(R)-(+)-Citronellic acid

Base Information

• Chemical Name: (R)-(+)-Citronellic acid
• CAS No.: 18951-85-4
• Molecular Formula: C10H18 O2
• Molecular Weight: 170.252
• Hs Code.: 2916190090
• European Community (EC) Number: 627-267-1
• DSSTox Substance ID: DTXSID50426458
• Nikkaji Number: J66.848F
• Wikidata: Q82239370
• Mol file: 18951-85-4.mol

Synonyms:(R)-(+)-Citronellic acid;18951-85-4;(3R)-3,7-dimethyloct-6-enoic acid;(r)-citronellic acid;(R)-3,7-Dimethyloct-6-enoic acid;(+)-citronellic acid;(R)-3,7-dimethyl-6-octenoic acid;MFCD00075195;SCHEMBL712982;DTXSID50426458;CHEBI:144576;(R)-3,7-Dimethyloct-6-enoicacid;(R)-(+)-Citronellic acid, 98%;(3R)-3,7-dimethyl-6-octenoic acid;AKOS025294799;BS-42160;(R)-(+)-3,7-dimethyloct-6-enoic acid;6-Octenoic acid, 3,7-dimethyl-, (3R)-;CS-0142271;W19706;EN300-7831692;J-012228;Z1255486488

Chemical Property of (R)-(+)-Citronellic acid

Chemical Property:

• Vapor Pressure: 0.00454mmHg at 25°C
• Refractive Index: n20/D 1.4534(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
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ether, Ethyl Acetate, Methanol (Slightly)
• 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

(R)-(+)-Citronellic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 21-38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC=C(C)C)CC(=O)O
• Isomeric SMILES: C[C@H](CCC=C(C)C)CC(=O)O
• Uses: (R)-(+)-Citronellic Acid is an oxidized derivative of Citronellal (C525025), a monoterpene compound that is formed by the metabolism of plants.

Technology Process of (R)-(+)-Citronellic acid

There total 26 articles about (R)-(+)-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%

(R)-Citronellal (2385-77-5) → (R)-citronellic acid (18951-85-4,57030-77-0)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chloride; In water; tert-butyl alcohol; at 0 ℃;

DOI:10.1016/j.bmc.2020.115604

Reference yield: 99.0%

3-Methylene-7-methyloct-6-enoic Acid (55050-39-0) → (R)-citronellic acid (18951-85-4,57030-77-0)

Guidance literature:

With C₃₈H₃₆IrO₂P; hydrogen; caesium carbonate; In butan-1-ol; at 65 ℃; for 0.5h; under 2280.15 Torr; enantioselective reaction;

DOI:10.1039/c6sc03764j

Reference yield: 98.0%

pulegone (89-82-7,90449-51-7) → (R)-citronellic acid (18951-85-4,57030-77-0)

Guidance literature:

DOI:10.1016/S0040-4039(01)92354-8

upstream raw materials:

(R)-Citronellal

(3R)-citronellol

pulegone

(E)-geranic acid

Downstream raw materials:

(2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane

usaramine

(R)-3-methyl-6-(2-((5-methyl-2-(4-(trifluoromethoxy)phenyl)-1H-imidazol-1-yl)methyl)phenoxy)hexanoic acid

(R,E)-1¹,2⁶,7-trimethyl-5⁶-((4-methylpiperazin-1-yl)methyl)-5²,5³-dihydro-1¹H,5¹H-11-oxa-4-aza-5(2,1)-benzo[d]imidazola-2-(2,4)-pyridina-1(4,5)-pyrazolacycloundecaphan-3-one

Refernces

• 1、 Bartelt, Robert J.,Zilkowski, Bruce W.,Cosse, Allard A.,Schnupf, Udo,Vermillion, Karl,Momany, Frank A.. "Male-specific sesquiterpenes from phyllotreta flea beetles". . p. 585 - 595. Retrieved 2011.
• 2、 Valentine, Donald,Sun, Ruen C.,Toth, Katherine. "Enantioselective Hydrogenations of a Terpenic Acrylic Acid Catalyzed by Rhodium Complexes of Chiral Diphosphines". . p. 3703 - 3707. Retrieved 1980.
• 3、 Muto, Shin-Etsu,Bando, Masahiko,Mori, Kenji. "Synthesis and stereochemistry of the four himachalene-type sesquiterpenes isolated from the flea beetle (Aphthona flava) as pheromone candidates". . p. 1946 - 1952. Retrieved 2004.
• 4、 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.
• 5、 Goetz, Daniel B.,Holstein, Sarah A.,Varney, Michelle L.,Wiemer, David F.. "Amides as bioisosteres of triazole-based geranylgeranyl diphosphate synthase inhibitors". . . Retrieved 2020/07/10.