Acetoin

Base Information

• Chemical Name: Acetoin
• CAS No.: 513-86-0
• Deprecated CAS: 52217-02-4
• Molecular Formula: C₄H₈O₂
• Molecular Weight: 88.1063
• Hs Code.: 2914.40
• European Community (EC) Number: 208-174-1,682-499-0
• NSC Number: 89727,7609
• UN Number: 2621
• UNII: BG4D34CO2H
• DSSTox Substance ID: DTXSID0024399
• Nikkaji Number: J2.623I
• Wikipedia: Acetoin
• Wikidata: Q223083
• Metabolomics Workbench ID: 5426
• ChEMBL ID: CHEMBL3561873
• Mol file: 513-86-0.mol

Synonyms:3-hydroxy-2-butanone;3H-2B butanone;Acetoin;Acetylmethylcarbinol

Chemical Property of Acetoin

Chemical Property:

• Appearance/Colour: light-yellow colored liquid
• Vapor Pressure: 1.92mmHg at 25°C
• Melting Point: 15 °C (monomer)
• Refractive Index: 1.4170 - 1.4210
• Boiling Point: 145.4 °C at 760 mmHg
• PKA: 13.21±0.20(Predicted)
• Flash Point: 49.7 °C
• PSA: 37.30000
• Density: 0.983 g/cm³
• LogP: -0.04380
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.1 g/mL, clear
• Water Solubility.: SOLUBLE
• 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
• Transport DOT Label: Flammable Liquid Flammable Solid

Purity/Quality:

98% min ^*data from raw suppliers

Acetoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,F
• Statements: 10-36/38-38-11
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Food Additives
• Canonical SMILES: CC(C(=O)C)O
• Uses: 3-Hydroxy-2-butanone is a chemical used in food flavoring and fragrances. It acts as an intermediate of butanediol cycle in microorganisms. It is used as an aroma carrier in the preparation of flavors and essences. Acetoin is a produced via fermentation of wines, dairy products and sugars by fermentive bacteria. Acetoin is used in food flavoring and fragrances and is also found in some fruits and vegetables. Used as pharmaceutical intermediates, food spices; mainly for the preparation of cream, dairy, yogurt and strawberry spices.

Technology Process of Acetoin

There total 209 articles about 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: 93.4%

sodium pyruvate (113-24-6) + benzaldehyde (100-52-7) → (R)-1-hydroxy-1-phenyl-2-propanone (1798-60-3) + 3-hydroxy-2-butanon (513-86-0,52217-02-4,51555-24-9)

Guidance literature:

With pyruvate decarboxylase; In octanol; water; at 4 ℃; for 40 - 395h; pH=6.5 - 8; Product distribution / selectivity; Enzymatic reaction; aqueous MOPS buffer;

Reference yield: 8.0%

2-hydroxy-3-butene (598-32-3) → acetaldol (107-89-1) + 1-Hydroxy-3-butanone (590-90-9) + 3-hydroxy-2-butanon (513-86-0,52217-02-4,51555-24-9) + crotonaldehyde (123-73-9,4170-30-3)

Guidance literature:

hydrogenchloride; lithium tetrachloropalladate(II); p-benzoquinone; In water; at 25 ℃; for 0.5h; Further byproducts given;

DOI:10.1021/jo00293a031

Reference yield: 8.0%

2-hydroxy-3-butene (598-32-3) → acetaldol (107-89-1) + 1-Hydroxy-3-butanone (590-90-9) + 3-hydroxy-2-butanon (513-86-0,52217-02-4,51555-24-9) + methyl vinyl ketone (78-94-4,25038-87-3) + crotonaldehyde (123-73-9,4170-30-3)

Guidance literature:

With hydrogenchloride; lithium tetrachloropalladate(II); p-benzoquinone; In water; at 25 ℃; for 0.5h; Rate constant; Mechanism; Kinetics; equilibrium constants;

DOI:10.1021/jo00293a031

upstream raw materials:

methyl magnesium iodide

2-hydroxy-propionitrile

formaldehyd

LACTIC ACID

Downstream raw materials:

4,5-dimethylimidazole

2.3-butanediol

3-acetoxy-2-butanone

N,N'-bis(cyclohexyl)-2,3-butanediimine

Refernces

• 1、 Merlic, Craig A.,Baur, Andreas,Yamada, Ken,Brown, Stuart E.. "Synthesis of quadruply carbon-13 labeled tetramethyltetrathiafulvalene". . p. 2677 - 2685. Retrieved 2000.
• 2、 v.Pechmann,Dahl. "-". . p. 2421. Retrieved 1890.
• 3、 Fett, Roseane,Brighente, Ines Maria Costa,Yunes, Rosendo Augusto. "Influence of Calcium Ions on the Mechanism of Oxime Formation from Acetoin". . p. 1639 - 1643. Retrieved 1996.
• 4、 Vermeer, Wilhelmus A. H.,Fulford, Anthony,Johnston, Peter,Wells, Peter B.. "New Enantioselective Reactions catalysed by Cinchonidine-modified Platinum". . p. 1053 - 1054. Retrieved 1993.
• 5、 Vartzouma,Louloudi,Butler,Hadjiliadis. "Practical tethering of vitamin B1 on a silica surface via its phosphate group and evaluation of its activity". . p. 522 - 523. Retrieved 2002.
• 6、 Bricker,Vail. "-". . p. 585,587. Retrieved 1951.
• 7、 Poblete,Mucientes,Villarreal,Santiago,Cabanas,Gabaldon. "Oxidation of 2,3-butanediol by alkaline hexacyanoferrate(III) using Ru(III) or Ru(VI) as catalyst". . p. 597 - 602. Retrieved 2006.
• 8、 D?ring, Manuel,Sieber, Volker,Simon, Robert C.,Tafertshofer, Georg,Zachos, Ioannis. "carba Nicotinamide Adenine Dinucleotide Phosphate: Robust Cofactor for Redox Biocatalysis". supporting information. p. 14701 - 14706. Retrieved 2021/05/13.
• 9、 Guo, Ze-Wang,Ou, Xiao-Yang,Xu, Pei,Gao, Hui-Fang,Zhang, Liao-Yuan,Zong, Min-Hua,Lou, Wen-Yong. "Energy- And cost-effective non-sterilized fermentation of 2,3-butanediol by an engineered: Klebsiella pneumoniae OU7 with an anti-microbial contamination system". . p. 8584 - 8593. Retrieved 2020/12/31.