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
Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1.	1997 Dec 12	9463521
Alpha,beta-unsaturated aldehydes increase glutathione S-transferase mRNA and protein: correlation with activation of the antioxidant response element.	1998 Nov 1	9799558
Cancer risk assessment for crotonaldehyde and 2-hexenal: an approach.	1999	10626223
Structural and kinetic determinants of aldehyde reduction by aldose reductase.	1999 Jan 5	9890881
Defensive chemistry of an aposematic bug, Pachycoris stallii Uhler and volatile compounds of its host plant Croton californicus Muell.-Arg.	2001 Feb	14768810
Characterization of the glutathione binding site of aldose reductase.	2001 Jan 30	11306073
Selective protection by stably transfected human ALDH3A1 (but not human ALDH1A1) against toxicity of aliphatic aldehydes in V79 cells.	2001 Jan 30	11306050
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 Nov 2	11524419
[Effect of N-oxidized pyridine derivatives on lipid peroxidation in the livers of rats].	2003	12669519
Modulating carbonyl cytotoxicity in intact rat hepatocytes by inhibiting carbonyl-metabolizing enzymes. I. Aliphatic alkenals.	2003 Feb 1	12604195
Volatile components and aroma active compounds in aqueous essence and fresh pink guava fruit puree (Psidium guajava L.) by GC-MS and multidimensional GC/GC-O.	2003 Feb 26	12590492
Volatiles from leaves, fruits, and virgin oil from Olea europaea Cv. Olivastra Seggianese from Italy.	2003 Feb 26	12590485
The olfactory responses of the antenna and maxillary palp of the fleshfly, Neobellieria bullata (Diptera: Sarcophagidae), and their sensitivity to blockage of nitric oxide synthase.	2003 Mar	12770002
Volatile fractions from three cultivars of Olea europaea L. collected in two different seasons.	2003 Mar 26	12643664
Thermodynamic study of two different chewing-gum bases by inverse gas chromatography.	2003 May 9	12830920
Analysis of a model reaction system containing cysteine and (E)-2-methyl-2-butenal, (E)-2-hexenal, or mesityl oxide.	2003 Nov 19	14611186
Characterization of a hydroperoxide lyase gene and effect of C6-volatiles on expression of genes of the oxylipin metabolism in Citrus.	2003 Oct	14610891
Alpha,beta-unsaturated carbonyl compounds: induction of oxidative DNA damage in mammalian cells.	2003 Sep	12960416
Investigation of long-range female sex pheromone of the European tarnished plant bug, Lygus rugulipennis: chemical, electrophysiological, and field studies.	2004 Aug	15537156
Aroma extract dilution analysis of cv. Meeker (Rubus idaeus L.) red raspberries from Oregon and Washington.	2004 Aug 11	15291490
EAG and behavioral responses of Helicoverpa armigera males to volatiles from poplar leaves and their combinations with sex pheromone.	2004 Dec	15547967
cis-3-Hexenal production in tobacco is stimulated by 16-carbon monounsaturated fatty acids.	2004 Jan	14732275
Stereochemical course of the generation of 3-mercaptohexanal and 3-mercaptohexanol by beta-lyase-catalyzed cleavage of cysteine conjugates.	2004 Jan 14	14709022
Electrophysiological characterisation of olfactory sensilla in the black bean aphid, Aphis fabae.	2004 Jul	15234625
Off-vine grape drying effect on volatile compounds and aromatic series in must from Pedro Ximénez grape variety.	2004 Jun 16	15186115
[New derivatives of triazino- and imidazoindole with hepatoprotective activity].	2004 May-Jun	15354541
Electroantennogram responses of the three migratory forms of the damson-hop aphid, Phorodon humuli, to aphid pheromones and plant volatiles.	2004 Nov	15607511
Enhancement of attraction to sex pheromones of Spodoptera exigua by volatile compounds produced by host plants.	2004 Oct	15609835
Some unusual minor volatile components of tomato.	2004 Oct 6	15453697
Stimulation of the lipoxygenase pathway is associated with systemic resistance induced in bean by a nonpathogenic Pseudomonas strain.	2004 Sep	15384491
A simple and efficient system for green note compound biogenesis by use of certain lipoxygenase and hydroperoxide lyase sources.	2005 Aug 24	16104814
Rapid determination of C6-aldehydes in tomato plant emission by gas chromatography-mass spectrometry and solid-phase microextraction with on-fiber derivatization.	2005 Feb	15754825
Screening for key odorants in Moroccan green olives by gas chromatography-olfactometry/aroma extract dilution analysis.	2005 Feb 23	15713037
How rainfall, relative humidity and temperature influence volatile emissions from apple trees in situ.	2005 Jul	15949824
Volatile C6-aldehydes and Allo-ocimene activate defense genes and induce resistance against Botrytis cinerea in Arabidopsis thaliana.	2005 Jul	15879447
Effect of soybean lipoxygenase on volatile generation and inhibition of Aspergillus flavus mycelial growth.	2005 Jun 15	15941315
Further field evaluation of synthetic herbivore-induced plant volatiles as attractants for beneficial insects.	2005 Mar	15898496
[Analysis and identification of Liriomyza sativae-attractants from cowpea and kidney bean volatiles].	2005 May	16110669
Carcinogenic potential of trans-2-hexenal is based on epigenetic effect.	2005 May-Jun	15875776
Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.	2005 Oct	15936080
The involvement of volatile infochemicals from spider mites and from food-plants in prey location of the generalist predatory mite Neoseiulus californicus.	2005 Sep	16132210
Analysis of volatile compounds from various types of barley cultivars.	2005 Sep 21	16159182
Influence of rearing conditions on the volatile compounds of cooked fillets of Silurus glanis (European catfish).	2005 Sep 7	16131131
Comet fluorescence in situ hybridization analysis for oxidative stress-induced DNA damage in colon cancer relevant genes.	2007 Apr	17192441
Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress.	2009 Mar 16	18845131
Effects of environmental novelty on fear-related behavior and stress responses of rats to emotionally relevant odors.	2009 May 16	19103229
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.	2010 Sep	20491607
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 Jul 6	21515296
Human aldo-keto reductases 1B1 and 1B10: a comparative study on their enzyme activity toward electrophilic carbonyl compounds.	2011 May 30	21329684
Murine hepatic aldehyde dehydrogenase 1a1 is a major contributor to oxidation of aldehydes formed by lipid peroxidation.	2011 May 30	21256123

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

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

(E)-2-HEXEN-1-AL

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