Geranic acid

Base Information

• Chemical Name: Geranic acid
• CAS No.: 4698-08-2
• Molecular Formula: C10H16 O2
• Molecular Weight: 168.236
• European Community (EC) Number: 207-299-9
• UNII: 10797G3M5Y
• ChEMBL ID: CHEMBL170190
• DSSTox Substance ID: DTXSID10109997
• Metabolomics Workbench ID: 1124
• Nikkaji Number: J400F,J607F
• NSC Number: 229335
• Wikidata: Q4381113
• Wikipedia: Geranic_acid
• Mol file: 4698-08-2.mol

Synonyms:decaprenoic acid;decaprenoic acid, (E)-isomer;decaprenoic acid, (Z)-isomer;geranic acid

Chemical Property of Geranic acid

Chemical Property:

• Melting Point: 81 °C
• Boiling Point: 295.3°Cat760mmHg
• PKA: 5.17±0.33(Predicted)
• Flash Point: 201.1°C
• PSA: 37.30000
• Density: 0.96g/cm³
• LogP: 2.76370
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 208

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(=CCCC(=CC(=O)O)C)C
• Isomeric SMILES: CC(=CCC/C(=C/C(=O)O)/C)C

Technology Process of Geranic acid

There total 24 articles about Geranic 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: 93.0%

(E)-3,7-Dimethyl-octa-2,6-dienoic acid 3-methyl-but-2-enyl ester (106262-58-2) → (E)-geranic acid (4698-08-2)

Guidance literature:

With Pd(PPh₃)(OAc)2; triethylammonium formate; In 1,4-dioxane; for 4.5h; Heating;

DOI:10.1016/S0040-4039(00)84535-9

Reference yield: 92.0%

Geraniol (106-24-1) → (E)-geranic acid (4698-08-2)

Guidance literature:

With [Rh(1,3,4,5-tetramethylimidazole-2-ylidene)(trop₂NH)][trifluoromethanesulfonate]; potassium tert-butylate; dinitrogen monoxide; In tetrahydrofuran; toluene; at 50 ℃; under 750.075 Torr; Schlenk technique;

DOI:10.1002/anie.201509288

Reference yield: 91.0%

3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) → (E)-geranic acid (4698-08-2)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; acetone; at 20 ℃; for 5h;

DOI:10.1016/j.cclet.2018.02.006

upstream raw materials:

(E/Z)-3,7-dimethyl-2,6-octadienal

3-Benzenesulfonyl-3,7-dimethyl-oct-6-enoic acid ethyl ester

cis-3,7-dimethyl-2,6-octadienal

3,7-dimethyl-2,6-octadienal

Downstream raw materials:

methyl geranate

(R)-citronellic acid

(S)-(-)-citronellic acid

(2E)-3,7-dimethyl-2,6-octadienoyl chloride

Refernces

• 1、 -. "Method for preparing geranic acid by oxidizing citral". Paragraph 0035-0070. . Retrieved 2021/01/24.
• 2、 Han, Sheng,Wang, Ying,Wei, Yongge,Wu, Zhikang,Yu, Han. "Highly efficient oxidation of alcohols to carboxylic acids using a polyoxometalate-supported chromium(iii) catalyst and CO2". . p. 3150 - 3154. Retrieved 2020/06/19.