Apiole

Base Information

• Chemical Name: Apiole
• CAS No.: 523-80-8
• Deprecated CAS: 83382-66-5
• Molecular Formula: C12H14 O4
• Molecular Weight: 222.241
• Hs Code.: 2932999099
• European Community (EC) Number: 208-349-2
• NSC Number: 9070
• UNII: QQ67504PXO
• DSSTox Substance ID: DTXSID4041236
• Nikkaji Number: J6.635D
• Wikipedia: Apiole
• Wikidata: Q21071561
• Metabolomics Workbench ID: 46202
• ChEMBL ID: CHEMBL1560118
• Mol file: 523-80-8.mol

Synonyms:1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene;4,7-dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole;apiole

Chemical Property of Apiole

Chemical Property:

• Vapor Pressure: 0.00293mmHg at 25°C
• Melting Point: 29°C
• Refractive Index: nD20 1.536-1.538
• Boiling Point: 294°C
• Flash Point: 117.2°C
• PSA: 36.92000
• Density: 1.151g/cm³
• LogP: 2.16100
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 222.08920892
• Heavy Atom Count: 16
• Complexity: 243

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Apioline ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2C(=C(C(=C1)CC=C)OC)OCO2
• Uses: antipyretic, diuretic, insecticide Apioline is extracted from essential oil from the roots of Illicium Ianceolatum and is known to exhibit antinociceptive and anti-inflammatory properties.

Technology Process of Apiole

There total 8 articles about Apiole 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: 68.0%

1,4-dimethoxy-2,3-methylenedioxybenzene (23731-75-1) + allyl tosylate (4873-09-0) → apiol (523-80-8)

Guidance literature:

{(norbornadiene)rhodium(I)(NCCH₃)2}(PF₆); In toluene; at 0 ℃; for 15h;

DOI:10.1055/s-2003-40859

Reference yield:

6-allyl-2,3-methylenedioxyphenol (109073-00-9) → apiol (523-80-8)

Guidance literature:

With sodium hydroxide; dipotassium peroxodisulfate; Erwaermen des Reaktionsprodukts in Methanol mit Dimethylsulfat und wss. Kalilauge;

DOI:10.1039/jr9380001602

Reference yield:

4-allyloxy-benzo[1,3]dioxole (857579-63-6) → apiol (523-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 220 °C

2: aq. NaOH solution; aqueous potassium peroxo disulfate solution / Erwaermen des Reaktionsprodukts in Methanol mit Dimethylsulfat und wss. Kalilauge

With sodium hydroxide; dipotassium peroxodisulfate;

DOI:10.1039/jr9380001602

upstream raw materials:

6-allyl-2,3-methylenedioxyphenol

1-methyl-4-nitrosobenzene

1,4-dimethoxy-2,3-methylenedioxybenzene

allyl tosylate

Downstream raw materials:

3-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-5-(3-hydroxy-4-methoxyphenyl)-1,2,4-oxadiazole

3-(2,5-dimethoxy-3,4-methylenedioxybenzyl)-5-(3-hydroxy-4-methoxyphenyl)-1,2,4-oxadiazole

3-(2,5-dimethoxy-3,4-methylenedioxy-6-chlorophenyl)-5-(3-hydroxy-4-methoxyphenyl)-1,2,4-oxadiazole

3,4-methylenedioxy-2,4',5-trimethoxy-3'-O-t-butyldimethylsilylstilbene

Refernces