Calceolarioside A

Base Information

• Chemical Name: Calceolarioside A
• CAS No.: 84744-28-5
• Molecular Formula: C23H26 O11
• Molecular Weight: 478.453
• ChEMBL ID: CHEMBL481635
• DSSTox Substance ID: DTXSID001316527
• Metabolomics Workbench ID: 138114
• Nikkaji Number: J410.465J
• Wikidata: Q104253151
• Mol file: 84744-28-5.mol

Synonyms:calceolarioside;calceolarioside A

Chemical Property of Calceolarioside A

Chemical Property:

• Vapor Pressure: 6.18E-26mmHg at 25°C
• Boiling Point: 784.7°C at 760 mmHg
• PKA: 9.31±0.10(Predicted)
• Flash Point: 269.8°C
• PSA: 186.37000
• Density: 1.58g/cm³
• LogP: 0.13230
• Storage Temp.: ?20°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 478.14751164
• Heavy Atom Count: 34
• Complexity: 673

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

Calceolarioside A ≥95% (LC/MS-ELSD) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CCOC2C(C(C(C(O2)CO)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O)O)O

Technology Process of Calceolarioside A

There total 21 articles about Calceolarioside A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 4-Ο-(E)-3,4-bis(tert-butyldimethylsilyloxy)caffeoyl-β-D-glucopyranoside → calceolarioside A (84744-28-5)

Guidance literature:

With pyridine; triethylamine tris(hydrogen fluoride); triethylamine; at 20 ℃; for 3h;

DOI:10.1055/s-0036-1591753

Reference yield: 35.0%

3,4-bis(allyloxy)phenylethyl 4-O-((trans)-3,4-bis(allyloxy)cinnamoyl)-6-O-alloc-β-D-glucopyranoside → calceolarioside A (84744-28-5)

Guidance literature:

With palladium 10% on activated carbon; In methanol; water; Inert atmosphere; Reflux;

DOI:10.1016/j.ejmech.2015.03.038

Reference yield:

Lavandulifolioside (131903-54-3) → Acteoside (61276-17-3,97747-56-3,138604-99-6,145306-71-4) + calceolarioside A (84744-28-5)

Guidance literature:

With hydrogenchloride; at 70 ℃; for 2h; Yield given. Yields of byproduct given;

DOI:10.1016/0031-9422(91)85288-B

upstream raw materials:

Acteoside

Lavandulifolioside

3,4-dihydroxy-β-phenethyl-O-β-D-glucopyranosyl-(1->3)-O-α-rhamnopyranosyl-(1->6)-4-caffeoyl-β-D-glucopyranoside

p-tolyl 3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-thio-β-D-glucopyranoside

Refernces

• 1、 Liu, Ying-Guo,Li, Xiaxi,Xiong, De-Cai,Yu, Binhan,Pu, Xiaoping,Ye, Xin-Shan. "Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents". . p. 313 - 323. Retrieved 2015/03/31.
• 2、 Mulani, Shaheen K.,Guh, Jih-Hwa,Mong, Kwok-Kong Tony. "A general synthetic strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides". . p. 2926 - 2937. Retrieved 2014/05/06.