Citronellol

Citronellol: Citronellol

(+)-Citronellol (left) and (-)-citronellol

IUPAC name

3,7-Dimethyloct-6-en-1-ol

Other names

(±)-β-Citronellol;
3,7-Dimethyl-6-octen-1-ol

Identifiers

CAS number 106-22-9^Y

ChemSpider 13850135^Y

UNII P01OUT964K^Y

KEGG C09849^Y

ChEBI CHEBI:50462^Y

ChEMBL CHEMBL395827^Y

Jmol-3D images Image 1
Image 2

SMILES

OCC[C@@H](CC/C=C(/C)C)C
C\C(C)=C\CCC(C)CCO

InChI

InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3^Y
Key: QMVPMAAFGQKVCJ-UHFFFAOYSA-N^Y
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

Properties

Molecular formula C₁₀H₂₀O

Molar mass 156.27 g mol⁻¹

Density 0.855 g/cm³

Boiling point
225 °C, 498 K, 437 °F

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Citronellol, or dihydrogeraniol, 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 found in the oils of rose (18-55%) and Pelargonium geraniums.^[1]

Citronellol is used in perfumes and insect repellents,^[2] and as a mite attractant.^[3] It is also a raw material for the production of rose oxide. The United States FDA considers citronellol as generally recognized as safe (GRAS) for food use.^[3] Citronellol should be avoided by people with perfume allergy.^[4]

See also

Citronellal

Geraniol

Rhodinol

Pelargonium graveolens

Perfume allergy

References

^ Lawless, J., The Illustrated Encyclopedia of Essential Oils ISBN 1-85230-661-0

^ Taylor WG, Schreck CE. (1985). "Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (-)-citronellol". J Pharm Sci. 74 (5): 534–539. doi:10.1002/jps.2600740508. PMID 2862274.

^ ^a ^b US EPA Citronellol Fact Sheet

^ Survey and health assessment of chemical substances in massage oils

Categories:
Alcohols
Alkenes
Perfume ingredients
Flavors
Monoterpenes

Citronellol
(+)-Citronellol (left) and (-)-citronellol
IUPAC name 3,7-Dimethyloct-6-en-1-ol
Other names (±)-β-Citronellol; 3,7-Dimethyl-6-octen-1-ol
Identifiers
CAS number	106-22-9^Y
ChemSpider	13850135^Y
UNII	P01OUT964K^Y
KEGG	C09849^Y
ChEBI	CHEBI:50462^Y
ChEMBL	CHEMBL395827^Y
Jmol-3D images	Image 1 Image 2
SMILES OCC[C@@H](CC/C=C(/C)C)C C\C(C)=C\CCC(C)CCO
InChI InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3^Y Key: QMVPMAAFGQKVCJ-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₁₀H₂₀O
Molar mass	156.27 g mol⁻¹
Density	0.855 g/cm³
Boiling point	225 °C, 498 K, 437 °F
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Citronellol — Général Nom IUPAC 3,7 diméthyloct 6 èn 1 ol No CAS … Wikipédia en Français
Citronellol — [zu Citrus] das, s, ungesättigter Terpenalkohol, (CH3)2C = CH (CH2)2 CH(CH3) CH2 CH2OH; farblose Flüssigkeit mit zartem Rosengeruch. Citronellol kommt (in zwei optisch aktiven Isomeren) in mehreren ätherischen Ölen, z. B. im Geraniumöl, vor und … Universal-Lexikon
Citronellol — Strukturformel Allgemeines Name Citronellol Andere N … Deutsch Wikipedia
citronellol — citronelolis statusas T sritis chemija formulė (CH₃)₂C=CHCH₂CH₂CH(CH₃)CH₂CH₂OH atitikmenys: angl. citronellol rus. цитронеллол ryšiai: sinonimas – 3,7 dimetil 6 okten 1 olis … Chemijos terminų aiškinamasis žodynas
citronellol — noun Etymology: International Scientific Vocabulary, from New Latin citronella Date: 1872 an unsaturated liquid alcohol C10H20O with a roselike odor that is found in two optically active forms in many essential oils (as rose oil) and is used in… … New Collegiate Dictionary
citronellol — /si treuh nel awl, ol/, n. a clear, colorless liquid mixture of isomeric alcohols having the formula C10H20O, usually obtained from an essential oil, as citronella oil, and having a roselike odor: used chiefly as a scent in the manufacture of… … Universalium
citronellol — noun A natural acyclic monoterpenoid, occurring in citronella oils and used in perfumes and insect repellents … Wiktionary
Citronellöl — Citronẹll|öl, Zitronellöl … Universal-Lexikon
citronellol — cit·ro·nel·lol nel .ȯl, .ōl n an unsaturated liquid alcohol C10H20O with a roselike odor that is found in two optically active forms in many essential oils (as rose oil) and is used in perfumery and soaps … Medical dictionary
citronellol — cit·ro·nel·lol … English syllables

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Citronellol

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