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Showing NP-Card for Diacetone alcohol (NP0045135)

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Record Information
Version2.0
Created at2022-03-10 18:58:34 UTC
Updated at2022-03-10 22:20:26 UTC
NP-MRD IDNP0045135
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiacetone alcohol
DescriptionDiacetone alcohol, sometimes referred to as DAA, belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. Diacetone alcohol is an organic compound with the chemical formula CH3C(O)CH2C(OH)(CH3)2. Diacetone alcohol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a colorless liquid, used as a solvent and a common synthetic intermediate used for the preparation of other compounds. Diacetone alcohol is found in the highest concentration in cow milk but it has also been detected, not quantified, in several different foods, such as fruits, mung beans, papaya, and soybeans Diacetone alcohol has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ). Diacetone alcohol is commercially used in cellulose ester lacquers, particularly of the brushing type, where it produces brilliant gloss and a hard film and where its lack of odor is desirable. It is used in lacquer thinners, dopes, wood stains, wood preservatives and printing pastes, in coating compositions for paper and textiles, permanent markers, in making artificial silk and leather, in imitation gold leaf, in celluloid cements, as a preservative for animal tissue, in metal cleaning compounds, in the manufacture of photographic film, and in hydraulic brake fluids, where it is usually mixed with an equal volume of castor oil.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045135 (Diacetone alcohol)


  Mrv1652303202019012D          

  8  7  0  0  0  0            999 V2000
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    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
    2.2539    0.8250    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
  5  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
M  END
Download

3D MOL for NP0045135 (Diacetone alcohol)

     RDKit          3D

 20 19  0  0  0  0  0  0  0  0999 V2000
    2.3521    0.0639    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4503   -0.6444   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6658   -1.8210   -0.7431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3028    0.0515   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959    0.1792   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -1.1355    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341    1.1868    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015    0.7407   -1.0176 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9597   -0.1319    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3935   -0.3528    0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014    1.1539    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -0.4468   -2.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5732    1.0898   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0505   -2.0082   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1558   -1.3298    1.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403   -1.1667    0.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1788    0.8726    1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3637    2.1308    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7690    1.4316    1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437    0.1363   -1.7900 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  1  0
  5  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  6 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
M  END
Download

3D SDF for NP0045135 (Diacetone alcohol)


  Mrv1652303202019012D          

  8  7  0  0  0  0            999 V2000
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    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
    2.2539    0.8250    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
  5  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045135

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3

> <INCHI_KEY>
SWXVUIWOUIDPGS-UHFFFAOYSA-N

> <FORMULA>
C6H12O2

> <MOLECULAR_WEIGHT>
116.1583

> <EXACT_MASS>
116.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
12.756689577594068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-4-methylpentan-2-one

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
0.22319619166666715

> <ALOGPS_LOGS>
0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.683655977286275

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.21409238536788

> <JCHEM_PKA_STRONGEST_BASIC>
-2.704592899158584

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
31.653399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diacetone alcohol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045135 (Diacetone alcohol)

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PDB for NP0045135 (Diacetone alcohol)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.207   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    5    6                                                       
CONECT    5    1    4    7                                                  
CONECT    6    2    3    4    8                                             
CONECT    7    5                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0045135 (Diacetone alcohol)
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SMILES for NP0045135 (Diacetone alcohol)
CC(=O)CC(C)(C)O
Download
INCHI for NP0045135 (Diacetone alcohol)
InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
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View in JSmol
Synonyms
ValueSource
2-Methyl-2-pentanol-4-oneChEBI
4-Hydroxy-2-keto-4-methylpentaneChEBI
4-Hydroxy-4-methyl-2-pentanoneChEBI
4-Hydroxy-4-methylpentan-2-oneChEBI
AcetonyldimethylcarbinolChEBI
DiacetonalkoholChEBI
Diacetone-alcoolChEBI
Diacetonyl alcoholChEBI
Dimethyl acetonyl carbinolChEBI
(CH3)2C(OH)CH2C(O)CH3HMDB
2-Hydroxy-2-methyl-4-pentanoneHMDB
2-Methyl-3-pentanol-4-oneHMDB
4-Hydroxy-4-methyl pentan-2-oneHMDB
4-Hydroxy-4-methyl-pentan-2-ONHMDB
4-Hydroxy-4-methylpentanoneHMDB
4-Hydroxy-4-methylpentanone-2HMDB
4-Idrossi-4-metil-pentan-2-oneHMDB
4-Methyl-2-pentanon-4-olHMDB
4-Methyl-4-hydroxy-2-pentanoneHMDB
DiacetonalcoholHMDB
DiacetonalcoolHMDB
DiacetoneHMDB
DiacetonealcoolHMDB
Diketone alcoholHMDB
Hydroxy-4-methyl-2-pentanoneHMDB
PyrantonHMDB
Pyranton aHMDB
PyratonHMDB
TyrantonHMDB
Diacetone alcoholMeSH
Chemical FormulaC6H12O2
Average Mass116.1583 Da
Monoisotopic Mass116.08373 Da
IUPAC Name4-hydroxy-4-methylpentan-2-one
Traditional Namediacetone alcohol
CAS Registry Number123-42-2
SMILES
CC(=O)CC(C)(C)O
InChI Identifier
InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
InChI KeySWXVUIWOUIDPGS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Angelica gigasLOTUS Database
Asarum canadenseLOTUS Database
Bistorta manshuriensisLOTUS Database
Cannabis sativaNULL
      Not Available
Carica papaya L.FooDB
Glycine maxFooDB
Glycyrrhiza glabraLOTUS Database
Gossypium hirsutumLOTUS Database
Jasminum sambacLOTUS Database
Nelumbo nuciferaLOTUS Database
Rubus arcticusPlant
Streptomyces globisporusLOTUS Database
Streptomyces olivaceusLOTUS Database
Tamarix aphyllaLOTUS Database
Vigna radiataFooDB
Vitis viniferaLOTUS Database
Xylopia parvifloraPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentBeta-hydroxy ketones  
Alternative Parents
Substituents
  • Beta-hydroxy ketone
    • 

  • Tertiary alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • 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
logP0.04ALOGPS
logP0.22ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)15.21ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity31.65 m³·mol⁻¹ChemAxon
Polarizability12.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031511  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008104  
KNApSAcK IDNot Available
Chemspider ID13838151  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiacetone_alcohol  
METLIN IDNot Available
PubChem Compound31256  
PDB IDNot Available
ChEBI ID55381  
Good Scents IDNot Available
References
General References
  1. Gouinguene SP, Stadler E: Oviposition in Delia platura (Diptera, Anthomyiidae): the role of volatile and contact cues of bean. J Chem Ecol. 2006 Jul;32(7):1399-413. doi: 10.1007/s10886-006-9058-3. Epub 2006 May 23. [PubMed:16718565  ] 
  2. Kitulagodage M, Astheimer LB, Buttemer WA: Diacetone alcohol, a dispersant solvent, contributes to acute toxicity of a fipronil-based insecticide in a passerine bird. Ecotoxicol Environ Saf. 2008 Oct;71(2):597-600. doi: 10.1016/j.ecoenv.2007.11.001. Epub 2007 Dec 21. [PubMed:18155147  ] 
  3. Finidori-Logli V, Bagneres AG, Clement JL: Role of plant volatiles in the search for a host by parasitoidDiglyphus isaea (Hymenoptera: Eulophidae). J Chem Ecol. 1996 Mar;22(3):541-58. doi: 10.1007/BF02033654. [PubMed:24227491  ]