CITRONELLOL
Citronellol is a volatile monoterpenic primary alcohol mainly found in the essential oil of plants such as Pelargonium graveolens, Cymbopogon winterianus and Rosa damascena.
Citronellol is an aromatic alcohol, possessing a wonderful aroma, abundance, and fresh floral scent, like roses.
Citronellol is extensively used in the fragrance and cosmetics industry as a key ingredient in perfumes, soaps, lotions, and deodorants due to its pleasant scent profile and good stability in formulations.
CAS Number: 106-22-9
EC Number: 231-415-7
Molecular Weight: 156.27
Molecular Formula: C10H20O
Synonyms: Citronellol, 106-22-9, 3,7-Dimethyloct-6-en-1-ol, Cephrol, 6-Octen-1-ol, 3,7-dimethyl-, 3,7-DIMETHYL-6-OCTEN-1-OL, Elenol, Rodinol, 2,3-Dihydrogeraniol, 2,6-Dimethyl-2-octen-8-ol, Citronellol, dl-, Dihydrogeraniol, DTXSID3026726, 565OK72VNF, CHEBI:50462, DTXCID006726, RefChem:29968, Citronellol (ex. Java citronella oil), 203-375-0, 247-737-6, beta-Citronellol, DL-Citronellol, (+/-)-beta-Citronellol, .beta.-Citronellol, C10H20O, 26489-01-0, MFCD00002935, NSC 8779, NSC-8779, 3,7-dimethyl-oct-6-en-1-ol, NSC8779, ST069325, b-citronellol, Insect Repellent, CAS-106-22-9, D-Citronellol;(R)-(+)-beta-Citronellol, (+/-)-beta-Citronellol analytical standard, (+/-)-Citronellol;(+/-)-beta-Citronellol, Citronellol (natural), (+-)-beta-citronellol, (+-)-CITRONELLOL, (R)-(+)-.beta.-Citronellol, nardus, UNII-565OK72VNF, mite attractant, rac-Citronellol, .BETA.-CITRONELLOL, (R)-, CCRIS 7452, Levo-citronellol, acyclic monoterpenoid, EINECS 203-375-0, EINECS 247-737-6, pelargonium geraniums, (-)-b-Citronellol, BRN 1721507, geranium oil saponified, Citronellol (Standard), AI3-25080, beta-Citronellol, 95%, (+-)-beta;-Citronellol, EC 203-375-0, (S)-(?)-beta-Citronellol, SCHEMBL21320, 4-01-00-02188 (Beilstein Handbook Reference), 6-Octen-1-ol,7-dimethyl-, MLS002415719, Citronellol mixture of isomers, SCHEMBL538858, 3,7-dimethyl-oct-6-en1-ol, CHEMBL395827, orb1304390, orb3025762, CITRONELLOL, (+/-)-, HSDB 6805, ()-Citronellol;()--Citronellol, .BETA.-CITRONELLOL [MI], MSK3305, WLN: Q2Y1&3UY1&1, beta-CITRONELLOL, (+/-)-, HMS2267B17, HMS6019L07, Citronellol, >=95%, FCC, FG, HY-W010201R, Tox21_202119, Tox21_300003, (+/-)-.BETA.-CITRONELLOL, BBL009826, BDBM50037035, s5584, SBB012357, STK085542, AKOS005393175, CCG-266265, CS-W010917, EBC-152348, HY-W010201, (+/-)-3,7-dimethyl-6-octen-1-ol, (+/-)-3,7-dimethyloct-6-en-1-ol, .BETA.-CITRONELLOL, (+/-)-, NCGC00091348-01, NCGC00091348-02, NCGC00091348-03, NCGC00091348-04, NCGC00254145-01, NCGC00259668-01, AS-14688, BP-21491, FC175239, SMR000112138, SY011260, DB-060123, DB-074976, DB-307766, (+/-)-beta-Citronellol, analytical standard, NS00093536, 6-Octen-1-ol, 3,7-dimethyl-, (+/-)-, EN300-1270486, F791077, Q27122080, Z87001681, (+/-)-beta-Citronellol, primary pharmaceutical reference standard, ( inverted exclamation markA)-|A-Citronellol; 3,7-Dimethyl-6-octen-1-ol
Citronellol is a naturally occurring monoterpenoid alcohol widely present in essential oils such as rose, geranium, and citronella oil, where it contributes a characteristic sweet, floral, and rose-like aroma.
Citronellol is extensively used in the fragrance and cosmetics industry as a key ingredient in perfumes, soaps, lotions, and deodorants due to its pleasant scent profile and good stability in formulations.
In addition to its aromatic properties, citronellol exhibits mild antimicrobial and insect-repellent activity, making it valuable in household products and natural repellent formulations.
Citronellol is a natural, aromatic compound widely utilized in cosmetics and personal care products for its pleasant scent.
Citronellol imparts a floral and citrusy aroma.
Apart from its aromatic qualities, citronellol also possesses potential antimicrobial properties.
Often found in skincare, haircare, and perfumes, Citronellol enhances the sensory experience of products.
Despite Citronellol's generally recognized safety, individuals with fragrance sensitivities should exercise caution.
The chemical formula of Citronellol is C10H20O and it appears as a clear liquid.
Citronellol is an aromatic alcohol, possessing a wonderful aroma, abundance, and fresh floral scent, like roses.
Citronellol is found in the oils of rose, eucalyptus, citriodora, geranium, lavender, basil, and citronella.
Chemically, Citronellol is a cyclic monoterpenoid.
Citronellol is a volatile monoterpenic primary alcohol mainly found in the essential oil of plants such as Pelargonium graveolens, Cymbopogon winterianus and Rosa damascena.
Citronellol is also one of the glycosidically bound aroma compounds in ginger.
Citronellol is a natural acyclic monoterpenoid.
Both enantiomers occur in nature.
(+)-Citronellol, which is found in citronella oils, including Cymbopogon nardus (50%), is the more common isomer.
(−)-Citronellol is widespread, but particularly abundant in the oils of rose (18–55%) and Pelargonium geraniums.
Citronellol is a compound found in natural essential oils belonging to the lemon and rose family.
In the cosmetics industry, Citronellol is widely used to impart a pleasant scent and provide a refreshing effect.
Citronellol's natural insect repellent properties add another benefit to skincare products.
Citronellol offers users a refreshing and soothing fragrance experience in various cosmetic formulations.
Uses of Citronellol:
Citronellol is widely used in the fragrance and personal care industries due to its pleasant floral and rose-like aroma, making it a key ingredient in perfumes, deodorants, soaps, and cosmetic formulations such as creams and lotions.
Citronellol is also commonly applied in household products including detergents, air fresheners, and cleaning agents to enhance scent profiles.
In addition, citronellol is utilized in insect repellent formulations because of its ability to help deter mosquitoes and other insects.
In the flavor industry, Citronellol is used in small amounts to improve aroma and contribute to the overall sensory quality of food and beverage products.
Citronellol is used as a fragrance component or scent enhancer.
Citronellol has lower skin permeability and therefore lasts longer as a fragrance.
Citronellol is also used as a mosquito repellent in various products.
Citronellol is used in creams, lotions, shaving creams, and bath products.
Citronellol is used in perfumes and as a fragrance in cleaning products.
In many applications, one of the enantiomers is preferred.
Citronellol is a component of citronella oil, an insect repellant.
The racemic material is described as having a floral, leathery, waxy, and rose aroma.
The dextro enantiomer, (R)-citronellol is described as citronella, rose, leafy, and oily, whilst the laevo enantiomer is described as floral, rose, waxy, geranium, and powdery.
Citronellol is used as a raw material for the production of rose oxide.
Citronellol is also a precursor to many commercial and potential fragrances such as citronellol acetate, citronellyl oxyacetaldehyde, citronellyl methyl acetal, and ethyl citronellyl oxalate.[2]
Citronellol is used in the personal care and cosmetic industry for its pleasing, citrusy scent.
Skin care:
In skin care products, Citronellol can mask unpleasant odors of the formulation.
Citronellol also has potential antimicrobial properties and is often included in moisturizers, toners, and creams to provide an overall refreshing experience
Hair care:
In haircare, citronellol adds a delightful fragrance to shampoos, conditioners, and styling products.
Citronellol's aromatic qualities create a sensorial experience during hair care routines, leaving a subtle, pleasant scent on the hair
Cosmetic products:
Citronellol is a popular ingredient in cosmetics, contributing its pleasant fragrance to various makeup formulations.
Citronellol can commonly be found in cosmetic products like foundations and lipsticks
Industry Uses:
Intermediates
Other (specify)
Flavoring and nutrient
Odor agents
Fragrance
Consumer Uses:
Fragrance
Odor agents
Flavoring and nutrient
Origin of Citronellol:
Citronellol is derived from natural sources like citronella, rose, or geranium oils through a process called steam distillation or solvent extraction.
In steam distillation, plant material is heated, and the volatile compounds, including citronellol, are collected.
Alternatively, solvent extraction involves dissolving the essential oil in a solvent and then evaporating the solvent, leaving behind citronellol.
This method preserves Citronellol's aromatic properties, making it a sought-after ingredient in cosmetics.
Preparation of Citronellol:
Several million kilograms of citronellol are produced annually.
Citronellol is mainly obtained by partial hydrogenation of geraniol or nerol over copper chromite catalyst.
Hydrogenation of both C=C bonds using a nickel catalyst gives tetrahydrogeraniol, yet another commercial fragrance.
Homogeneous catalysts have been investigated for the production of enantiomers.
History of Citronellol:
Citronellol has been used for centuries through its natural occurrence in essential oils such as rose, geranium, and citronella, which were historically valued in perfumery, traditional medicine, and aromatic applications.
Citronellol itself was identified and studied more precisely in the late 19th century with the advancement of organic chemistry and analytical techniques for essential oils.
During the 20th century, improvements in distillation and chemical synthesis enabled the large-scale production of citronellol, making it widely accessible for industrial use.
Today, Citronellol remains an essential ingredient in modern fragrance, cosmetic, and household product formulations.
Stability and Reactivity of Citronellol:
Chemical stability:
Stable under normal conditions.
Reactivity:
Reacts with strong oxidizing agents.
May undergo oxidation when exposed to air.
Conditions to avoid:
Heat.
Open flames.
Prolonged exposure to air.
Light.
Incompatible materials:
Strong oxidizing agents.
Strong acids.
Hazardous decomposition products:
Carbon monoxide (CO) may form.
Carbon dioxide (CO₂) may be generated.
Irritating organic fumes may be released.
Handling and Storage of Citronellol:
Handling:
Use with adequate ventilation.
Avoid inhalation.
Avoid prolonged skin contact.
Storage:
Store in tightly closed containers.
Keep in a cool, dry, and well-ventilated area.
Protect from light.
First Aid Measures of Citronellol:
Inhalation:
Move to fresh air.
Keep at rest.
Skin contact:
Wash thoroughly with soap and water.
Eye contact:
Rinse cautiously with water for several minutes.
Ingestion:
Rinse mouth.
Do not induce vomiting.
Seek medical advice if needed.
Firefighting Measures of Citronellol:
Suitable extinguishing media:
Foam.
Dry chemical.
Carbon dioxide (CO₂).
Water spray.
Hazards:
Flammable liquid.
Combustion may produce irritating fumes.
Carbon oxides may be generated.
Protection:
Use self-contained breathing apparatus.
Accidental Release Measures of Citronellol:
Precautions:
Eliminate ignition sources.
Ensure adequate ventilation.
Avoid contact.
Cleanup:
Absorb with inert material such as sand or earth.
Collect in suitable containers.
Exposure Controls / Personal Protection of Citronellol:
Ventilation:
Ensure adequate ventilation.
Use local exhaust if necessary.
Hand protection:
Wear chemical-resistant gloves.
Eye protection:
Use safety goggles.
Skin protection:
Wear protective clothing.
Hygiene measures:
Wash hands after handling.
Avoid prolonged exposure.
Identifiers of Citronellol:
Synonym(s): β-Rhodinol, (S)-3,7-Dimethyl-6-octen-1-ol
Linear Formula: (CH3)2C=CHCH2CH2CH(CH3)CH2CH2OH
CAS Number: 7540-51-4
Molecular Weight: 156.27
FEMA Number: 2309
Enzyme Commission number: 203-375-0
Beilstein: 1721505
EC Number: 231-415-7
MDL number: MFCD00063214
PubChem Substance ID: 329830473
Flavis number: 02.011
NACRES: NA.21
CAS Number:
106-22-9
1117-61-9 (R)
7540-51-4 (S)
Beilstein Reference: 1362474
ChEBI: CHEBI:50462
ChEMBL: ChEMBL395827
ChemSpider: 13850135
ECHA InfoCard: 100.003.069
EC Number: 247-737-6
KEGG: C09849
PubChem CID: 8842
UNII:
565OK72VNF
P01OUT964K (R)
8RSY5Y5658 (S)
CompTox Dashboard (EPA): DTXSID3026726
InChI:
InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3
Key: QMVPMAAFGQKVCJ-UHFFFAOYSA-N
InChI=1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1
Key: QMVPMAAFGQKVCJ-SNVBAGLBBU
InChI=1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3
Key: QMVPMAAFGQKVCJ-UHFFFAOYAO
SMILES:
OCC[C@@H](CC/C=C(/C)C)C
C\C(C)=C\CCC(C)CCO
Linear Formula: (CH3)2C=CHCH2CH2CH(CH3)CH2CH2OH
CAS Number: 106-22-9
Molecular Weight: 156.27
FEMA Number: 2309
Council of Europe no.: 59
UNSPSC Code: 12164502
PubChem Substance ID: 24900995
Flavis number: 2.011
EC Number: 203-375-0
NACRES: NA.21
MDL number: MFCD00002935
Organoleptic: waxy; floral; rose
Grade: FG, Kosher
Biological source: synthetic
Food allergen: no known allergens
Properties of Citronellol:
Chemical formula: C10H20O
Molar mass: 156.269 g·mol−1
Density: 0.855 g/cm3
Boiling point: 225 °C (437 °F; 498 K)
Viscosity: 11.1 mPa s
biological source: synthetic
Quality Level: 400
vapor pressure: ~0.02 mmHg ( 25 °C)
Assay: 99%
refractive index: n20/D 1.456 (lit.)
bp: 225-226 °C (lit.)
density: 0.856 g/mL at 25 °C (lit.)
Organoleptic: floral; waxy; rose
SMILES string: C[C@H](CCO)CC\C=C(\C)C
InChI: 1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m0/s1
InChI key: QMVPMAAFGQKVCJ-JTQLQIEISA-N
Molecular Weight: 156.26 g/mol
XLogP3-AA: 3.2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 5
Exact Mass: 156.151415257 Da
Monoisotopic Mass: 156.151415257 Da
Topological Polar Surface Area: 20.2 Ų
Heavy Atom Count: 11
Complexity: 112
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Names of Citronellol:
IUPAC name:
3,7-Dimethyloct-6-en-1-ol
Other names:
(±)-β-Citronellol
Cephrol
Corol
