21499-23-0

Basic information

• Product Name: (+)-PHYLLODULCIN
• Synonyms: PHYLLODULCIN;(3R)-3-(3-Hydroxy-4-methoxyphenyl)-8-hydroxyisochroman-1-one;(3R)-3β-(3-Hydroxy-4-methoxyphenyl)-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one;(3R)-Phyllodulcin;(R)-3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one;R-(+)-Phyllodulcin;(+)-Praeruptorin;Praeruptorin
• CAS NO: 21499-23-0
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28
• Product Categories: Miscellaneous Natural Products
• Mol File: 21499-23-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 540.6°Cat760mmHg
• Flash Point: 206.2°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 2.66E-12mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: (+)-PHYLLODULCIN(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-PHYLLODULCIN(21499-23-0)
• EPA Substance Registry System: (+)-PHYLLODULCIN(21499-23-0)

Safety Data

• Hazardous Substances Data: 21499-23-0(Hazardous Substances Data)

Usage

General Description

(+)-PHYLLODULCIN is a natural sweetener and a natural product found in the leaves of sweet plants, such as the West African shrub Dioscoreophyllum cumminsii, which is known for its intensely sweet taste. It is a low-calorie sweetener, around 2000 times sweeter than sucrose, and has been found to have potential applications as a sugar substitute in the food industry. Research has also shown that (+)-PHYLLODULCIN has beneficial effects on glucose metabolism and insulin sensitivity, making it a potential candidate for the development of new treatments for diabetes and obesity. Furthermore, (+)-PHYLLODULCIN has been found to have antioxidant properties, which may have potential health benefits.

InChI:InChI=1/C16H14O5/c1-20-13-6-5-9(7-12(13)18)14-8-10-3-2-4-11(17)15(10)16(19)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m1/s1

Upstream product

• 172484-39-8 (3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 
• 946002-05-7 (R)-8-hydroxy-3-(4-methoxy-3-(methoxymethoxy)phenyl)-3,4-dihydroisocoumarin 
• 946001-97-4 (1R)-2-{2-[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-3-methoxyphenyl}-1-(4-methoxy-3-(methoxymethoxy)phenyl)ethanol 
• 946001-52-1 (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)-4,5-dihydrooxazole 
• 50463-84-8 2-methoxy-6-methylbenzoyl chloride 
• 6161-65-5 2-methoxy-6-methyl-benzoic acid 
• 621-59-0 isovanillin 
• 179260-97-0 Triisopropyl-(2-methoxy-5-vinyl-phenoxy)-silane 
• 179260-96-9 4-methoxy-3-(triisopropylsilyloxy)-benzaldehyde 
• 179261-00-8 Triisopropyl-((S)-2-methoxy-5-oxiranyl-phenoxy)-silane 
• 179260-99-2 Toluene-4-sulfonic acid (S)-2-hydroxy-2-(4-methoxy-3-triisopropylsilanyloxy-phenyl)-ethyl ester 
• 179260-98-1 (S)-1-(4-Methoxy-3-triisopropylsilanyloxy-phenyl)-ethane-1,2-diol 
• 118842-88-9 (3-acetyloxy-2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide 
• 66380-87-8 (+/-)-3-(3-benzyloxy-4-methoxyphenyl)-3,4-dihydro-8-hydroxy-1H-2-benzopyran-1-one 

Downstream Products

• 80394-88-3 Thunberginol G 
• 147666-80-6 Thunberginol A 
• 183619-71-8 3'-Hydroxyhydrangeaic acid 
• 183619-68-3 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-8-(tert-butyl-dimethyl-silanyloxy)-isochromen-1-one 

Relevant articles and documents

Asymmetric synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins from (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline

Reaction of the laterally lithiated (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline with p-tolualdehyde gave an inseparable mixture of the addition products in low diastereoselectivity. However, the (S,S)-product cyclized to the corresponding 3,4-di

Enantiodifferentiation in taste perception of the phyllodulcins

Both enantiomers of phyllodulcin 1 have been prepared. Ester 2 was synthesized in a Wittig reaction from O-benzyl isovanillin. The corresponding stilbene carboxylic acid 3 could be cyclized with CF3CO2H to produce the 3'-benzyl ether