Phyllodulcin

Base Information

• Chemical Name: Phyllodulcin
• CAS No.: 21499-23-0
• Molecular Formula: C16H14 O5
• Molecular Weight: 286.284
• Hs Code.: 2932209090
• UNII: 9DDW04R41V
• DSSTox Substance ID: DTXSID10944103
• Nikkaji Number: J16.341D
• Wikipedia: Phyllodulcin
• Wikidata: Q5961163
• Metabolomics Workbench ID: 68199
• ChEMBL ID: CHEMBL303483
• Mol file: 21499-23-0.mol

Synonyms:phyllodulcin;phyllodulcin, (R)-isomer

Chemical Property of Phyllodulcin

Chemical Property:

• Vapor Pressure: 2.66E-12mmHg at 25°C
• Boiling Point: 540.6°Cat760mmHg
• Flash Point: 206.2°C
• PSA: 75.99000
• Density: 1.37g/cm³
• LogP: 2.56060
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 286.08412354
• Heavy Atom Count: 21
• Complexity: 385

Purity/Quality:

99% ^*data from raw suppliers

(R)-8-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)isochroman-1-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2CC3=C(C(=CC=C3)O)C(=O)O2)O
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@H]2CC3=C(C(=CC=C3)O)C(=O)O2)O
• General Description: (+)-PHYLLODULCIN is a naturally occurring sweet-tasting dihydroisocoumarin derivative, structurally characterized by an 8-hydroxy-3-(3-hydroxy-4-methoxyphenyl) substitution. It is of pharmacological interest due to its potential applications as a sweetener and antifungal agent. (+)-PHYLLODULCIN can be efficiently synthesized via benzamide-directed ortho metalation strategies, which provide a versatile route to alkoxy-substituted isocoumarins that are otherwise challenging to produce through traditional methods. Its stereochemistry is defined by the (R)-configuration at the 3-position, contributing to its biological activity.

Technology Process of Phyllodulcin

There total 20 articles about Phyllodulcin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R)-8-hydroxy-3-(4-methoxy-3-(methoxymethoxy)phenyl)-3,4-dihydroisocoumarin (946002-05-7) → phyllodulcin (21499-23-0)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2007.04.092

Reference yield: 99.0%

(3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one (172484-39-8) → phyllodulcin (21499-23-0)

Guidance literature:

With sodium ethanolate; In ethanol; for 0.05h; Heating;

DOI:10.1016/0957-4166(95)00367-X

Reference yield: 95.0%

(R)-8-Hydroxy-3-(4-methoxy-3-triisopropylsilanyloxy-phenyl)-isochroman-1-one → phyllodulcin (21499-23-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;

DOI:10.1021/jo9603385

upstream raw materials:

(3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one

(R)-8-hydroxy-3-(4-methoxy-3-(methoxymethoxy)phenyl)-3,4-dihydroisocoumarin

(1R)-2-{2-[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-3-methoxyphenyl}-1-(4-methoxy-3-(methoxymethoxy)phenyl)ethanol

(S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)-4,5-dihydrooxazole

Downstream raw materials:

Thunberginol G

3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-8-(tert-butyl-dimethyl-silanyloxy)-isochromen-1-one

3'-Hydroxyhydrangeaic acid

Thunberginol A

Refernces

Ortho-Lithiated Tertiary Benzamides. Chain Extension via o-Toluamide Anion and General Synthesis of Isocoumarins Including Hydrangenol and Phyllodulcin

10.1021/jo00179a002

The research focuses on the synthesis of 3-aryl-3,4-dihydroisocoumarin derivatives, including the natural products hydrangenol and phyllodulcin, using a benzamide directed ortho metalation strategy. The purpose of the study was to develop an efficient and general method for synthesizing these compounds, which are of pharmacological interest due to their potential antifungal and sweetening properties. The researchers utilized various benzamides, such as N,N-diethyl-2-methylbenzamide and N,N-dimethyl-2-methoxybenzamide, along with reagents like lithium diisopropylamide (LDA) and sec-butyl lithium, to achieve the desired metalation and subsequent reactions. The conclusions drawn from the study indicate that the benzamide directed metalation approach is a powerful and adaptable method for synthesizing alkoxy-substituted isocoumarins, which are difficult to prepare by classical routes.

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