2-HEXENAL, (2E)-

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10O
Molecular Weight	98.143
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC\C=C\C=O

InChI

InChIKey=MBDOYVRWFFCFHM-SNAWJCMRSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30614691 | https://www.ncbi.nlm.nih.gov/pubmed/28048941

2-Hexenal belongs to the aldehyde and exists in two isomeric forms: cis (Z) and greater importance form, trans (E). Trans-2-hexenal was studied as a potential antifungal compound that can inhibits Aspergillus flavus Spore Germination. The inhibition takes place by the disruption of mitochondrial energy metabolism and the induction of early apoptosis. Besides, trans-2-hexenal can be an alternative fumigation agent for controlling M. incognita on tomato crops. Botanical nematicides have recently received increasing interest because of the high risks of some traditional nematicides to human health and the environment.

Approval Year

PubMed

Title	Date	PubMed
Mixture of cis-3-hexenol and trans-2-hexenal attenuates behavioral and stress responses induced by 2,5-dihydro-2,4,5-trimethylthiazoline and electric footshock stress in rats.	2011-07-06	21515296
Human aldo-keto reductases 1B1 and 1B10: a comparative study on their enzyme activity toward electrophilic carbonyl compounds.	2011-05-30	21329684
Murine hepatic aldehyde dehydrogenase 1a1 is a major contributor to oxidation of aldehydes formed by lipid peroxidation.	2011-05-30	21256123
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.	2010-09	20491607
Effects of environmental novelty on fear-related behavior and stress responses of rats to emotionally relevant odors.	2009-05-16	19103229
Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress.	2009-03-16	18845131
Comet fluorescence in situ hybridization analysis for oxidative stress-induced DNA damage in colon cancer relevant genes.	2007-04	17192441
Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.	2005-10	15936080
Analysis of volatile compounds from various types of barley cultivars.	2005-09-21	16159182
Influence of rearing conditions on the volatile compounds of cooked fillets of Silurus glanis (European catfish).	2005-09-07	16131131
The involvement of volatile infochemicals from spider mites and from food-plants in prey location of the generalist predatory mite Neoseiulus californicus.	2005-09	16132210
A simple and efficient system for green note compound biogenesis by use of certain lipoxygenase and hydroperoxide lyase sources.	2005-08-24	16104814
How rainfall, relative humidity and temperature influence volatile emissions from apple trees in situ.	2005-07	15949824
Volatile C6-aldehydes and Allo-ocimene activate defense genes and induce resistance against Botrytis cinerea in Arabidopsis thaliana.	2005-07	15879447
Effect of soybean lipoxygenase on volatile generation and inhibition of Aspergillus flavus mycelial growth.	2005-06-15	15941315
Carcinogenic potential of trans-2-hexenal is based on epigenetic effect.	2005-05-07	15875776
[Analysis and identification of Liriomyza sativae-attractants from cowpea and kidney bean volatiles].	2005-05	16110669
Further field evaluation of synthetic herbivore-induced plant volatiles as attractants for beneficial insects.	2005-03	15898496
Screening for key odorants in Moroccan green olives by gas chromatography-olfactometry/aroma extract dilution analysis.	2005-02-23	15713037
Rapid determination of C6-aldehydes in tomato plant emission by gas chromatography-mass spectrometry and solid-phase microextraction with on-fiber derivatization.	2005-02	15754825
EAG and behavioral responses of Helicoverpa armigera males to volatiles from poplar leaves and their combinations with sex pheromone.	2004-12	15547967
Electroantennogram responses of the three migratory forms of the damson-hop aphid, Phorodon humuli, to aphid pheromones and plant volatiles.	2004-11	15607511
Some unusual minor volatile components of tomato.	2004-10-06	15453697
Enhancement of attraction to sex pheromones of Spodoptera exigua by volatile compounds produced by host plants.	2004-10	15609835
[New derivatives of triazino- and imidazoindole with hepatoprotective activity].	2004-09-10	15354541
Stimulation of the lipoxygenase pathway is associated with systemic resistance induced in bean by a nonpathogenic Pseudomonas strain.	2004-09	15384491
Identification of a specific isoform of tomato lipoxygenase (TomloxC) involved in the generation of fatty acid-derived flavor compounds.	2004-09	15347800
Aroma extract dilution analysis of cv. Meeker (Rubus idaeus L.) red raspberries from Oregon and Washington.	2004-08-11	15291490
Investigation of long-range female sex pheromone of the European tarnished plant bug, Lygus rugulipennis: chemical, electrophysiological, and field studies.	2004-08	15537156
Transient release of oxygenated volatile organic compounds during light-dark transitions in Grey poplar leaves.	2004-08	15299129
Hydroperoxide-lyase activity in mint leaves. Volatile C6-aldehyde production from hydroperoxy-fatty acids.	2004-07-01	15196770
Electrophysiological characterisation of olfactory sensilla in the black bean aphid, Aphis fabae.	2004-07	15234625
Variation of the essential oil content and composition in leaves from cultivated plants of Hypericum androsaemum L.	2004-06-19	15202597
Off-vine grape drying effect on volatile compounds and aromatic series in must from Pedro Ximénez grape variety.	2004-06-16	15186115
Formation of volatile compounds in model experiments with crude leek (Allium ampeloprasum Var. Lancelot) enzyme extract and linoleic acid or linolenic acid.	2004-04-21	15080639
[Attraction effect of main volatile components from tea shoots and flowers on Sphaerophoria menthastri (Diptera: Syrphidae) and Chrysopa septempunctata (Neuroptera: Chrysopidae)].	2004-04	15334958
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.	2004-03-24	15030218
The "heterolytic hydroperoxide lyase" is an isomerase producing a short-lived fatty acid hemiacetal.	2004-02-27	14984738
Volatile constituents from the leaves of Callicarpa japonica Thunb. and their antibacterial activities.	2004-02-25	14969531
Stereochemical course of the generation of 3-mercaptohexanal and 3-mercaptohexanol by beta-lyase-catalyzed cleavage of cysteine conjugates.	2004-01-14	14709022
cis-3-Hexenal production in tobacco is stimulated by 16-carbon monounsaturated fatty acids.	2004-01	14732275
Cardiac toxic effects of trans-2-hexenal are mediated by induction of cardiomyocyte apoptotic pathways.	2003	14734831
Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. A new role for leukotriene B4 12-hydroxydehydrogenase/15-oxoprostaglandin 13-reductase.	2001-11-02	11524419
Defensive chemistry of an aposematic bug, Pachycoris stallii Uhler and volatile compounds of its host plant Croton californicus Muell.-Arg.	2001-02	14768810
Characterization of the glutathione binding site of aldose reductase.	2001-01-30	11306073
Selective protection by stably transfected human ALDH3A1 (but not human ALDH1A1) against toxicity of aliphatic aldehydes in V79 cells.	2001-01-30	11306050
Structural and kinetic determinants of aldehyde reduction by aldose reductase.	1999-01-05	9890881
Cancer risk assessment for crotonaldehyde and 2-hexenal: an approach.	1999	10626223
Alpha,beta-unsaturated aldehydes increase glutathione S-transferase mRNA and protein: correlation with activation of the antioxidant response element.	1998-11-01	9799558
Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1.	1997-12-12	9463521

Patents

Sample Use Guides

In Vitro Use Guide

sublethal doses of ( E)-2-hexenal disturbed pyruvate metabolism and reduced the intracellular soluble protein content of A. flavus spores during the early stage of germination, and MIC treatment decreased acetyl-CoA and ATP contents by 65.7 ± 3.7% and 53.9 ± 4.0% ( P < 0.05), respectively.

Name

Type

Language

2-HEXENAL, (2E)-

Systematic Name

English

(E)-2-HEXEN-1-AL

Preferred Name

English

LEAF ALDEHYDE

Common Name

English

2-HEXENAL [FHFI]

Common Name

English

(E)-2-HEXEN-1-AL [FCC]

Common Name

English

(2E)-HEXENAL

Systematic Name

English

2-HEXENAL

Systematic Name

English

TRANS-2 HEXENAL

Systematic Name

English

.ALPHA.-.BETA.-HEXYLENEALDEHYDE

Common Name

English

HEXEN-2-AL

Systematic Name

English

2-HEXENAL, TRANS-

Systematic Name

English

2-HEXENAL, (E)-

Systematic Name

English

GREEN LEAF ALDEHYDE

Common Name

English

TRANS-2-HEXENAL

Systematic Name

English

.BETA.-PROPYL ACROLEIN

Systematic Name

English

(2E)-2-HEXENAL

Systematic Name

English

TRANS-2-HEXEN-1-AL

Systematic Name

English

FEMA NO. 2560

Code

English

(E)-2-HEXENAL

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 172.515