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Geraniol structure
Geraniol structure

Geraniol

Iupac Name:(2E)-3,7-dimethylocta-2,6-dien-1-ol
CAS No.: 106-24-1
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+
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

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
  • 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...
  • 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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