4906-24-5

Basic information

• Product Name: 3-ACETOXY-2-BUTANONE
• Synonyms: SEC-BUTAN-3-ONYL ACETATE;3-ACETOXY-2-BUTANONE;ACETYL METHYL CARBINYL ACETATE;2-ACETOXY-3-BUTANONE;FEMA 3526;2-Ketobutan-3-yl acetate;3-oxo-2-butyl acetate;Acetoin acetate
• CAS NO: 4906-24-5
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14
• Product Categories: Organics;ketone
• Mol File: 4906-24-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 56-58°C 30mm
• Flash Point: 66°C
• Appearance: /
• Density: 1,02 g/cm3
• Vapor Pressure: 2.07mmHg at 25°C
• Refractive Index: 1.4135
• BRN: 1756882
• CAS DataBase Reference: 3-ACETOXY-2-BUTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETOXY-2-BUTANONE(4906-24-5)
• EPA Substance Registry System: 3-ACETOXY-2-BUTANONE(4906-24-5)

Safety Data

• Statements: 36/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4906-24-5(Hazardous Substances Data)

Usage

uses

3-Acetoxy-2-butanone can be used as an edible spice, mainly for the preparation of milk and dairy flavors.

Identification

▼▲ CAS.No.:? 4906-24-5? FL.No.:? 9.186 FEMA.No.:? 3526 NAS.No.:? 3526 CoE.No.:? 608 EINECS.No.:? n/a? JECFA.No.:? 406

Regulatory Status

CoE: Approved. Bev.: 1 ppm; Food: 10 ppm FDA: n/a FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1998).

Usage

Reported uses (ppm): (FEMA, 1994) ▼▲ Food Category? Usual? Max.? Alcoholic.beverages? 5.37 20 Baked.goods? 10.6 49.3 Frozen.dairy? 5.37 20 Gelatins,puddings? 5.38 20 Nonalcoholic.beverages? 5 20 Soft.candy? 9.91 47.8

Natural occurrence

Reported found in pineapple (Ananas comoscus), roasted chicken, red wine, cocoa, arctic bramble (Rubus articus L.) and pawpaw (Asimina triloba L. Dunal).

Occurrence

3-Acetoxy-2-butanone is reported found in pineapple (Ananas comoscus), roasted chicken, red wine, cocoa, arctic bramble (Rubus articus L.) and pawpaw (Asimina triloba L. Dunal).

Aroma threshold values

Detection at 5.0%: sweet, fruity, estry, chemical, pineapple, apple, banana with a ketonic nuance.

Taste threshold values

Taste characteristics at 100 ppm: fruity body, fleshy, rimy, grape, and winey.

General Description

2-Acetoxy-3-butanone occurs naturally in paw paw fruit. It is also reported to be formed by the reaction between cysteine and 2,5-dimethyl-4-hydroxy-3(2H)-furanone.

InChI:InChI=1/C6H10O3/c1-4(7)5(2)9-6(3)8/h5H,1-3H3

Upstream product

• 108-24-7 acetic anhydride 
• 1029272-42-1 (2R,3S)-2,3-butanediol 
• 79-20-9 acetic acid methyl ester 
• 513-86-0 3-hydroxy-2-butanon 
• 127-08-2 potassium acetate 
• 4091-39-8 3-chloro-2-butanone 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 2028-63-9 but-3-yn-2-ol 
• 814-75-5 3-bromo-butanone 
• 7338-73-0 3-hydroxy-3-methyl-2,4-pentanedione 
• 78-93-3 butanone 
• 638-38-0 manganese triacetate 
• 82237-14-7 2,2-diethoxy-4,5-dimethyl-2-phenoxy-1,3,2λ⁵-dioxaphosphole 

Downstream Products

• 78-94-4 methyl vinyl ketone 

Relevant articles and documents

A multicatalyst system for the one-pot desymmetrization/oxidation of meso-1,2-alkane diols

Two is better than one: We demonstrate the viability of an organocatalytic reaction sequence along a short peptide backbone that carries two independent catalytic functionalities, which allow the rapid, one-pot acylative desymmetrization and oxidation of meso-alkane-1,2-diols to the corresponding acetylated acetoins with good yields and enantioselectivities (see scheme). Copyright

One-Pot desymmetrization of meso-l,2-hydrocarbon diols through acylation and oxidation

Avoid racemization! Short lipophilic oligopeptides utilizing nucleophilic N-jt-methyl histidine residues catalyze the desymmetrization of wieso-l,2-diols with enantiomeric ratios of up to 94:6. Direct one-pot oxidation, which avoids the well-known racemiz

Asymmetric Reduction of 1-Acetoxy-2-alkanones with Baker's Yeast: Purification and Characterization of α-Acetoxy Ketone Reductase

An α-acetoxy ketone reducing enzyme has been purified and characterized from the cell-free extract of bakers' yeast (Saccharomyces cerevisiae). Only one NADPH-dependent dehydrogenase that catalyzed the reduction of α-acetoxy ketone was found in bakers' yeast. The molecular weight of the enzyme was estimated to be 36 kDa by SDS-polyacrylamide gel electrophoresis. The enzyme was composed of a single polypeptide chain. The enzyme had reducing activity for both aliphatic and aromatic α-acetoxy ketones, although no reducing activity toward α-chloro ketones and α-hydroxy ketones was found. The enzyme catalyzed the reduction of not only α-acetoxy ketones, but also β-keto esters. Studies on the chromatographic behavior and stereospecificity indicated that the enzyme was identical with one of the β-keto ester reductases purified from bakers' yeast.