CITRONELLIC ACID

Base Information

• Chemical Name: CITRONELLIC ACID
• CAS No.: 502-47-6
• Deprecated CAS: 57030-77-0
• Molecular Formula: C10H18 O2
• Molecular Weight: 170.252
• Hs Code.: 29161995
• European Community (EC) Number: 207-939-7
• UNII: 1JJT408R87
• DSSTox Substance ID: DTXSID1047106
• Nikkaji Number: J11.776E
• Wikidata: Q2182744
• Metabolomics Workbench ID: 174
• ChEMBL ID: CHEMBL2288023
• Mol file: 502-47-6.mol

Synonyms:Citronellicacid (6CI);3,7-Dimethyl-6-octenoic acid;Rhodinic acid;

Chemical Property of CITRONELLIC ACID

Chemical Property:

• Appearance/Colour: COLORLESS LIQUID
• Vapor Pressure: 0.00454mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• Boiling Point: 257 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 163.2 °C
• PSA: 37.30000
• Density: 0.935 g/cm³
• LogP: 2.84360
• Water Solubility.: Insoluble in water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 170.130679813
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

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

Citronellic Acid >95.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 21-38
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(CCC=C(C)C)CC(=O)O
• Uses: Citronellic acid was used in synthesis of stereoisomers of 3,11- dimethylnonacosan-2-one and 29-hydroxy-3,11-dimethylnonacosan-2-one.

Technology Process of CITRONELLIC ACID

There total 19 articles about CITRONELLIC 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: 94.0%

3,7-dimethyl-oct-6-enal (106-23-0,26489-02-1) → racemic citronellic acid (502-47-6,57030-77-0)

Guidance literature:

With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene; In water; at 50 ℃; for 12h; under 760.051 Torr; Sealed tube;

DOI:10.1002/anie.201604847

Reference yield: 92.0%

Citronellol (106-22-9) → racemic citronellic acid (502-47-6,57030-77-0)

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: 92.0%

nerolic acid (4613-38-1) → racemic citronellic acid (502-47-6,57030-77-0)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; at 70 ℃; for 3h;

DOI:10.1016/S0040-4039(00)78461-9

upstream raw materials:

6-amino-3,7-dimethyl-octanoic acid

(R)-Citronellal

geranic acid

Citronellol

Downstream raw materials:

benzyl 3,7-dimethyloct-6-enoate

tert-butyl 5,9-dimethyl-3-oxo-2-(triphenylphosphoranylidene)-8-decenoate

N-benzyl-3,7-dimethyloct-6-en-1-amine

4-[(2-allyloxycarbonylamino-ethyl)-benzyl-carbamoyl]-2-citronellyl-amino-butyric acid methyl ester

Refernces

• 1、 -. "Method for preparing carboxylic acid by catalyzing aldehyde oxidation with N-heterocyclic carbene". Paragraph 0043; 0094-0099; 0101-0106. . Retrieved 2020/11/25.
• 2、 Oda, Shinobu,Nakanishi, Mami,Ishikawa, Asako,Baba, Toshiki. "Modified liquid–liquid interface cultivation system with floating microspheres and binder micro-pieces for slow-growing or unicellular microorganisms: Application to interfacial bioconversions with an actinomycete and yeasts". . p. 1 - 8. Retrieved 2019/02/13.