Alphitolic acid

Base Information

• Chemical Name: Alphitolic acid
• CAS No.: 19533-92-7
• Molecular Formula: C30H46O4
• Molecular Weight: 470.68
• ChEMBL ID: CHEMBL511805
• Metabolomics Workbench ID: 141035
• Nikkaji Number: J16.653G
• Wikidata: Q27136070
• Mol file: 19533-92-7.mol

Synonyms:alphitolic acid

Chemical Property of Alphitolic acid

Chemical Property:

• Boiling Point: 578.6 °C at 760 mmHg
• Flash Point: 317.8 °C
• PSA: 77.76000
• Density: 1.15 g/cm³
• LogP: 6.06030
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 472.35526001
• Heavy Atom Count: 34
• Complexity: 894

Purity/Quality:

99%, ^*data from raw suppliers

Alphitolicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C(C3(CC2)C)(CCC5C4(CC(C(C5(C)C)O)O)C)C)C(=O)O
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@H]4[C@]([C@@]3(CC2)C)(CC[C@@H]5[C@@]4(C[C@H]([C@@H](C5(C)C)O)O)C)C)C(=O)O

Technology Process of Alphitolic acid

There total 11 articles about Alphitolic 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: 97.0%

2α,3β-diacetoxylup-20(29)-en-28-oic acid (67911-65-3) → alphitolic acid (19533-92-7,97762-86-2)

Guidance literature:

2α,3β-diacetoxylup-20(29)-en-28-oic acid; With water; sodium hydroxide; In methanol; at 20 ℃; for 2h;

With hydrogenchloride; In water; at 0 ℃; pH=3;

DOI:10.1016/j.tet.2009.07.047

Reference yield: 83.0%

2-O-tert-butyldimethylsilylalphitolic acid → alphitolic acid (19533-92-7,97762-86-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Reflux;

DOI:10.1021/acs.jnatprod.8b00986

Reference yield:

2α-hydroxy-3β-[(O-β-D-xylopyranosyl-(1->2)-β-D-glucopyranosyl)oxy]lup-20(29)-en-28-oic acid α-L-rhamnopyranosyl ester (1379682-87-7) → alphitolic acid (19533-92-7,97762-86-2)

Guidance literature:

With hydrogenchloride; water; In 1,4-dioxane; at 95 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.phytol.2011.04.010

upstream raw materials:

2α,3β-diacetoxylup-20(29)-en-28-oic acid

2α-hydroxy-3β-[(O-β-D-xylopyranosyl-(1->2)-β-D-glucopyranosyl)oxy]lup-20(29)-en-28-oic acid α-L-rhamnopyranosyl ester

3β-[(O-α-L-arabinopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->2)-β-D-glucopyranosyl)oxy]-2α-hydroxylup-20(29)-en-28-oic acid α-L-rhamnopyranosyl ester

3β-[(O-α-L-arabinopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->4)]-β-D-glucopyranosyl)oxy]-2α-hydroxylup-20(29)-en-28-oic acid α-L-rhamnopyranosyl ester

Refernces

• 1、 Yokosuka, Akihito,Kawakami, Sachiko,Haraguchi, Mitsue,Mimaki, Yoshihiro. "Seven new triterpene glycosides from the pericarps of Stryphnodendron fissuratum". experimental part. p. 259 - 266. Retrieved 2012/05/04.