Hydrangenol

Base Information

• Chemical Name: Hydrangenol
• CAS No.: 480-47-7
• Molecular Formula: C15H12O4
• Molecular Weight: 256.258
• UNII: TL8PI7PHV1
• DSSTox Substance ID: DTXSID20963981
• Nikkaji Number: J12.398F
• Wikipedia: Hydrangenol
• Wikidata: Q5954317
• Metabolomics Workbench ID: 68120
• ChEMBL ID: CHEMBL69299
• Mol file: 480-47-7.mol

Synonyms:hydrangenol

Chemical Property of Hydrangenol

Chemical Property:

• Vapor Pressure: 8.86E-12mmHg at 25°C
• Refractive Index: 1.661
• Boiling Point: 528.3 °C at 760 mmHg
• Flash Point: 206.4 °C
• PSA: 66.76000
• Density: 1.386 g/cm³
• LogP: 2.55200
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 256.07355886
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

97% ^*data from raw suppliers

Hydrangenol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(=O)C2=C1C=CC=C2O)C3=CC=C(C=C3)O
• General Description: Hydrangenol is a naturally occurring 3-aryl-3,4-dihydroisocoumarin derivative with potential pharmacological applications, including antifungal and sweetening properties. It can be efficiently synthesized using a benzamide-directed ortho metalation strategy, which provides a versatile and general method for producing structurally complex isocoumarins that are otherwise challenging to obtain through traditional synthetic routes.

Technology Process of Hydrangenol

There total 35 articles about Hydrangenol 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: 94.0%

(+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin (82780-51-6) → hydrangenol (480-47-7)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 25 ℃;

DOI:10.1016/S0040-4039(00)87180-4

Reference yield: 84.0%

3-(4'-benzyloxyphenyl)-8-hydroxy-3,4-dihydro-2-benzopyran-1-one (637774-32-4) → hydrangenol (480-47-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; under 3750.3 Torr;

DOI:10.1016/j.tet.2003.09.046

Reference yield: 81.0%

6-<2-(4-benzyloxyphenyl)ethenyl>salicylic acid → hydrangenol (480-47-7)

Guidance literature:

With hydrogenchloride; In methanol; for 4h; Heating;

DOI:10.3987/COM-92-S16

upstream raw materials:

Hydrangeaic acid

Hydrangenol-8-O-glucoside

(+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin

3-(4'-benzyloxyphenyl)-8-hydroxy-3,4-dihydro-2-benzopyran-1-one

Downstream raw materials:

2-hydroxy-6-methylbenzoic acid

4-hydroxy-benzoic acid

8-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-isochroman-1-one

lunularic acid

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.