3-O-Dodecylcarbomethylascorbic acid

Base Information

• Chemical Name: 3-O-Dodecylcarbomethylascorbic acid
• CAS No.: 133794-57-7
• Molecular Formula: C₂₀H₃₄O₇
• Molecular Weight: 386.486
• DSSTox Substance ID: DTXSID8020547
• Nikkaji Number: J420.356I
• Wikidata: Q63088201
• Mol file: 133794-57-7.mol

Synonyms:3-O-Dodecylcarbomethylascorbic acid;133794-57-7;3-O-Dodecylcarbomethyl-L-ascorbic acid;CCRIS 7480;(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-3-(2-oxotetradecoxy)-2H-furan-5-one;3-O-DODECYLCARBOMETHYLASCORBICACID;(5R)-5-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-4-[(2-oxododecyl)oxy]furan-2(5H)-one;SCHEMBL9193740;DTXSID8020547;3-O-(2-Oxotetradecyl)-L-ascorbic acid;LS-185106;Q63088201

Chemical Property of 3-O-Dodecylcarbomethylascorbic acid

Chemical Property:

• Vapor Pressure: 2.72E-18mmHg at 25°C
• Boiling Point: 625.9°Cat760mmHg
• Flash Point: 215.4°C
• PSA: 113.29000
• Density: 1.16g/cm³
• LogP: 2.93130
• XLogP3: 4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 16
• Exact Mass: 386.23045342
• Heavy Atom Count: 27
• Complexity: 487

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCC(=O)COC1=C(C(=O)OC1C(CO)O)O
• Isomeric SMILES: CCCCCCCCCCCCC(=O)COC1=C(C(=O)O[C@@H]1[C@H](CO)O)O

Technology Process of 3-O-Dodecylcarbomethylascorbic acid

There total 6 articles about 3-O-Dodecylcarbomethylascorbic 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: 83.0%

(R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-4-(2-oxo-tetradecyloxy)-5H-furan-2-one (133794-51-1) → (R)-5-((R)-1,2-Dihydroxy-ethyl)-3-hydroxy-4-(2-oxo-tetradecyloxy)-5H-furan-2-one (133794-57-7)

Guidance literature:

With hydrogenchloride; In methanol; at 50 ℃; for 2h;

DOI:10.1021/jm00111a034

Reference yield:

5,6-O-isopropylidene-D-isoascorbic acid (50271-42-6) → (R)-5-((R)-1,2-Dihydroxy-ethyl)-3-hydroxy-4-(2-oxo-tetradecyloxy)-5H-furan-2-one (133794-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / NaHCO₃ / dimethylsulfoxide / 50 °C

2: 83 percent / 2 M HCl / methanol / 2 h / 50 °C

With hydrogenchloride; sodium hydrogencarbonate; In methanol; dimethyl sulfoxide;

DOI:10.1021/jm00111a034

Reference yield:

1-tetradecene (1120-36-1) → (R)-5-((R)-1,2-Dihydroxy-ethyl)-3-hydroxy-4-(2-oxo-tetradecyloxy)-5H-furan-2-one (133794-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1: AcOH, aq. NaBrO₂ / dioxane / 12 h / Ambient temperature

2: 33 percent / NaHCO₃ / dimethylsulfoxide / 50 °C

3: 83 percent / 2 M HCl / methanol / 2 h / 50 °C

With hydrogenchloride; sodium bromite; sodium hydrogencarbonate; acetic acid; In 1,4-dioxane; methanol; dimethyl sulfoxide;

DOI:10.1021/jm00111a034

upstream raw materials:

(R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-4-(2-oxo-tetradecyloxy)-5H-furan-2-one

5,6-O-isopropylidene-D-isoascorbic acid

1-tetradecene

1-bromotetradecan-2-one

Refernces

• 1、 Nihro, Yasunori,Miyataka, Hideki,Sudo, Tadamitsu,Matsumoto, Hitoshi,Satoh, Toshio. "3-O-Alkylascorbic Acids as Free-Radical Quenchers: Synthesis and Inhibitory Effect on Lipid Peroxidation". . p. 2152 - 2157. Retrieved 2007/10/02.