(S)-(-)-Citronellic acid

Base Information

• Chemical Name: (S)-(-)-Citronellic acid
• CAS No.: 2111-53-7
• Molecular Formula: C10H18 O2
• Molecular Weight: 170.252
• Hs Code.: 2916190090
• European Community (EC) Number: 623-663-3
• Nikkaji Number: J66.847H
• Wikidata: Q105009585
• Mol file: 2111-53-7.mol

Synonyms:(S)-(-)-Citronellic acid;2111-53-7;(S)-(-)-3,7-Dimethyl-6-octenoic acid;(3S)-3,7-dimethyloct-6-enoic acid;(s)-citronellic acid;(-)-citronellic acid;(?)-Citronellic acid;SCHEMBL714852;CHEBI:144575;GJWSUKYXUMVMGX-VIFPVBQESA-N;(S)-(-)-Citronellic acid, 98%;(S)-3,7-dimethyl-6-octenoic acid;(S)-3,7-Dimethyloct-6-enoic acid;(3S)-3,7-dimethyl-6-octenoic acid;(s)-(-)-3,7-dimethyl-oct-6-enoic acid;6-Octenoic acid, 3,7-dimethyl-, (3S)-;J-013855

Chemical Property of (S)-(-)-Citronellic acid

Chemical Property:

• Vapor Pressure: 0.00454mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Boiling Point: 257°Cat760mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 163.2°C
• PSA: 37.30000
• Density: 0.935g/cm³
• LogP: 2.84360
• 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:

99%, ^*data from raw suppliers

(S)-(?)-Citronellic acid 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 38

MSDS Files:

Useful:

• Canonical SMILES: CC(CCC=C(C)C)CC(=O)O
• Isomeric SMILES: C[C@@H](CCC=C(C)C)CC(=O)O
• Uses: (S)-(-)-Citronellic acid may be used in the synthesis of trisubstituted piperidine substructures of the veratramine and jervine type, that can be building blocks for developing cyclopamine analogs.

Technology Process of (S)-(-)-Citronellic acid

There total 20 articles about (S)-(-)-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: 99.0%

(S)-Citronellal (5949-05-3) → (S)-(-)-citronellic acid (2111-53-7,57030-77-0)

Guidance literature:

With silver nitrate; sodium hydroxide; In water; pH=14; Inert atmosphere;

DOI:10.1021/jo2026228

Reference yield: 75.0%

(S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) → (S)-(-)-citronellic acid (2111-53-7,57030-77-0)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c6ob01599a

Reference yield: 43.0%

(S)-Citronellal (5949-05-3) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) + (S)-(-)-citronellic acid (2111-53-7,57030-77-0)

Guidance literature:

With Fusarium concentricum; In dimethyl sulfoxide; at 28 - 30 ℃; for 120h; Reagent/catalyst; Microbiological reaction;

DOI:10.1002/cbdv.201300112

upstream raw materials:

(E)-geranic acid

(S)-Citronellal

3-Methylene-7-methyloct-6-enoic Acid

nerolic acid

Refernces

• 1、 Santaniello, Enzo,Manzocchi, Ada,Biondi, Pier Antonio,Secchi, Camillo,Simonic, Tatijana. "Stereospecificity of Pig Kidney and Pea Seedling Diamino Oxidases on 2-Methyl-1,4-diaminobutane". . p. 803 - 804. Retrieved 1984.
• 2、 Boudreault, Pierre-Luc,Comeau, Christian,Derbali, Rabeb Mouna,Grandbois, Michel,Poulet, Sylvain,Ries, Benjamin,Riniker, Sereina,Sarret, Philippe,Stadelmann, Thomas,Tremblay, Jacob,C?té, Jér?me,Fr?hlich, Ulrike,Leclair, Grégoire,Marsault, éric. "Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- And C-Methylations Fine-Tune Conformation and Properties". . p. 5365 - 5383. Retrieved 2021/05/04.
• 3、 -. "PPAR AGONISTS, COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF". Page/Page column 104-105. . Retrieved 2017/04/23.