You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:37 UTC
Update Date2018-05-20 00:19:01 UTC
HMDB IDHMDB0031646
Secondary Accession Numbers
  • HMDB31646
Metabolite Identification
Common NameAcetic anhydride
DescriptionAcetic anhydride is an esterification 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 yields ethyl acetate: (CH3CO)2O + CH3CH2OH → CH3CO2CH2CH3 + CH3COOH. 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
Structure
Thumb
Synonyms
ValueSource
AcetanhydrideChEBI
Acetic acid anhydrideChEBI
Acetyl oxideChEBI
Anhydride acetiqueChEBI
EssigsaeureanhydridChEBI
Ethanoic anhydrateChEBI
Ethanoic anhydrideChEBI
Acetate anhydrideGenerator
Ethanoic anhydric acidGenerator
(CH3CO)2OHMDB
Acetic acid, anhydrideHMDB
Acetic oxideHMDB
Acetyl acetateHMDB
Acetyl anhydrideHMDB
Acetyl etherHMDB
Acetyltrimethyl-silaneHMDB
Anhydrid kyseliny octoveHMDB
Anidride aceticaHMDB
AzijnzuuranhydrideHMDB
Octowy bezwodnikHMDB
Acetic anhydride, 3H-labeledMeSH
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Nameacetyl acetate
Traditional Nameacetic anhydride
CAS Registry Number108-24-7
SMILES
CC(=O)OC(C)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
InChI KeyWFDIJRYMOXRFFG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-73 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility120 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
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
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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008300
KNApSAcK IDNot Available
Chemspider ID7630
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetic_anhydride
METLIN IDNot Available
PubChem Compound7918
PDB IDNot Available
ChEBI ID36610
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lou W, Zong M, Fan X, Lu J, Du W: [Asymmetric microbial reduction of organosilyl ketone with immobilized Saccharomyces cerevisiae cells]. Wei Sheng Wu Xue Bao. 2002 Aug;42(4):484-9. [PubMed:12557557 ]
  2. Pratap R, Ram VJ: An efficient de novo synthesis of partially reduced phenanthrenes through C-C insertion. J Org Chem. 2007 Sep 14;72(19):7402-5. Epub 2007 Aug 18. [PubMed:17705542 ]
  3. Li N, Zong MH, Liu C, Peng HS, Wu HC: (R)-oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins. Biotechnol Lett. 2003 Feb;25(3):219-22. [PubMed:12882574 ]
  4. Huang SR, Liu SL, Zong MH, Xu R: Synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide catalyzed with (R)-oxynitrilase from loquat seed meal. Biotechnol Lett. 2005 Jan;27(2):79-82. [PubMed:15703868 ]
  5. Goel A, Verma D, Dixit M, Raghunandan R, Maulik PR: Acetyltrimethylsilane: a novel reagent for the transformation of 2H-pyran-2-ones to unsymmetrical biaryls. J Org Chem. 2006 Jan 20;71(2):804-7. [PubMed:16408998 ]
  6. Martin D, Illa O, Baceiredo A, Bertrand G, Ortuno RM, Branchadell V: Theoretical and experimental investigation of the basicity of phosphino(silyl)carbenes. J Org Chem. 2005 Jul 8;70(14):5671-7. [PubMed:15989352 ]
  7. Zhang BB, Cheng J, Lou WY, Wang P, Zong MH: Efficient anti-Prelog enantioselective reduction of acetyltrimethylsilane to (R)-1-trimethylsilylethanol by immobilized Candida parapsilosis CCTCC M203011 cells in ionic liquid-based biphasic systems. Microb Cell Fact. 2012 Aug 16;11:108. doi: 10.1186/1475-2859-11-108. [PubMed:22897972 ]
  8. Lefebvre O, Brigaud T, Portella C: Acetyltrimethylsilane, trifluoromethyltrimethylsilane, and prenyl esters: a three-component system for the synthesis of gem-difluoroanalogues of monoterpenes. J Org Chem. 2001 Jun 15;66(12):4348-51. [PubMed:11397175 ]
  9. Xiao ZJ, Zong MH, Lou WY: Highly enantioselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to enantiopure (R)-4-(trimethylsilyl)-3-butyn-2-ol using a novel strain Acetobacter sp. CCTCC M209061. Bioresour Technol. 2009 Dec;100(23):5560-5. doi: 10.1016/j.biortech.2009.06.006. Epub 2009 Jun 28. [PubMed:19564106 ]
  10. Xu R, Zong MH, Liu YY, He J, Zhang YY, Lou WY: Enzymatic enantioselective transcyanation of silicon-containing aliphatic ketone with (S)-hydroxynitrile lyase from Manihot esculenta. Appl Microbiol Biotechnol. 2004 Nov;66(1):27-33. Epub 2004 Aug 12. [PubMed:15309340 ]
  11. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .