Acetic anhydride (CHEM004138)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:35:41 UTC
Update Date2016-10-28 10:00:52 UTC
Accession NumberCHEM004138
Identification
Common NameAcetic anhydride
ClassSmall Molecule
DescriptionAn acyclic carboxylic anhydride derived from acetic acid.
Contaminant Sources
  • Clean Air Act Chemicals
  • DEA Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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
Chemical FormulaC4H6O3
Average Molecular Mass102.089 g/mol
Monoisotopic Mass102.032 g/mol
CAS Registry Number108-24-7
IUPAC Nameacetyl acetate
Traditional Nameacetic anhydride
SMILESCC(=O)OC(C)=O
InChI IdentifierInChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
InChI KeyWFDIJRYMOXRFFG-UHFFFAOYSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-883c860e5905aab2532dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-9800000000-e55e60193ad8b633285aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-9800000000-5d2524434f33a1e79cc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8850b43805e8bf48f1f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfu-9600000000-2bf62658103ef9ea5137Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9600000000-0941637364d795b5d5dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-6c6e84d48837a0409c37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-8dc97f621de1cc9e2c11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-6aa1f4078505fa3b0971Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-87bbaed151efac084591Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac084591Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031646
FooDB IDFDB008300
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcetic_anhydride
Chemspider ID7630
ChEBI ID36610
PubChem Compound ID7918
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25704707
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25857991
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26139873
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26256347
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.