(R)-acetoin

Base Information

• Chemical Name: (R)-acetoin
• CAS No.: 53584-56-8
• Molecular Formula: C4H8O2
• Molecular Weight: 88.1063
• Nikkaji Number: J52.647I
• Wikidata: Q27098190
• Metabolomics Workbench ID: 5468
• Mol file: 53584-56-8.mol

Synonyms:(R)-acetoin;(R)-dimethylketol;(3R)-3-hydroxybutan-2-one;(R)-2-acetoin;(R)-3-hydroxy-2-butanone;(R)-3-hydroxybutan-2-one;(-)-acetoin;D-(-)-acetoin;53584-56-8;d-acetoin;r-acetoin;R,3-HYDROXYBUTAN-2-ONE;3R-Hydroxybutan-2-one;(R)-(-)-Acetoin;(-)-3-Hydroxybutan-2-one;2-Butanone, 3-hydroxy-, (R)-;2-Butanone, 3-hydroxy-, (3R)-;levorotatory acetoin;(R)-acetylmethylcarbinol;(R)-3-hydroxy-butan-2-one;CHEBI:15686;LMFA12000064;DB04364;C00810;A934541;Q27098190

Chemical Property of (R)-acetoin

Chemical Property:

• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 88.052429494
• Heavy Atom Count: 6
• Complexity: 58.6

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)C)O
• Isomeric SMILES: C[C@H](C(=O)C)O

Technology Process of (R)-acetoin

There total 52 articles about (R)-acetoin 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: 50.0%

dimethylglyoxal (431-03-8) → (2R,3S)-2,3-butanediol (1029272-42-1) + (R,R)-2,3-butandiol (24347-58-8) + (S)-acetoin (78183-56-9,51555-24-9) + (R)-acetoin (53584-56-8,51555-24-9)

Guidance literature:

With hydrogen; Pt/Al₂O₃; cinchonine; In toluene; for 1.91667h; under 80256.4 Torr; Yield given. Further byproducts given. Title compound not separated from byproducts;

DOI:10.1039/a801390j

Reference yield: 50.0%

dimethylglyoxal (431-03-8) → (2S,3S)-butane-2,3-diol (19132-06-0) + (2R,3S)-2,3-butanediol (1029272-42-1) + (R,R)-2,3-butandiol (24347-58-8) + (S)-acetoin (78183-56-9,51555-24-9) + (R)-acetoin (53584-56-8,51555-24-9)

Guidance literature:

With hydrogen; Pt/Al₂O₃; cinchonine; In toluene; for 1.91667h; under 80256.4 Torr; Rate constant; Product distribution; different reaction times;

DOI:10.1039/a801390j

Reference yield: 50.0%

dimethylglyoxal (431-03-8) → (2S,3S)-butane-2,3-diol (19132-06-0) + (2R,3S)-2,3-butanediol (1029272-42-1) + (R,R)-2,3-butandiol (24347-58-8) + (R)-acetoin (53584-56-8,51555-24-9)

Guidance literature:

With hydrogen; Pt/Al₂O₃; cinchonine; In toluene; for 1.91667h; under 80256.4 Torr; Further byproducts given. Yields of byproduct given;

DOI:10.1039/a801390j

upstream raw materials:

D-xylose

(2R,3S)-2,3-butanediol

d,l-2,3-butanediol

LACTIC ACID

Downstream raw materials:

3-O-MTPA-2-butanone

(R,R)-2,3-butandiol

(R)-3-oxobutan-2-yl benzoate

Refernces

• 1、 Ji, Fangling,Feng, Yanbin,Li, Mingyang,Yang, Yongliang,Wang, Tianqi,Wang, Jingyun,Bao, Yongming,Xue, Song. "Studies on structure-function relationships of acetolactate decarboxylase from: Enterobacter cloacae". . p. 39066 - 39073. Retrieved 2018/11/30.
• 2、 Margitfalvi, József L.,Tálas, Emília. "Enantioselective hydrogenation of activated ketones in the presence of Pt-cinchona catalysts. Is the proton transfer concept valid?". . p. 142 - 145. Retrieved 2014/01/17.