3-O-Ethyl-L-ascorbic acid

Base Information

• Chemical Name: 3-O-Ethyl-L-ascorbic acid
• CAS No.: 86404-04-8
• Molecular Formula: C8H12O6
• Molecular Weight: 204.18
• Hs Code.: 2932209090
• European Community (EC) Number: 617-849-3
• UNII: 6MW60CB71P
• DSSTox Substance ID: DTXSID8020595
• Nikkaji Number: J486.253H
• Wikidata: Q27265176
• RXCUI: 1373720
• Mol file: 86404-04-8.mol

Synonyms:3-O-ETHYL ASCORBIC ACID;3-O-ethyl-L-ascorbic acid;3-O-ethylascorbic acid;vitamin C ethyl

Chemical Property of 3-O-Ethyl-L-ascorbic acid

Chemical Property:

• Vapor Pressure: 1.84E-14mmHg at 25°C
• Melting Point: 112.0 to 116.0 °C
• Refractive Index: 1.555
• Boiling Point: 551.5 °C at 760 mmHg
• PKA: 8.89±0.40(Predicted)
• Flash Point: 228.5 °C
• PSA: 96.22000
• Density: 1.46 g/cm³
• LogP: -0.92890
• Storage Temp.: 0-10°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 204.06338810
• Heavy Atom Count: 14
• Complexity: 259

Purity/Quality:

98% ^*data from raw suppliers

3-O-Ethyl-L-ascorbic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C(=O)OC1C(CO)O)O
• Isomeric SMILES: CCOC1=C(C(=O)O[C@@H]1[C@H](CO)O)O
• Description: 3-O-Ethyl ascorbic acid ether, also called VC ethyl ether, is an ascorbic acid derivative. Ascorbic acid is a naturally occurring antioxidant and free radical scavenger, a reducing agent in the conversion process of biological enzymes, and has a preventive effect on some chronic diseases (cancer, diabetes and allergic skin diseases). From the molecular structure of ascorbic acid, it can be seen that compared to the 2-position enol hydroxyl group, the 3-position enol hydroxyl group has higher activity on electrophiles, and it is the product of 3-O-alkylation during O-alkylation modification. Mainly. 3-O-Ethyl ascorbate ether is a product of ascorbic acid-3-O-ethylation. It has a simple molecular structure and is easily absorbed by the skin. After entering the dermis through the stratum corneum of the skin, it is easily decomposed by the biological enzymes in the human body. The effect of ascorbic acid effectively solves the fat solubility problem of ascorbic acid, and is widely used in cosmetics as a whitening agent and antioxidant.
• Uses: Vitamin C ethyl ether (VC ethyl ether) is a lipophilic and hydrophilic amphoteric vitamin C derivative. It not only retains the redox effect of vitamin C but is also very stable. It is a non-discoloring vitamin C derivative. It is a lipophilic and lookchem amphoteric substance, which not only makes it extremely convenient to use in the formula, but also makes it easy to penetrate the stratum corneum into the dermis. After entering the skin, it is easily decomposed by biological enzymes to play the role of vitamin C, thereby Improve its bioavailability. 3-O-Ethyl-L-ascorbic Acid could be a useful stabilizing agent for a para-hydroxyacetophenone solution. 3-O-Ethyl-L-ascorbic Acid could be a useful stabilizing agent for a para-?hydroxyacetophenone solution.

Technology Process of 3-O-Ethyl-L-ascorbic acid

There total 10 articles about 3-O-Ethyl-L-ascorbic 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: 98.0%

(R)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-ethoxy-3-hydroxyfuran-2(5H)-one (86404-03-7) → 3‐O‐ethyl‐L‐ascorbic acid (86404-04-8)

Guidance literature:

With hydrogenchloride; In methanol; at 60 ℃; for 3h;

DOI:10.1021/jm00087a017

Reference yield: 76.0%

ethanol (64-17-5) + ascorbic acid (50-81-7,98966-42-8) → 3‐O‐ethyl‐L‐ascorbic acid (86404-04-8)

Guidance literature:

ascorbic acid; With tetrabutylammomium bromide; tin(IV) chloride; In ethyl acetate; at 40 ℃;

ethanol; With triethylamine; Diethyl carbonate; at 45 ℃; for 5h;

With hydrogenchloride; In water; at 55 ℃; pH=2; Temperature; pH-value;

Reference yield: 69.0%

ethyl bromide (74-96-4) + ascorbic acid (50-81-7,98966-42-8) → 3‐O‐ethyl‐L‐ascorbic acid (86404-04-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Product distribution / selectivity;

upstream raw materials:

(R)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-ethoxy-3-hydroxyfuran-2(5H)-one

diethyl sulfate

ascorbic acid

Ethyl methanesulfonate

Refernces

• 1、 -. "a method for manufacturing 3-O-alkyl-ascorbic acid". Paragraph 0130; 0140-0144; 0157-0160. . Retrieved 2021/12/03.
• 2、 -. "Method for synthesizing 3-O-alkyl-5,6-O-isopropylidene ascorbic acid by using circulation method". Paragraph 0043; 0044. . Retrieved 2019/10/29.