Isovanillin

Base Information

• Chemical Name: Isovanillin
• CAS No.: 621-59-0
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: 29124900
• European Community (EC) Number: 210-694-9
• NSC Number: 82996
• UNII: 4A9N90H9X6
• DSSTox Substance ID: DTXSID7049423
• Nikkaji Number: J57.879G
• Wikipedia: Isovanillin
• Wikidata: Q412986
• Metabolomics Workbench ID: 129998
• ChEMBL ID: CHEMBL275563
• Mol file: 621-59-0.mol

Synonyms:iso-vanillin;isovanillin;isovanillin, potassium salt

Chemical Property of Isovanillin

Chemical Property:

• Appearance/Colour: light tan cyrstalline solid
• Vapor Pressure: 0.000384mmHg at 25°C
• Melting Point: 113-116 °C
• Refractive Index: 1.587
• Boiling Point: 308.1 °C at 760 mmHg
• PKA: pK1:8.889 (25°C)
• Flash Point: 119.9 °C
• PSA: 46.53000
• Density: 1.231 g/cm³
• LogP: 1.21330
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Sensitive.: Air Sensitive
• Solubility.: Soluble in acetone and methanol.
• Water Solubility.: 2.27g/L at 20℃
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 135

Purity/Quality:

99% ^*data from raw suppliers

Isovanillin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=O)O
• Uses: 3-Hydroxy-4-methoxybenzaldehyde was used as starting reagent during the two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 and glycitein synthesis.

Technology Process of Isovanillin

There total 112 articles about Isovanillin 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%

3-hydroxy-4-methoxybenzyl alcohol (4383-06-6) → isovanillin (621-59-0)

Guidance literature:

With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate; In dichloromethane;

DOI:10.1021/jo981322c

Reference yield: 99.0%

3-benzyloxy-4-methoxybenzaldehyde (6346-05-0) → isovanillin (621-59-0)

Guidance literature:

With iron(III) chloride on silica; In neat (no solvent); at 30 ℃; for 1h;

DOI:10.1021/jo00335a045

Reference yield: 99.0%

O-methoxymethylisovanillin (5779-98-6) → isovanillin (621-59-0)

Guidance literature:

With β‐cyclodextrin; In water; at 60 ℃; for 0.15h; Microwave irradiation;

DOI:10.1039/c5ra15996b

upstream raw materials:

3-ethoxy-4-methoxybenzaldehyde

Isochavibetol

3-(3-acetoxy-4-methoxyphenyl)acrylic acid

opianic acid

Downstream raw materials:

(Z)-2-methoxy-5-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)phenyl acetate

Isochavibetol

3-ethoxy-4-methoxybenzaldehyde

(E)-1-(2,4-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-prop-2-en-1-one

Refernces

• 1、 -. "Method for synthesizing isovanillin". Paragraph 0019; 0031-0039; 0041-0051. . Retrieved 2021/07/31.
• 2、 Grimm, Christopher,Kroutil, Wolfgang,Pompei, Simona,Schiller, Christine,Schober, Lukas. "Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives". supporting information. p. 16906 - 16910. Retrieved 2021/07/02.