Picroside II CAS 39012-20-9

Introduction:Basic information about Picroside II CAS 39012-20-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Picroside II Basic information

Product Name:Picroside II
Synonyms:6'-VANILLOYL CATALPOL;AMPHICOSIDE;PICROSIDE II;PICROSID II;beta-d-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl, [1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha)]-;AMPHICOSIDE II;PICROSIDE ò;(1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-1a,1b,2,5a,6,6a-Hexahydro-6-((4-hydroxy-3-methoxybenzoyl)oxy)-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl-beta-D-glucopyranoside
CAS:39012-20-9
MF:C23H28O13
MW:512.46
EINECS:254-247-6
Product Categories:Inhibitors;Miscellaneous Natural Products;Iridoids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File:39012-20-9.mol

Picroside II Chemical Properties

Melting point 145 - 155oC
Boiling point 780.8±60.0 °C(Predicted)
density 1.66±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,2-8°C
solubility ethanol: soluble1mg/mL, clear, colorless
pka8.07±0.20(Predicted)
form Solid
color Pale Yellow
InChIKeyAKNILCMFRRDTEY-MRFBWRKESA-N
SMILESC12(CO)OC1C(C1C=COC(O[C@H]3[C@H](O)[C@H]([C@H](O)[C@@H](CO)O3)O)C21)OC(=O)C1=CC=C(O)C(OC)=C1 |&1:12,13,15,16,18,r|

Safety Information

Safety Statements 24/25
WGK Germany 3
HS Code 29389090
Storage Class13 - Non Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral

Picroside II Usage And Synthesis

UsesPicroside II similar to Picroside I (P437635), acts as an oxygen free radical scavenger and thus promotes anti-inflammatory activity and may be used in the treatment of arthritis or ischemic injury.
Chemical PropertiesYellow needle-shaped crystals, soluble in methanol, derived from Picrorhizoma Coptidis.
UsesPicroside II similar to Picroside I (P437635), acts as an oxygen free radical scavenger and thus promotes anti-inflammatory activity and may be used in the treatment of arthritis or ischemic injury.
DefinitionChEBI: Picroside ii is a tannin.
Biological ActivityPicroside II displaysmany anti-cancer properties such as anti-metastatic, anti-angiogenic, and anti-apoptotic activities in both in vitro and in vivo studies.It also exerts antioxidant, anti-inflammatory, and antidiarrheal effectsagainst acute oxidative injuries such as severe acute pancreatitis-inducedintestinal barrier injury. PII has protective effects onischemia/reperfusion (I/R)-induced injury by interacting with differentmechanisms in various in vitro and in vivo models.', 'Phytochemical found in Traditional Chinese Medicine herbal preparations. Picroside II, a glucoside, is reported to have hepatoprotective, cardioprotective, and neuroprotective properties.
in vivo

Picroside II (0-20 mg/kg, i.g., given in two doses) protects liver cells from damage and prevents apoptosis[1].
Picroside II (20 mg/kg, intravenous injection, given in four doses) inhibits the activation of NLRP3 inflammasome and NF-κB pathway in mice, reducing the inflammatory response in sepsis and enhancing immune function[3].
Picroside II (20 mg/kg, intraperitoneal injection, a single dose) protects the blood-brain barrier by inhibiting oxidative signaling pathways in a rat model of ischemia-reperfusion injury[4].
Picroside II (5-20 mg/kg, i.g., once a day for seven days) has anti-lipid peroxidation effects and protects against mitochondrial damage in mice with liver injury[5].

Animal Model:DGalN and LPS(HY-D1056)-induced acute liver injury in mice[1]
Dosage:0, 5, 10, 20 mg/kg; administered 10 min before and 4 h after D-GalN and LPS administration
Administration:i.g.
Result:Reduced the levels of alanine aminotransferase and aspartate aminotransferase in the serum, decreased MDA content, had a dose-dependent effect on hepatocyte apoptosis, and upregulated the expression of the bcl-2 gene.
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Animal Model:Sepsis mouse model[3]
Dosage:20 mg/kg; four times injected (2 h, 14 h, 26 h and 38 h after CLP)
Administration:Intravenous injection (i.v.)
Result:Improved survival, reduced sepsis-related infiltration and attenuated lung injury, enhanced bacterial clearance, reduced IL-6, IL-1β, and TNF-α levels, inhibited splenic lymphocyte apoptosis, reduced p-NF-κB (p65) expression, and reduced IL-1β and caspase-1 levels.
Animal Model:Rats with cerebral ischemia-reperfusion injury[4]
Dosage:20 mg/kg; single dose
Administration:Intraperitoneal injection (i.p.)
Result:Reduced the nervous system score, neuronal injury, BBB damage, ROS content and NADPH oxidase activity, down-regulated the protein levels of Rac-1, Nox2, ROCK, MLCK and MMP-2, and up-regulated the expression of claudin-5.
Animal Model:Mouse model of liver injury induced by CCl4, D-GalN and AP[5]
Dosage:5, 10, 20mg/kg; daily; 7 days
Administration:i.g.
Result:Reduced the high levels of ALT and AST in serum caused by CCl4, D-GalN and AP, significantly alleviated liver cell damage, reduced MDA, and increased SOD and GSH-Px content in a dose-dependent manner, inhibited AP-induced liver toxicity in mice, enhanced ATPase activity, and improved mitochondrial swelling.

Picroside II Preparation Products And Raw materials