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Citronellol

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Citronellol Basic information

Product Name:
Citronellol
CAS:
106-22-9
MF:
C10H20O
MW:
156.27
EINECS:
203-375-0
Mol File:
106-22-9.mol
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Citronellol Chemical Properties

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 | DL-CITRONELLOL
refractive index 
n20/D 1.456(lit.)
Flash point:
209 °F
storage temp. 
2-8°C
pka
15.13±0.10(Predicted)
form 
Liquid
color 
Clear almost colorless
Water Solubility 
SLIGHTLY SOLUBLE
JECFA Number
1219
Merck 
14,2330
BRN 
1721507
Stability:
Stable. Incompatible with oxidizing agents.
InChIKey
QMVPMAAFGQKVCJ-UHFFFAOYSA-N
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
Citronellol (106-22-9)
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Safety Information

Hazard Codes 
Xi,N
Risk Statements 
36/37/38-51/53-43-36/38
Safety Statements 
26-36-24/25-61-37-24
RIDADR 
UN 3082 9 / PGIII
WGK Germany 
1
RTECS 
RH3400000
Hazard Note 
Irritant
TSCA 
Yes
HazardClass 
9
HS Code 
29052220
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).

MSDS

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Citronellol Usage And Synthesis

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.

Chemical Properties

colourless liquid with a characteristic, rose-like, smell

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.

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.

Uses

Perfumery, flavoring agent.

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.

Preparation

By reduction of citronellal or geraniol or by fractional distillation of such essential oils as geranium and citronella (Bedoukian, 1967).

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.

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.

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.

Chemical 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.

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.]

References

https://eic.rsc.org/magnificent-molecules/citronellol/2000020.article
https://en.wikipedia.org/wiki/Citronellol

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Jiangxi Baolin Natural Spices Co.Ltd. Gold
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Jiangxi Zhonghuan New Material Co., Ltd. Gold
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J & K SCIENTIFIC LTD.
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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Email:
sh@meryer.com
Chembest Research Laboratories Limited
Tel:
021-20908456-
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sales@BioChemBest.com
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