Queen substance

Base Information

• Chemical Name: Queen substance
• CAS No.: 2575-01-1
• Molecular Formula: C10H16 O3
• Molecular Weight: 184.235
• Hs Code.: 2918300090
• UNII: 618LR3X900
• Nikkaji Number: J1.525C,J2.370.988K
• Wikidata: Q27263314
• Metabolomics Workbench ID: 1589
• Mol file: 2575-01-1.mol

Synonyms:9-ODA cpd;9-oxodec-2-enoic acid;9-oxodecenoic acid;9ODA cpd

Chemical Property of Queen substance

Chemical Property:

• Boiling Point: 369.7°Cat760mmHg
• Flash Point: 191.6°C
• PSA: 54.37000
• Density: 1.029g/cm³
• LogP: 2.16670
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 194

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CCCCCC=CC(=O)O
• Isomeric SMILES: CC(=O)CCCCC/C=C/C(=O)O

Technology Process of Queen substance

There total 106 articles about Queen substance 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: 85.0%

(E)-(+/-)-9-Hydroxy-2-decensaeure (4448-33-3) → (E)-9-oxo-dec-2-enoic acid (334-20-3,2575-01-1,29282-32-4)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; at 50 ℃; for 1h;

DOI:10.1023/A:1019683830012

Reference yield: 82.0%

(E)-9-Oxo-2-decanoic acid methyl ester (1189-64-6) → (E)-9-oxo-dec-2-enoic acid (334-20-3,2575-01-1,29282-32-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; for 5h; Heating;

DOI:10.1055/s-1988-27461

Reference yield: 81.5%

ethyl 9-oxo-trans-2-decenoate (57221-88-2) → (E)-9-oxo-dec-2-enoic acid (334-20-3,2575-01-1,29282-32-4)

Guidance literature:

With potassium hydroxide; In ethanol; for 3.5h; Heating;

upstream raw materials:

Decen-(2^c+t)-on-⁽⁹⁾-saeure-⁽¹⁾-methylester

(Z)-9-Oxo-dec-2-enoic acid ethyl ester

2-mercapto-4-(4'-methoxyphenyl)thiazole

7-oxo-octanal

Downstream raw materials:

(E)-9-Oxo-2-decanoic acid methyl ester

decane-1,9-diol

1-decanoic acid

2E-nonene-1,9-dioic acid

Refernces

• 1、 Ishmuratov,Vydrina,Nasibullina,Yakovleva,Muslukhov,Tolstikov. "New approach to the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee, from the telomer of butadiene and water". . p. 789 - 791. Retrieved 2011.
• 2、 Ebert. "A two-step synthesis of the 'Queen substance' of the honey bee". . p. 1527 - 1531. Retrieved 1991.
• 3、 Tamaru et al.. "". . p. 919. Retrieved 1978.
• 4、 Kemme, Susanne T.,?mejkal, Tomá?,Breita, Bernhard. "Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence". supporting information; experimental part. p. 989 - 994. Retrieved 2009/05/27.