Perilloside A

Base Information

• Chemical Name: Perilloside A
• CAS No.: 141206-20-4
• Molecular Formula: C16H26 O6
• Molecular Weight: 314.37404
• DSSTox Substance ID: DTXSID00931027
• Nikkaji Number: J923.987A
• Wikidata: Q82906534
• Mol file: 141206-20-4.mol

Synonyms:perilloside A

Chemical Property of Perilloside A

Chemical Property:

• Vapor Pressure: 7.28E-12mmHg at 25°C
• Boiling Point: 494.8°Cat760mmHg
• Flash Point: 253°C
• PSA: 99.38000
• Density: 1.26g/cm³
• LogP: 0.10550
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 314.17293854
• Heavy Atom Count: 22
• Complexity: 421

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC(=CC1)COC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: CC(=C)[C@H]1CCC(=CC1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of Perilloside A

There total 8 articles about Perilloside 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: 95.0%

2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-5-hydroxy-6-((S)-4-isopropenyl-cyclohex-1-enylmethoxy)-tetrahydro-pyran-4-yl ester (200501-84-4) → (S)-(-)-perillyl β-D-glucopyranoside (141206-20-4)

Guidance literature:

With Amberlite IRA₄₀₀ (OH^-); In methanol; for 16h; Heating;

DOI:10.1016/S0040-4039(97)10315-X

Reference yield: 20.7%

D-glucose (50-99-7) + (-)-perillyl alcohol (536-59-4,18457-55-1) → (S)-(-)-perillyl β-D-glucopyranoside (141206-20-4)

Guidance literature:

With whole-cell of E_. coli BL₂₁ culture; at 25 ℃; for 72h; pH=7.0; aq. buffer; Enzymatic reaction;

DOI:10.1002/chem.200800548

Reference yield:

3,4,6-tri-O-pivaloyl-D-glucal (149198-97-0,104445-19-4) → (S)-(-)-perillyl β-D-glucopyranoside (141206-20-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / 2,2-dimethyldioxirane / acetone

2: 68 percent / SiO₂, molecular sieves 3 Angstroem / benzene / 24 h / Ambient temperature

3: 95 percent / Amberlite IRA₄₀₀ (OH^-) / methanol / 16 h / Heating

With 2,2-dimethyldioxirane; 3 A molecular sieve; Amberlite IRA₄₀₀ (OH^-); silica gel; In methanol; acetone; benzene;

DOI:10.1016/S0040-4039(97)10315-X

upstream raw materials:

(-)-perillyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-5-hydroxy-6-((S)-4-isopropenyl-cyclohex-1-enylmethoxy)-tetrahydro-pyran-4-yl ester

3,4,6-tri-O-pivaloyl-D-glucal

(1S,3R,4R,5S,6R)-3-((pivaloyloxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane-4,5-diyl bis(2,2-dimethylpropanoate)

Refernces

• 1、 Matsushita, Yoh-Ichi,Sugamoto, Kazuhiro,Kita, Yoshio,Matsui, Takanao. "Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-D-glucopyranose". . p. 8709 - 8712. Retrieved 2007/10/03.