857054-03-6

Basic information

• Product Name: 2H-Furo[2,3-c]pyran-2-one
• Synonyms: 2H-Furo[2,3-c]pyran-2-one;Karrikin 2
• CAS NO: 857054-03-6
• Molecular Formula: C₇H₄O₃
• Molecular Weight: 136.10486
• Product Categories: Heterocycles
• Mol File: 857054-03-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Acetonitrile (Slightly), Chloroform (Sparingly), Methanol
• CAS DataBase Reference: 2H-Furo[2,3-c]pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Furo[2,3-c]pyran-2-one(857054-03-6)
• EPA Substance Registry System: 2H-Furo[2,3-c]pyran-2-one(857054-03-6)

Safety Data

• Hazardous Substances Data: 857054-03-6(Hazardous Substances Data)

Usage

Description

2H-Furo[2,3-c]pyran-2-one, also known as KAR2, is a compound found in smoke that plays a crucial role in promoting seed germination in a wide range of plant species. It is part of a group of compounds called "the karrikins," named after "karrik," an aboriginal word for smoke.
Used in Agriculture:
2H-Furo[2,3-c]pyran-2-one is used as a seed germination promoter for enhancing the growth of plants in agricultural settings. Its presence in smoke from forest fires, when not too frequent, contributes to the rapid germination and growth of plants in ecosystems, making it a beneficial compound for agricultural practices.
Used in Ecosystem Restoration:
2H-Furo[2,3-c]pyran-2-one is used as a natural growth stimulant for promoting the recovery of ecosystems after forest fires. By encouraging the germination and growth of plants, it helps restore the balance and health of ecosystems that have been affected by fires, provided they occur at appropriate intervals.

Upstream product

• 952058-03-6 (4S)-4,5-dihydro-4-ethoxycarbonyloxy-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 
• 952058-02-5 (4S,7R,7aR)-4,7-bis(ethoxycarbonyloxy)-4,5,7,7a-tetrahydro-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 
• 20590-54-9 1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose 
• 89282-30-4 3-hydroxyl-4H-pyran-4-thione 
• 1061751-15-2 ethyl 5-(dimethylamino)methylene-4-[2-(dimethylamino)vinyl]-2-oxo-2,5-dihydrofuran-3-carboxylate 
• 1030604-39-7 C₁₂H₁₅NO₅ 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 20590-53-8 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose 
• 87-72-9 D-Xylose 
• 1238180-83-0 n-butyl D-xyloside 

Downstream Products

• 857054-02-5 3-methyl-2H-furo[2,3-c]pyran-2-one 
• 1030604-48-8 3-phenyl-2H-furo[2,3-c]pyran-2-one 

Relevant articles and documents

From Biomass to the Karrikins via Selective Catalytic Oxidation of Hemicellulose-Derived Butyl Xylosides and Glucosides

Members of the karrikin family of bioactive small molecules are known to promote germination of a range of plants following large scale fires. As a result, they are relevant and interesting compounds. This report describes their synthesis from a biomass-derived product stream. During work to fractionate biomass with the goal of obtaining high quality lignins, an interesting co-product stream derived from the hemicellulose in the biomass, was obtained. Whilst many applications of this co-product stream can be proposed, in this case the major monosaccharides have been converted to relevant karrikins in short reaction sequences. Key results include a highly selective catalytic oxidation reaction, conversion of the resulting ketone to a butenolide by two alternative approaches, a selective acetal reductive opening reaction, X-ray crystallographic analysis of two compounds and detailed comparison of the final products with previous literature reports. Only through successful use of all the components generated during biomass refining, can economic sustainability be potentially achieved.

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.

Preparation of 2H-furo[2,3-c]pyran-2-one derivatives and evaluation of their germination-promoting activity

The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), has recently been identified as the germination stimulant present in smoke that promotes the germination of seeds from a wide range of plant species. In this paper, we describe the preparation of a number of analogues of 1 and compare their efficacy in promoting seed germination of three highly smoke-responsive plant species, Lactuca sativa L. cv. Grand Rapids (Asteraceae), Emmenanthe penduliflora Benth. (Hydrophyllaceae), and Solanum orbiculatum Poir. (Solanaceae). The results show that the methyl substituent at C-3 in 1 is important for germination-promoting activity while substitution at C-7 reduces activity. In contrast, bioactivity is mostly retained with analogues substituted at C-4 or C-5.