(+)-5,6-O-Isopropylidene-L-ascorbic acid

Base Information

• Chemical Name: (+)-5,6-O-Isopropylidene-L-ascorbic acid
• CAS No.: 15042-01-0
• Molecular Formula: C9H12O6
• Molecular Weight: 216.191
• Hs Code.: 2932999099
• Mol file: 15042-01-0.mol

Synonyms:(5R)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxyfuran-2(5H)-one;(5R)-5-[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyfuran-2(5H)-one;5,6-O,O-isopropylidene-L-ascorbic acid;

Chemical Property of (+)-5,6-O-Isopropylidene-L-ascorbic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 217 °C (dec.)
• Refractive Index: 10 ° (C=5, MeOH)
• Boiling Point: 395.216 °C at 760 mmHg
• PKA: 3.99±0.10(Predicted)
• Flash Point: 160.964 °C
• PSA: 85.22000
• Density: 1.518 g/cm³
• LogP: 0.39090
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: Acetone, DMSO, Ethanol, Methanol

Purity/Quality:

98%, ^*data from raw suppliers

Ascorbic Acid Acetonide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

Technology Process of (+)-5,6-O-Isopropylidene-L-ascorbic acid

There total 15 articles about (+)-5,6-O-Isopropylidene-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: 100.0%

2,2-dimethoxy-propane (77-76-9) + ascorbic acid (50-81-7,98966-42-8) → 5,6-O-isopropylidene-L-ascorbic acid (15042-01-0)

Guidance literature:

With hydrogenchloride; acetone; for 1h;

DOI:10.1016/S0957-4166(97)00258-9

Reference yield: 100.0%

acetone (67-64-1) + ascorbic acid (50-81-7,98966-42-8) → 5,6-O-isopropylidene-L-ascorbic acid (15042-01-0)

Guidance literature:

With Amberlite IR-120; for 2h; Heating;

Reference yield: 99.0%

(R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one (127392-14-7) → (S)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5H-furan-2-one (15042-01-0,15042-06-5,50271-42-6,64550-45-4,127514-13-0)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In ethanol; under 760 Torr;

upstream raw materials:

ascorbic acid

acetone

2,2-dimethoxy-propane

acryloyl chloride

Downstream raw materials:

calcium bis[(2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)acetate]

5,6-O-isopropylidene-2-O-(2-chlorobenzyl)-L-ascorbic acid

5,6-O-isopropylidene-2-O-(4-chlorobenzyl)-L-ascorbic acid

5,6-O-isopropylidene-2-O-(4-bromobenzyl)-L-ascorbic acid

Refernces

• 1、 Richardson, Alistair T.,Cho, Jung,McGhie, Tony K.,Larsen, David S.,Schaffer, Robert J.,Espley, Richard V.,Perry, Nigel B.. "Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris)". . . Retrieved 2020.
• 2、 Burtea, Alexander,Rychnovsky, Scott D.. "Biosynthesis-Inspired Approach to Kujounin A2 Using a Stereoselective Tsuji-Trost Alkylation". . p. 5849 - 5852. Retrieved 2018.
• 3、 Abell, Andrew D.,Ratcliffe, Maureen J.,Gerrard, Juliet. "Ascorbic acid-based inhibitors of α-amylases". . p. 1703 - 1706. Retrieved 1998.
• 4、 Bueno, Manuel,Molina, Inmaculada,Galbis, Juan A.. "1,4-Dioxane-2,5-dione-type monomers derived from l-ascorbic and d-isoascorbic acids. Synthesis and polymerisation". . p. 2100 - 2104. Retrieved 2009.
• 5、 Quelever, Gilles,Kachidian, Philippe,Melon, Christophe,Garino, Cedrik,Laras, Younes,Pietrancosta, Nicolas,Sheha, Mahmoud,Kraus, Jean Louis. "Enhanced delivery of γ-secretase inhibitor DAPT into the brain via an ascorbic acid mediated strategy". . p. 2450 - 2457. Retrieved 2005.
• 6、 Solingapuram Sai, Kiran Kumar,Bashetti, Nagaraju,Chen, Xiaofei,Norman, Skylar,Hines, Justin W.,Meka, Omsai,Kumar, J. V. Shanmukha,Devanathan, Sriram,Deep, Gagan,Furdui, Cristina M.,Mintz, Akiva. "Initial biological evaluations of 18F-KS1, a novel ascorbate derivative to image oxidative stress in cancer". . . Retrieved 2019.
• 7、 Ito, Hideyuki,Iwaoka, Yuji,Matsuno, Hiroaki,Miura, Kaori,Tai, Akihiro. "Antiallergic activity of 6-deoxy-2-o-methyl-6-(N-hexadecanoyl)amino-l-ascorbic acid". . . Retrieved 2021.
• 8、 Muripiti, Venkanna,Brijesh, Lohchania,Rachamalla, Hari Krishnareddy,Marepally, Srujan Kumar,Banerjee, Rajkumar,Patri, Srilakshmi V.. "α-Tocopherol-ascorbic acid hybrid antioxidant based cationic amphiphile for gene delivery: Design, synthesis and transfection". . p. 178 - 191. Retrieved 2019.
• 9、 Raveendran, Varsha,Suresh Babu, Adukamparai Rajukrishnan,Renuka, Neeroli Kizhakayil. "Mint leaf derived carbon dots for dual analyte detection of Fe(iii) and ascorbic acid". . p. 12070 - 12077. Retrieved 2019.
• 10、 -. "COMPOUND, ANTI-ALLERGY DRUG, AND MEDIATOR RELEASE INHIBITOR". Paragraph 0062-0063. . Retrieved 2021/07/17.