| Identification | More | [Name]
CITRONELLOL | [CAS]
26489-01-0 | [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]
26489-01-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
77-83 °C(lit.)
| [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)
| [refractive index ]
n20/D 1.456(lit.)
| [Fp ]
209 °F
| [storage temp. ]
2-8°C
| [Contact allergens]
L-Citronellol is a constituent of rose and geranium
oils. d-Citronellol occurs in Ceylon and Java citronella
oils. As a fragrance allergen, citronellol has to be mentioned
by name in cosmetics within the EU. | [CAS DataBase Reference]
26489-01-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [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 . | [WGK Germany ]
1
| [RTECS ]
RH3400000
|
| Hazard Information | Back Directory | [Chemical Properties]
The enantiomers (3R)-(+)-citronellol and (3S)-(?)-citronellol
occur in many essential oils.
(?)-Citronellol isolated from natural sources is often named rhodinol. At
present, the name rhodinol is also used for the isopropenyl isomer α-citronellol
or a mixture of the two isomers.
In many natural products, citronellol occurs as a mixture of its two enantiomers;
the pure (+) or (?) formis seldom found. (?)-Citronellol is the predominant enantiomer
in geranium and rose oils, both of whichmay contain up to 50% citronellols.
Citronellol is a colorless liquid with a sweet rose-like odor. The odor of (?)-
citronellol is more delicate than that of (+)-citronellol.
Citronellol undergoes the typical reactions of primary alcohols. Compared with
geraniol, which contains one more double bond, citronellol is relatively stable.
Citronellol is converted into citronellal by dehydrogenation or oxidation; hydrogenation
yields 3,7-dimethyloctan-l-ol. Citronellyl esters are easily prepared by
esterification with acid anhydrides. | [Definition]
ChEBI: Citronellol is a monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7. It has a role as a plant metabolite. | [Preparation]
(?)-Citronellol is still obtained mainly from geranium oil by
saponification followed by fractional distillation (“rhodinol”). Although of high
odor quality, this grade does not possess the true (?)-citronellol odor due to
impurities. Much larger quantities of (+)-citronellol and racemic citronellol are
used and are prepared by partial or total synthesis.
1) Synthesis from citronellal: Citronellal can be hydrogenated to citronellol
by the use of special catalysts and/or special hydrogenation techniques,
for example, [122]. The citronellal that is used as the starting material
may originate from synthetic production or from isolation of essential
oils. Citronellal from citronella oil yields (+)-citronellol; the corresponding
material from citronellal from Eucalyptus citriodora oil is racemic. Pure
(+)-citronellol is also obtained from (+)-citronellal, which is produced as an
intermediate of (?)-menthol. By this asymmetric technology,
pure (?)-citronellal and, therefore, pure (?)-citronellol are also available.
2) Synthesis of racemic or slightly dextrorotatory citronellol from geraniol
fractions of essential oils: This citronellol is produced by catalytic hydrogenation of saponified geraniol fractions (also containing (+)-
citronellol) obtained from Java citronella oil, followed by fractional
distillation. Selective hydrogenation of the double bond in the 2-position
of geraniol in geraniol–citronellol mixtures isolated from essential oils
can be achieved by using Raney cobalt as a catalyst; overhydrogenation to
3,7-dimethyloctan-l-ol can be largely avoided by this method.
3) Synthesis of racemic citronellol from synthetic geraniol, nerol, or citral: A considerable
amount of commercial synthetic racemic citronellol is produced by
partial hydrogenation of synthetic geraniol and/or nerol. Another starting
material is citral, which can be hydrogenated, for example, in the presence
of a catalyst system consisting of transition metals and amines.
4) Preparation of (?)-citronellol from optically active pinenes: (+)-cis-Pinane is
readily synthesized by hydrogenation of (+)-α-pinene or (+)-β-pinene and is
then pyrolyzed to give (+)-3,7-dimethyl-1,6-octadiene. This compound can
be converted into (?)-citronellol (97% purity) by reaction with triisobutylaluminumor
diisobutylaluminumhydride, followed by air oxidation and hydrolysis
of the resulting aluminum alcoholate. |
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