591-12-8

Basic information

• Product Name: alpha-Angelica lactone
• Synonyms: FEMA 3293;3-PENTEN-4-OLIDE;4-HYDROXY-3-PENTANOIC ACID GAMMA-LACTONE;4-HYDROXY-3-PENTENOIC ACID GAMMA-LACTONE;4-HYDROXY-3-PENTENOIC ACID G-LACTONE;4-HYDROXY-3-PENTENOIC ACID LACTONE;ALPHA-ANGELICALACTONE;ANGELICALACTONE
• CAS NO: 591-12-8
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.1
• EINECS: 209-701-8
• Product Categories: Miscellaneous Natural Products
• Mol File: 591-12-8.mol

Chemical Properties

• Melting Point: 13-17 °C(lit.)
• Boiling Point: 55-56 °C12 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: White crystalline with rich aroma of tonka beans and chocolate flavor
• Density: 1.092 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.023mmHg at 25°C
• Refractive Index: n20/D 1.448(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate
• PKA: pK1:4.3 (25°C)
• Water Solubility: 5 g/100 mL (25 ºC)
• Merck: 14,647
• BRN: 108394
• CAS DataBase Reference: alpha-Angelica lactone(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Angelica lactone(591-12-8)
• EPA Substance Registry System: alpha-Angelica lactone(591-12-8)

Safety Data

• Safety Statements: 24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 2
• RTECS: LU5075000
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 591-12-8(Hazardous Substances Data)

Usage

Uses

Used in Cancer Chemoprevention:
α-Angelica lactone serves as a cancer chemopreventive agent, playing a crucial role in the synthesis of glutathione and the activity of detoxification enzymes such as glutathione-S-transferase and UDP-glucuronosyltransferase in various organs, including the esophagus, stomach, intestine, and liver.
Used in Tobacco Flavoring:
In the tobacco industry, α-Angelica lactone is utilized as a flavoring agent due to its natural occurrence in tobacco and its sweet, herbaceous odor that resembles the characteristic taste of tobacco.
Used in Oral Care Formulations:
α-Angelica lactone is employed in oral care formulations to enhance and round out the mint notes, providing a pleasant and refreshing taste experience.
Used in Coffee Flavors:
alpha-Angelica lactone is also used in the flavor industry, specifically for adding depth and complexity to coffee flavors, contributing to a richer and more enjoyable taste.

Preparation

By dry distillation of levulinic acid

Biochem/physiol Actions

Plant-derived cancer chemopreventive agent. Increases the synthesis of glutathione and the activity of glutathione-S-transferase and UDP-glucunonosyltransferase detoxification enzymes in esophagus, stomach, intestine, and liver.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits acrid smoke and irritating fumes.

InChI:InChI=1/C5H6O2/c1-4-2-3-5(6)7-4/h2H,3H2,1H3

Upstream product

• 591-11-7 5-methyl-5H-furan-2-one 
• 98198-39-1 prop-2-yn-1-ylpropanedioic acid 
• 6089-09-4 4-pentynoic acid 
• 743369-26-8 zinc(II) carbonate 
• 123-76-2 levulinic acid 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 22414-24-0 2,5-dihydro-2,5-dimethoxy-2-methylfuran 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 10008-73-8 5-methylenedihydrofuran-2-one 
• 36781-65-4 pent-3-ynoic acid 
• 9004-34-6 cellulose 
• 10489-79-9 α-D-fructofuranose 
• 492-61-5 β-D-glucose 
• 57-48-7 D-Fructose 

Downstream Products

• 624-45-3 levulinic acid methyl ester 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 1487-57-6 4,5-Dihydro-5-methoxy-5-methylfuran-2(3H)-one 
• 854875-89-1 3-((Ξ)-4-amino-benzylidene)-5-methyl-3H-furan-2-one 
• 2833-29-6 4,5-Dihydro-5-ethoxy-5-methylfuran-2(3H)-one 
• 4405-05-4 2-acetonyl-3-phenyl-acrylic acid 
• 84417-34-5 4-oxo-n-pentano-p-toluidide 
• 3269-96-3 3-((Ξ)-4-hydroxy-benzylidene)-5-methyl-3H-furan-2-one 
• 38711-12-5 3-(4-methoxy-benzylidene)-5-methyl-3H-furan-2-one 
• 36805-02-4 5-methyl-3-((Ξ)-vanillylidene)-3H-furan-2-one 
• 591-11-7 5-methyl-5H-furan-2-one 
• 1070-35-5 Allyl 4-Oxopentanoate 
• 23132-35-6 levulinanilide 
• 92453-69-5 1,4-bis-levulinoyloxy-benzene 

Relevant articles and documents

Renewable bio-based routes to γ-valerolactone in the presence of hafnium nanocrystalline or hierarchical microcrystalline zeotype catalysts

Different renewable bio-based routes leading to the versatile bioproduct γ-valerolactone (GVL) were studied in integrated fashions, starting from furfural (Fur), α-angelica lactone (AnL) and levulinic acid (LA), in the presence of multifunctional hafnium-

Synthesis of renewable alkylated naphthalenes with benzaldehyde and angelica lactone

Herein, we report a new route for the synthesis of renewable alkylated naphthalenes (ANs) with benzaldehyde and angelica lactone, two platform compounds that can be derived from lignocellulose.

Construction of Enantioenriched γ,γ-Disubstituted Butenolides Enabled by Chiral Amine and Lewis Acid Cascade Cocatalysis

Herein we report a cascade cocatalysis strategy for the facile construction of chiral γ,γ-disubstituted butenolides. The synthetic manifold employs simple alkynoic acids instead of the preformed silyloxy furans or 5-substituted furan-2(3H)-ones. In situ formed 5-substituted furan-2(3H)-ones by AgNO3 or Ph3PAuCl/AgOTf catalyzed cyclization of alkynoic acids can smoothly engage in the subsequent chiral diphenylprolinol TMS-ether catalyzed Michael and Michael-aldol reactions. The cascade process serves as a general approach to chiral quaternary γ,γ-disubstituted butenolides.

Esterification of levulinic acid over Sn(II) exchanged Keggin heteropolyacid salts: An efficient route to obtain bioaditives

In this paper, we describe a process to add value to the biomass derivatives (i.e., levulinic acid), converting it to bioadditives over solid Sn(II) exchanged Keggin heteropolyacid salts. These solid catalysts are an attractive alternative to the traditional soluble and corrosive Br?nsted acid catalysts. Among Sn(II) heteropoly salts, the Sn1.5PW12O40 was the most active and selective catalyst, achieving high conversions (ca. 90 %) and selectivity (90–97 %) for alkyl esters and angelica lactone, the main reaction products. The impacts of the main reaction parameters (i.e., catalyst load, temperature, and the molar ratio of alcohol to acid) were investigated. The use of renewable raw material, and an efficient and recyclable catalyst are the main positive features of this process. The Sn1.5PW12O40 catalyst was easily recovered and reused without loss activity.

Regioselective β-Arylation of α-Angelica Lactone through Isomerization/Addition under Mild Conditions

The conversion of biomass-based platform molecules into various high-value chemicals greatly promotes the utilization of renewable biomass resources. Herein, an example of Rh-catalyzed β-arylation of levulinic-acid-derived α-angelica lactone was reported, providing the γ-lactone-structure products with high regioselectivity. Both arylboronic and alkenylboronic acids could be applied in this transformation. This reaction tolerated a variety of synthetically important functional groups. Moreover, the obtained γ-lactone products could be readily converted to high-value products such as 1,4-diols and γ-methoxy-carboxylates.

Lewis-Pair-Mediated Selective Dimerization and Polymerization of Lignocellulose-Based β-Angelica Lactone into Biofuel and Acrylic Bioplastic

This contribution reports an unprecedentedly efficient dimerization and the first successful polymerization of lignocellulose-based β-angelica lactone (β-AL) by utilizing a selective Lewis pair (LP) catalytic system, thereby establishing a versatile bio-refinery platform wherein two products, including a dimer for high-quality gasoline-like biofuel (C8–C9 branched alkanes, yield=87 %) and a heat- and solvent-resistant acrylic bioplastic (Mn up to 26.0 kg mol?1), can be synthesized from one feedstock by one catalytic system. The underlying reason for exquisite selectivity of the LP catalytic system toward dimerization and polymerization was explored mechanistically.

Efficient synthesis of niobium pentoxide nanowires and application in ethanolysis of furfuryl alcohol

Nb2O5 nanowires with high specific surface area and crystallinity were prepared by using ammonium oxalate and an acetic acid solvent system. The nanomaterial was applied in ethanolysis of furfuryl alcohol (FA), and the yield of the product, 2-(ethoxymethyl)furan (FEE), achieved was up to 79.6%. Compared to mesoporous Nb2O5 materials and other porous materials, the residence time of FEE on the surface of the catalyst is shorter, and the yield of ethyl levulinate (EL) is lower. Furthermore, a high temperature calcination treatment can change the acid sites and acidity type distribution on the nanowire surface. By XRD, NH3-TPD, IR, and TG-DTA determination methods, it was found that the weak and medium-strong acid sites on the surface of Nb2O5 nanowires were reduced after a 300 °C treatment, and the amount of strong acid was relatively higher. According to the catalytic performance test data and acidity determination, it was concluded that more weak acid and medium-strong acid sites improve the conversion of furfuryl alcohol to FEE, and the strong acid sites promote further conversion of FEE to EL.

CATALYST FOR PRODUCING GAMMA-VALEROLACTONE, METHOD FOR PREPARING THE SAME AND METHOD FOR MANUFACTURING GAMMA-VALEROLACTONE USING THE SAME

Disclosed are a heteropolyacid catalyst for producing gamma-valerolactone, which is supported on M-Beta zeolite (M=Sn, Ti, Zr or Hf), and a method for preparing the same and a method for manufacturing gamma-valerolactone using the catalyst. The catalyst has an effect of producing gamma-valerolactone from biomass-derived furfural at a high yield through a one-pot process.

Butenolide Derivatives of Biobased Furans: Sustainable Synthetic Dyes

The dye and pigment manufacturing industry is one of the most polluting in the world. Each year, over one million tons of petrochemical colorants are produced globally, the synthesis of which generates a large amount of waste. Naturally occurring, plant-based dyes, on the other hand, are resource intensive to produce (land, water, energy), and are generally less effective as colorants. Between these two extremes would be synthetic dyes that are fully sourced from biomass-derived intermediates. The present work describes the synthesis of such compounds, containing strong chromophores that lead to bright colors in the yellow to red region of the visible spectrum. The study was originally motivated by an early report of an unidentified halomethylfurfural derivative which resulted from hydrolysis in the presence of barium carbonate, now characterized as a butenolide of 5-(hydroxymethyl)furfural (HMF). The method has been generalized for the synthesis of dyes from other biobased platform molecules, and a mechanism is proposed.

The phosphinoboration of 2-diphenylphosphino benzaldehyde and related aldimines

We have investigated the addition of a simple phosphinoboronate ester, Ph2PBpin (pin = 1,2-O2C2Me4), to 2-diphenylphosphinobenzaldehyde (2-Ph2PC6H4C(O)H) and related aldimine derivatives (2-Ph2PC6H4C(NR)H) as a simple and effective strategy for generating unique diphosphine ligands bearing a pendant Lewis-acid Bpin group. These reactions proceed selectively to give one new product where the phosphide fragment has added to the aldehyde (or imine) carbon atom and the electron-deficient boron group has added to the electron-rich heteroatom. Preliminary studies show these new compounds can ligate to Pd(II) and Pt(II) metal centres. These novel metal complexes, as well as the organic soluble [MCl2(coe)]2 (M = Pd, Pt, coe = cis-cyclooctene) compounds, have been shown to be effective precatalysts in the cyclisation of alkynoic acids to give the corresponding exo-dig cyclic lactones. Reactions employing these metal complexes also generated unusual endo-dig cyclic lactones not traditionally observed in these cyclisation reactions. For instance, reactions of 4-pentynoic acid also afforded significant amounts of α-angelica lactone, a biologically-important compound traditionally prepared via the catalytic dehydration and cyclisation of levulinic acid.