoside, used to treat inflammation, jaundice and hepatic disorders. When given in doses of 500 mg/kg either alone or in combination with radiation, geniposidic acid exhibits a more notable inhibitory activity factor against implanted tumor growth. In rabbits, geniposidic acid increases the number of intimal foam cells, the intima/media thickness ratio, and plaque area. In rabbits, geniposidic acid (100 μg/mL) alleviates EC shedding and corrects abnormalities in aortic morphology. Rabbits' smooth muscle cell proliferation is significantly slowed down by geniposidic acid (100 μg/mL). The migration of SMCs from the upper chamber is obviously inhibited by geniposidic acid.

Physicochemical Properties

Molecular Formula	C16H22O10
Molecular Weight	374.34
Exact Mass	374.121
Elemental Analysis	C, 51.34; H, 5.92; O, 42.74
CAS #	27741-01-1
Related CAS #	27741-01-1
PubChem CID	443354
Appearance	White to off-white solid powder
Density	1.6±0.1 g/cm3
Boiling Point	684.1±55.0 °C at 760 mmHg
Flash Point	250.9±25.0 °C
Vapour Pressure	0.0±4.8 mmHg at 25°C
Index of Refraction	1.660
LogP	-1.68
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	5
Heavy Atom Count	26
Complexity	602
Defined Atom Stereocenter Count	8
SMILES	O([C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])[C@@]1([H])[C@]2([H])C(C([H])([H])O[H])=C([H])C([H])([H])[C@]2([H])C(C(=O)O[H])=C([H])O1
InChi Key	ZJDOESGVOWAULF-OGJQONSISA-N
InChi Code	InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9-,10-,11-,12+,13-,15+,16+/m1/s1
Chemical Name	(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
Synonyms	Geniposidic acid
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	Human Endogenous Metabolite
ln Vitro	Geniposidic acid increases survival rate of rats with fulminant hepatic failure. Geniposidic acid attenuates the following effects: GalN/LPS increases serum aminotransferase activity, serum tumor necrosis factor-α level and hepatic lipid peroxidation and decreases hepatic glutathione content. Geniposidic acid augmentes increases in serum interleukin-6 level, heme oxygenase-1 and NF-E2-related factor 2 protein expression in rats with fulminant hepatic failure. Geniposidic acid decreases cleaved caspase-8 and caspase-3 protein expression and shows significantly fewer apoptotic cells in rats with fulminant hepatic failure. Geniposidic acid increases Bcl-xL protein expression and decreased Bax protein expression in rats with fulminant hepatic failure. Geniposidic acid treatment enhances phosphorylation of signal transducer and activator of transcription 3 in rats with fulminant hepatic failure.[3]
ln Vivo	Geniposidic acid shows a more remarkable inhibitory activity factor against implanted tumor growth when the doses of 500 mg/kg are given alone or combined with irradiation. [1] In rabbits, geniposidic acid increases the number of intimal foam cells, intima/media thickness ratio, and plaque area. In rabbits, geniposidic acid (100 g/mL) improves aortic morphology disorders and reduces ECs shedding. Rabbits' smooth muscle cell proliferation is significantly inhibited by geniposidic acid (100 g/mL). A clear inhibition of SMC migration from the upper chamber is produced by geniposidic acid.[2] The following effects of geniposidic acid are lessened: GalN/LPS raises serum tumor necrosis factor-α levels, hepatic lipid peroxidation, and serum aminotransferase activity while lowering glutathione levels in the liver. In rats with fulminant hepatic failure, geniposidic acid enhances increases in serum interleukin-6 level, heme oxygenase-1, and NF-E2-related factor 2 protein expression. In rats with fulminant hepatic failure, geniposidic acid significantly reduces cleaved caspase-8 and caspase-3 protein expression and the number of apoptotic cells. In rats with fulminant hepatic failure, geniposidic acid increases Bcl-xL protein expression and decreases Bax protein expression. In rats with fulminant hepatic failure, geniposidic acid treatment increases the phosphorylation of signal transducer and activator of transcription 3.
References	[1]. Cancer Lett . 1997 Feb 26;113(1-2):31-7. [2]. Pharm Biol . 2015 Feb;53(2):280-5. [3]. Cancer Lett . 1997 Feb 26;113(1-2):31-7.
Additional Infomation	Geniposidic acid is a terpene glycoside. Geniposidic acid has been reported in Scyphiphora hydrophyllacea, Veronica kellereri, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO: ~16 mg/mL (~42.7 mM) Water: <1 mg/mL Ethanol: ~2 mg/mL (~5.3 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 3 mg/mL (8.01 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 30.0 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: ≥ 3 mg/mL (8.01 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 30.0 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: ≥ 3 mg/mL (8.01 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 30.0 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	2.6714 mL	13.3568 mL	26.7137 mL
	5 mM	0.5343 mL	2.6714 mL	5.3427 mL
	10 mM	0.2671 mL	1.3357 mL	2.6714 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.