76974-79-3

Basic information

• Product Name: rac-GR24
• Synonyms: (3AR*,8BS*,E)-3-(((R*)-4-METHYL-5-OXO-2,5-DIHYDROFURAN-2-YLOXY)METHYLENE)-3,3A,4,8B-TETRAHYDRO-2H-INDENO[1,2-B]FURAN-2-ONE;Strigolactones;strigolactone;rac-GR24;GR24
• CAS NO: 76974-79-3
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29000
• Mol File: 76974-79-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 567.7°C at 760 mmHg
• Flash Point: 255°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 6.66E-13mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: rac-GR24(CAS DataBase Reference)
• NIST Chemistry Reference: rac-GR24(76974-79-3)
• EPA Substance Registry System: rac-GR24(76974-79-3)

Safety Data

• Hazardous Substances Data: 76974-79-3(Hazardous Substances Data)

Usage

Uses

Strigolactone GR24 is a terpenoid lactone that stimulates communication with arbuscular mycorrhizal fungi. It is also a plant hormone that stimulates and regulates shoot branching.

InChI:InChI=1/C17H14O5/c1-9-6-14(21-16(9)18)20-8-13-12-7-10-4-2-3-5-11(10)15(12)22-17(13)19/h2-6,8,12,14-15H,7H2,1H3/b13-8+/t12-,14+,15-/m1/s1

Upstream product

• 59488-94-7 2-bromo-4-methyl-2H-furan-5-one 
• 107-31-3 Methyl formate 
• 4471-33-4 cis-3,3a,4,8b-tetrahydro-2H-indeno<1,2-b>furan-2-one 

Relevant articles and documents

Contalactone, a contaminant formed during chemical synthesis of the strigolactone reference GR24 is also a strigolactone mimic

Strigolactone (SL) plant hormones control plant architecture and are key players in both symbiotic and parasitic interactions. GR24, a synthetic SL analog, is the worldwide reference compound used in all bioassays for investigating the role of SLs in plant development and in rhizospheric interactions. In 2012, the first characterization of the SL receptor reported the detection of an unknown compound after incubation of GR24 samples with the SL receptor. We reveal here the origin of this compound (P270), which comes from a by-product formed during GR24 chemical synthesis. We present the identification of this by-product, named contalactone. A proposed chemical pathway for its formation is provided as well as an evaluation of its bioactivity on pea, Arabidopsis, root parasitic plant seeds and AM fungi, characterizing it as a SL mimic. Quality of GR24 samples can be easily checked by carrying out microscale hydrolysis in a basic aqueous medium to easily detect P270 as indicator of the presence of the contalactone impurity. In all cases, before being used for bioassays, GR24 must be careful purified by preparative HPLC.