Geraniol CAS 106-24-1
Introduction：Basic information about Geraniol CAS 106-24-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Geraniol Basic informationDescription References
| Product Name: | Geraniol |
| Synonyms: | LEMONOL;GERANIOL;GERANIOL 60;GERANIOL 600;GERANIOL 70;GERANIOL 80;GERANIOL 90;GERANIOL 902 |
| CAS: | 106-24-1 |
| MF: | C10H18O |
| MW: | 154.25 |
| EINECS: | 203-377-1 |
| Product Categories: | Steroid Metabolism;Acyclic;Alkenes;Allium sativum (Garlic);Building Blocks;Cancer Research;Chemical Synthesis;Chemopreventive Agents;Citrus aurantium (Seville orange);Elettaria Cardamomum (Cardamom);Enzyme Inhibitors;Humulus lupulus (Hops);Lavandula angustifolia (Lavendar tea);Metabolic Pathways;Metabolomics;Nutrition Research;Ocimum basilicum (Basil);Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);s wort);Terpenoid Metabolism;Terpenoids;Vaccinium myrtillus (Bilberry);Acyclic Monoterpenes;Biochemistry;Terpenes;Zingiber officinale (Ginger) |
| Mol File: | 106-24-1.mol |
Geraniol Chemical Properties
| Melting point | -15 °C |
| Boiling point | 229-230 °C (lit.) |
| density | 0.879 g/mL at 20 °C (lit.) |
| vapor density | 5.31 (vs air) |
| vapor pressure | ~0.2 mm Hg ( 20 °C) |
| refractive index | n |
| FEMA | 2507 | GERANIOL |
| Fp | 216 °F |
| storage temp. | 2-8°C |
| solubility | water: soluble0.1g/L at 25°C |
| pka | 14.45±0.10(Predicted) |
| form | Liquid |
| color | Clear colorless to pale yellow |
| Specific Gravity | 0.878～0.885 (20/4℃) |
| Odor | at 100.00 %. sweet floral fruity rose waxy citrus |
| Odor Type | floral |
| biological source | synthetic |
| Water Solubility | PRACTICALLY INSOLUBLE |
| Merck | 14,4403 |
| JECFA Number | 1223 |
| BRN | 1722456 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Major Application | flavors and fragrances |
| Cosmetics Ingredients Functions | TONIC PERFUMING |
| InChI | 1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+ |
| InChIKey | GLZPCOQZEFWAFX-JXMROGBWSA-N |
| SMILES | C\C(C)=C\CC\C(C)=C\CO |
| LogP | 2.6 at 25℃ |
| CAS DataBase Reference | 106-24-1(CAS DataBase Reference) |
| NIST Chemistry Reference | 2,6-Octadien-1-ol, 3,7-dimethyl-, (E)-(106-24-1) |
| EPA Substance Registry System | trans-Geraniol (106-24-1) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38-43-41-36-52/53-38 |
| Safety Statements | 26-36-24/25-36/37-61-36/37/39 |
| RIDADR | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 1 |
| RTECS | RG5830000 |
| Hazard Note | Irritant |
| TSCA | TSCA listed |
| HS Code | 29052900 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Eye Dam. 1 Skin Irrit. 2 Skin Sens. 1 |
| Hazardous Substances Data | 106-24-1(Hazardous Substances Data) |
| toxicity | The acute oral LD50 value in rats was reported as 3.6 g/kg (Jenner, Hagan, Taylor, Cook & Fitzhugh, 1964) and as 4.8 g/kg, while the iv UD 50 in rabbits was reported as 50 mg/kg (Yamawkai, 1962). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Moreno, 1972). |
| Description | Geraniol is a kind of monoterpenoid as well as alcohol. It is mainly existed in plant oils such as rose oil, palmarosa oil, and citronella oil. It can also be found in plants such as geraniums and lemongrass. It has a rose-like scent and is therefore used in perfumes as well as many kinds of flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, and blueberry. Another major application of geraniol is being used as an effective plant-based insect repellent for treatment of mosquitoes, house flies, stable flies, cockroaches, fire ants, fleas and lone star ticks. On the other hand, its scent can also attract bees. |
| References | https://en.wikipedia.org/wiki/Geraniolhttps://pubchem.ncbi.nlm.nih.gov/compound/geraniol#section=Top |
| Description | Geraniol has a characteristic rose-like odor. Geraniol may be preparedby fractional distillation from those essential oils rich ingeraniol, or synthetically from myrcene; commercial geraniol cannotbe classified according to its alcohol content, as most of therecurring impurities are alcoholic in nature (nerol, citronellol, tetrahydrogeraniol).Gas-chromatography techniques may be usefullyemployed to determine the geraniol content in a product. |
| Chemical Properties | Geraniol has a characteristic rose-like odor The physical constants vary for the various commercial products, depending on the total geraniol content; specifc gravity and refractive index may be indicative of the purity of the product Commercial geraniol cannot be classifed according to its alcohol content, as most of the recurring impurities are alcoholic in nature (nerol, citronellol, tetrahydrogeraniol) Gas chromatography techniques may be usefully employed to determine the gera- niol content in a product. |
| Chemical Properties | Geraniol occurs in nearlyall terpene-containing essential oils, frequently as an ester. Palmarosa oil contains70–85% geraniol; geranium oils and rose oils also contain large quantities. Geraniolis a colorless liquid, with a floral, rose-like odor. Since geraniol is an acyclic, doubly unsaturated alcohol, it can undergo a numberof reactions, such as rearrangement and cyclization. Rearrangement in thepresence of copper catalysts yields citronellal. In the presence of mineral acids, itcyclizes to form monocyclic terpene hydrocarbons, cyclogeraniol being obtainedif the hydroxy function is protected. Partial hydrogenation leads to citronellol,and complete hydrogenation of the double bonds yields 3,7-dimethyloctan-l-ol(tetrahydrogeraniol). Citral may be obtained from geraniol by oxidation or bycatalytic dehydrogenation. Geranyl esters are prepared by esterification. Geraniol is one of the most frequently used terpenoid fragrance materials.It can be used in all floral, rose-like compositions and does not discolor soaps. Inflavor compositions, geraniol is used in small quantities to accentuate citrus notes.It is an important intermediate in the manufacture of geranyl esters, citronellol,and citral. |
| Chemical Properties | colourless to pale yellow liquid with an odour of roses |
| Occurrence | The presence of geraniol in nature has been reported in more than 160 essential oils: ginger grass, lemongrass, Ceylon and Java citronella, tuberose, oak musk, orris, champaca, ylang-ylang, mace, nutmeg, sassafras, Cayenne Bois-de-Rose, Acacia farnesiana, geramium clary sage, spike, lavandin, lavender, jasmine, coriander, carrot, myrrh, eucalyptus, lime, mandarin petitgrain, bergamot petitgrain, bergamot, lemon, orange and others The essential oils of palmarosa and Cymbopogon winterianus contain the highest levels of geraniol (approx 80 to 95%) Also reported in numerous other sources including apple juice, citrus peel oils and juices, bilberry, cranberry, other berries, guava, papaya, cinnamon, ginger, corn mint oil, mustard, nutmeg, mace, milk, coffee, tea, whiskey, honey, passion fruit, plums, mushrooms, mango, starfruit, cardamom, coriander leaf and seeds, litchi, Ocimum basilicum, myrtle leaf, rosemary, clary sage, Spanish sage and chamomile oil |
| Uses | Geraniol is used in the synthesis of insect repellant. It is also used in the synthesis of Angelicoin A and Herecinone J, which inhibit collagen-induced platelet aggregation. |
| Uses | Geraniol was used in field evaluation of synthetic herbivore-induced plant volatiles as attractants to beneficial insects.It was used to evaluate the tumor-suppressive potency of isoprenoids in vitro and in vivo. |
| Uses | geraniol is perfuming and with tonic properties. It is a primary constituent in many essential oils, including citronella, lavender, lemongrass, orange flower, and ylang-ylang. |
| Definition | ChEBI: A monoterpenoid consisting of two prenyl units linked head-to-tail and functionalised with a hydroxy group at its tail end. |
| Preparation | A convenient route for the production of geraniol and nerol consistsof the hydrogenation of citral, which is used in large quantities as an intermediatein the synthesis of vitamin A. Large-scale processes have, therefore, been developedfor producing geraniol. Currently, these are far more important than isolationfrom essential oils. Nevertheless, some geraniol is still isolated from essentialoils for perfumery purposes. 1) Isolation from essential oils: Geraniol is isolated from citronella oils and frompalmarosa oil. Fractional distillation of, for example, Java citronella oil (if necessary,after saponification of the esters present) yields a fraction containingabout 60% geraniol, as well as citronellol and sesquiterpenes.Aproductwith a higher geraniol content and slightly different odor quality foruse in fine fragrances is obtained by fractionating palmarosa oil after saponificationof the geranyl esters. 2) Synthesis from β-pinene: Pyrolysis of β-pinene yields myrcene, which is convertedinto a mixture of predominantly geranyl, neryl, and linalyl chloride byaddition of hydrogen chloride in the presence of small amounts of catalyst, forexample, copper(I) chloride and an organic quaternary ammonium salt.After removal of the catalyst, the mixture is reacted with sodium acetate inthe presence of a nitrogen base (e.g., triethylamine) and converted to geranylacetate, neryl acetate, and a small amount of linalyl acetate. Geraniol is obtained after saponification and fractional distillation of theresulting alcohols.3) Synthesis from linalool: A 96% pure synthetic geraniol prepared by isomerizationof linalool has become commercially available. Orthovanadates are usedas catalysts, to give a >90% yield of a geraniol–nerol mixture. Geraniolof high purity is finally obtained by fractional distillation.A considerable portion of commercially available geraniol is produced by amodified process: linalool obtained in a purity of about 65% from α-pinene isconverted into linalyl borates, which rearrange in the presence of vanadatesas catalysts to give geranyl and neryl borates. The alcohols are obtained byhydrolysis of the esters. 4) Synthesis from citral: Citral has very recently come to be produced petrochemicallyin very large quantities, so partial hydrogenation of citral hasbecome a very economical route for the production of geraniol. A highselectivity for this reaction can be achieved by the use of special catalysts[106] or by special reaction techniques. |
| Aroma threshold values | Detection: 4 to 75 ppb. |
| Taste threshold values | Taste characteristics at 10 ppm: sweet foral rose, citrus with fruity, waxy nuances. |
| General Description | Colorless to pale yellow oily liquid with a sweet rose odor. |
| Reactivity Profile | An unsaturated aliphatic hydrocarbon and an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. |
| Flammability and Explosibility | Non flammable |
| Anticancer Research | Starting from antitumor activity against several cell lines by an arrest occurring atthe G0/G1 cell cycle and ultimately with an increase of apoptosis, this molecule wasfound to interfere with the mevalonic cycle enzyme. Suppression of prenylation ofproteins leads to the inhibition of DNA synthesis, and the suppression of 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) leads to a reduction of the mevalonate pool andthus limits protein isoprenylation. In the same way, a reduction of cholesterol biodisponibilitywas controlled (Pattanayak et al. 2009; Ni et al. 2012; Dahham et al.2016). |
| Safety Profile | Poison by intravenous route. Moderately toxic by ingestion, subcutaneous, and intramuscular routes. A severe human skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. |
| Synthesis | By fractional distillation from those essential oils rich in geraniol, or synthetically from myrcene. |
| Metabolism | Geraniol is metabolized in the rabbit by ω-oxidation and by reduction of an α β-unsaturated bond (Parke, 1968). The products of geraniol metabolism are 'Hildebrandt acid' and 7-carboxy-3-methylocta-6-enoic acid. The latter acid is optically active (Williams, 1959). |
| Purification Methods | Purify geraniol by ascending chromatography or by thin layer chromatography on plates of kieselguhr G with acetone/water/liquid paraffin (130:70:1) as solvent system. Hexane/ethyl acetate (1:4) is also suitable. Also purify it by GLC on a silicone-treated column of Carbowax 20M (10%) on Chromosorb W (60-80 mesh). [Porter Pure Appl Chem 20 499 1969.] Store it in full, tightly sealed containers in the cool and protect from light. It has a pleasant odour. [cf p 681, Beilstein 1 IV 2277.] |
Geraniol Preparation Products And Raw materials
| Raw materials | Calcium chloride-->Citral-->Linalool-->Citronellol-->NEROL-->Eucalyptus Citriodara Oil-->Amalgam sodium-->Citronella oil-->Myrcene-->Terpinen-4-ol |
| Preparation Products | Citral-->Citronellol-->Citronellal-->NEROL-->Rhodinol-->Geranyl acetate-->GERANYL BUTYRATE-->Geranyl formate-->FEMA 2510-->3,7-DIMETHYL-1-OCTANOL-->2,4,5-TRIMETHYLANILINE-->1,3-Benzenediol, 4-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-5-pentyl--->3-Ethoxy-3,7-dimethyl-1,6-octadiene-->TRANS,TRANS-2,6-DIMETHYL-2,6-OCTADIENE-1,8-DIOL)-->GERANYL ISOVALERATE |
