Gondoic Acid

Base Information

• Chemical Name: Gondoic Acid
• CAS No.: 5561-99-9
• Molecular Formula: C20H38 O2
• Molecular Weight: 310.521
• Hs Code.: 3823.11
• UNII: UDX6WPL94T
• DSSTox Substance ID: DTXSID30970949
• Nikkaji Number: J12.741H
• Wikipedia: 11-Eicosenoic_acid
• Wikidata: Q416618
• NCI Thesaurus Code: C68361,C68370
• Metabolomics Workbench ID: 518
• ChEMBL ID: CHEMBL4640620
• Mol file: 5561-99-9.mol

Synonyms:cis-11-eicosenoic acid;eicosenoic acid

Chemical Property of Gondoic Acid

Chemical Property:

• Appearance/Colour: yellowish paste
• Vapor Pressure: 1.84E-08mmHg at 25°C
• Melting Point: 25 - 32 C
• Refractive Index: n20/D 1.4606(lit.)
• Boiling Point: 426.3oC at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 110 ºC
• PSA: 37.30000
• Density: 0.883
• LogP: 6.88870
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 17
• Exact Mass: 310.287180451
• Heavy Atom Count: 22
• Complexity: 258

Purity/Quality:

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

(11Z)-11-EicosenoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Not regulated UN NO.
• Hazard Codes: Not regulated UN NO.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCC=CCCCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCCC(=O)O
• Description: Gondoic acid is a mono unsaturated omega-9 fatty acid found in a variety of plant oils and nuts. It is the main acid component of jojoba oil.
• Uses: (11Z)-11-Eicosenoic Acid, is a monostaturated fatty acid. The combined C20:1 isomers constitute 70% of the total fatty acid pool in jojoba seed oil isolated from plants in the Arizona desert.

Technology Process of Gondoic Acid

There total 5 articles about Gondoic Acid 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:

calopusin A (1359947-89-9) → (R,R)-2,3-butandiol (24347-58-8) + 11-eicosenoic acid (5561-99-9)

Guidance literature:

calopusin A; With potassium hydroxide; In methanol; for 2h; Reflux;

With water; In methanol;

DOI:10.1007/s11745-012-3657-2

Reference yield:

Oleic aldehyde (2423-10-1) → 11-eicosenoic acid (5561-99-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 87.5 percent / p-toluenesulfonic acid / benzene / 20 h / Heating

2: 1.) 9-BBN / 1.) THF, 25 deg C, 3 h, 2.) methanol, reflux, 2 h

3: 1.) 9-BBN, 2.) lithium diisopropylamide, 3.) NaOH, H₂O₂

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; toluene-4-sulfonic acid; lithium diisopropyl amide; In benzene;

Reference yield:

behenolic acid (506-35-4) → 11-eicosenoic acid (5561-99-9,62322-84-3,2462-94-4)

Guidance literature:

With potassium hydroxide; at 260 ℃;

upstream raw materials:

behenolic acid

(Z)-1-bromo-9-octadecene

sodium diethylmalonate

Oleic aldehyde

Downstream raw materials:

cis-11-eicosenamide

trans-11-eicosenoic acid

(11Z)-icosenanilide

(11Z)-11-icosenoic acid methyl ester

Refernces

• 1、 Dhillon, Ranjit S.,Singh, Rupinder P.,Singh, Jasvinder. "Pheromones via organoboranes: Part IV - Synthesis of (Z)-9-tricosene (Muscalure)". . p. 718 - 721. Retrieved 2007/10/03.