4-Hydroxy-3,5-dimethoxy-cinnamyl alcohol

Base Information

• Chemical Name: 4-Hydroxy-3,5-dimethoxy-cinnamyl alcohol
• CAS No.: 537-33-7
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• DSSTox Substance ID: DTXSID10895025
• Wikidata: Q105159849,Q105159850
• Mol file: 537-33-7.mol

Synonyms:DTXSID10895025;4-hydroxy-3,5-dimethoxy-cinnamyl alcohol;4-(3-Hydroxy-1-propen-1-yl)-2,6-dimethoxyphenol

Chemical Property of 4-Hydroxy-3,5-dimethoxy-cinnamyl alcohol

Chemical Property:

• Vapor Pressure: 1.32E-06mmHg at 25°C
• Melting Point: 61-65 °C(lit.)
• Boiling Point: 384.7°Cat760mmHg
• PKA: 10.00±0.40(Predicted)
• Flash Point: 186.4°C
• PSA: 58.92000
• Density: 1.205g/cm³
• LogP: 1.41490
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

99%, ^*data from raw suppliers

Sinapyl alcohol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C=CCO
• Description: Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which are precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenoids and coumarins.
• Uses: Sinapyl alcohol, a monolignol, is a primary lignin monomer. It has been evaluated for anti-inflammatory and antinociceptive activities. It participates in the initial stages in the biosynthesis of lignin. Coupling reactions of sinapyl alcohol and sinapyl p-hydroxybenzoate has been reported. Preparation of sinapyl alcohol by selective 1,2-reduction of corresponding cinnamate esters using diisobutylaluminium hydride as reducing agent has been studied. Sinapyl Alcohol is useful for producing nail polish made of wood. Sinapyl alcohol may be employed in the preparation of lignin, a highly stable biopolymer.

Technology Process of 4-Hydroxy-3,5-dimethoxy-cinnamyl alcohol

There total 10 articles about 4-Hydroxy-3,5-dimethoxy-cinnamyl alcohol 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%

4-hydroxy-3,5-dimethoxycinnamic acid methyl ester (42041-51-0,67460-46-2,20733-94-2) → Syringenin (20675-96-1,104330-63-4,537-33-7)

Guidance literature:

With 1-bromo-butane; lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 20 ℃; Cooling with acetone-dry ice; Inert atmosphere;

DOI:10.1039/c5gc01334h

Reference yield:

lignin (9005-53-2) → p-cresol (106-44-5) + 2-Methoxy-4-methylphenol (93-51-6) + 4-hydroxymethyl-2-methoxyphenol (498-00-0) + Apocynol (2480-86-6) + Syringenin (20675-96-1,104330-63-4,537-33-7) + vanillin (121-33-5,8014-42-4) + phenol (108-95-2,27073-41-2)

Guidance literature:

lignin; With titanium(IV) oxide; In water; for 5h; UV-irradiation;

With hydrogen; In methanol; at 20 ℃; for 24h; under 7498.84 Torr;

DOI:10.1039/d0gc00052c

Reference yield:

1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2'-methoxyphenoxy)-1,3-propanediol (92409-34-2) → sinapinaldehyde (4206-58-0,87345-53-7,20649-43-8) + 1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one (5650-43-1) + Syringenin (20675-96-1,104330-63-4,537-33-7) + 2-methoxy-phenol (90-05-1) + 3-hydroxy-1-(3,5-dimethoxy-4-hydroxyphenyl)-propan-1-one (136196-47-9)

Guidance literature:

With hydrazine hydrate; iso-butanol; at 80 ℃; for 24h; Inert atmosphere; Sealed tube; Irradiation; Green chemistry;

DOI:10.1039/d1gc01953h

upstream raw materials:

syringin

(E)-sinapinaldehyde

3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

5-hydroxyconiferyl alcohol

Downstream raw materials:

3’,4’,5’-trimethoxycinnamyl alcohol

C₂₁H₂₄O₇

C₃₁H₃₆O₁₁

C₃₂H₃₈O₁₂

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