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

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

Uses

Used in the Food Industry:
(+)-PHYLLODULCIN is used as a sugar substitute for its intense sweetness, offering a low-calorie alternative to traditional sugars. This makes it an attractive option for consumers seeking to reduce their sugar intake or for those with dietary restrictions.
Used in Diabetes and Obesity Treatments:
(+)-PHYLLODULCIN is used as a potential therapeutic agent due to its beneficial effects on glucose metabolism and insulin sensitivity. Research indicates that it may contribute to the development of new treatments for diabetes and obesity, helping to manage and alleviate symptoms associated with these conditions.
Used in Health and Wellness Applications:
(+)-PHYLLODULCIN is used for its antioxidant properties, which may provide a range of health benefits. Antioxidants are known to combat oxidative stress and may contribute to the prevention of various diseases and the promotion of overall health.

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 
• 50463-84-8 2-methoxy-6-methylbenzoyl chloride 
• 6161-65-5 2-methoxy-6-methyl-benzoic acid 
• 621-59-0 isovanillin 
• 179260-96-9 4-methoxy-3-(triisopropylsilyloxy)-benzaldehyde 
• 66380-87-8 (+/-)-3-(3-benzyloxy-4-methoxyphenyl)-3,4-dihydro-8-hydroxy-1H-2-benzopyran-1-one 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 172484-36-5 (E)-ethyl 6-<2-(3-benzyloxy-4-methoxyphenyl)ethenyl>-2-hydroxybenzoate 
• 172484-37-6 (E)-6-<2-(3-benzyloxy-4-methoxyphenyl)ethenyl>-2-hydroxybenzoic acid 
• 179260-98-1 (S)-1-(4-Methoxy-3-triisopropylsilanyloxy-phenyl)-ethane-1,2-diol 
• 179260-99-2 Toluene-4-sulfonic acid (S)-2-hydroxy-2-(4-methoxy-3-triisopropylsilanyloxy-phenyl)-ethyl ester 
• 179261-00-8 Triisopropyl-((S)-2-methoxy-5-oxiranyl-phenoxy)-silane 
• 179260-97-0 Triisopropyl-(2-methoxy-5-vinyl-phenoxy)-silane 

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

Highly enantioselective synthesis of natural phyllodulcin

(S)-[4-Methoxy-3-[(triisopropylsilyl)oxy]phenyl)oxirane (prepared from isovanillin by consecutive silylation, olefination, Sharpless asymmetric cis-dihydroxylation, and dehydration) reacted with [3-(methoxymethoxy)phenyl]lithium (prepared from 3-bromophenol by consecutive methoxymethylation and bromine-lithium exchange) to yield (R)-1-[4-methoxy-3-[(triisopropylsilyl)oxy]phenyl)2-[3-(methoxymethoxy )phenyl]ethanol. The last compound underwent selective hydrogen-metal exchange with excess of butyllithium affording (after carbonation, lactonization, and deprotection of phenolic groups) the title compound [(R)-3,4-dihydro-8-hydroxy-3-(4-methoxy-3-hydroxyphenyl)isocoumarin].

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