| Identification | More | [Name]
Citronellol | [CAS]
106-22-9 | [Synonyms]
2,6-DIMETHYL-2-OCTEN-8-OL
3,7-DIMETHYL-6-OCTEN-1-OL
3,7-DIMETHYL-OCT-6-EN-1-OL
6-OCTEN-1-OL, 3,7-DIMETHYL
(+/-)-BETA-CITRONELLOL
BETA-CITRONELLOL
(+/-)-CITRONELLOL
CITRONELLOL
CITRONELLOL 80
CITRONELLOL 90/92
CITRONELLOL 96
CITRONELLOL 96/98
CITRONELLOL AJ
CITRONELLOL, DL-B-
CITRONELLOL EXTRA
CITRONELLOL PRIME
DL-B-CITRONELLOL
DL-CITRONELLOL
FEMA 2307
FEMA 2309 | [EINECS(EC#)]
203-375-0 | [Molecular Formula]
C10H20O | [MDL Number]
MFCD00002935 | [Molecular Weight]
156.27 | [MOL File]
106-22-9.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless liquid with a characteristic, rose-like, smell | [Melting point ]
77-83 °C(lit.)
| [alpha ]
-0.3～+0.3°(D/20℃)(neat) | [Boiling point ]
225 °C(lit.)
| [density ]
0.857 g/mL at 25 °C(lit.)
| [vapor density ]
5.4 (vs air)
| [vapor pressure ]
~0.02 mm Hg ( 25 °C)
| [FEMA ]
2309 | [refractive index ]
n20/D 1.456(lit.)
| [Fp ]
209 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform, Methanol (Sparingly) | [form ]
Liquid | [pka]
15.13±0.10(Predicted) | [color ]
Clear almost colorless | [Odor]
at 100.00 %. floral leather waxy rose bud citrus | [Stability:]
Stable. Incompatible with oxidizing agents. | [Odor Type]
floral | [Water Solubility ]
SLIGHTLY SOLUBLE | [JECFA Number]
1219 | [Merck ]
14,2330 | [BRN ]
1721507 | [InChIKey]
QMVPMAAFGQKVCJ-UHFFFAOYSA-N | [LogP]
3.41 at 25℃ | [Uses]
citronellol is a constituent of plant essential oils. Found abundantly in eucalyptus oil. It is used for masking odor or providing a fragrance component to a cosmetic product. | [CAS DataBase Reference]
106-22-9(CAS DataBase Reference) | [NIST Chemistry Reference]
6-Octen-1-ol, 3,7-dimethyl-(106-22-9) | [EPA Substance Registry System]
106-22-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,N | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1
| [RTECS ]
RH3400000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29052220 | [Safety Profile]
Poison by intravenous
route. Moderately toxic by ingestion, skin
contact, and intramuscular routes. A severe
skin irritant. A combustible liquid. When
heated to decomposition it emits acrid
smoke and irritating fumes. See also
ALCOHOLS. | [Hazardous Substances Data]
106-22-9(Hazardous Substances Data) | [Toxicity]
The acute oral LD50 value in rats was reported as 3.45 g/kg (3.21-3.69 g/kg) (Moreno, 1973). The acute dermal LE>50 value in rabbits was reported as 2.65 g/kg (1.78-3.52 g/kg) (Moreno, 1973). The im LD50 value in mice was reported as 4 g/kg (Northover & Verghese, 1962). |
| Questions and Answers (Q&A) | Back Directory | [Description]
Citronellol is a kind of natural occurring acyclic monoterpenoid which can be found in citronella oils such as Cymbopogon nardus ((+)-citronellol) and rose oils and Pelargonium geraniums ((-)-citronellol). In addition to be extracted from natural oils, it can also be manufactured by the hydrogenation of geraniol or nerol. It is mainly used in perfumes and insects repellents as well as being used as a mite attractant. It should be noted that it is an excellent mosquito repellent at short distances. Combination with beta-cyclodextrin can make it has an average duration time of 1.5 hour against the mosquitoes. It can also be used for the manufacture of rose oxide. One of its most common applications is for adding floral and citrus notes to perfumes, soaps and cosmetics.
| [References]
https://eic.rsc.org/magnificent-molecules/citronellol/2000020.article
https://en.wikipedia.org/wiki/Citronellol
|
| Hazard Information | Back Directory | [Chemical Properties]
Citronellol has a characteristic rose-like odor. Because odor plays such an important part in selecting this material,
there may be special grades of citronellol that do not meet the Essential Oil Association specification. These limits have been broadened
enough to include best qualities of commercial citronellol and chemically pure citronellol. l-Citronellol has a sweet, peach-like
flavor; d-citronellol has a bitter taste. | [Chemical Properties]
colourless liquid with a characteristic, rose-like, smell | [Occurrence]
l-Citronellol has been found in the plants of the Rosaceae family; d- and dl-citronellol have been identified in
Verbenaceae, Labiatae, Rutaceae, Geraniaceae and others; citronellol has been reported in about 70 essential oils and in the oil of
Rosa bourbonia; the Bulgarian rose oil has been reported to contain more than 50% l-citronellol, whereas East African geranium
contains more than 80% of the d-isomer; the natural product is always optically active. Reported found in guava fruit, orange, bilberry,
blackcurrant, nutmeg, ginger, corn mint oil (Mentha arvensis L. var. piperascens), mustard, pennyroyal oil (Mentha pulegium
L.), hop oil, tea, coriander seed, cardamom, beer, rum, and apple juice. | [Definition]
ChEBI: A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7. | [Preparation]
By reduction of citronellal or geraniol or by fractional distillation of such essential oils as geranium and citronella (Bedoukian, 1967). | [Aroma threshold values]
Detection at 11 ppb to 2.2 ppm; l-form, 40 ppb | [Taste threshold values]
Taste characteristics at 20 ppm: floral, rose, sweet and green with fruity citrus nuances. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 60, p. 2260, 1995 DOI: 10.1021/jo00112a056
Synthesis, p. 391, 1976
Tetrahedron Letters, 30, p. 5677, 1989 DOI: 10.1016/S0040-4039(00)76168-5 | [General Description]
Citronellol is a volatile monoterpenic primary alcohol mainly found in the essential oil of plants such as Pelargonium graveolens, Cymbopogon winterianus and Rosa damascena. It is also one of the glycosidically bound aroma compounds in ginger. | [Flammability and Explosibility]
Nonflammable | [Synthesis]
It is generally accepted to distinguish rhodinol as the product isolated from geranium consisting of a mixture of l-citronellol
and geraniol, whereas the name l-citronellol should be used to indicate the corresponding synthetic product with the highest
level of purity; dl-citronellol can be prepared by catalytic hydrogenation of geraniol or by oxidation of allo-cyrnene; l-citronellol is
prepared from (+) d-pinene via (+) cis-pinene to (+) 2,6-dimethyl-2,7-octadiene and, finally, isolating l-citronellol by hydrolysis of the
aluminum-organo compound. | [storage]
4°C, protect from light | [Purification Methods]
Purify them bydistillation through a cannon packed (Ni) column and the main cut collected at 84o/14mm and redistilled. Also purify via the benzoate. [IR: Eschenazi J Org Chem 26 3072 1961, Naves Bull Soc Chim Fr 505 1951, Beilstein 1 IV 2188.] |
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