Cassiaside C

Base Information

• Chemical Name: Cassiaside C
• CAS No.: 119170-52-4
• Molecular Formula: C₂₇H₃₂O₁₅
• Molecular Weight: 596.542
• DSSTox Substance ID: DTXSID201317838
• Nikkaji Number: J2.402.988C
• Wikidata: Q105005848
• Metabolomics Workbench ID: 132981
• ChEMBL ID: CHEMBL3634701
• Mol file: 119170-52-4.mol

Synonyms:cassiaside C

Chemical Property of Cassiaside C

Chemical Property:

• Melting Point: 235-237 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Boiling Point: 932.2±65.0 °C(Predicted)
• PKA: 6.88±0.20(Predicted)
• PSA: 238.20000
• Density: 1.69±0.1 g/cm3(Predicted)
• LogP: -2.02830
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 7
• Exact Mass: 596.17412031
• Heavy Atom Count: 42
• Complexity: 979

Purity/Quality:

≥98% ^*data from raw suppliers

CassiasideC(NewProduct) 98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=CC3=CC(=CC(=C3C(=C2C(=O)O1)O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)OC
• Isomeric SMILES: CC1=CC2=CC3=CC(=CC(=C3C(=C2C(=O)O1)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)OC
• Description: Cassiaside C belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. Cassiaside C has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make cassiaside C a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cassiaside C.

Technology Process of Cassiaside C

There total 6 articles about Cassiaside C 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: 97.0%

toralactone 9-O-yl 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranoside (590368-09-5) → cassiaside C (119170-52-4)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at 20 ℃; for 20h;

DOI:10.1021/jo034223u

Reference yield:

10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-on-9-O-methyllactone (71602-63-6) → cassiaside C (119170-52-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / BBr₃ / CH₂Cl₂ / 7 h / 20 °C

2: tetrabutylammonium bromide; borate buffer / CHCl₃ / 12 h / 52 °C / pH 10.8

3: 85 percent / aq. HCl / methanol; CH₂Cl₂ / 18 h / 20 °C

4: 92 percent / TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 0 - 20 °C

5: 97 percent / K₂CO₃ / tetrahydrofuran; methanol / 20 h / 20 °C

With hydrogenchloride; borate buffer; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; boron tribromide; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1021/jo034223u

Reference yield:

2,4-dimethoxy-6-methylbenzoic acid (3686-57-5) → cassiaside C (119170-52-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran; cyclohexane / 0.33 h / -78 °C

1.2: 32 percent / tetrahydrofuran; cyclohexane / -78 - 20 °C

2.1: 85 percent / BBr₃ / CH₂Cl₂ / 7 h / 20 °C

3.1: tetrabutylammonium bromide; borate buffer / CHCl₃ / 12 h / 52 °C / pH 10.8

4.1: 85 percent / aq. HCl / methanol; CH₂Cl₂ / 18 h / 20 °C

5.1: 92 percent / TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 0 - 20 °C

6.1: 97 percent / K₂CO₃ / tetrahydrofuran; methanol / 20 h / 20 °C

With hydrogenchloride; borate buffer; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; boron tribromide; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; chloroform; cyclohexane;

DOI:10.1021/jo034223u

upstream raw materials:

toralactone 9-O-yl 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranoside

10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-on-9-O-methyllactone

2,4-dimethoxy-6-methylbenzoic acid

Toralactone

Downstream raw materials:

Toralactone

Refernces