18445-71-1

Basic information

• Product Name: penitricin B
• Synonyms: penitricin B;(E)-4-Hydroxy-2-butenal
• CAS NO: 18445-71-1
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 0
• Mol File: 18445-71-1.mol

Chemical Properties

• Boiling Point: 238.5°Cat760mmHg
• Flash Point: 97.4°C
• Appearance: /
• Density: 1.037g/cm³
• Vapor Pressure: 0.00748mmHg at 25°C
• Refractive Index: 1.451
• CAS DataBase Reference: penitricin B(CAS DataBase Reference)
• NIST Chemistry Reference: penitricin B(18445-71-1)
• EPA Substance Registry System: penitricin B(18445-71-1)

Safety Data

• Hazardous Substances Data: 18445-71-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Penitricin B is used as an antimicrobial agent for its ability to inhibit the growth of various pathogenic microorganisms, making it a promising candidate for the development of new antibiotics.
Used in Organic Synthesis:
(2E)-4-Hydroxy-2-butenal, a component of penitricin B, is used as a reactant in organic reactions such as Henry reaction, [4+2] annulation (Robinson annulation), and asymmetric Michael addition, contributing to the synthesis of various organic compounds.

InChI:InChI=1/C4H6O2/c5-3-1-2-4-6/h1-3,6H,4H2/b2-1+

Upstream product

• 1708-29-8 2,5-dihydrofuran 
• 152522-71-9 trans-4,4-dimethoxy-2-butenol 
• 23147-58-2 glycolaldehyde dimer 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 

Downstream Products

• 1072925-39-3 C₁₂H₁₄O₂ 
• 1072925-40-6 C₁₃H₁₆O₃ 
• 128372-49-6 4-(4-Methoxy-phenyl)-tetrahydro-furan-2-ol 
• 1072925-55-3 4-(4-dimethylaminophenyl)-tetrahydrofuran-2-ol 
• 1072925-48-4 C₁₂H₁₆O₄ 
• 1072925-41-7 C₁₂H₁₃ClO₂ 
• 1072925-42-8 C₁₂H₁₃FO₂ 
• 1391761-46-8 C₁₃H₁₅NO₄ 
• 1391761-45-7 C₁₃H₁₅NO₄ 
• 1391761-35-5 C₁₂H₁₃NO₄ 
• 1391761-34-4 C₁₂H₁₃NO₄ 

Relevant articles and documents

Organocatalyzed Michael-Henry reactions: Enantioselective synthesis of cyclopentanecarbaldehydes via the dienamine organocatalysis of a succinaldehyde surrogate

Asymmetric formal [3+2] cycloadditions of 4-hydroxybut-2-enal, a succinaldehyde surrogate, and nitroalkenes with an organocatalyst provided cyclopentanecarbaldehydes containing four consecutive stereogenic centers with excellent enantioselectivities.

Structural Definition of Early Lysine and Histidine Adduction Chemistry of 4-Hydroxynonenal

The lipid peroxidation product trans-4-hydroxy-2-nonenal (HNE) has been implicated in the covalent modification of low-density lipoproteins (LDL) thought to contribute to the overaccumulation of LDL in the arterial wall in the initial stages of atherosclerosis. Proposals for the exact stuctures of "early" protein side-chain modifications until now have been based on indirect evidence. In this paper, the structures of first-formed His- and Lys-based adducts were elucidated by correlating NMR spectral properties with those obtained on models with reduced chiral center content, in some cases following hydride reduction. In this manner, we could confirm unambiguously the structure of a HNE-His imidazole(Nτ) Michael adduct, stabilized as a cyclic hemiacetal and isolated from a neutral aqueous 1:1 stoichiometry reaction mixture. In the case of Lys/amine reactivity, where an excess of amine is needed to avert HNE aldol condensation, the predominance of a 1:1 Michael adduct in homogeneous aqueous solution and a 1:2 Michael-Schiff base adduct under two-phase aqueous-organic conditions could be verified by isolation of the respective borohydride-reduced forms. The 1:2 adduct, shown to exist as the cyclic hemiaminal, could represent a stable lysine-based cross-link in certain protein microenvironments.

Anodic Oxidation of Unsaturated Aliphatic Ethers in Aqueous Electrolytes

2,5-Dihydrofuran 1 was galvanostatically oxidized in aqueous electrolytes on Pt and PbO2 anodes at current densities of 10 to 50 mA cm-2.Under acidic conditions maleic dialdehyde 2 was obtained on both electrodes with a current efficiency (c.e.) of up to 50percent.In the alkaline region (pH 10) 4-hydroxy crotonic aldehyde 3 (Pt) or 2,5-dihydrofuranone 4 (PbO2) become the main products with c.e.'s of 29percent and 27percent, respectively, depending on the anode material.The influence of pH and of the anode material are discussed in detail. 2,3-Dihydrofuran 7, vinyl ethyl ether 8 and for comparison, furan 9 were studied in addition.

Acetylenic antibiotics

Antimicrobial activity is exhibited by compounds having the formula STR1 wherein R1 is hydrogen or aryl; R2 is hydroxymethyl, carboxyaldehyde, propenalyl, 3-hydroxy-1-propenyl, or 3-hydroxy-1,2-epoxypropyl; and n is 2 and m is 1 or n