(+)-Citronellol (left) and (−)-citronellol (right)
| |
R-(+)-Citronellol
| |
S-(−)-Citronellol
| |
Names | |
---|---|
IUPAC name
3,7-Dimethyloct-6-en-1-ol
| |
Other names
(±)-β-Citronellol; Cephrol, Corol
| |
Identifiers | |
3D model (
JSmol)
|
|
1362474 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.069 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII |
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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 |
Hazards | |
GHS labelling: | |
Warning | |
H315, H317, H319 | |
P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P501 | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Citronellol, or dihydrogeraniol, is a natural acyclic mono terpenoid. 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. [1]
Several million kilograms of citronellol are produced annually. It is mainly obtained by hydrogenation of geraniol or nerol over copper chromite catalyst. [2] Homogeneous catalysts are used for the production of enantiomers. [3] [4]
Citronellol is used in perfumes and as a fragrance in cleaning products. In many applications, one of the enantiomers is preferred. It is a component of citronella oil, an insect repellant. [2]
Citronellol is used as a raw material for the production of rose oxide. [2] [5] It is also a precursor to many commercial and potential fragrances such as citronellol acetate, citronellyl oxyacetaldehyde, citronellyl methyl acetal, and ethyl citronellyl oxalate. [2]
The United States FDA considers citronellol as generally recognized as safe (GRAS) for food use. [6] Citronellol is subject to restrictions on its use in perfumery, [7] as some people may become sensitised to it, but the degree to which citronellol can cause an allergic reaction in humans is disputed. [8] [9]
In terms of dermal safety, citronellol has been evaluated as an insect repellent. [10]
(+)-Citronellol (left) and (−)-citronellol (right)
| |
R-(+)-Citronellol
| |
S-(−)-Citronellol
| |
Names | |
---|---|
IUPAC name
3,7-Dimethyloct-6-en-1-ol
| |
Other names
(±)-β-Citronellol; Cephrol, Corol
| |
Identifiers | |
3D model (
JSmol)
|
|
1362474 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.069 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII |
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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 |
Hazards | |
GHS labelling: | |
Warning | |
H315, H317, H319 | |
P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P501 | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Citronellol, or dihydrogeraniol, is a natural acyclic mono terpenoid. 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. [1]
Several million kilograms of citronellol are produced annually. It is mainly obtained by hydrogenation of geraniol or nerol over copper chromite catalyst. [2] Homogeneous catalysts are used for the production of enantiomers. [3] [4]
Citronellol is used in perfumes and as a fragrance in cleaning products. In many applications, one of the enantiomers is preferred. It is a component of citronella oil, an insect repellant. [2]
Citronellol is used as a raw material for the production of rose oxide. [2] [5] It is also a precursor to many commercial and potential fragrances such as citronellol acetate, citronellyl oxyacetaldehyde, citronellyl methyl acetal, and ethyl citronellyl oxalate. [2]
The United States FDA considers citronellol as generally recognized as safe (GRAS) for food use. [6] Citronellol is subject to restrictions on its use in perfumery, [7] as some people may become sensitised to it, but the degree to which citronellol can cause an allergic reaction in humans is disputed. [8] [9]
In terms of dermal safety, citronellol has been evaluated as an insect repellent. [10]