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Showing NP-Card for acetic anhydride (NP0289701)

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Record Information
Version2.0
Created at2022-09-09 20:01:06 UTC
Updated at2022-09-09 20:01:06 UTC
NP-MRD IDNP0289701
Secondary Accession NumbersNone
Natural Product Identification
Common Nameacetic anhydride
DescriptionAcetic anhydride, also known as (CH3CO)2O or acetyl acetate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. It is also used as a wood preservative via autoclave impregnation to make a longer lasting timber. Acetic anhydride is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetic anhydride is a sharp and vinegar tasting compound. Outside of the human body,. Its largest application is for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials. acetic anhydride is found in Vitis vinifera. acetic anhydride was first documented in 2015 (PMID: 25704707). Because of its reactivity toward water, alcohol foam or carbon dioxide are preferred for fire suppression (PMID: 25857991) (PMID: 26139873) (PMID: 26256347).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0289701 (acetic anhydride)


  Mrv0541 05061306032D          

  7  6  0  0  0  0            999 V2000
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
M  END
Download

3D MOL for NP0289701 (acetic anhydride)

     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.5285    0.2139    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1965   -0.4432    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0973   -1.6846    0.2837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033    0.2705    0.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361   -0.3544    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5014    0.4528    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529   -1.5880    0.2631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1884   -0.3145   -0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239    0.2507    1.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036    1.2628   -0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025    1.2329   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528   -0.1637   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6958    0.8647    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  6 11  1  0
  6 12  1  0
  6 13  1  0
M  END
Download

3D SDF for NP0289701 (acetic anhydride)


  Mrv0541 05061306032D          

  7  6  0  0  0  0            999 V2000
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3

> <INCHI_KEY>
WFDIJRYMOXRFFG-UHFFFAOYSA-N

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.0886

> <EXACT_MASS>
102.031694058

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.423829713825054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
acetyl acetate

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.3125194183333333

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.945086711302831

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
22.082000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetic anhydride

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0289701 (acetic anhydride)

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PDB for NP0289701 (acetic anhydride)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5    7                                                  
CONECT    4    2    6    7                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0289701 (acetic anhydride)
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SMILES for NP0289701 (acetic anhydride)
CC(=O)OC(C)=O
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INCHI for NP0289701 (acetic anhydride)
InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
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View in JSmol
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 Mass102.0886 Da
Monoisotopic Mass102.03169 Da
IUPAC Nameacetyl acetate
Traditional Nameacetic anhydride
CAS Registry NumberNot Available
SMILES
CC(=O)OC(C)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
InChI KeyWFDIJRYMOXRFFG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Vitis viniferaLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031646  
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  
Good Scents IDNot Available
References
General References
  1. Bartz J, Goebel JT, Giovanaz MA, Zavareze Eda R, Schirmer MA, Dias AR: Acetylation of barnyardgrass starch with acetic anhydride under iodine catalysis. Food Chem. 2015 Jul 1;178:236-42. doi: 10.1016/j.foodchem.2015.01.095. Epub 2015  Jan 28. [PubMed:25704707  ] 
  2. Bozic M, Vivod V, Kavcic S, Leitgeb M, Kokol V: New findings about the lipase acetylation of nanofibrillated cellulose using acetic anhydride as acyl donor. Carbohydr Polym. 2015 Jul 10;125:340-51. doi: 10.1016/j.carbpol.2015.02.061. Epub  2015 Mar 7. [PubMed:25857991  ] 
  3. Wani IA, Sogi DS, Gill BS: Physico-chemical properties of acetylated starches from Indian black gram (Phaseolus mungo L.) cultivars. J Food Sci Technol. 2015 Jul;52(7):4078-89. doi: 10.1007/s13197-014-1480-x. Epub  2014 Aug 7. [PubMed:26139873  ] 
  4. Chai W, Liu X, Zou J, Zhang X, Li B, Yin T: Pomelo peel modified with acetic anhydride and styrene as new sorbents for removal of oil pollution. Carbohydr Polym. 2015 Nov 5;132:245-51. doi: 10.1016/j.carbpol.2015.06.060. Epub  2015 Jun 25. [PubMed:26256347  ] 
  5. LOTUS database [Link]