Methyl geranate

Base Information

• Chemical Name: Methyl geranate
• CAS No.: 1189-09-9
• Molecular Formula: C11H18 O2
• Molecular Weight: 182.263
• Hs Code.: 2916190090
• European Community (EC) Number: 214-712-6
• UNII: 26YR95MGP2
• DSSTox Substance ID: DTXSID40274147
• Nikkaji Number: J113.654B,J101.936H
• Wikidata: Q27254138
• Metabolomics Workbench ID: 78563
• Mol file: 1189-09-9.mol

Synonyms:Methyl geranate;1189-09-9;methyl (2E)-3,7-dimethylocta-2,6-dienoate;E-Methylgeranate;methyl geraniate;2,6-Octadienoic acid, 3,7-dimethyl-, methyl ester, (E)-;Methyl (E)-geranate;2,6-Octadienoic acid, 3,7-dimethyl-, methyl ester;UNII-26YR95MGP2;26YR95MGP2;Geranic acid methyl ester;Methyl (E)-3,7-dimethylocta-2,6-dienoate;2349-14-6;2,6-Octadienoic acid, 3,7-dimethyl-, methyl ester, (2E)-;EINECS 214-712-6;3,7-Dimethyl-2,6-octadienoic acid methyl ester;Methyl 3,7-dimethyl-2,6-octadienoate;Methyl-trans-geranate;DTXSID4047129;Methyl trans-geranate;methyl-(E)-geranate;Methyl geranate, AldrichCPR;trans-Geranic acid methyl ester;methyl geranate, No Antioxidant;DTXCID2027129;DTXSID40274147;ACOBBFVLNKYODD-CSKARUKUSA-N;CHEBI:166666;BAA18909;Tox21_302707;MFCD00036571;NCGC00256733-01;GERANIC ACID METHYL ESTER, TRANS-;CS-0453000;methyl (E) - 3,7 - dimethylocta - 2,6 - dienoate;Q27254138;(2E)-3,7-dimethyl-octa-2,6-dienoic acid methyl ester;OCTA-2,6-DIENOATE, 3,7-DIMETHYL-, METHYL (E)-;2,6-OCTADIENOIC ACID, 3,7-DIMETHYL-, METHYL ESTER, TRANS-

Chemical Property of Methyl geranate

Chemical Property:

• Vapor Pressure: 0.0257mmHg at 25°C
• Refractive Index: 1.4690
• Boiling Point: 247.4°Cat760mmHg
• Flash Point: 109.6°C
• PSA: 26.30000
• Density: 0.909g/cm³
• LogP: 2.85210
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 182.130679813
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

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

METHYL GERANATE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CC(=O)OC)C)C
• Isomeric SMILES: CC(=CCC/C(=C/C(=O)OC)/C)C
• Uses: Methyl geranate is a key link between the lavender aspect and the geranium character for a fougere note. It gives excellent effects in many florals to develop richness and naturalness and should be tried in colognes especially with neroli and green notes in combination with galbanum. Usage levels: 0.5-10%. It is useful in imparting a natural note in re-constituted oils.

Technology Process of Methyl geranate

There total 50 articles about Methyl geranate 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: 91.0%

methanol (67-56-1) + Geraniol (106-24-1) → methyl geranate (1189-09-9)

Guidance literature:

With Rh(trop2N)(PPh₃); methacrylic acid methyl ester; In tetrahydrofuran; at -30 - 25 ℃; for 4h; chemoselective reaction;

DOI:10.1002/anie.200804757

Reference yield: 87.0%

methanol (67-56-1) + 3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) → methyl geranate (1189-09-9)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.150972

Reference yield: 75.0%

methanol (67-56-1) + (E)-geranic acid (4698-08-2) → methyl geranate (1189-09-9)

Guidance literature:

Acidic conditions;

DOI:10.1007/s00706-016-1797-4

upstream raw materials:

ethynyl methyl ether

6-Methyl-hept-5-en-2-on

trimethyl phosphonoacetate

(E)-7-Bromo-3,7-dimethyl-oct-2-enoic acid methyl ester

Downstream raw materials:

5-(2,2-Dimethyl-propionyl)-2,6,6-trimethyl-cyclohex-2-enecarboxylic acid methyl ester

(E)-7-Chloro-3,7-dimethyl-6-phenylsulfanyl-oct-2-enoic acid methyl ester

(E)-6-Chloro-3,7-dimethyl-7-phenylsulfanyl-oct-2-enoic acid methyl ester

(E)-3,7-Dimethyl-6-phenylsulfanyl-octa-2,7-dienoic acid methyl ester

Refernces

• 1、 Comeskey, Daniel J.,Rowan, Daryl D.,Matich, Adam J.. "Synthesis of d8-geranyl diphosphate". . p. 47 - 54. Retrieved 2006.
• 2、 Meng, Zhanchao,Fürstner, Alois. "Total Synthesis of (-)-Sinulariadiolide. A Transannular Approach". . p. 805 - 809. Retrieved 2019.
• 3、 Howard,Stevens. "". . p. 161,163. Retrieved 1960.
• 4、 Berkessel, Albrecht,Biswas, Animesh,Harnying, Wacharee,Sudkaow, Panyapon. "N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading". supporting information. p. 19631 - 19636. Retrieved 2021/08/09.