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Trans-2-Pentenal, also known as pentenal, is an α,β-unsaturated aldehyde that is characterized by its clear colorless to yellow liquid appearance. It has been found to increase [Ca2+] in cultured neonatal rat trigeminal ganglion (TG) neurons and has been studied for its gas-phase reactions with NO3 radicals in pure N2.

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  • 1576-87-0 Structure
  • Basic information

    1. Product Name: trans-2-Pentenal
    2. Synonyms: (2E)-2-Pentenal;(E)-2-pentenal;(E)-pent-2-enal;2-(E)-pentenal;FEMA 3218;T2 PENTENAL;TRANS-2-PENTEN-1-AL;TRANS-2-PENTENAL
    3. CAS NO:1576-87-0
    4. Molecular Formula: C5H8O
    5. Molecular Weight: 84.12
    6. EINECS: 216-414-1
    7. Product Categories: N/A
    8. Mol File: 1576-87-0.mol
  • Chemical Properties

    1. Melting Point: -101.15°C (estimate)
    2. Boiling Point: 80-81 °C160 mm Hg(lit.)
    3. Flash Point: 73 °F
    4. Appearance: Clear colorless to yellow/Liquid
    5. Density: 0.86 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 11.451mmHg at 25°C
    7. Refractive Index: n20/D 1.440-1.446(lit.)
    8. Storage Temp.: 0-6°C
    9. Solubility: N/A
    10. Water Solubility: Insoluble
    11. Sensitive: Air Sensitive
    12. BRN: 1719742
    13. CAS DataBase Reference: trans-2-Pentenal(CAS DataBase Reference)
    14. NIST Chemistry Reference: trans-2-Pentenal(1576-87-0)
    15. EPA Substance Registry System: trans-2-Pentenal(1576-87-0)
  • Safety Data

    1. Hazard Codes: Xi,F
    2. Statements: 10-36/37/38-11
    3. Safety Statements: 29-37/39-26-16
    4. RIDADR: UN 1989 3/PG 2
    5. WGK Germany: 3
    6. RTECS: SB1560000
    7. F: 10
    8. HazardClass: 3
    9. PackingGroup: II
    10. Hazardous Substances Data: 1576-87-0(Hazardous Substances Data)

1576-87-0 Usage

Uses

Used in Chemical Synthesis:
Trans-2-Pentenal is used as a chemical intermediate for the synthesis of various compounds due to its reactive α,β-unsaturated aldehyde functional group. This makes it a versatile building block in the creation of complex organic molecules.
Used in Pharmaceutical Research:
In the field of pharmaceutical research, trans-2-Pentenal is utilized as a starting material for the development of new drugs, particularly those targeting the nervous system. Its ability to increase [Ca2+] in neurons suggests potential applications in the treatment of neurological disorders.
Used in Material Science:
Trans-2-Pentenal's reactive nature also makes it a candidate for use in material science, where it can be employed in the development of new polymers and other advanced materials with specific properties.
Used in Environmental Chemistry:
The study of gas-phase reactions of NO3 radicals with pentenal contributes to the understanding of atmospheric chemistry and pollution control. This knowledge can be applied in the development of strategies to mitigate air pollution and its effects on human health and the environment.

Safety Profile

Mutation data reported. When heated to decompositionit emits acrid smoke and irritating vapors.

Check Digit Verification of cas no

The CAS Registry Mumber 1576-87-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,7 and 6 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1576-87:
(6*1)+(5*5)+(4*7)+(3*6)+(2*8)+(1*7)=100
100 % 10 = 0
So 1576-87-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O/c1-2-3-4-5-6/h3-5H,2H2,1H3/b4-3+

1576-87-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (P1790)  trans-2-Pentenal  >95.0%(GC)

  • 1576-87-0

  • 5g

  • 280.00CNY

  • Detail
  • TCI America

  • (P1790)  trans-2-Pentenal  >95.0%(GC)

  • 1576-87-0

  • 25g

  • 865.00CNY

  • Detail
  • Alfa Aesar

  • (L06108)  trans-2-Pentenal, 96%   

  • 1576-87-0

  • 5g

  • 347.0CNY

  • Detail
  • Alfa Aesar

  • (L06108)  trans-2-Pentenal, 96%   

  • 1576-87-0

  • 25g

  • 1399.0CNY

  • Detail
  • Sigma-Aldrich

  • (94575)  trans-2-Pentenal  analytical standard

  • 1576-87-0

  • 94575-1ML

  • 521.82CNY

  • Detail

1576-87-0Relevant articles and documents

Isolation and Structure of Pseurotin A, a Microbial Metabolite of Pseudeurotium ovalis Stolk with an Unusual Heterospirocyclic System

Bloch, Peter,Tamm, Christoph

, p. 304 - 315 (1981)

The structure and absolute configuration of pseurotin A, a new metabolite, isolated from culture filtrates of Pseudeurotium ovalis Stolk (Ascomycetes) has been shown to be (1'S,2'S,5S,8S,9R,3'Z)-8-benzoyl-2(1',2-dihydroxy-3'-hexenyl)-9-hydroxy-8-methoxy-1-oxa-7-azaspironon-2-ene-4,6-dione (1).

Chromium-Catalyzed Production of Diols From Olefins

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Paragraph 0111, (2021/03/19)

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

C-GLUCOSIDE DERIVATIVE CONTAINING FUSED PHENYL RING OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PROCESS FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

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Paragraph 0359-0360, (2018/12/04)

The present disclosure relates to C-glycoside derivatives having a fused phenyl ring or pharmaceutical acceptable salts thereof, a method for preparing the same, a pharmaceutical composition comprising the same, a use thereof and a method for dual inhibition of SGLT1 and SGLT2 using the same. A novel compound of the present disclosure has a dual inhibitory activity against SGLT1 and SGLT2, thus being valuably used as a diabetes therapeutic agent.

Catalytic Reactions of Homo- and Cross-Condensation of Ethanal and Propanal

Martsinkevich,Bruk,Dashko,Afaunov,Flid,Sedov

, p. 1032 - 1035 (2019/01/03)

Abstract: Processes of catalytic homocondensation of propanal and its cross-condensation with ethanal and methanal in the presence of aniline and amino acids have been studied. The dependence of the conversion of the reactants and selectivity of the homo/heterocondensation process on the catalyst nature and temperature has been revealed. It has been shown that the maximum acrolein selectivity is reached in the case of using benzoyl-substituted derivatives in water, with the proportion of the products of further condensation decreasing. The selectivity for the ethanal homocondensation product 2-butenal decreases simultaneously as a result of the formation of linear and branched oligomers of successive condensation.

Highly practical and efficient preparation of aldehydes and ketones from aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst

Zhang, Mengqi,Zhai, Yongyan,Ru, Shi,Zang, Dejin,Han, Sheng,Yu, Han,Wei, Yongge

supporting information, p. 10164 - 10167 (2018/09/13)

Herein, we divulge an efficient protocol for aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst, (NH4)5[IMo6O24]. The catalyst system is compatible with a wide range of groups and exhibits high selectivity, and shows excellent stability and reusability, thus serving as a potentially greener alternative to the classical transformations.

Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction

Meazza, Marta,Potter, Michael,Pitak, Mateusz B.,Coles, Simon J.,Mazzanti, Andrea,Rios, Ramon

supporting information, p. 719 - 725 (2017/02/05)

A method for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines was developed. The resulting cyclohexenes (three C–C bonds were formed) were obtained in good yields with good diastereoselectivities and excellent enantioselectivities.

Evidence for isomerizing hydroformylation of butadiene. A combined experimental and computational study

Maji, Tapan,Mendis, Camina H.,Thompson, Ward H.,Tunge, Jon A.

, p. 145 - 152 (2016/09/09)

The (DIOP)rhodium-catalyzed hydroformylation of butadiene has been shown to give among the highest selectivities for formation of adipaldehyde, which is useful for the synthesis of nylon. Herein, isomerizing hydroformylation is shown to be a mechanism that is partially responsible for this selectivity and density functional theory studies are used to reveal the detailed pathway for the requisite alkene isomerization.

Lipid-derived aldehyde degradation under thermal conditions

Zamora, Rosario,Navarro, José L.,Aguilar, Isabel,Hidalgo, Francisco J.

, p. 89 - 96 (2015/02/19)

Nucleophilic degradation produced by reactive carbonyls plays a major role in food quality and safety. Nevertheless, these reactions are complex because reactive carbonyls are usually involved in various competitive reactions. This study describes the thermal degradation of 2-alkenals (2-pentenal and 2-octenal) and 2,4-alkadienals (2,4-heptadienal and 2,4-decadienal) in an attempt to both clarify the stability of aldehydes and determine new compounds that might also play a role in nucleophile/aldehyde reactions. The obtained results showed that alkenals and alkadienals decomposed rapidly in the presence of buffer and air to produce formaldehyde, acetaldehyde, and the aldehydes corresponding to the breakage of the carboncarbon double bonds: propanal, hexanal, 2-pentenal, 2-octenal, glyoxal, and fumaraldehyde. The activation energy of double bond breakage was relatively low (~25 kJ/mol) and the yield of alkanals (10-18%) was higher than that of 2-alkenals (~1%). All these results indicate that these reactions should be considered in order to fully understand the range of nucleophile/aldehyde adducts produced.

Thiol-functionalized fructose-derived nanoporous carbon as a support for gold nanoparticles and its application for aerobic oxidation of alcohols in water

Mahyari, Mojtaba,Shaabani, Ahmad,Behbahani, Mohammad,Bagheri, Akbar

, p. 576 - 583 (2014/08/05)

Gold nanoparticles supported on thiol-functionalized fructose-derived nanoporous carbon (AuNPs@thiol-Fru-d-NPS) were found to be a simple bench-top, biocompatible, recyclable and selective catalytic system for the aerobic oxidation of various types of alcohols into their corresponding aldehydes and ketones at room temperature under the environmentally friendly conditions with excellent yields. Copyright

Biooxidation of Primary Alcohols to Aldehydes through Hydrogen Transfer Employing Janibacter terrae

Orbegozo, Thomas,De Vries, Johannes G.,Kroutil, Wolfgang

experimental part, p. 3445 - 3448 (2010/09/05)

Chemoselective oxidations still represent a challenge for chemists. Lyophilized cells of Janibacter terrae were employed for the chemoselective oxidation of primary alcohols to the corresponding aldehydes by hydrogen transfer with the use of acetaldehyde as the hydrogen acceptor. Secondary alcohol moieties were transformed at a much slower rate. The substrate spectrum encompasses substituted benzyl alcohols, whereby substrates with a substituent in the meta position were well tolerated, whereas only very small substituants were tolerated in the ortho position. Furthermore, nalkanols and allylic alcohols were transformed with good conversions. The biocatalyst was compatible with DMSO as a water miscible organic solvent up to 30 % v/v.

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