Picroside II - analytical standard, ≥98%(HPLC) , CAS No.39012-20-9

CAS: 39012-20-9 Cat. No.: P117966 Molecular Weight: 512.46 EC Number: 254-247-6

GRADE & PURITY Analytical standard, ≥98%(HPLC)

Synonyms

AMPHICOSIDE II | Picrosid II, HPLC Grade | [2-(Hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxy-3-methoxybenzoate | BCP29556 | Amphicoside | AS-56421 | Picroside II | PicrosideII | Pi

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Phytochemical found in Traditional Chinese Medicine herbal preparations. Picroside II, a glucoside, is reported to have hepatoprotective, cardioprotective, and neuroprotective properties.

Specifications

Synonyms

AMPHICOSIDE II | Picrosid II, HPLC Grade | [2-(Hydroxymethyl)-10-[3, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3, 9-dioxatricyclo[4.4.0.02, 4]dec-7-en-5-yl] 4-hydroxy-3-methoxybenzoate | BCP29556 | Amphicoside | AS-56421 | Picroside II | PicrosideII | Pi

Specifications & Purity

analytical standard, ≥98%(HPLC)

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Purity

≥98%(HPLC)

Names and Identifiers

• Canonical Smiles: COC1=C(C=CC(=C1)C(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O
• IUPAC Name: [2-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxy-3-methoxybenzoate
• InChIKey: AKNILCMFRRDTEY-UHFFFAOYSA-N
• INCHI: 1S/C23H28O13/c1-31-12-6-9(2-3-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3
• Isomeric SMILES: COC1=C(C=CC(=C1)C(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O
• Molecular Weight: 512.46
• Reaxy-Rn: 27516222
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27516222&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Tannins
      • Subclass Hydrolyzable tannins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Tannins
• Subclass: Hydrolyzable tannins
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydrolyzable tannins
• Alternative Parents: Hexoses p-Hydroxybenzoic acid alkyl esters O-glycosyl compounds M-methoxybenzoic acids and derivatives Methoxyphenols Anisoles Phenoxy compounds Benzoyl derivatives Methoxybenzenes 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Oxanes Secondary alcohols Carboxylic acid esters Epoxides Dialkyl ethers Acetals Oxacyclic compounds Polyols Monocarboxylic acids and derivatives Organic oxides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hydrolyzable tannin - Hexose monosaccharide - P-hydroxybenzoic acid alkyl ester - P-hydroxybenzoic acid ester - O-glycosyl compound - Glycosyl compound - M-methoxybenzoic acid or derivatives - Methoxyphenol - Benzoate ester - Benzoic acid or derivatives - Phenoxy compound - Phenol ether - Anisole - Methoxybenzene - Benzoyl - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Alkyl aryl ether - Oxane - Monosaccharide - Benzenoid - Monocyclic benzene moiety - Secondary alcohol - Carboxylic acid ester - Polyol - Ether - Oxirane - Dialkyl ether - Carboxylic acid derivative - Acetal - Organoheterocyclic compound - Oxacycle - Monocarboxylic acid or derivatives - Primary alcohol - Alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 512.500 g/mol
• XLogP3: -1.400
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 8
• Exact Mass: 512.153 Da
• Monoisotopic Mass: 512.153 Da
• Topological Polar Surface Area: 197.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 839.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 11
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xuehua Piao, Xiaodan Sui, Baohai Liu, Tingfang Cui, Zinan Qi.  (2021)  Picroside II Improves Severe Acute Pancreatitis-Induced Hepatocellular Injury in Rats by Affecting JAK2/STAT3 Phosphorylation Signaling.  Biomed Research International,      [PMID:34368363] [10.1155/2021/9945149]

2. Wenjing Wang, Lu Wang, Lina Zou, Gaiping Li, Baoxian Ye.  (2015)  A novel voltammetric sensor based on poly(l-Citrulline)/SWCNTs composite film modified electrode for sensitive determination of picroside II.  TALANTA,      [PMID:26838418] [10.1016/j.talanta.2015.12.055]