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W241512

Sigma-Aldrich

Ethyl acetoacetate

greener alternative

natural, ≥97%, FG

Synonym(s):

Acetoacetic ester

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About This Item

Linear Formula:
CH3COCH2COOC2H5
CAS Number:
Molecular Weight:
130.14
FEMA Number:
2415
Beilstein:
385838
EC Number:
Council of Europe no.:
240c
MDL number:
UNSPSC Code:
12164502
PubChem Substance ID:
Flavis number:
9.402
NACRES:
NA.21

grade

FG
Fragrance grade
Halal
Kosher
natural

Quality Level

Agency

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117

vapor density

4.48 (vs air)

vapor pressure

1 mmHg ( 28.5 °C)

Assay

≥97%

autoignition temp.

580 °F

expl. lim.

9.5 %

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

refractive index

n20/D 1.418-1.421

bp

181 °C (lit.)

mp

−43 °C (lit.)

solubility

water: soluble 35 part
organic solvents: soluble

density

1.029 g/mL at 20 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

greener alternative category

Organoleptic

apple; fatty; green; fruity

SMILES string

CCOC(=O)CC(C)=O

InChI

1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3

InChI key

XYIBRDXRRQCHLP-UHFFFAOYSA-N

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product is a Biobased products, showing key improvements in Green Chemistry Principles “Less Hazardous Chemical Syntheses” and “Use of Renewable Feedstock”.

Application


  • Benchtop (19)F Nuclear Magnetic Resonance (NMR) Spectroscopy Provides Mechanistic Insight into the Biginelli Condensation toward the Chemical Synthesis of Novel Trifluorinated Dihydro- and Tetrahydropyrimidinones as Antiproliferative Agents.: This study explores the use of Ethyl acetoacetate in the synthesis of novel trifluorinated compounds with potential antiproliferative properties against cancer cells. The research employs advanced NMR spectroscopy to elucidate the reaction mechanism (Chen et al., 2023, Chen et al., 2023).

  • Synthesis and Characterization of New Dihydronaphthalene Candidates as Potent Cytotoxic Agents against MCF-7 Human Cancer Cells.: This article discusses the creation of dihydronaphthalene derivatives using Ethyl acetoacetate, highlighting their significant cytotoxic activity against breast cancer cells. The synthesized compounds show promise for further development as chemotherapeutic agents (Ahmed et al., 2020, Ahmed et al., 2020).

  • Synthesis and characterization of new 4H-chromene-3-carboxylates ensuring potent elastase inhibition activity along with their molecular docking and chemoinformatics properties.: Utilizing Ethyl acetoacetate, this research focuses on developing 4H-chromene derivatives that exhibit strong elastase inhibition, a key enzyme implicated in various inflammatory diseases. The study integrates molecular docking and chemoinformatics for detailed analysis (Dige et al., 2020, Dige et al., 2020).

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

164.3 °F - closed cup

Flash Point(C)

73.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Structures of the reaction products of tetraalkoxytitanium with acetylacetone and ethyl acetoacetate.
Yamamoto A and Kambara .
Journal of the American Chemical Society, 79(!6), 4344-4348 (1957)
Reaction of aromatic amines and ethyl acetoacetate promoted by zeolite HSZ-360. Phosgene-free synthesis of symmetric diphenylureas.
Bigi F and Zambonin E.
Chemical Communications (Cambridge, England), 4, 513-514 (1998)
Oxygen vs carbon alkylation of ethyl acetoacetate.
Le Noble WJ and Morris HF.
The Journal of Organic Chemistry, 34(6), 1969-1973 (1969)
Gas-phase proton NMR studies of keto-enol tautomerism of acetylacetone, methyl acetoacetate, and ethyl acetoacetate.
Folkendt MM, et al.
The Journal of Physical Chemistry, 89 (15) , 3347-3352 (1985)
Lipase CAL-B does not catalyze a promiscuous decarboxylative aldol addition or Knoevenagel reaction.
Evitt AS and Bornscheuer UT.
Green Chemistry, 13(5), 1141-1142 (2011)

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