(2E,4E)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid

Base Information

• Chemical Name: (2E,4E)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid
• CAS No.: 53092-52-7
• Deprecated CAS: 40596-67-6
• Molecular Formula: C16H28 O3
• Molecular Weight: 268.397
• Hs Code.: 2918990090
• European Community (EC) Number: 258-355-4
• UNII: MB9LR353F8
• DSSTox Substance ID: DTXSID10886034
• Wikidata: Q27085172
• Pharos Ligand ID: 9K9JN8YLLBPZ
• ChEMBL ID: CHEMBL289635
• Mol file: 53092-52-7.mol

Synonyms:Methoprene acid;53092-52-7;2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, (2E,4E)-;ZR-725;UNII-MB9LR353F8;(2E,4E)-11-METHOXY-3,7,11-TRIMETHYLDODECA-2,4-DIENOIC ACID;MB9LR353F8;EINECS 258-355-4;(+-)-(2E,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid;C16H28O3;S Methoprene acid;Spectrum5_001945;D0CT1F;BSPBio_001416;BML2-E11;CHEMBL289635;GTPL2812;SCHEMBL3052148;SCHEMBL3052151;(2E,4E)-(+-)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid;2,4-Dodecadienoic acid, 11-methoxy-3,7,11-trimethyl-, (E,E)-(.+.)-;CHEBI:91685;DTXSID10886034;HMS1361G18;HMS1791G18;HMS1989G18;HMS3402G18;Methoprene acid, >=98% (TLC);AKOS037645613;AS-6176;IDI1_033886;NCGC00161329-01;NCGC00161329-02;NCGC00161329-03;NCGC00161329-04;BRD-A41145729-001-02-7;Q27085172;(2E,4E)-(1)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid;2,4-DODECADIENOIC ACID, 11-METHOXY-3,7,11-TRIMETHYL-, (E,E)-;TRANS,TRANS-11-METHOXY-3,7,11-TRIMETHYL-2,4-DODECADIENOIC ACID;2,4-DODECADIENOIC ACID, 11-METHOXY-3,7,11-TRIMETHYL-, (E,E)-(+/-)-

Chemical Property of (2E,4E)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid

Chemical Property:

• Vapor Pressure: 2.62E-07mmHg at 25°C
• Boiling Point: 394.1°Cat760mmHg
• PKA: 4.96±0.33(Predicted)
• Flash Point: 134.2°C
• PSA: 46.53000
• Density: 0.954g/cm³
• LogP: 4.19500
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO or Ethanol
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 268.20384475
• Heavy Atom Count: 19
• Complexity: 327

Purity/Quality:

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

Methoprene acid ≥98% (TLC) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCCC(C)(C)OC)CC=CC(=CC(=O)O)C
• Isomeric SMILES: CC(CCCC(C)(C)OC)C/C=C/C(=C/C(=O)O)/C
• Description: Methoprene Acid (53093-52-7) is an analog of insect juvenile hormone which acts as an insect growth regulator. Binds directly and selectively to the retinoid X receptor (RXR) acting as a transcriptional activator in both insect and mammalian cells with no activity at RAR.1?Negatively regulates thrombosis and hemostasis.2?Induces neurosteroid biosynthesis in human glial GI-1 cells.3?Increases the expression of the brown-fat-uncoupling-protein-1 gene (ucp-1).4
• Uses: Methoprene Acid is an analog of insect juvenile hormone which acts as an insect growth regulator.

Technology Process of (2E,4E)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid

There total 4 articles about (2E,4E)-11-Methoxy-3,7,11-trimethyldodeca-2,4-dienoic 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:

6-(6-Methoxy-2,6-dimethyl-heptyl)-4-methyl-3,6-dihydro-pyran-2-one (52313-82-3) → Methoprene acid (53092-52-7,207597-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOEt / ethanol

2: (i) PhSH, (ii) NH₃

With sodium ethanolate; In ethanol;

DOI:10.1021/jo00889a001

Reference yield:

(2Z,4E)-11-methoxy-3,7,11-trimethyl-dodeca-2,4-dienoic acid (53023-65-7,207597-76-0) → Methoprene acid (53092-52-7,207597-76-0)

Guidance literature:

Multistep reaction; (i) PhSH, (ii) NH₃;

DOI:10.1021/jo00889a001

Reference yield:

→ S-(4E)-3,7,11-Trimethyl-11-methoxy-2,4-dodecadiensaeure (40596-67-6,41915-75-7,53023-65-7,53092-52-7,56374-19-7,84889-18-9,207597-76-0)

Guidance literature:

S-(-)-7-Methoxydihydrocitronellal, Diisopropyl-3-isopropoxycarbonyl-2-methyl-2-propenylphosphonat, NaH;

DOI:10.1021/jf60217a019

upstream raw materials:

(2Z,4E)-11-methoxy-3,7,11-trimethyl-dodeca-2,4-dienoic acid

6-(6-Methoxy-2,6-dimethyl-heptyl)-4-methyl-3,6-dihydro-pyran-2-one

Downstream raw materials:

methoprene

Refernces