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Showing NP-Card for Acetoin (NP0000723)

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Record Information
Version1.0
Created at2006-05-22 15:12:44 UTC
Updated at2022-01-10 20:15:22 UTC
NP-MRD IDNP0000723
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetoin
DescriptionAcetoin, also known as dimethylketol or 2,3-butanolone, belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Thus, acetoin is considered to be an oxygenated hydrocarbon lipid molecule. Acetoin is used as an external energy store by a number of fermentive bacteria. Acetoin, along with diacetyl, is one of the compounds giving butter its characteristic flavor. Acetoin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Acetoin is used as a food flavoring (in baked goods) and a fragrance. Acetoin is a sweet, buttery, and creamy tasting compound. Outside of the human body, Acetoin has been detected, but not quantified in several different foods, such as cocoa and cocoa products, evergreen blackberries, orange bell peppers, tortilla chips, and pomes. This could make acetoin a potential biomarker for the consumption of these foods. Constituent of beer, wine, fresh or cooked apple, fresh or cooked leak, corn, honey, cocoa, butter, cheeses, roasted coffee and other foodstuffs. Acetoin, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and ulcerative colitis; acetoin has also been linked to the inborn metabolic disorder celiac disease. Acetoin is a colorless or pale yellow to green yellow liquid with a pleasant, buttery odor. It can be found in apples, butter, yogurt, asparagus, black currants, blackberry, wheat, broccoli, brussels sprouts, cantaloupe.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000723 (Acetoin)


  Mrv1652305271900012D          

  6  5  0  0  0  0            999 V2000
   31.6657  -15.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0946  -14.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3802  -15.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3802  -16.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8090  -15.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0946  -15.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000723 (Acetoin)

HMDB0003243
     RDKit          3D
Acetoin
 14 13  0  0  0  0  0  0  0  0999 V2000
    1.8848    0.3626    0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631    0.0025   -0.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    0.2065   -1.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4904   -0.5850   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.1519   -0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3961   -0.7083    1.3485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598    1.4508    0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8174   -0.0198   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035   -0.2062    1.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528   -1.6256   -0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.2893   -1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    1.2383   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187   -0.0154    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.0371    1.8312 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
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
M  END
Download

3D SDF for NP0000723 (Acetoin)


  Mrv1652305271900012D          

  6  5  0  0  0  0            999 V2000
   31.6657  -15.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0946  -14.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3802  -15.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3802  -16.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8090  -15.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0946  -15.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000723

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3

> <INCHI_KEY>
ROWKJAVDOGWPAT-UHFFFAOYSA-N

> <FORMULA>
C4H8O2

> <MOLECULAR_WEIGHT>
88.1051

> <EXACT_MASS>
88.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.143149969881287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxybutan-2-one

> <ALOGPS_LOGP>
-0.66

> <JCHEM_LOGP>
-0.1422039953333334

> <ALOGPS_LOGS>
0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.81975350602122

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.723456226493909

> <JCHEM_PKA_STRONGEST_BASIC>
-3.357098011793852

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
22.3909

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetoin

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000723 (Acetoin)

HMDB0003243
     RDKit          3D
Acetoin
 14 13  0  0  0  0  0  0  0  0999 V2000
    1.8848    0.3626    0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631    0.0025   -0.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    0.2065   -1.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4904   -0.5850   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.1519   -0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3961   -0.7083    1.3485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598    1.4508    0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8174   -0.0198   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035   -0.2062    1.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528   -1.6256   -0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.2893   -1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    1.2383   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5187   -0.0154    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.0371    1.8312 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
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
M  END
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PDB for NP0000723 (Acetoin)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      59.109 -28.016   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      61.777 -26.476   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      60.443 -28.786   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      60.443 -30.326   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      63.110 -28.786   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      61.777 -28.016   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    6                                                            
CONECT    3    1    4    6                                                  
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    2    3    5                                                  
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for NP0000723 (Acetoin)

COMPND    HMDB0003243
HETATM    1  C1  UNL     1       1.885   0.363   0.319  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.763   0.003  -0.592  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.917   0.206  -1.783  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.490  -0.585  -0.034  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.718   0.152  -0.471  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.396  -0.708   1.349  1.00  0.00           O  
HETATM    7  H1  UNL     1       1.960   1.451   0.490  1.00  0.00           H  
HETATM    8  H2  UNL     1       2.817  -0.020  -0.192  1.00  0.00           H  
HETATM    9  H3  UNL     1       1.803  -0.206   1.279  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.553  -1.626  -0.454  1.00  0.00           H  
HETATM   11  H5  UNL     1      -2.107  -0.289  -1.435  1.00  0.00           H  
HETATM   12  H6  UNL     1      -1.560   1.238  -0.591  1.00  0.00           H  
HETATM   13  H7  UNL     1      -2.519  -0.015   0.284  1.00  0.00           H  
HETATM   14  H8  UNL     1      -0.802   0.037   1.831  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    3    4
CONECT    4    5    6   10
CONECT    5   11   12   13
CONECT    6   14
END
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SMILES for NP0000723 (Acetoin)

CC(O)C(C)=O
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INCHI for NP0000723 (Acetoin)

InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3
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View in JSmol
Synonyms
ValueSource
(S)-2-AcetoinChEBI
1-Hydroxyethyl methyl ketoneChEBI
2,3-ButanoloneChEBI
2-AcetoinChEBI
2-Hydroxy-3-butanoneChEBI
3-Hydroxy-2-butanoneChEBI
3-Hydroxybutan-2-oneChEBI
Acetyl methyl carbinolChEBI
DimethylketolChEBI
gamma-Hydroxy-beta-oxobutaneChEBI
g-Hydroxy-b-oxobutaneGenerator
Γ-hydroxy-β-oxobutaneGenerator
(R)-2-AcetoinHMDB
(R)-3-Hydroxy-2-butanoneHMDB
(R)-3-Hydroxybutan-2-oneHMDB
(R)-AcetoinHMDB
(R)-DimethylketolHMDB
2-Butanol-3-oneHMDB
2-Hydroxy-3-oxobutaneHMDB
3-Hydroxyl-2-butanoneHMDB
AcetoineHMDB
b-OxobutaneHMDB
beta-OxobutaneHMDB
AcetylmethylcarbinolHMDB
3H-2b ButanoneHMDB
AcetoinMeSH
Chemical FormulaC4H8O2
Average Mass88.1051 Da
Monoisotopic Mass88.05243 Da
IUPAC Name3-hydroxybutan-2-one
Traditional Nameacetoin
CAS Registry Number513-86-0
SMILES
CC(O)C(C)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3
InChI KeyROWKJAVDOGWPAT-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-10View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-01-10View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Zinat2021-11-15View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Zinat2021-11-15View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-08-23View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Allium ampeloprasumLOTUS Database
Allium cepaFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Aloe arborescensLOTUS Database
Camellia sinensisLOTUS Database
Capsicum annuumFooDB
Cocos nuciferaFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Corynebacterium glutamicumLOTUS Database
Daphne odoraLOTUS Database
Daucus carota ssp. sativusFooDB
Ficus caricaFooDB
Glycine maxFooDB
Glycyrrhiza glabraLOTUS Database
Helianthus annuusLOTUS Database
Helianthus annuus L.FooDB
Litchi chinensisLOTUS Database
Litsea cubebaKNApSAcK Database
Malpighia emarginataLOTUS Database
Mentha spicataFooDB
Plumeria rubraLOTUS Database
Prunus persicaLOTUS Database
Rubus idaeusFooDB
Sergia lucensLOTUS Database
Streptomyces avermitilisLOTUS Database
Streptomyces virginiaeLOTUS Database
Theobroma cacaoFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Trifolium pratenseLOTUS Database
Vaccinium myrtillusFooDB
Vigna radiataFooDB
Vitis viniferaLOTUS Database
Zea mays L.FooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Skin microbiota)KNApSAcK Database
Serratia odoriferaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAcyloins
Alternative Parents
Substituents
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point15 °CNot Available
Boiling Point147.00 to 148.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.360The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility473 g/LALOGPS
logP-0.66ALOGPS
logP-0.14ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)13.72ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.39 m³·mol⁻¹ChemAxon
Polarizability9.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003243
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011799
KNApSAcK IDC00050424
Chemspider ID21105851
KEGG Compound IDC00466
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetoin
METLIN ID103
PubChem Compound179
PDB IDNot Available
ChEBI ID15688
Good Scents IDrw1007331
References
General References
  1. Hirooka EY, Muller EE, Freitas JC, Vicente E, Yoshimoto Y, Bergdoll MS: Enterotoxigenicity of Staphylococcus intermedius of canine origin. Int J Food Microbiol. 1988 Dec;7(3):185-91. [PubMed:3275321 ]
  2. Walker V, Mills GA: Urinary organic acid excretion by babies born before 33 weeks of gestation. Clin Chem. 1989 Jul;35(7):1460-6. [PubMed:2758593 ]
  3. Walker V, Mills GA, Hall MA, Lowes JA: Carbohydrate fermentation by gut microflora in preterm neonates. Arch Dis Child. 1989 Oct;64(10 Spec No):1367-73. [PubMed:2589871 ]
  4. Otsuka M, Ohmori S: Simple and sensitive determination of diacetyl and acetoin in biological samples and alcoholic drinks by gas chromatography with electron-capture detection. J Chromatogr. 1992 Jun 10;577(2):215-20. [PubMed:1400754 ]
  5. Bhadury D, Nolvachai Y, Marriott PJ, Tanner J, Tuck KL: Detection of Volatiles from Raw Beef Meat from Different Packaging Systems Using Solid-Phase Microextraction GC-Accurate Mass Spectrometry. Foods. 2021 Aug 27;10(9). pii: foods10092018. doi: 10.3390/foods10092018. [PubMed:34574128 ]
  6. Yuan H, Xu Y, Chen Y, Zhan Y, Wei X, Li L, Wang D, He P, Li S, Chen S: Metabolomics analysis reveals global acetoin stress response of Bacillus licheniformis. Metabolomics. 2019 Feb 20;15(3):25. doi: 10.1007/s11306-019-1492-7. [PubMed:30830499 ]