857054-02-5

Basic information

• Product Name: 3-METHYL-2H-FURO[2,3-C]PYRAN-2-ONE
• Synonyms: 3-METHYL-2H-FURO[2,3-C]PYRAN-2-ONE;KAR1;Karrikinolide
• CAS NO: 857054-02-5
• Molecular Formula: C8H6O3
• Molecular Weight: 150.13144
• Product Categories: Heterocycles
• Mol File: 857054-02-5.mol

Chemical Properties

• Melting Point: 116-118°C
• Boiling Point: 411.3±28.0 °C(Predicted)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• Storage Temp.: -20?C Freezer
• CAS DataBase Reference: 3-METHYL-2H-FURO[2,3-C]PYRAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-2H-FURO[2,3-C]PYRAN-2-ONE(857054-02-5)
• EPA Substance Registry System: 3-METHYL-2H-FURO[2,3-C]PYRAN-2-ONE(857054-02-5)

Safety Data

• Hazardous Substances Data: 857054-02-5(Hazardous Substances Data)

Upstream product

• 857054-14-9 4-thioxo-4H-pyran-3-yl-2-chloropropanoate 
• 108-24-7 acetic anhydride 
• 952058-08-1 2-oxo-2H-furo[2,3-c]pyran-3-carbaldehyde 
• 857054-03-6 2H-furo[2,3-c]pyran-2-one 
• 952058-02-5 (4S,7R,7aR)-4,7-bis(ethoxycarbonyloxy)-4,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-2-one 
• 952058-03-6 (4S)-4,5-dihydro-4-ethoxycarbonyloxy-2H-furo[2,3-c]pyran-2-one 
• 952057-96-4 (Z)-3-deoxy-3-C-[(ethoxycarbonyl)methylene]-1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-erythro-pentose 
• 952057-98-6 (4S,7S,7aR)-4,7-dihydroxy-4,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-2-one 
• 952057-99-7 (4S,7S,7aR)-4,7-diacetoxy-4,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-2-one 
• 952058-00-3 (4S)-4-acetoxy-4,5-dihydro-2H-furo[2,3-c]pyran-2-one 
• 20590-54-9 1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose 
• 863969-71-5 2-chloro-propionic acid 4-oxo-4H-pyran-3-yl ester 
• 496-63-9 3-hydroxy-pyran-4-one 
• 89282-30-4 3-hydroxyl-4H-pyran-4-thione 

Downstream Products

• 1030604-54-6 C₁₁H₁₄O₃Si 
• 949158-56-9 3-methyl-4,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-2-one 
• 1379764-80-3 C₁₆H₁₂O₆ 
• 1379764-79-0 C₁₆H₁₂O₆ 
• 1262683-60-2 7-⁽³⁾H-3-methyl-2H-furo[2,3-c]pyran-2-one 

Relevant articles and documents

Synthesis of Karrikinolide Using the Aldol-Type Acetal Addition Reaction

A short step total synthesis of karrikinolide has been achieved. Both α and α′ positions of O-acylated acetol were alkylated by the boron-mediated aldol-type acetal addition reaction. The one-pot sequence including the Arbuzov reaction, intramolecular Horner-Wadsworth-Emmons reaction, acidic hydrolysis of acetals, and pyran formation provided karrikinolide. This procedure was applicable to the gram-scale synthesis of karrikinolide.

New and scalable access to karrikin (KAR1) and evaluation of its potential application on corn germination

Karrikin (KAR1), also named ‘karrikinolide’, was isolated in 2004 from smoke water and identified as a very potent germination stimulant as well as controlling early seedling development for a large variety of plant species. We reported herein an unprecedented and scalable synthesis of Karrikin (KAR1) based on an elegant and efficient 6-endo-dig cyclization. Moreover, we evaluated the effect of KAR1 on corn seeds germination, we carried out additional studies on the uptake of this butenolide into corn seeds, and the main soil chemiodynamic properties (i.e., persistence and mobility) were calculated or estimated. Finally, we provided a rationalization of the experimental results by building a homology model of corn KAI2, using as template the X-ray of the KAI2 protein from Arabidopsis thaliana.

Discovery of cytochrome bc1 complex inhibitors inspired by the natural product karrikinolide

The cytochrome bc1 complex (cyt bc1 or complex III) is a promising target of numerous antibiotics and fungicides. With an aim to indentify new lead structures for the bc1 complex, a series of novel inhibitors were discovered from the natural product karrikinolide for the first time. Extensive screening results suggested variable inhibitory activities of these compounds against succinate-cytochrome reductase [SCR, a mixture of respiratory complex II (SQR) and complex III (the bc1 complex)], implying the essential role of a 4-substituted phenyl group for the high potency. Exceptionally, compound 12g showed excellent inhibition potency having an IC50 value in the sub-micromolar range, demonstrating its higher potency than the commercial control amisulbrom by over two orders of magnitude. Further experiments inferred that these newly prepared compounds mainly target the bc1 complex. Seemingly, this work has presented a new lead scaffold for further development of bc1 complex inhibitors.

Karrikins from plant smoke modulate bacterial quorum sensing

The discovery that plant smoke contains germination stimuli has led to the identification of a new class of signaling molecules named karrikins. Here we report a potential second role for these molecules: in various bacterial species-A. tumefaciens, P. aeruginosa and V. harveyi-they modulate bacterial quorum-sensing (QS), with very different outcomes. the Partner Organisations 2014.

Efficient synthesis of karrikinolide via Cu(II)-catalyzed lactonization

The efficient total synthesis of karrikinolide (KAR1), a potent plant growth regulator discovered in smoke from burning plant material, is described. 3-Hydroxy-4-pyranone, prepared from d-xylose, was subjected to a Cu(II)-catalyzed transesterification-Wittig lactonization to afford the dihydrofuropyran in good yield. Finally, radical bromination, followed by olefin formation, provided KAR1 in acceptable yield.

Synthesis of the seed germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-ones utilizing direct and regioselective Ti-crossed aldol addition

3-Methyl-2H-furo[2,3-c]pyran-2-ones 1 and 2, a unique and remarkable seed germination stimulant, and its analogue were synthesized using direct and regioselective Ti-crossed aldol addition between dihydro-2H-pyran-3(4H)-ones and methyl pyruvate as the key step, followed by furanone formation.

Synthesis of butenolides as seed germination stimulants

Syntheses of a series of novel butenolides as seed germination stimulants are described. The key steps include the cyclization reaction of enamine 4 to form a pyran ring, the efficient halogenating reaction and the selective lithiation reaction of butenolides.

Synthesis of the germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds from carbohydrates

An efficacious synthetic route to the recently identified, potent germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds, using carbohydrate substrates, is described. D-Xylose and D-glucuronic acid γ-lactone were used in the preparation of the parent heterocycle and its 5-methoxycarbonyl analogue, respectively. These compounds were elaborated using various methods to furnish the natural product and a suite of its analogues. The germination stimulant was thus prepared on a multi-gram scale in nine steps from inexpensive, commercially available 1,2-O-isopropylidene-D-xylofuranose in an overall yield of 30 %, vastly improving upon the only method published to date. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

VINYLOGOUS 4H-PYRONES AND THEIR USE IN PROMOTING PLANT GROWTH

This invention resides in a hitherto unknown class of chemical compounds, 2H-furo[2,3-c]pyran-2-ones including derivatives and analogues thereof. It includes methods for making compounds within said class and includes, without limitation, at least the intermediates employed in the generation of said compounds. The invention also relates to the use of vinylogous 4H-pyrones, including but not limited to the hitherto unknown 2H-furo[2,3-c]pyran-2-ones. In one aspect the invention resides in a method comprising the step of: exposing biological plant material to at least a compound of the invention to promoting bioactivity within said material. In another aspect the invention resides in methods for promoting growth of plant material in, for example, smoke-responsive plant species by exposing said material to a compound of the invention. More specifically, the invention relates to the use of said compounds for promoting seed germination of a plant, for example, a smoke-responsive plant.

Synthesis of the seed germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2- one

3-Methyl-2H-furo[2,3-c]pyran-2-one 1 was recently identified as the key agent in smoke, responsible for promoting the seed germination of a diverse range of fire-dependent and fire-independent plant species from around the world. The synthesis of this novel compound, obtained in three steps from pyromeconic acid, is described.