77636-08-9

Usage

Uses

Used in Perfume and Fragrance Industry:
Toddanone is used as a fragrance ingredient for its fruity, sweet odor, contributing to the overall scent profile of perfumes and fragrances.
Used in Food Industry:
Toddanone is used as a flavoring agent for its distinctive fruity and sweet taste, enhancing the flavor of various food products.
Used in Paint and Coating Industry:
Toddanone is used as a solvent in the manufacturing process of paints and coatings, aiding in the application and performance of these products.
Used in Industrial Cleaning Products:
Toddanone is used as a solvent in the production of industrial cleaning products, helping to dissolve and remove dirt, grease, and other contaminants.
Used in Pharmaceutical Industry:
Toddanone is used in the synthesis of pharmaceuticals, playing a crucial role in the development of new medications.
Used as a Chemical Intermediate:
Toddanone is used in the production of other compounds, serving as a key intermediate in various chemical reactions and processes.

Upstream product

• 77636-05-6 5,7-dimethoxy-6-(2',3'-epoxy-3'-methylbutyl)coumarin 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 78548-01-3 5,7-dimethoxy-6-(2,3-dihydroxy-3-methylbut-3-enyl)-2H-1-benzopyran-2-one 
• 134052-24-7 5,7-dimethoxy-6-(2-hydroxy-3-methylbut-3-enyl)-2H-1-benzopyran-2-one 
• 137764-14-8 (+)-toddanol 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 1176645-57-0 (-)-toddalolactone 3′-O-β-D-glucopyranoside 
• 77636-09-0 5-hydroxy-6-(3'-methylbut-2'-enyl)-7-acetoxycoumarin 
• 77636-12-5 7-acetoxy-5-methoxy-6-(3'-methyl-2'-butenyl)coumarin 
• 77636-11-4 7-hydroxy-5-methoxy-6-(3'-methyl-2'-butenyl)coumarin 
• 115-18-4 2-methyl-3-buten-2-ol 
• 4335-12-0 toddaculin 
• 77636-10-3 5,7-diacetoxy-6-(3'-methylbut-2'-enyl)coumarin 

Relevant academic research and scientific papers

TODDANOL AND TODDANONE, TWO COUMARINS FROM TODDALIA ASIATICA

Key Word Index - Toddalia asiatica; Rutaceae; roots; toddanol; toddanone; structural analysis. Two new constituents isolated from the roots of Toddalia asiatica and designated as toddanol and toddanone have been characterized as 5,7-dimethoxy-6-(2-hydroxy-3-methylbut-3-enyl)coumarin (1) and 5,7-dimethoxy-6-(3-methyl-2-oxobutanyl)coumarin (3), respectively, by spectral analysis and interconversion experiments.

Compounds from Toddalia asiatica: Immunosuppressant Activity and Absolute Configurations

In a screening of an extract library from plants used in Traditional Chinese Medicine the MeOH extract of Toddalia asiatica inhibited proliferation of human primary T cells with an IC50 of 25.8 μg/mL. Activity in the extract was tracked by HPLC activity profiling, and a total of 15 compounds were characterized. Three compounds, toddalic acid (6) and both enantiomers (7a and 7b) of toddanolic acid (7), were new natural products, and two recently published compounds, (2′R)-toddalolactone 3′-O-β-d-glucopyranoside (10) and (2′S)-toddalolactone 2′-O-β-d-glucopyranoside (11), were described in detail for the first time. The absolute configurations of compounds 8, 9, 10, 12, 13, and 15 were determined by comparison of experimental and calculated ECD spectra. For glucosides 9 and 10, ECD data and chiral-phase HPLC of the aglycones after enzymatic hydrolysis confirmed the results. Nitidine chloride (4) inhibited proliferation of primary human T cells with an IC50 of 0.4 μM.

The Absolute Stereochemistries of (+)-Toddalolactone and its Related Chiral Coumarins from Toddalia asiatica (L.) Lam. (T. aculeata Pers.) and their Optical Purities

The absolute stereochemistries of (+)-toddalolactone (+)-1 and its related chiral coumarins (+)-toddanol (+)-2, (+)-6-(2-hydroxy-3-methoxy-3-methylbutyl)-5,7-dimethoxycoumarin (+)-3, (+)-6-(3-chloro-2-hydroxy-3-methylbutyl)-5,7-dimethoxycoumarin (+)-4 an

Synthesis of Toddanol and Toddanone

A synthetic approach to confirm the structures of toddanol (1) and toddanone (2) has been provided.In addition, coumurrayin (12), sibiricin (13), isosiribicin (14), toddaculin (8) and aculeatin (9) have also been synthesised.