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Showing NP-Card for 2-Hexenal (NP0002780)

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Record Information
Version2.0
Created at2020-11-23 19:40:15 UTC
Updated at2021-08-19 23:59:22 UTC
NP-MRD IDNP0002780
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hexenal
Provided ByBMRBBMRB logo
Description2-Hexenal, also known as (e)-hex-2-enal or b-propyl acrolein, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, 2-hexenal is considered to be a fatty aldehyde. 2-Hexenal is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2-Hexenal is found in Aethus indicus, Ageratum conyzoides, Aloe arborescens, Aristolochia debilis, Basella alba, Thea sinensis , Capillipedium parviflorum, Capparis spinosa, Citrus limon, Citrus sinensis, Clinopodium serpyllifolium, Dianthus caryophyllus L. , Echinophora tenuifolia, Euploea sylvester, Farfugium japonicum, Gonioctena viminalis, Lonicera japonica, Micromeria maderensis, Nelumbo nucifera, Nepeta racemosa, Origanum sipyleum, Origanum vulgare, Peristeria elata, Petasites albus , Pimenta racemosa, Quercus agrifolia, Riptortus clavatus, Robinia pseudoacacia, Salvia sclarea, Brassica hirta and Thymus longicaulis. 2-Hexenal was first documented in 2011 (PMID: 21548650). Based on a literature review a small amount of articles have been published on 2-Hexenal (PMID: 22177713) (PMID: 22417509).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002780 (2-Hexenal)


     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -3.1461   -0.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757    0.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2052    0.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652    0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7275   -0.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4424    1.2262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -1.7147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165   -0.5406    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793   -1.4184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720    1.5225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5016    1.8188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0911   -1.1220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7438    2.0663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785   -1.9021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194   -1.3095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  1  8  1  6
  1  9  1  0
  1 10  1  0
  2 11  1  1
  2 12  1  0
  3 13  1  1
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
Download

3D MOL for NP0002780 (2-Hexenal)

NP0002780
     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.7055   -0.2762    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    0.0667    0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.1293   -0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689    0.4720   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -0.3318   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    0.0300    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    1.1084    0.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -1.0594   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -0.7195    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900    0.6226   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8488   -0.6087    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287    1.0797    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.8524   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.8728   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286    1.3919    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8443   -1.2540   -0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1535   -0.6304   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
Download

3D SDF for NP0002780 (2-Hexenal)


     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -3.1461   -0.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757    0.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2052    0.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652    0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7275   -0.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4424    1.2262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -1.7147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165   -0.5406    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793   -1.4184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720    1.5225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5016    1.8188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0911   -1.1220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7438    2.0663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785   -1.9021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194   -1.3095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  1  8  1  6
  1  9  1  0
  1 10  1  0
  2 11  1  1
  2 12  1  0
  3 13  1  1
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
> <DATABASE_ID>
NP0002780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+

> <INCHI_KEY>
MBDOYVRWFFCFHM-SNAWJCMRSA-N

> <FORMULA>
C6H10O

> <MOLECULAR_WEIGHT>
98.145

> <EXACT_MASS>
98.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.572393136597263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-hex-2-enal

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.650103365

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.201821978414376

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
31.241499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(E)-2-hexenal

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002780 (2-Hexenal)

NP0002780
     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.7055   -0.2762    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    0.0667    0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.1293   -0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689    0.4720   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -0.3318   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    0.0300    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    1.1084    0.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -1.0594   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -0.7195    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900    0.6226   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8488   -0.6087    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287    1.0797    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.8524   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.8728   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286    1.3919    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8443   -1.2540   -0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1535   -0.6304   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
Download

PDB for NP0002780 (2-Hexenal)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0      -5.896   4.896   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.562   5.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.228   4.896   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.895   5.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.561   4.896   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.772   5.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.106   4.896   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    3    1                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
Download

3D PDB for NP0002780 (2-Hexenal)

COMPND    NP0002780
HETATM    1  C1  UNL     1      -2.705  -0.276   0.188  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.294   0.067   0.552  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.376   0.129  -0.663  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.969   0.472  -0.171  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.995  -0.332  -0.364  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.327   0.030   0.135  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.513   1.108   0.754  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.785  -1.059  -0.586  1.00  0.00           H  
HETATM    9  H2  UNL     1      -3.175  -0.720   1.114  1.00  0.00           H  
HETATM   10  H3  UNL     1      -3.290   0.623  -0.097  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.849  -0.609   1.311  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.329   1.080   1.043  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.738   0.852  -1.406  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.388  -0.873  -1.130  1.00  0.00           H  
HETATM   15  H8  UNL     1       1.129   1.392   0.357  1.00  0.00           H  
HETATM   16  H9  UNL     1       1.844  -1.254  -0.891  1.00  0.00           H  
HETATM   17  H10 UNL     1       4.153  -0.630  -0.027  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4   13   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7   17
END
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SMILES for NP0002780 (2-Hexenal)

CCC\C=C\C=O
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INCHI for NP0002780 (2-Hexenal)

InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+
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View in JSmol
Synonyms
ValueSource
(e)-2-HexenalChEBI
(e)-Hex--2-enalChEBI
(e)-Hex-2-enalChEBI
2-trans-HexenalChEBI
3-PropylacroleinChEBI
beta-Propyl acroleinChEBI
beta-PropylacroleinChEBI
Leaf aldehydeChEBI
trans-2-HexenalChEBI
b-Propyl acroleinGenerator
Β-propyl acroleinGenerator
b-PropylacroleinGenerator
Β-propylacroleinGenerator
Hex-2-en-1-alHMDB
2-Hexenal, eHMDB
(2E)-2-HexenalHMDB
(2E)-HexenalHMDB
(e)-2-Hexen-1-alHMDB
2-Hexen-1-alHMDB
Hex-2-enalHMDB
trans-2-Hexen-1-alHMDB
2-HexenaldehydeHMDB
3-Propyl-acroleinHMDB
Hexen-2-alHMDB
Hexen-2-en-1-alHMDB
Hexylenic aldehydeHMDB
alpha,beta-HexylenaldehydeHMDB
Α,β-hexylenaldehydeHMDB
Green leaf aldehydeHMDB
2-HexenalMeSH
Chemical FormulaC6H10O
Average Mass98.1450 Da
Monoisotopic Mass98.07316 Da
IUPAC Name(2E)-hex-2-enal
Traditional Name(E)-2-hexenal
CAS Registry NumberNot Available
SMILES
CCC\C=C\C=O
InChI Identifier
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+
InChI KeyMBDOYVRWFFCFHM-SNAWJCMRSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aethus indicusLOTUS Database
Ageratum conyzoidesLOTUS Database
Aloe arborescensLOTUS Database
Aloe arborescens var. natalensisKNApSAcK Database
Arctium lappaFooDB
Aristolochia debilisLOTUS Database
Basella albaLOTUS Database
Brassica hirtaKNApSAcK Database
Brassica oleracea var. botrytisFooDB
Camellia sinensisPlant
Cannabis sativaCannabisDB
      Not Available
Capillipedium parviflorumLOTUS Database
Capparis spinosaLOTUS Database
Citrus limonLOTUS Database
Citrus sinensisLOTUS Database
Citrus sinensis L.KNApSAcK Database
Clinopodium serpyllifoliumLOTUS Database
Cucumis sativus L.FooDB
Dianthus caryophyllusPlant
Dianthus caryophyllus L.KNApSAcK Database
Echinophora tenuifoliaLOTUS Database
Euploea sylvesterLOTUS Database
Farfugium japonicumLOTUS Database
Ginkgo bilobaFooDB
Glycine maxFooDB
Gonioctena viminalisLOTUS Database
Juglans regiaFooDB
Lonicera japonicaLOTUS Database
Malus pumilaFooDB
Mangifera indicaKNApSAcK Database
Medicago sativaKNApSAcK Database
Micromeria maderensisLOTUS Database
Myrtus communisKNApSAcK Database
Nelumbo nuciferaLOTUS Database
Nepeta racemosaLOTUS Database
Ocotea sinuataKNApSAcK Database
Olea europaeaKNApSAcK Database
Origanum onitesFooDB
Origanum sipyleumLOTUS Database
Origanum vulgareLOTUS Database
Peristeria elataLOTUS Database
Petasites albusPlant
Pimenta racemosaLOTUS Database
Polygonum minusKNApSAcK Database
Prunus aviumFooDB
    • Bernalte, M. J., Hernandez, M. T., Vidal-Aragon, M. C. & Sabio, E. (1999) Physical, chemical, fla...
Quercus agrifoliaLOTUS Database
Ribes nigrumFooDB
Riptortus clavatusLOTUS Database
Robinia pseudoacaciaLOTUS Database
Salvia sclareaLOTUS Database
Sambucus nigraFooDB
Sinapis albaPlant
Solanum lycopersicum Mill.KNApSAcK Database
Thea sinensisKNApSAcK Database
Thymus longicaulisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentMedium-chain aldehydes
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point47.00 °C. @ 17.00 mm HgThe Good Scents Company Information System
Water Solubility5261 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.790 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP1.8ALOGPS
logP1.65ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.24 m³·mol⁻¹ChemAxon
Polarizability11.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031496
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004502
KNApSAcK IDC00000351
Chemspider ID4444608
KEGG Compound IDC08497
BioCyc IDTRANS-2-HEXENAL
BiGG IDNot Available
Wikipedia LinkCis-3-Hexenal
METLIN IDNot Available
PubChem Compound5281168
PDB IDNot Available
ChEBI ID28913
Good Scents IDrw1013831
References
General References
  1. Sakamaki K, Ishizaki S, Ohkubo Y, Tateno Y, Fujita A: Identification of the medicinal off-flavor compound formed from ascorbic acid and (E)-hex-2-enal. J Agric Food Chem. 2011 Jun 22;59(12):6667-71. doi: 10.1021/jf200846h. Epub 2011 May 23. [PubMed:21548650 ]
  2. Joo MJ, Merkel C, Auras R, Almenar E: Development and characterization of antimicrobial poly(l-lactic acid) containing trans-2-hexenal trapped in cyclodextrins. Int J Food Microbiol. 2012 Feb 15;153(3):297-305. doi: 10.1016/j.ijfoodmicro.2011.11.015. Epub 2011 Nov 29. [PubMed:22177713 ]
  3. De Lucca AJ, Carter-Wientjes CH, Boue S, Bhatnagar D: Volatile trans-2-hexenal, a soybean aldehyde, inhibits Aspergillus flavus growth and aflatoxin production in corn. J Food Sci. 2011 Aug;76(6):M381-6. doi: 10.1111/j.1750-3841.2011.02250.x. [PubMed:22417509 ]