Record Information
Version1.0
Creation date2010-04-08 22:08:01 UTC
Update date2015-07-20 22:20:48 UTC
Primary IDFDB008300
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetic anhydride
DescriptionEsterification agent for use in prepn. of modified food starch and for acetylation of monoglycerides Acetic anhydride is a versatile reagent for acetylations, the introduction of acetyl groups to organic substrates. In these conversions, acetic anhydride is viewed as a source of CH3CO+. Alcohols and amines are readily acetylated. For example, the reaction of acetic anhydride with ethanol is:; Acetic anhydride is an irritant and flammable. Because of its reactivity toward water, alcohol foam or carbon dioxide are preferred for fire suppression. The vapour of acetic anhydride is harmful.; Acetic anhydride is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with the moisture in the air.; As indicated by its organic chemistry, Ac2O is mainly used for acetylations leading to commercially significant materials. Its largest application is for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials. Similarly it is used in the production of aspirin, acetyl salicylic acid, which is prepared by the acetylation of salicylic acid. It is also used as a wood preservative via autoclave impregnation to make a longer lasting timber. Because of its use for the synthesis of heroin by the diacetylation of morphine, acetic anhydride (known as 'AA' in clandestine chemistry circles) is listed as a U.S. DEA List II Precursor, and restricted in many other countries. The largest markets for diverted acetic anhydride continue to be heroin laboratories in Afghanistan.
CAS Number108-24-7
Structure
Thumb
Synonyms
SynonymSource
(CH3CO)2OChEBI
(MeCO)2OChEBI
Ac2OChEBI
AcetanhydrideChEBI
Acetic acid anhydrideChEBI
Acetyl acetateChEBI
Acetyl oxideChEBI
Anhydride acetiqueChEBI
EssigsaeureanhydridChEBI
Ethanoic anhydrateChEBI
Ethanoic anhydrideChEBI
Acetate anhydrideGenerator
Acetyl acetic acidGenerator
Ethanoic anhydric acidGenerator
Acetic acid, anhydrideHMDB
Acetic oxideHMDB
Acetyl anhydrideHMDB
Acetyl etherHMDB
Acetyltrimethyl-silaneHMDB
Anhydrid kyseliny octoveHMDB
Anidride aceticaHMDB
AzijnzuuranhydrideHMDB
Octowy bezwodnikHMDB
Acetic anhydride, 3H-labeledHMDB
Acetic anhydride [UN1715] [Corrosive]biospider
Silane, acetyltrimethyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility119 g/LALOGPS
logP0.11ALOGPS
logP-0.31ChemAxon
logS0.07ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.08 m³·mol⁻¹ChemAxon
Polarizability9.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H6O3
IUPAC nameacetyl acetate
InChI IdentifierInChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
InChI KeyWFDIJRYMOXRFFG-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OC(C)=O
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
Classification
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
  • Carboxylic acid anhydride
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 47.06%; H 5.92%; O 47.02%DFC
Melting PointMp -73°DFC
Boiling PointBp15 44°DFC
Experimental Water Solubility120 mg/mL at 20 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd154 1.09DFC
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-883c860e5905aab2532dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-9800000000-e55e60193ad8b633285aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-9800000000-5d2524434f33a1e79cc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8850b43805e8bf48f1f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfu-9600000000-2bf62658103ef9ea5137View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9600000000-0941637364d795b5d5dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-6c6e84d48837a0409c37View in MoNA
ChemSpider ID7630
ChEMBL IDCHEMBL1305819
KEGG Compound IDNot Available
Pubchem Compound ID7918
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31646
CRC / DFC (Dictionary of Food Compounds) IDDFR94-Z:DFR94-Z
EAFUS ID19
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1097401
SuperScent IDNot Available
Wikipedia IDAcetic_anhydride
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sharp
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vinegar
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference