Hexadecyl 3,4,5-trihydroxybenzoate

Base Information

• Chemical Name: Hexadecyl 3,4,5-trihydroxybenzoate
• CAS No.: 5026-65-3
• Molecular Formula: C23H38O5
• Molecular Weight: 394.552
• Hs Code.: 29339990
• European Community (EC) Number: 225-715-7
• UNII: X1J85N35ZO
• DSSTox Substance ID: DTXSID00198254
• Nikkaji Number: J151.209I
• Wikidata: Q27293315
• ChEMBL ID: CHEMBL464675
• Mol file: 5026-65-3.mol

Synonyms:Hexadecyl 3,4,5-trihydroxybenzoate;5026-65-3;Cetyl gallate;Hexadecyl Gallate;Gallic Acid Cetyl Ester;n-cetylgallate;n-Hexadecyl-gallate;Gallic acid, hexadecyl ester;UNII-X1J85N35ZO;CHEMBL464675;X1J85N35ZO;Benzoic acid, 3,4,5-trihydroxy-, hexadecyl ester;EINECS 225-715-7;Cetylgallat;Hexadecyl3,4,5-trihydroxybenzoate;MFCD00016428;NIPAGALLIN CE;PROGALLIN CE;PALMITYL GALLATE;3,4,5-Trihydroxybenzoic acid hexadecyl ester;D01VEP;Gallic Acid Hexadecyl Ester;SCHEMBL36506;Gallic acid n-hexadecyl ester;1-HEXADECANOL, GALLATE;GALLIC ACID, CETYL ESTER;DTXSID00198254;BDBM50250973;Hexadecyl 3,4,5-trihydroxybenzoate #;AS-61822;LS-38404;CS-0319969;FT-0635517;G0013;D90705;A828042;Q27293315

Chemical Property of Hexadecyl 3,4,5-trihydroxybenzoate

Chemical Property:

• Vapor Pressure: 2.92E-13mmHg at 25°C
• Melting Point: 100 °C
• Refractive Index: 1.523
• Boiling Point: 562.6 °C at 760 mmHg
• Flash Point: 185.1 °C
• PSA: 86.99000
• Density: 1.065 g/cm³
• LogP: 6.44150
• Storage Temp.: 2-8°C
• XLogP3: 8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 17
• Exact Mass: 394.27192431
• Heavy Atom Count: 28
• Complexity: 375

Purity/Quality:

98%,99%, ^*data from raw suppliers

Hexadecyl3,4,5-Trihydroxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C,F
• Hazard Codes: Xi,C,F

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCOC(=O)C1=CC(=C(C(=C1)O)O)O

Technology Process of Hexadecyl 3,4,5-trihydroxybenzoate

There total 2 articles about Hexadecyl 3,4,5-trihydroxybenzoate 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: 73.0%

1-Hexadecanol (36653-82-4,124-29-8) + 3,4,5-trihydroxybenzoic acid (149-91-7) → 3,4,5-trihydroxybenzoic acid hexadecyl ester (5026-65-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 10h;

DOI:10.1007/s10600-021-03276-3

Reference yield:

→ 3,4,5-trihydroxybenzoic acid hexadecyl ester (5026-65-3)

Guidance literature:

With palladium on activated charcoal; ethanol; Hydrogenation;

DOI:10.1021/ja01207a043

Reference yield:

3,4,5-trihydroxybenzoic acid hexadecyl ester (5026-65-3) → hexadecyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-dihydroxybenzoate (1329454-70-7)

Guidance literature:

Multi-step reaction with 3 steps

1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C

2: boron trifluoride diethyl etherate / dichloromethane

3: trifluoroacetic acid / 24 h / 20 °C

With camphor-10-sulfonic acid; boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane; chloroform;

DOI:10.1016/j.tet.2011.07.046

upstream raw materials:

1-Hexadecanol

3,4,5-trihydroxybenzoic acid

Downstream raw materials:

hexadecyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-dihydroxybenzoate

hexadecyl 3-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4,5-dihydroxybenzoate

hexadecyl 3-O-(β-D-glucopyranosyl)-4,5-dihydroxybenzoate

hexadecyl 3-O-(β-D-glucopyranosyluronate)-4,5-dihydroxybenzoate

Refernces

• 1、 Savi, Luciane A.,Leal, Paulo C.,Vieira, Tiago O.,Rosso, Rober,Nunes, Ricardo J.,Yunes, Rosendo A.,Creczynski-Pasa, Tania B.,Barardi, Celia R. M.,Simoes, Claudia Maria Oliveira. "Evaluation of anti-herpetic and antioxidant activities, and cytotoxic and genotoxic effects of synthetic alkyl-esters of gallic acid". . p. 66 - 75. Retrieved 2007/10/03.