(-)-Citronellol

Base Information

• Chemical Name: (-)-Citronellol
• CAS No.: 7540-51-4
• Molecular Formula: C10H20O
• Molecular Weight: 156.268
• Hs Code.: 29052220
• European Community (EC) Number: 231-415-7
• UNII: 8RSY5Y5658
• DSSTox Substance ID: DTXSID1041550
• Nikkaji Number: J67.958E
• Wikidata: Q27105229
• RXCUI: 2050062
• Metabolomics Workbench ID: 28011
• ChEMBL ID: CHEMBL1907995
• Mol file: 7540-51-4.mol

Synonyms:7540-51-4;(S)-3,7-dimethyloct-6-en-1-ol;(-)-beta-Citronellol;l-Citronellol;(-)-Citronellol;(S)-(-)-citronellol;beta-Rhodinol;(3S)-3,7-dimethyloct-6-en-1-ol;(S)-(-)-beta-Citronellol;(S)-citronellol;6-Octen-1-ol, 3,7-dimethyl-, (3S)-;(-)-3,7-Dimethyloct-6-en-1-ol;(S)-(-)-3,7-Dimethyl-6-octen-1-ol;(3S)-citronellol;6-Octen-1-ol, 3,7-dimethyl-, (S)-;(S)-3,7-Dimethyl-6-octen-1-ol;CHEBI:88;UNII-8RSY5Y5658;3S,7-dimethyloct-6-en-1-ol;DTXSID1041550;8RSY5Y5658;EINECS 231-415-7;FEMA No. 2309;6-Octen-1-ol, 3,7-dimethyl-, (-)-;AI3-09552;MFCD00063214;(3s)-3,7-dimethyl-6-octen-1-ol;(S)-(-)-beta-Citronellol, 99%, FG;laevo-citronellol;(S) -citronellol;(s)-beta-citronellol;(-)-fA-Citronellol;(-)-(s)-citronellol;CITRONELLOL, L-;beta-Citronellol, (S)-;(-)-(S)-beta-citronellol;SCHEMBL301394;CHEMBL1907995;DTXCID9021550;(-)-.BETA.-CITRONELLOL;.BETA.-CITRONELLOL, (S)-;Tox21_300711;(S)-(-)-beta-Citronellol, 99%;AKOS015902396;(S)-(-)-.BETA.-CITRONELLOL;CS-W016231;LMPR0102010012;LS-2078;NCGC00248147-01;NCGC00254618-01;AC-26774;AS-57118;(-)-beta-Citronellol, analytical standard;CAS-7540-51-4;C2254;C3619;F16553;Q27105229;( - ) - 3,7 - dimethyloct - 6 - en - 1 - ol

Chemical Property of (-)-Citronellol

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: ~0.02 mm Hg ( 25 °C)
• Melting Point: 77-83oC(lit.)
• Refractive Index: n20/D 1.456
• 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 (Soluble), Ethyl Acetate (Slightly), Methanol (Soluble)
• Water Solubility.: SLIGHTLY SOLUBLE
• 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

L-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

Useful:

• Canonical SMILES: CC(CCC=C(C)C)CCO
• Isomeric SMILES: C[C@@H](CCC=C(C)C)CCO
• Uses: L-Citronellol as fragrance ingredient.

Technology Process of (-)-Citronellol

There total 43 articles about (-)-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: 99.0%

Geraniol (106-24-1) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Guidance literature:

With bis(norbornadiene)rhodium(l)tetrafluoroborate; (R_C,S_Fc,S_P)-1-[2-(1-N,N-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-dicyclohexylphosphinoferrocene; hydrogen; In dichloromethane; at 20 ℃; for 20h; under 19001.3 Torr; enantioselective reaction; Inert atmosphere; Autoclave;

DOI:10.1039/c3cc47727d

Reference yield: 98.59%

3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Guidance literature:

With dichloro(1,5-cyclooctadiene)ruthenium(II); (R)-(+)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; niobium pentachloride; HSiPh₃; In toluene; at 40 ℃; for 3h; Reagent/catalyst; Solvent; Temperature; enantioselective reaction; Catalytic behavior; Glovebox; Sealed tube; Inert atmosphere;

Reference yield: 96.0%

(S)-Citronellal (5949-05-3) → (S)-3,7-dimethyl-6-octen-1-ol (7540-51-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1271/bbb.68.1768

upstream raw materials:

ethanol

(S)-Citronellal

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

3,7-dimethyl-oct-6-enal

Downstream raw materials:

(S)-Citronellal

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

5-(4-Decyloxy-phenyl)-2-((S)-3,7-dimethyl-oct-6-enyloxy)-pyrimidine

(4R)-4-methylhexanoic acid

Refernces

A Short Synthesis of Natural (-)-Oblongolide via an Intramolecular or a Transannular Diels-Alder Reaction

10.1021/jo00123a011

The study presents a concise synthesis of the natural product (-)-oblongolide, a norsesquiterpene lactone, using either an intramolecular Diels-Alder (IMDA) reaction or a transannular Diels-Alder (TDA) reaction as key steps. The synthesis begins with (-)-citronellol, which is transformed into a series of intermediates through various chemical reactions. Key intermediates include methyl (2E,4E,10E)-(S)-(+)-11-(tert-butoxycarbonyl)-7-methylundeca-2,4,10-trienoate (7), obtained via sequential Lemieux-Johnson oxidation, Wittig olefination, pyridinium dichromate oxidation, and Wadsworth-Emmons-Horner alkenation. A regioselective reduction of 7 yields tert-butyl (2E,8E,10E)-(S)-(+)-2,6-dimethyl-12-hydroxydodeca-2,8,10-trienoate (8), which then undergoes the IMDA reaction to form oblongolide (1). Alternatively, the macrocyclic lactone derived from 8 undergoes a TDA reaction to produce oblongolide with higher stereoselectivity and yield. The study highlights the importance of steric control in achieving the desired stereochemistry and the efficiency of the TDA reaction compared to the IMDA reaction.

Synthesis of Retiferol RAD1 and RAD2, the Lead Representatives of a New Class of des-CD Analogs of Cholecalciferol

10.1006/bioo.1995.1002

The study investigates the design and total convergent synthesis of new analogs of cholecalciferol (vitamin D) with the CD-ring system replaced by a two-carbon aliphatic spacer. The researchers aimed to simplify the structure of vitamin D-based therapeutics by identifying the essential structural parts responsible for its activity. The key chemicals involved include vitamin D derivatives, such as vitamin D3 and 1α-hydroxyvitamin D3, which serve as precursors for the ring fragments. The chain fragment is derived from S-(-)-β-citronellol, a natural monoterpene. The synthesized compounds, RAD and RAD2, are designed as des-CD analogs of 25-OH-D3 and 1,25-(OH)2D3, respectively, with an unnatural configuration at C-20. The study employs various reagents and conditions, such as imidazole, t-BuMe2SiCl, MCPBA, lithium triethylborohydride, and pyridinium chlorochromate, to achieve the desired modifications and coupling of the ring and chain fragments. The results provide insights into the potential for developing more effective therapeutic agents based on the simplified structure of vitamin D.