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Geraniol

Base Information Edit
  • Chemical Name:Geraniol
  • CAS No.:106-24-1
  • Deprecated CAS:8007-13-4,491611-08-6
  • Molecular Formula:C10H18O
  • Molecular Weight:154.252
  • Hs Code.:29052900
  • European Community (EC) Number:203-377-1
  • NSC Number:46105,9279
  • UNII:L837108USY
  • DSSTox Substance ID:DTXSID8026727
  • Nikkaji Number:J297.798B,J3.240I
  • Wikipedia:Geraniol
  • Wikidata:Q410836
  • NCI Thesaurus Code:C63668
  • RXCUI:1368875
  • Pharos Ligand ID:C59LZQWG7A27
  • Metabolomics Workbench ID:28015
  • ChEMBL ID:CHEMBL25719
  • Mol file:106-24-1.mol
Geraniol

Synonyms:geraniol;geraniol, (E)-isomer;geraniol, (Z)-isomer;geraniol, 1-(14)C-labeled, (E)-isomer;geraniol, 2-(14)C-labeled, (E)-isomer;geraniol, titanium (4+) salt;nerol

Suppliers and Price of Geraniol
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • Geraniol
  • 10g
  • $ 418.00
  • TRC
  • Geraniol
  • 5g
  • $ 55.00
  • TCI Chemical
  • Geraniol >96.0%(GC)
  • 25mL
  • $ 19.00
  • TCI Chemical
  • Geraniol >96.0%(GC)
  • 100mL
  • $ 45.00
  • TCI Chemical
  • Geraniol >96.0%(GC)
  • 500mL
  • $ 112.00
  • Sigma-Aldrich
  • Geraniol natural, ≥97%, FG
  • 9 kg
  • $ 1190.00
  • Sigma-Aldrich
  • Geraniol ≥97%, FCC, FG
  • 20 kg
  • $ 704.00
  • Sigma-Aldrich
  • Geraniol ≥97%, FCC, FG
  • 20kg-k
  • $ 682.00
  • Sigma-Aldrich
  • Geraniol natural, ≥97%, FG
  • 4 kg
  • $ 552.00
  • Sigma-Aldrich
  • Geraniol natural, ≥97%, FG
  • 4kg-k
  • $ 535.00
Total 204 raw suppliers
Chemical Property of Geraniol Edit
Chemical Property:
  • Appearance/Colour:colourless to pale yellow liquid with an odour of roses 
  • Vapor Pressure:0.013mmHg at 25°C 
  • Melting Point:-15 °C 
  • Refractive Index:n20/D 1.474(lit.)  
  • Boiling Point:229.499 °C at 760 mmHg 
  • PKA:14.45±0.10(Predicted) 
  • Flash Point:76.667 °C 
  • PSA:20.23000 
  • Density:0.867 g/cm3 
  • LogP:2.67140 
  • Storage Temp.:2-8°C 
  • Solubility.:water: soluble0.1g/L at 25°C 
  • Water Solubility.:PRACTICALLY INSOLUBLE 
  • XLogP3:2.9
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:1
  • Rotatable Bond Count:4
  • Exact Mass:154.135765193
  • Heavy Atom Count:11
  • Complexity:150
Purity/Quality:

99% *data from raw suppliers

Geraniol *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes: Xi:Irritant;
     
  • Statements: R36/37/38:; 
  • Safety Statements: S24/25:; 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Other Classes -> Alcohols and Polyols, Other
  • Canonical SMILES:CC(=CCCC(=CCO)C)C
  • Isomeric SMILES:CC(=CCC/C(=C/CO)/C)C
  • General Description Geraniol is a monoterpenoid alcohol widely used in organic synthesis, particularly in the production of sesquiterpenes like (-)-delobanone and oligoprenols, due to its role as a key intermediate in Sharpless epoxidation and allyl-allyl coupling reactions. It is also significant in hydrogenation processes, where it forms as an unsaturated alcohol (UALC) during the hydrogenation of citral, though its stability can be affected by temperature and CO adsorption. Geraniol's versatility in synthetic chemistry underscores its importance in constructing complex molecular frameworks and bioactive compounds.
Technology Process of Geraniol

There total 227 articles about Geraniol 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:
Guidance literature:
With 15-crown-5; (1-(2-(2,3-diisopropyl-1-methylguanidino)ethyl)-3-mesityl-1,3-dihydro-2H-imidazol-2-ylidene)copper(I) chloride; hydrogen; sodium t-butanolate; In 1,4-dioxane; at 60 ℃; for 24h; Inert atmosphere;
DOI:10.1021/jacs.1c09626
Guidance literature:
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine; In N,N-dimethyl-formamide; for 72h; Inert atmosphere; Glovebox; UV-irradiation;
DOI:10.1002/anie.201208066
Guidance literature:
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine; In N,N-dimethyl-formamide; for 72h; Inert atmosphere; Glovebox; UV-irradiation;
DOI:10.1002/anie.201208066
Refernces Edit

Synthesis of (-)-delobanone

10.1021/jo001737+

The research focuses on the synthesis of (-)-delobanone, a sesquiterpene, using a novel approach that involves the preparation of alkenyl cyclopropane 2 from the Sharpless-derived epoxide 1. The key reactants include geraniol, which undergoes Sharpless epoxidation to form an epoxide, followed by sulfonylation to produce benzenesulfonate 11. This is then reacted with lithioacetonitrile to yield nitrile 9, which is further transformed into aldehyde 8 through a DIBAL-H reduction. The aldehyde is converted into an alkenyl cyclopropane 2 via a Wittig reaction. The final step involves the irradiation of 2 in the presence of Fe(CO)5 under a CO atmosphere to achieve the ring expansion, resulting in (-)-delobanone 3. Throughout the synthesis, various analytical techniques were employed, including NMR, IR, MS, and optical rotation measurements, to monitor the progress and confirm the structures of the intermediates and final product. The research also discusses the potential challenges and the successful optimization of the reaction conditions to achieve high yields and selectivity.

An improved convergent strategy for the synthesis of oligoprenols

10.1002/hlca.200890211

The present study aimed to develop a practical and highly regio- and stereoselective method for the synthesis of oligoisoprenols, essential precursors for the synthesis of biologically important isoprenoids. The convergent synthetic strategy described is characterized by iterative allyl-allyl couplings of monomers derived from commercially available geraniol and repeated reductive elimination of p-toluenesulfonyl (Ts) groups. The study successfully demonstrated the use of this approach to synthesize (all-trans)-oligoisoprenols, such as (all-trans)-octaprenol and (all-trans)-decaprenol, which is more efficient and practical compared to previous methods. The key chemicals used in the process include geraniol, p-toluenesulfonyl, allyl bromide, allyl sulfone, and various reducing agents such as Li/EtNH2, Na/EtOH, Na/naphthalene, and LiHBEt3/Pd(dppp)Cl2. The study concluded that the developed convergent strategy is an effective method for the synthesis of long linear polyprene backbones.

Liquid-phase hydrogenation of citral over Pt/SiO2 catalysts - I. Temperature effects on activity and selectivity

10.1006/jcat.1999.2803

The research investigates the liquid-phase hydrogenation of citral over Pt/SiO2 catalysts, aiming to understand the effects of temperature on the reaction's activity and selectivity. Citral, an a,?-unsaturated aldehyde with a conjugated C==C-C==O bond system and an isolated C==C bond, is hydrogenated to produce various products like unsaturated alcohols (UALC), partially saturated aldehydes (PSALD), and completely saturated alcohols (SAT). The study finds that the reaction rate exhibits an unusual activity minimum at 373 K, attributed to the interplay between the decomposition of unsaturated alcohols (geraniol and nerol) and the desorption of CO. At lower temperatures (298 K), the reaction rate decreases significantly due to CO accumulation blocking active sites, while at higher temperatures (373 K and above), the enhanced CO desorption rate allows for stable activity and conventional Arrhenius behavior. The researchers propose a kinetic model based on Langmuir–Hinshelwood kinetics, incorporating dissociative adsorption of hydrogen, competitive adsorption between hydrogen and organic compounds, and the addition of a second hydrogen atom as the rate-determining step. The model successfully describes the observed product distributions and the unusual temperature dependence of the reaction rate.

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