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Showing NP-Card for (2E,4E)-2,4-Hexadienoic acid (NP0141346)

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Record Information
Version1.0
Created at2022-07-19 21:26:14 UTC
Updated at2022-07-19 21:34:40 UTC
NP-MRD IDNP0141346
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2E,4E)-2,4-Hexadienoic acid
Description(2E,4E)-2,4-Hexadienoic acid, also known as (e,e)-sa or (e,e)-2,4-hexadienoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms (2E,4E)-2,4-Hexadienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Antimicrobial agent against a wide variety of microorganisms, especies yeasts and moulds. Preservative action more efficient in acidic foods (2E,4E)-2,4-Hexadienoic acid is a bland tasting compound. Outside of the human body, (2E,4E)-2,4-Hexadienoic acid is a potentially toxic compound. Preservative for many foodstuffs. Generally used as K salt or (less frequently) as Ca salt. These are fatty acids whose chain contains at least one CC double bond (2E,4E)-2,4-Hexadienoic acid belongs to the family of Unsaturated Fatty Acids. (2E,4E)-2,4-Hexadienoic acid is found in Foeniculum vulgare, Prunus domestica and Schisandra chinensis. It was first documented in 1994 (PMID: 7979442). Typical usage levels 500-2000 ppm (PMID: 11413487) (PMID: 16902246) (PMID: 20544305) (PMID: 11206806).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0141346 ((2E,4E)-2,4-Hexadienoic acid)


  Mrv0541 02241219072D          

  8  7  0  0  0  0            999 V2000
    0.7132   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279    0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for NP0141346 ((2E,4E)-2,4-Hexadienoic acid)

     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -3.0188   -0.4952    0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192   -0.6067    0.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7525    0.1262   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974    0.0046   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948    0.7213   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9484    0.6052   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7151    1.2746   -1.4540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982   -0.2961    0.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561   -0.1223   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876    0.2577    1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5037   -1.4683    0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202   -1.2882    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752    0.8289   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1568   -0.6899    0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    1.4101   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1283   -0.2621    1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  8 16  1  0
M  END
Download

3D SDF for NP0141346 ((2E,4E)-2,4-Hexadienoic acid)


  Mrv0541 02241219072D          

  8  7  0  0  0  0            999 V2000
    0.7132   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279    0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0141346

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+

> <INCHI_KEY>
WSWCOQWTEOXDQX-MQQKCMAXSA-N

> <FORMULA>
C6H8O2

> <MOLECULAR_WEIGHT>
112.1265

> <EXACT_MASS>
112.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
11.79749525845454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E)-hexa-2,4-dienoic acid

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
1.4467979606666663

> <ALOGPS_LOGS>
-0.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.007006715873307

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
33.2835

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sorbic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0141346 ((2E,4E)-2,4-Hexadienoic acid)

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PDB for NP0141346 ((2E,4E)-2,4-Hexadienoic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.331  -1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.668  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.000  -1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.665  -0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.000  -1.154   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.665   1.154   0.000  0.00  0.00           O+0
CONECT    1    6    2                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0141346 ((2E,4E)-2,4-Hexadienoic acid)
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SMILES for NP0141346 ((2E,4E)-2,4-Hexadienoic acid)
C\C=C\C=C\C(O)=O
Download
INCHI for NP0141346 ((2E,4E)-2,4-Hexadienoic acid)
InChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+
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View in JSmol
Synonyms
ValueSource
(e,e)-1,3-Pentadiene-1-carboxylic acidChEBI
(e,e)-2,4-Hexadienoic acidChEBI
(e,e)-SAChEBI
(e,e)-Sorbic acidChEBI
1,3-Pentadiene-1-carboxylic acidChEBI
alpha-trans-gamma-trans-Sorbic acidChEBI
SAChEBI
trans,trans-2,4-Hexadienoic acidChEBI
trans,trans-SAChEBI
trans,trans-Sorbic acidChEBI
(e,e)-1,3-Pentadiene-1-carboxylateGenerator
(e,e)-2,4-HexadienoateGenerator
(e,e)-SorbateGenerator
1,3-Pentadiene-1-carboxylateGenerator
a-trans-g-trans-SorbateGenerator
a-trans-g-trans-Sorbic acidGenerator
alpha-trans-gamma-trans-SorbateGenerator
Α-trans-γ-trans-sorbateGenerator
Α-trans-γ-trans-sorbic acidGenerator
trans,trans-2,4-HexadienoateGenerator
trans,trans-SorbateGenerator
(2E,4E)-2,4-HexadienoateGenerator
SorbateHMDB
(2-Butenylidene)-acetic acidHMDB
(2-Butenylidene)acetic acidHMDB
(2E,4E)-Hexa-2,4-dienoic acidHMDB
2, 4-Hexadienoic acid potassium saltHMDB
2,4-Hexadienoic acidHMDB
2-Propenylacrylic acidHMDB
2E,4E-Hexadienoic acidHMDB
Acidum sorbicumHMDB
alpha-trans-Laquo gammaraquo -trans-sorbic acidHMDB
Crotylidene acetic acidHMDB
Crotylidene-acetic acidHMDB
FEMA 3921HMDB
Hexa-2,4-dienoic acidHMDB
Hexadienic acidHMDB
Hexadienoic acidHMDB
Hexadienoic acid, (e,e)HMDB
Hexadienoic acid1,3-pentadiene-1-carboxylic acidHMDB
PanosorbHMDB
PreservastatHMDB
Sorbic acid (NF)HMDB
Sorbic acid, potassium saltHMDB
SorbistatHMDB
trans-trans-2,4-Hexadienoic acidHMDB
(2E,4E)-2,4-Hexadienoic acidChEBI
Acid, sorbicMeSH
Sorbate, sodiumMeSH
Sorbate, potassiumMeSH
Acid, propenylacrylicMeSH
Potassium sorbateMeSH
Sodium sorbateMeSH
Acid, hexadienoicMeSH
Propenylacrylic acidMeSH
Chemical FormulaC6H8O2
Average Mass112.1265 Da
Monoisotopic Mass112.05243 Da
IUPAC Name(2E,4E)-hexa-2,4-dienoic acid
Traditional Namesorbic acid
CAS Registry NumberNot Available
SMILES
C\C=C\C=C\C(O)=O
InChI Identifier
InChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+
InChI KeyWSWCOQWTEOXDQX-MQQKCMAXSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-07-19View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-07-19View Spectrum
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
Foeniculum vulgareLOTUS Database
Prunus domesticaLOTUS Database
Schisandra chinensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentMedium-chain fatty acids  
Alternative Parents
Substituents
  • Medium-chain fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Straight chain fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • 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
logP1.77ALOGPS
logP1.45ChemAxon
logS-0.81ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.28 m³·mol⁻¹ChemAxon
Polarizability11.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029581  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000738  
KNApSAcK IDNot Available
Chemspider ID558605  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSorbic acid  
METLIN IDNot Available
PubChem Compound643460  
PDB IDNot Available
ChEBI ID38358  
Good Scents IDNot Available
References
General References
  1. Morrow JD, Minton TA, Awad JA, Roberts LJ: Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans following the application of sorbic acid. Arch Dermatol. 1994 Nov;130(11):1408-12. [PubMed:7979442  ] 
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  4. Guo YJ, Pan ZZ, Chen CQ, Hu YH, Liu FJ, Shi Y, Yan JH, Chen QX: Inhibitory effects of fatty acids on the activity of mushroom tyrosinase. Appl Biochem Biotechnol. 2010 Nov;162(6):1564-73. doi: 10.1007/s12010-010-8938-8. Epub 2010 Jun 11. [PubMed:20544305  ] 
  5. Cigic IK, Plavec J, Mozina SS, Zupancic-Kralj L: Characterisation of sorbate geometrical isomers. J Chromatogr A. 2001 Jan 5;905(1-2):359-66. doi: 10.1016/s0021-9673(00)00996-1. [PubMed:11206806  ]