Identification	Physical Data	Spectra
Route of Synthesis (ROS)	Safety and Hazards	Other Data

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Identification

Product Name	(E,E)-2,4-Hexadienal
IUPAC Name	(2E,4E)-hexa-2,4-dienal
Molecular Structure
CAS Registry Number	142-83-6
EINECS Number	205-564-3
MDL Number	MFCD00007004
Beilstein Registry Number	1698401
Synonyms	trans,trans-2,4-Hexadienal, 2,4-Hexadienal, trans,trans-2,4-hexadienal;CAS Number: 142-83-6
Molecular Formula	C6H8O
Molecular Weight	96.12
InChI	InChI=1S/C6H8O/c1-2-3-4-5-6-7/h2-6H,1H3/b3-2+,5-4+
InChI Key	BATOPAZDIZEVQF-MQQKCMAXSA-N
Canonical SMILES	C/C=C/C=C/C=O

Patent Information
Patent ID	Title	Publication Date
US2018/305276	METHOD FOR PRODUCING 2,4-DIENAL ACETAL COMPOUND AND 2,4-DIENAL COMPOUND	2018
CN106256816	A α, β – unsaturated carbonyl compound isomer E – Z – isomer of preparation (by machine translation)	2016
EP2832233	1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents	2015
WO2003/95403	POLYUNSATURATED LINEAR ALDEHYDES AND THEIR DERIVATIVES WITH ANTI-RADICAL AND ANTI-TUMORAL ACTIVITY	2003
US4073813	Process for the preparation of unsaturated alcohols	1978

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Physical Data

Appearance	Yellow to red liquid
Solubility	It is Insoluble in water, but soluble in ethanol.
Boiling Point	69 °C20 mm Hg(lit.)
Refractive index	1.5560 (estimate)
Sensitivity	Air Sensitive

Melting Point, °C

-18

-17.5 – -16.5

Boiling Point, °C	Pressure (Boiling Point), Torr
60
75 – 76	30
33 – 34	0.3
68 – 68.5	20
47 – 47.5	7
173 – 174	754

Density, g·cm-3	Reference Temperature, °C	Measurement Temperature, °C
173 – 174	20	20
0.9087	0	22

Refractive Index	Wavelength (Refractive Index), nm	Temperature (Refractive Index), °C
1.5346		20
1.5391	589	20.5
1.5367	589	27
1.5425	589	20
1.5372	589	22

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Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Coupling Nuclei	Solvents (NMR Spectroscopy)	Frequency (NMR Spectroscopy), MHz	Original Text (NMR Spectroscopy)
Chemical shifts, Spectrum	1H		chloroform-d1	400
Chemical shifts	1H		chloroform-d1	500	1H-NMR (500 MHz, CDCl3): δ=1.92 (3H, d, J=5.2 Hz), 6.06 (1H, dd, J=7.9, 15.4 Hz), 6.18-6.44 (2H, m), 7.00-7.16 (1H, m), 9.54 (1H, d, J=7.9 Hz) ppm
Chemical shifts	1H			399.9
Chemical shifts	1H		CDCl3	400
	1H	1H	CDCl3	400
Chemical shifts	13C		CDCl3	100
Spectrum	1H		CDCl3	400
Chemical shifts	1H		CD2Cl2
Chemical shifts	13C		pentane
Chemical shifts	13C		triethylamine
Chemical shifts	13C		dimethylsulfoxide-d6
Chemical shifts	1H		CD3CN

Description (IR Spectroscopy)	Solvent (IR Spectroscopy)	Comment (IR Spectroscopy)
Bands	neat liquid
Bands	KBr	1682 cm**(-1)
Spectrum	neat (no solvent)	3100 – 50 cm**(-1)
Bands	CCl4	3035 – 298 cm**(-1)
Bands	neat (no solvent)	1680 – 1600 cm**(-1)
Spectrum	CHCl3	2000 – 1429 cm**(-1)

Description (Mass Spectrometry)

gas chromatography mass spectrometry (GCMS), electron impact (EI), spectrum

gas chromatography mass spectrometry (GCMS), electron impact (EI), IT (ion trap), spectrum

spectrum

Description (UV/VIS Spectroscopy)	Solvent (UV/VIS Spectroscopy)	Comment (UV/VIS Spectroscopy)	Absorption Maxima (UV/VIS), nm	Ext./Abs. Coefficient, l·mol-1cm-1
Spectrum	gas
Absorption cross-section		gas
Absorption maxima	ethanol		271
Spectrum	various solvent(s)	500-200nm
Spectrum	diethyl ether, 2-methyl-butane	500 – 200 nm, Ratio of solvents: 5:5:2(alcohol)
Absorption maxima	various solvent(s)		253
Absorption maxima	diethyl ether, 2-methyl-butane	Ratio of solvents: 5:5:2(alcohol)	267	31900
Absorption maxima	2,2,4-trimethyl-pentane		261

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Route of Synthesis (ROS)

Conditions	Yield
With oxygen; Pd561phen60(OAc)180 In acetic acid at 60℃; for 2h;	100%
With (1,10-phenanthrolino)2-tetrapalladium(CO)(acetate)4; oxygen In benzene at 50℃; for 24h;	96%
With 1,4-diaza-bicyclo[2.2.2]octane; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; oxygen; 1,3-di(4-pyridyl)propane; copper(II) perchlorate In dimethyl sulfoxide at 20℃; under 760 Torr; for 2h;	85%

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Safety and Hazards

Pictogram(s)
Signal	Danger
GHS Hazard Statements	H226 (100%): Flammable liquid and vapor [Warning Flammable liquids] H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal] H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin] Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement Codes	P210, P233, P240, P241, P242, P243, P261, P264, P270, P272, P280, P301+P312, P302+P352, P303+P361+P353, P312, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P370+P378, P403+P235, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

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Other Data

Transportation	Class 6.1(8); Packaging Group: III; UN Number: 2922
	Under the room temperature and away from light
HS Code	291219
Storage	Under the room temperature and away from light
Shelf Life	2 years
Market Price	USD

Druglikeness
Lipinski rules component
Molecular Weight	96.1289
logP	1.511
HBA	1
HBD	0
Matching Lipinski Rules	4
Veber rules component
Polar Surface Area (PSA)	17.07
Rotatable Bond (RotB)	2
Matching Veber Rules	2

Bioactivity

In vitro: Efficacy

Quantitative Results

pX	Parameter	Value (qual)	Value (quant)	Unit	Target
10.5	amount		30 – 60	pM
4.28	activation percentage(relative to standard agonist)		108.71	%	Transient receptor potential cation channel subfamily V member 1 [human]:WildTransient receptor potential cation channel subfamily A member 1 [human]:Wild
4.06	activation percentage(relative to standard agonist)		92	%	Transient receptor potential cation channel subfamily A member 1 [human]:Wild
4.02	Km (Michaelis constant)(Michaelis-Menton constant)		95.7	µM	Aldo-keto reductase family 1 member B10:Wild
	kcat(Catalytic constant)	=	82.8	min-1	Aldo-keto reductase family 1 member B10:Wild
	score(stimulation of CCK secretion)	=	0.84	no unit

Quantitative Results
1 of 8	Target	Aldo-keto reductase family 1 member B10:Wild
	Biological material	HEK293T cell line
	Assay Description	Maximum velocity of the compound towards recombinant EGFP-aldo-keto reductase family 1 B10 protein transfected into 293T cell line upon incubation in 135mM sodium phosphate (pH 7.0), 0.2mM NADPH, 1.0mM beta-mercaptoethanol, 50mM KCl at 35 degree C for 20 min
	Results	1
2 of 8	Target	Aldo-keto reductase family 1 member B10:Wild
	Biological material	HEK293T cell line
	Assay Description	Ratio of catalytic constant of the compound to that of Michaelis-Menton constant towards aldo-keto reductase family 1 B10 protein
	Results	1
3 of 8	Biological material	human HL-60 cell line
	Assay Description	Effect : DNA adduct formation Bioassay : in vitro; RPMI 1640 medium; incub. in 5 percent CO2 atmosphere at 37 deg C for 4 h; cells incub. with or without NaBH4 on ice for 30 min; DNA-protein cross-link (DNAPC) levels determ.
4 of 8	Effect	Cytotoxic
	Assay Description	Target : Chinese hamster lung V79 fibroblasts Bioassay : cells incub. with title comp. for 1 h; cell suspension was mixed with tryphan blue solution and membrane integrity was examined microscopically
	Results	cytotoxicity (loss of membrane integrity) of cells was <15% in all incubation/post-incubation of title comp.
5 of 8	Effect	Cytotoxic
	Biological material	human Caco-2 cell line
	Assay Description	Bioassay : cells incub. with title comp. for 1 h; cell suspension was mixed with tryphan blue solution and membrane integrity was examined microscopically
	Results	viability (membrane integrity) of cells was >85% in all incubation/post-incubation of title comp.
6 of 8	Effect	Genotoxic
	Assay Description	Target : Chinese hamster lung V79 fibroblasts Bioassay : control: 0.1% DMSO; DNA migration is directly expressed as mean tail intensity (TI%); FPG: formamidopyrimidine-DNA glycosylase cells incub. with title comp. for 1 h; centrifuged, mixed with low melting agarose on slides; lysed; covered with FPG; alkaline single cell gel electrophoresis was performed; DNA damage was determined by comet assay
	Results	title comp. at 300 μmol/l caused distinct direct DNA breakage (TI% > 20) and FPG-sensitive sites became apparent, whereas at 100 μmol/l not effective; at 100 μmol/l FPG-sensitive sites was not observed; fig.
7 of 8	Effect	Oxidant
	Assay Description	Target : Chinese hamster lung V79 fibroblasts Bioassay : control: without title comp.; DTNB: NADPH/5.5′-dithiobis(2-nitribenzoic acid); tGSH: total glutathione (GSH); TNB: 5-thio-2-nitrobenzoate cells incubated with title comp. for 1 h at 37 deg C in incubation medium; centrifuged; DTNB solution added to supernatant; after addn. of glutathione reductase, TNB formation rate measured at 412 nm; tGSH determined by photometric determination of TNB
	Results	title comp. induced strong depletion of GSH levels to <20% of control during 1 h incubation; title comp. pretreated cells showed increase in tGSH (>30% of control) during 3 h post-incubation; fig.
8 of 8	Assay Description	Effect : biotransformation Target : CD-1 mouse liver microsomes Bioassay : in vitro; metabolism of title comp. tested; 50 μmol/l FeSO4; 2.0 mmol/l NADPH; phosphate buffer,pH 7.4; 37 deg C; incubated for 10 min; also in the presence of pyrazole or cyanamide; metabolites quantitated by HPLC
	Results	pyrazole significantly inhibited title comp. monoreduction and monooxidation; cyanamide did not decrease title comp. metabolism significantly

Toxicity/Safety Pharmacology

Quantitative Results

pX	Parameter	Value (qual)	Value (quant)	Unit
4.7	concentration (parameter)(LED)	=	1.9	%
1	number(Number of deaths)	Not active
	number(Number of deaths)	Active
	LD50(Lethal dose)	=	0.27	mL/kg
	LD50	=	0.3	g/kg
	number(Number of deaths)	Active
		=	74	µg/mL
		=	2.5	μM

Qualitative Results
1 of 3	Biological material	Tetrahymena pyriformis
	Assay Description	Toxic activity of compound in tetrahymena pyriformis
2 of 3	Biological material	Salmonella enterica serovar Typhimurium
	Assay Description	Mutagenicity in Salmonella typhimurium, in presence and absence of hamster liver S9 homogenate; 100-10000 ug/plate; Negative;AMES test
	Results	Mutagenicity not calculated
	Measurement	Mutagenicity
3 of 3	Effect	Cytotoxic
	Biological material	human HL-60 cell line
	Assay Description	Effect : cell viability Bioassay : in vitro; RPMI 1640 medium; incub. in 5 percent CO2 atmosphere at 37 deg C for 2-4 h; cell viability assessed by trypan blue exclusion assay

Use Pattern

(E,E)-2,4-Hexadienal CAS#: 142-83-6 as Food/food additives

(E,E)-2,4-Hexadienal CAS#: 142-83-6 in combination with 2,4-hexadien-1-ol

(E,E)-2,4-Hexadienal CAS#: 142-83-6 in combination with 2-methylbutanol

(E,E)-2,4-Hexadienal CAS#: 142-83-6 in combination with 3-methylbutanol

in combination with butyl acetate

in combination with cis-4- methyl-5-butyldihydro-2(3H)-furanone

in combination with trans-4-methyl-5-butyldihydro-2(3H)-furanone

(E,E)-2,4-Hexadienal CAS#: 142-83-6 used as an appetite-suppressing food product

cholecystokinin secretion-promoting composition

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