TRANS-2-HEXENAL

Iupac Name：(E)-hex-2-enal

Molecular Weight：98.143

Modify Date.: 2022-12-07 11:38

Introduction:

Trans-?2-?Hexenal can be used for the determination of low-molecular-weight carbonyl compounds which are reactive with biological nucleophiles in biological samples[1].

Liquid|Pale yellow to colourless oily liquid; Strong fruity, green, vegetable-like aroma

(2E)-hexenal is a 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices. It has a role as a flavouring agent, an antibacterial agent and a plant metabolite.

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1. Names and Identifiers

: 1.1 Name; TRANS-2-HEXENAL; 1.2 Synonyms; (2E)-2-Hexenal (2E)-hexenal (E)-2-hexanal (e)-2-hexena (E)-2-Hexenal (E)-hex-2-enal (E)-Hexenal 2-(E)-hexenal 2-Hexenal (E) 2-Hexenal, (2E)- 2-trans-Hexenal 3-propylacrolein EINECS 229-778-1 FEMA 2560 Hex-2(E)-enal HEXENAL-2 Leaf aldehyde MFCD00007008 T2 HEXENAL trans-2-HEXANAL TRANS-2-HEXEN-1-AL WITH GC trans-3-Propyalacrolein trans-Hex-2-enal VH1U4 &&E Form; View all

1.3 CAS No.: 6728-26-3

1.4 CID: 5281168

1.5 EINECS(EC#): 229-778-1

1.6 Molecular Formula: C6H10O (isomer)

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

1.8 InChIkey: MBDOYVRWFFCFHM-SNAWJCMRSA-N

1.9 Canonical Smiles: CCCC=CC=O

1.10 Isomers Smiles: CCC/C=C/C=O

2. Properties

2.1 Density: 0.846

2.1 Melting point: -78°C (estimate)

2.1 Boiling point: 146-149℃

2.1 Refractive index: 1.444-1.45

2.1 Flash Point: 35℃

2.2 Precise Quality: 98.07320

2.2 PSA: 17.07000

2.2 logP: 1.54160

2.2 VaporDensity: 3.4 (vs air)

2.3 Appearance: Liquid

2.4 Atmospheric OH Rate Constant: 4.40e-11 cm3/molecule*sec

2.5 Storage: 0-6°C

2.6 Chemical Properties: clear colorless to light yellow liquid

2.7 Color/Form: Clear colorless to light yellow

2.8 Water Solubility: Soluble in propylene glycol and most fixed oils; Very slightly soluble in water

2.9 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices.

4. Safety and Handling

4.1 Symbol: GHS02, GHS06

4.1 Hazard Codes: Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R10;R21/22

4.1 Safety Statements: S16;S36/37

4.1 Packing Group: III

4.1 Hazard Class: 3

4.1 Hazard Declaration: H226-H302-H311-H317

4.1 RIDADR: UN 1988

4.1 Caution Statement: P280-P312

4.1 WGK Germany: 2

4.1 RTECS: MP5900000

4.1 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MP5900000

CHEMICAL NAME :: 2-Hexenal, (E)-

CAS REGISTRY NUMBER :: 6728-26-3

BEILSTEIN REFERENCE NO. :: 1699684

LAST UPDATED :: 199709

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C6-H10-O

MOLECULAR WEIGHT :: 98.16

WISWESSER LINE NOTATION :: VH1U4 -T

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 780 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Vascular - regional or general arteriolar or venous dilation Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 180 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Vascular - regional or general arteriolar or venous dilation Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 685 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Vascular - regional or general arteriolar or venous dilation Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TEST SYSTEM :: Human

DOSE/DURATION :: 10 ppm/3D (Continuous)

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 390,161,1997

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 3

Skin sensitization, Category 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H226 Flammable liquid and vapour H302 Harmful if swallowed H311 Toxic in contact with skin H317 May cause an allergic skin reaction H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P273 Avoid release to the environment.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P391 Collect spillage.
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : liquid film

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

6728-26-3Total: 36 Synthesis Route

928-95-0 70 Suppliers

6728-26-3 113 Suppliers

Literatures:
McAllister, Graeme D.; Oswald, Magalie F.; Paxton, Richard J.; Raw, Steven A.; Taylor, Richard J.K. Tetrahedron, 2006 , vol. 62, # 28 p. 6681 - 6694
Yield: ~98%

928-94-9 23 Suppliers

6728-26-3 113 Suppliers

Literatures:
Vig; Sharma; Gupta Journal of the Indian Chemical Society, 1990 , vol. 67, # 1 p. 37 - 38
Yield: ~76%

927-77-5 31 Suppliers

6728-26-3 113 Suppliers

Literatures:
Chemische Berichte, , vol. 91, p. 1867,1876
Yield: null

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8. Precursor and Product

precursor:

28998-62-1

18318-83-7

96530-28-8

6789-80-6

85260-47-5

928-94-9

69112-21-6

20407-80-1

67746-30-9

101-33-7

928-96-1

58953-13-2

928-95-0

13419-69-7

927-77-5

View all

product :

79754-10-2

19269-28-4

13894-63-8

136954-25-1

69977-24-8

96185-13-6

27970-82-7

3208-16-0

96530-28-8

6789-80-6

51755-72-7

88015-70-7

1613-32-7

87016-08-8

99414-71-8

66-25-1

928-95-0

13419-69-7

56904-85-9

88257-43-6

3658-95-5

111-27-3

View all

9. Other Information

9.0 Usage: trans-2-Hexenal is used in evaluation of quality of protected designation of origin virgin olive oils by headspace solid-phase microextraction-gas chromatography using flame ionization detection and multivariate analysis. It was used in the multicomponent method for the determination of low-molecular-weight carbonyl compounds in biological samples.

9.1 BRN: 1699684

9.2 Descriptioin: Tans-2-Hexenal is a colorless to pale yellow clear liquid. It occurs naturally in tomatoes, banana and black tea. It gives a leafy, fruity, fatty, apple banana, strawberry note.1 It is mostly used as a flavoring agent in food. It is also used in air care products, cleaning and furnishing care products, laundry and dishwashing products.

9.3 Chemical Properties: clear colorless to light yellow liquid

9.4 Chemical Properties: (E)-2-Hexenal is the simplest straight-chain unsaturated aldehyde of interest for perfumes and flavors. It occurs in essential oils obtained from green leaves of many plants.
(E)-2-Hexenal is a colorless, sharp, herbal-green-smelling liquid with a slight acrolein-like pungency. Upon dilution, however, it smells pleasantly green and apple-like. The aldehyde can be synthesized by reacting butanal with vinyl ethyl ether in the presence of boron trifluoride, followed by hydrolysis of the reaction product with dilute sulfuric acid.
Biosynthetic methods for its production as natural flavor material have been developed.
(E)-2-Hexenal has an intense odor and is used in perfumes to obtain a green-leaf note and in fruit flavors for green nuances.

9.5 Uses: Also known as “leaf aldehyde,” it is of special interest because it is naturally present in numerous fruits and is also used as a food additive for flavoring. Feron et al. identified hexenal in about 80 different types of food.

9.6 Uses: trans-2-Hexen-1-al was used in evaluation of quality of protected designation of origin virgin olive oils by headspace solid-phase microextraction-gas chromatography using flame ionization detection and multivariate analysis. It was used in the multicomponent method for the determination of low-molecular-weight carbonyl compounds in biological samples.

9.7 Henrys Law Constant: 4.89e-05 atm-m3/mole

9.8 Mesh Entry Terms: 2-hexenal

9.9 Production: < 25,000 lb

9.10 Manufacturing Info: Food, beverage, and tobacco product manufacturing|2-Hexenal, (2E)-: ACTIVE|2-Hexenal: ACTIVE

9.11 Use Classification: Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty aldehydes [FA06]

10. Computational chemical data

Molecular Weight: 98.143g/mol
Molecular Formula: C₆H₁₀O
Compound Is Canonicalized: True
XLogP3-AA: 1.5
Exact Mass: 98.073164938
Monoisotopic Mass: 98.073164938
Complexity: 64.6
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 17.1
Heavy Atom Count: 7
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAACACggAICAAAAAACIAChSgAAAAAAgAAAICAAAAEgAAAAAAQAAAAAAgAAIAYIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What are the properties and applications of TRANS-2-HEXENAL? Mar 14 2023
TRANS-2-HEXENAL, also known as 2-Hexenal, is a colorless or pale yellow liquid at room temperature and pressure. It has a fruity aroma and is commonly used as an intermediate in organic synthesis and ..

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