D-Citronellol

Base Information

• Chemical Name: D-Citronellol
• CAS No.: 1117-61-9
• Molecular Formula: C10H20O
• Molecular Weight: 156.268
• Hs Code.: 2905290000
• European Community (EC) Number: 214-250-5
• UNII: P01OUT964K
• DSSTox Substance ID: DTXSID00880647
• Nikkaji Number: J67.959C
• Wikidata: Q418813
• RXCUI: 1310495
• Metabolomics Workbench ID: 28007
• ChEMBL ID: CHEMBL1907993
• Mol file: 1117-61-9.mol

Synonyms:beta-citronellol;citronellol;citronellol, (+-)-isomer;citronellol, (R)-isomer;citronellol, (S)-isomer;citronellol, titanium (+4) salt

Chemical Property of D-Citronellol

Chemical Property:

• Vapor Pressure: ~0.02 mm Hg ( 25 °C)
• Melting Point: -4.05°C (estimate)
• Refractive Index: n20/D 1.456(lit.)
• Boiling Point: 224.5 °C at 760 mmHg
• PKA: 15.13±0.10(Predicted)
• Flash Point: 98.3 °C
• PSA: 20.23000
• Density: 0.845 g/cm³
• LogP: 2.75130
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly, Sonicated), Ethyl Acetate, Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 156.151415257
• Heavy Atom Count: 11
• Complexity: 112

Purity/Quality:

99.9% ^*data from raw suppliers

D-Citronellol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(CCC=C(C)C)CCO
• Isomeric SMILES: C[C@H](CCC=C(C)C)CCO
• Description: (+)-β-Citronellol is a monoterpene that has been found in Cannabis. It inhibits degranulation of cultured mast cells by 21.3% when used at a concentration of 0.5 mM. Unlike (R)-citronellal, it does not reduce the perceived bitterness of caffeine when used at a concentration of 5.9 nM. Formulations containing (+)-β-citronellol have been used as fragrance ingredients in various cosmetics, toiletries, and cleaning products.
• Uses: (R)-(+)-β-Citronellol can undergo:Oxidation to form (R)-(+)-citronellal, an antifungal agent and (R)-(+)-citronellic acid. Intermolecular olefin aziridination with 2,2,2-trichloroethoxysulfonamide to form citronellol aziridine for ring-opening reactions.Series of reactions to form α2δ-ligands for treating generalized anxiety disorder and insomnia.

Technology Process of D-Citronellol

There total 74 articles about D-Citronellol 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: 100.0%

(R)-Citronellal (2385-77-5) → (3R)-citronellol (1117-61-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1016/j.tet.2015.04.107

Reference yield: 99.0%

cis-3,7-dimethyl-2,6-octadienal (106-26-3,96680-15-8) → (3R)-citronellol (1117-61-9)

Guidance literature:

With BF₄^(1-)*C₉₀H₁₃₀O₆P₂Rh⁽¹⁺⁾; hydrogen; In methanol; at 20 ℃; for 18h; under 22502.3 Torr; Reagent/catalyst; Temperature; Pressure; enantioselective reaction; Autoclave;

Reference yield: 97.0%

citronellol-tetrahydropyranyl ether (71841-73-1) → (3R)-citronellol (1117-61-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 55 ℃; for 3h;

DOI:10.1007/s10600-018-2379-y

upstream raw materials:

methanol

(R)-Citronellal

aluminum ethoxide

ethanol

Downstream raw materials:

3,7-dimethyl-6-octen-1-ol formate

citronellyl tiglate

(R)-Citronellal

(+)(R)-1-hydroxy-2.6-dimethyl-octen-⁽²⁾-oic acid-⁽⁸⁾

Refernces

• 1、 Daley, Christopher J.A.,Wiles, Jason A.,Bergens, Steven H.. "Application of [Ru((R)-BINAP)(MeCN)(1-3:5,6-η-C8H11)](BF4) as a catalyst precursor for enantioselective hydrogenations". . p. 1447 - 1456. Retrieved 1998.
• 2、 Ali,Allaoud,Karim,Roucoux,Mortreux. "Catalytic synthesis of (R) and (S) citronellol by homogeneous hydrogenation over amidophosphinephosphinite and diaminodiphosphine rhodium complexes". . p. 369 - 370. Retrieved 1995.
• 3、 Gramatica, Paola,Manitto, Paolo,Poli, Laura. "Chiral Synthetic Intermediates via Asymmetric Hydrogenation of α-Methyl-α,β-unsaturated Aldehydes by Baker's Yeast". . p. 4625 - 4628. Retrieved 1985.
• 4、 Kikukawa, Tadashi,Imaida, Motomasa,Tai, Akira. "SYNTHESIS OF THE SEX-ATTRACTANT OF PINE SAWFLIES (DIPRION SPECIES); (2S,3R,7R)- AND (2S,3R,7S)-3,7-DIMETHYLPENTADECAN-2-Ol". . p. 1799 - 1802. Retrieved 1982.
• 5、 Mori, Kenji,Akasaka, Kazuaki. "Pheromone synthesis. Part 258. Synthesis of the enantiomers of the beetle pheromones ethyl 4-methylheptanoate, 4-methyloctanoic acid and 4-methyl-1-nonanol, and HPLC analysis of their derivatives to determine their enantiomeric purities". . p. 182 - 187. Retrieved 2016.
• 6、 Takaya, Hidemasa,Ohta, Tetsuo,Sayo, Noboru,Kumobayashi, Hidenori,Akutagawa, Susumu,et al.. "Enantioselective Hydrogenation of Allylic and Homoallylic Alcohols". . p. 1596 - 1597. Retrieved 1987.
• 7、 Zhao, Cheng-Hua,Millar, Jocelyn G.,Pan, Kun-Hui,Cai-Sheng. "Responses of tea tussock moth, Euproctis pseudoconspersa, to its pheromone, (R)- 10,14-dimethylpentadecyl isobutyrate, and to the S-enantiomer of its pheromone". . p. 1347 - 1353. Retrieved 1998.
• 8、 Mori,Harashima. "Assignment of (6R*10R*)-relative stereochemistry to the major component of the sex pheromone of the maritime pine scale, Matsucoccus feytaudi". . p. 5995 - 5998. Retrieved 1991.
• 9、 Guerrero, Angel,Ramos, Victoria Elena,López, Sergio,Alvarez, José María,Domínguez, Aroa,Coca-Abia, María Milagro,Bosch, María Pilar,Quero, Carmen. "Enantioselective Synthesis and Activity of All Diastereoisomers of (E)-Phytal, a Pheromone Component of the Moroccan Locust, Dociostaurus maroccanus". . p. 72 - 80. Retrieved 2019/01/15.