Geraniol

Iupac Name：(2E)-3,7-dimethylocta-2,6-dien-1-ol

Molecular Weight：154.25

Modify Date.: 2022-11-29 10:30

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: Geraniol
1.2 Synonyms: (2E)-3,7-Dimethyl-2,6-octadien-1-ol (2E)-3,7-Dimethyl-2,6-octadienol (2E)-3,7-Dimethylocta-2,6-dien-1-ol (E)-3,7-Dimethylocta-2,6-dien-1-ol 2,6-octadien-1-ol, 3,7-dimethyl- 2,6-Octadien-1-ol, 3,7-dimethyl-, (2E)- 3,7-Dimethyl-2,6-octadien-1-ol 3,7-dimethyl-2,6-octadienol 3,7-Dimethylocta-2,6-dien-1-ol 3,7-dimethyl-trans-2,6-octadien-1-ol EINECS 203-377-1 FEMA 2507 GERANIOL 60 GERANIOL 600 GERANIOL 70 GERANIOL 80 GERANIOL 90 GERANIOL 902 Guaniol LEMONOL Meranol MFCD00002917 Q2UY1&3UY1&1 trans-3,7-Dimethyl-2,6-octadien-1-ol

1.3 CAS No.: 106-24-1

1.4 CID: 637566

1.5 EINECS(EC#): 203-377-1

1.6 Molecular Formula: C10H18O (isomer)

1.7 Inchi: InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+

1.8 InChkey: GLZPCOQZEFWAFX-JXMROGBWSA-N

1.9 Canonical Smiles: CC(=CCCC(=CCO)C)C

1.10 Isomers Smiles: CC(=CCC/C(=C/CO)/C)C

2. Properties

2.1 Density: 0.879 g/mL at 20 °C(lit.)

2.1 Melting point: -15 °C

2.1 Boiling point: 229-230 °C(lit.)

2.1 Refractive index: n20/D 1.474(lit.)

2.1 Flash Point: 216 °F

2.2 Precise Quality: 154.13600

2.2 PSA: 20.23000

2.2 logP: 2.67140

2.2 Solubility: 0.00 M

2.3 VaporDensity: 5.31 (vs air)

2.4 Appearance: Clear colorless to pale yellow Liquid

2.5 Storage: Ambient temperatures.

2.6 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.

2.7 Color/Form: Oil

2.8 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.9 Odor: Sweet rose odor

2.10 Odor Threshold: Aroma threshold values: Detection: 4 to 75 ppb.

2.11 pKa: 14.45±0.10(Predicted)

2.12 Water Solubility: Practically insoluble in water

2.13 Stability: Stable. Combustible. Incompatible with strong oxidizing agents.

2.14 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A monoterpenoid consisting of two prenyl units linked head-to-tail and functionalised with a hydroxy group at its tail end.

3.2 General Description: Colorless to pale yellow oily liquid with a sweet rose odor.

3.3 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

3.4 Usage: 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.

4. Safety and Handling

4.1 Symbol: GHS05;GHS07;

4.1 Hazard Codes: Xi

4.1 Signal Word: DANGER

4.1 Risk Statements: 36/37/38-43-41-36-52/53-38

4.1 Safety Statements: 26-36-24/25-36/37-61-36/37/39

4.1 Hazard Declaration: H315; H317; H318

4.1 RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution

4.1 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.

4.2 Caution Statement: P280-P305 + P351 + P338

4.2 WGK Germany: 1

4.2 RTECS: RG5830000

4.2 Toxicity: The acute oral LD 50 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 LD 50 value in rabbits was reported as > 5 g/kg (Moreno, 1972).

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Skin sensitization, Category 1

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H315 Causes skin irritation H317 May cause an allergic skin reaction H318 Causes serious eye damage
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : CCl4 solution

IR : liquid film

Raman : 4880 A,200 M,liquid

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

106-24-1Total: 162 Synthesis Route

78-70-6 233 Suppliers

106-24-1 170 Suppliers

Literatures:
Chemische Berichte, , vol. 31, p. 839 Chemische Berichte, , vol. 26, p. 2720 Journal fuer Praktische Chemie (Leipzig), , vol. <2>49, p. 190 Journal fuer Praktische Chemie (Leipzig), , vol. <2>56, p. 508 Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 116, p. 1253 Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 116, p. 1200 DE165894 ; Chemische Berichte, , vol. 39, p. 1782,1784
Yield: null

78-70-6 233 Suppliers

106-25-2 75 Suppliers

106-24-1 170 Suppliers

Literatures:
Zhurnal Obshchei Khimii, , vol. 28, p. 1458,1459 J. Gen. Chem. USSR (Engl. Transl.), , vol. 28, p. 1511,1512
Yield: null

78-70-6 233 Suppliers

106-25-2 75 Suppliers

106-24-1 170 Suppliers

98-55-5 126 Suppliers

Literatures:
Tetrahedron Letters, , vol. 24, # 35 p. 3741 - 3744
Yield: ~8%

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8. Precursor and Product

precursor:

141-27-5

106-25-2

624-15-7

123-35-3

115-18-4

78-79-5

502-47-6

115-95-7

110-93-0

763-10-0

105-87-3

78-70-6

126-91-0

View all

product :

51-77-4

1189-09-9

6138-90-5

3294-76-6

94-48-4

126-90-9

3779-61-1

126-91-0

5677-55-4

138-86-3

80-53-5

3608-21-7

6090-15-9

5585-39-7

123-35-3

5389-87-7

6247-66-1

99-87-6

502-65-8

3338-55-4

3796-70-1

689-67-8

106-21-8

2051-30-1

111-02-4

View all

9. Other Information

9.0 Merck: 14,4403

9.1 BRN: 1722456

9.2 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.

9.3 References: https://en.wikipedia.org/wiki/Geraniol https://pubchem.ncbi.nlm.nih.gov/compound/geraniol#section=Top

9.4 Description: Geraniol has a characteristic rose-like odor. Geraniol may be prepared by fractional distillation from those essential oils rich in geraniol, or synthetically from myrcene; commercial geraniol cannot be classified 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 geraniol content in a product.

9.5 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.

9.6 Chemical Properties: Geraniol occurs in nearly all terpene-containing essential oils, frequently as an ester. Palmarosa oil contains 70–85% geraniol; geranium oils and rose oils also contain large quantities. Geraniol is a colorless liquid, with a floral, rose-like odor.
Since geraniol is an acyclic, doubly unsaturated alcohol, it can undergo a number of reactions, such as rearrangement and cyclization. Rearrangement in the presence of copper catalysts yields citronellal. In the presence of mineral acids, it cyclizes to form monocyclic terpene hydrocarbons, cyclogeraniol being obtained if 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 by catalytic 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. In flavor 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.

9.7 Chemical Properties: colourless to pale yellow liquid with an odour of roses

9.8 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

9.9 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.

9.10 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.

9.11 Definition: ChEBI: A monoterpenoid consisting of two prenyl units linked head-to-tail and functionalised with a hydroxy group at its tail end.

9.12 Preparation: A convenient route for the production of geraniol and nerol consists of the hydrogenation of citral, which is used in large quantities as an intermediate in the synthesis of vitamin A. Large-scale processes have, therefore, been developed for producing geraniol. Currently, these are far more important than isolation from essential oils. Nevertheless, some geraniol is still isolated from essential oils for perfumery purposes.
1) Isolation from essential oils: Geraniol is isolated from citronella oils and from palmarosa oil. Fractional distillation of, for example, Java citronella oil (if necessary, after saponification of the esters present) yields a fraction containing about 60% geraniol, as well as citronellol and sesquiterpenes. Aproductwith a higher geraniol content and slightly different odor quality for use in fine fragrances is obtained by fractionating palmarosa oil after saponification of the geranyl esters.
2) Synthesis from β-pinene: Pyrolysis of β-pinene yields myrcene, which is converted into a mixture of predominantly geranyl, neryl, and linalyl chloride by addition of hydrogen chloride in the presence of small amounts of catalyst, for example, copper(I) chloride and an organic quaternary ammonium salt. After removal of the catalyst, the mixture is reacted with sodium acetate in the presence of a nitrogen base (e.g., triethylamine) and converted to geranyl acetate, neryl acetate, and a small amount of linalyl acetate.
Geraniol is obtained after saponification and fractional distillation of the resulting alcohols. 3) Synthesis from linalool: A 96% pure synthetic geraniol prepared by isomerization of linalool has become commercially available. Orthovanadates are used as catalysts, to give a >90% yield of a geraniol–nerol mixture. Geraniol of high purity is finally obtained by fractional distillation. A considerable portion of commercially available geraniol is produced by a modified process: linalool obtained in a purity of about 65% from α-pinene is converted into linalyl borates, which rearrange in the presence of vanadates as catalysts to give geranyl and neryl borates. The alcohols are obtained by hydrolysis of the esters.
4) Synthesis from citral: Citral has very recently come to be produced petrochemically in very large quantities, so partial hydrogenation of citral has become a very economical route for the production of geraniol. A high selectivity for this reaction can be achieved by the use of special catalysts [106] or by special reaction techniques.

9.13 Aroma threshold values: Detection: 4 to 75 ppb.

9.14 Taste threshold values: Taste characteristics at 10 ppm: sweet foral rose, citrus with fruity, waxy nuances.

9.15 General Description: Colorless to pale yellow oily liquid with a sweet rose odor.

9.16 Usage: 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.

9.17 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.

9.18 Flammability and Explosibility: Nonflammable

9.19 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).

9.20 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.

9.21 Synthesis: By fractional distillation from those essential oils rich in geraniol, or synthetically from myrcene.

9.22 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).

9.23 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.]

10. Computational chemical data

Molecular Weight: 154.25g/mol
Molecular Formula: C₁₀H₁₈O
Compound Is Canonicalized: True
XLogP3-AA: 2.9
Exact Mass: 154.135765193
Monoisotopic Mass: 154.135765193
Complexity: 150
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 20.2
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAADACggAICAAAAAgCAAiBCAAAAAAAgAAAACAAAAAgAFAIAAQAAEAAAgAAIEAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

How does geraniol inhibits efflux pumps? Jul 13 2021
Geraniol (a primary alcohol based on two isoprene units) was shown to enhance the activities of anti-bacterial agents in Lorenzi et al. (2009) . This group also sought to patent the use of the compound as an adjuvant in “Geraniol as a bacterial efflux pump inhibitor” [ EP2184061A1 ]. Nevertheless...
The antitumor effects of geraniol Jan 28 2021
Geraniol is a dietary monoterpene alcohol that is found in the essential oils of aromatic plants. To date, experimental evidence supports the therapeutic or preventive effects of geraniol on different types of cancer, such as breast, lung, colon, prostate, pancreatic, and hepatic cancer, and has re...

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