Quillaic acid

Base Information

• Chemical Name: Quillaic acid
• CAS No.: 631-01-6
• Molecular Formula: C30H46O5
• Molecular Weight: 486.692
• European Community (EC) Number: 211-149-8
• UNII: 69O8E4G02B
• DSSTox Substance ID: DTXSID001026576
• Nikkaji Number: J15.488A
• Wikidata: Q27108137
• Metabolomics Workbench ID: 72222
• ChEMBL ID: CHEMBL260060
• Mol file: 631-01-6.mol

Synonyms:(+)-quillaic acid;3 beta,16 alpha-dihydroxy-23-oxoolean-12-en-28-oic acid;quillaic acid;quillaja sapogenin

Chemical Property of Quillaic acid

Chemical Property:

• Vapor Pressure: 1.33E-17mmHg at 25°C
• Melting Point: 294℃
• Refractive Index: 1.575
• Boiling Point: 613.275 °C at 760 mmHg
• PKA: 4.41±0.70(Predicted)
• Flash Point: 338.716 °C
• PSA: 94.83000
• Density: 1.188 g/cm³
• LogP: 5.38340
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 486.33452456
• Heavy Atom Count: 35
• Complexity: 970

Purity/Quality:

98% ^*data from raw suppliers

Quillaic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C=O)O)C)C(=O)O)C
• Isomeric SMILES: C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)O)C)C)(C)C=O)O
• Uses: Quillaic Acid an unglycosylated saponin from the Quillaja saponaria bark is used as a topical antiinflammatory.

Technology Process of Quillaic acid

There total 18 articles about Quillaic acid 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:

3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl quilliac acid 28-O-(6-O-acetyl)-β-D-glucopyranosyl-(1->3)-[β-D-xylopyranosyl-(1->4)]-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside (1248822-17-4) → D-xylose (58-86-6) + D-Fucose (3615-37-0,478518-52-4) + L-Rhamnose (3615-41-6,478518-52-4) + D-Galactose (59-23-4) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4) + D-glucose + quillaic acid triterpene (631-01-6)

Guidance literature:

With hydrogenchloride; water; at 90 ℃; for 4h;

DOI:10.1248/cpb.58.412

Reference yield:

3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosylquillaic acid → D-glucose (50-99-7) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4) + quillaic acid triterpene (631-01-6)

Guidance literature:

With trifluoroacetic acid; In water; for 1h; Reflux;

DOI:10.1016/j.phytochem.2016.07.011

Reference yield:

(S)-1-phenyl-ethylamine (2627-86-3) + acetic anhydride (108-24-7) + 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosylquillaic acid → C24H31NO11 + quillaic acid triterpene (631-01-6) + Acetic acid (1R,2R,3R)-2,3,4-triacetoxy-1-{(S)-1-acetoxy-2-[acetyl-((S)-1-phenyl-ethyl)-amino]-ethyl}-butyl ester (79526-50-4,79549-65-8,79549-66-9,79549-67-0,79549-68-1,79617-01-9,83680-90-4,83680-91-5)

Guidance literature:

3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosylquillaic acid; With trifluoroacetic acid; In water; for 1h; Reflux;

(S)-1-phenyl-ethylamine; With sodium cyanoborohydride; In ethanol; water; at 40 ℃; for 4h;

acetic anhydride; With pyridine; at 20 ℃; for 24h;

DOI:10.1016/j.phytochem.2016.07.011

upstream raw materials:

3-O-β-D-galactopyranosyl-(1->2)-<β-D-xylopyranosyl-(1->3)>-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-<β-D-glucopyranosyl-(1->3)>-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside.

<16,28-dihydroxy-23,28-dioxoolean-12-en-3β-yl O-β-D-galactopyranosyl-(1->2)-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranosid>uronic

quillaic acid 3-O-β-D-galactopyranosyl-(1->2)-[β-D-galactopyranosyl-(1->3)]-β-D-glucuronopyranoside

quillaic acid 3-O-β-D-xylopyranosyl-(1->3)-β-D-glucuronopyranoside

Downstream raw materials:

1,2,7-trimethylnaphthalene

3β,16α,23-trihydroxyolean-12-en-28-oic acid

Refernces

• 1、 Chen, Qing,Luo, Jian-Guang,Kong, Ling-Yi. "New triterpenoid saponins from the roots of Gypsophila perfoliata Linn.". . p. 2206 - 2212. Retrieved 2011.
• 2、 Takahashi, Nobuyuki,Li, Wei,Koike, Kazuo. "Oleanane-type triterpenoid saponins from Silene armeria". . p. 77 - 85. Retrieved 2016/08/05.